Explore the allure of private and custom cycling vacations. Tailor your trip, choose your group, and set your own schedule. Read on to discover the reasons to opt for a private bike tour and explore fantastic destinations for your next adventure.
Friends and Family
Friends and family that bike together, stay together. There’s nothing better than cruising with your nearest and dearest, and booking a Private Trip means guaranteeing you will be traveling with your favorite people.
It’s simple!
Gather your group, choose from our variety of trips and dates, and we’ll reserve an open week exclusively for your adventure.
Exclusive ≠ expensive
For most of our trips, with 10 or more in your group, the price is as advertised! So gather your friends, family and anyone in between.
Flexibility
We always say it’s “Your Day, You Decide” and with our Private Trips, it’s your trip, with your group, on your schedule.
Trip Enhancements
Enhance your Private Trip with our exclusive Add-Ons. From inclusive wine and beer to travel assistance, our Private Trips offer a one-stop solution to enrich your adventure.
Sit back, relax
Every aspect of your trip is meticulously planned to match your style. Your Private Trip Coordinator takes care of every detail, and our guides prepare your bikes in advance—so you can simply enjoy your vacation.
Looking to elevate your company outing? California Wine Country offers a 3-day escape amidst lush vineyards, blending exquisite wines and farm-to-table cuisine. Cycle through picturesque landscapes, sampling the region’s finest wines, and indulge in the vibrant food scene. A Private Trip to Sonoma combines luxury, adventure, and team building for an unforgettable company retreat.
Experience Tuscany’s rolling roads, exceptional cycling, and delectable wine and cuisine. Delight in local delights, from Chianti Classico in Radda to perfecting the art of Cucina Italiana with a private pizza-making class, this trip has something for everyone in your group.
Discover the heart of the American Southwest in Santa Fe, a fantastic destination for a memorable short vacation with loved ones. Cycle through the land of canyons, mountains, and adobe architecture. Immerse in luxury accommodations, relish award-winning cuisine, and explore Southwestern culture in an exclusive and intimate setting.
Andalucia beckons as the quintessential Spanish adventure. Pedal through limestone peaks, savoring the region’s diverse gastronomy. Immerse yourself and savor the culture of southern Spain with a private flamenco, explore organic olive oil farms, and cycle through pristine natural parks—creating unforgettable memories with your group.
Journey through Central Europe on a tailored 6-Day Private Bike Tour, making the journey from Prague to Vienna an ideal choice for a remarkable family trip or family reunion. Explore Bohemian landscapes, Renaissance towns, and dense forests, all while immersing in the region’s rich culture and delectable cuisine. Experience Ceský Krumlov’s medieval charm, savor a wine-paired dinner in Austria’s oldest winery, and cycle along the picturesque Danube River—making this private tour a cycling escapade of a lifetime.
Make any of our regularly scheduled departures private just for you.
Choose a private bike tour for a unique adventure with your favorite people. Take the first step towards an unforgettable private cycling tour by filling out our Private Trip form below. Your next adventure awaits!
Are you ready to book an unforgettable bike tour? With our 2024 tour dates releasing soon, here are five incredible regions that are sure to get any traveler’s heart racing.
1.Amsterdam to Bruges: A Delightful Cycling Journey through Northern Europe
On one of our newest adventures, you’ll cycle from the sophisticated city of Amsterdam in the Netherlands to the charming town of Bruges in Belgium. Both destinations are cycling capitals, with tulip fields, windmills, and spring flowers adorning the landscapes. And when it comes to contemporary cultural delights, there will be plenty of opportunities to sample the finest chocolates, cheeses, and beers the region offers. This tour is excellent for both experienced riders and new cyclists alike. From picturesque canals to the serene countryside, this biking adventure promises a perfect blend of past and present.
2. Italy: A Feast for the Senses on Two Wheels
Imagine cycling through the picturesque landscapes of Italy, exploring its rich history, indulging in delicious cuisine, and experiencing the warmth of Italian hospitality. Our bike tours in Italy will take you on an unforgettable journey through each region’s best. In Tuscany, surrender your senses to the Allegria of Italy as you pedal through the picturesque Chianti region to the Val d’Orcia. Along the way, you can sample a Chianti Classico in Radda, perfect your Cucina Italiana at a private pizza-making class, and explore the breathtaking scenery of the Val d’Orcia and the walled town of Montalcino. For those seeking epic rides and incredible vistas, the Dolomites offer unparalleled cycling adventures. This mountainous region in Italy’s heart is famous for its challenging climbs and breathtaking scenery. Discover southern Puglia’s wild beauty and culinary secrets, also known as the “heel of Italy’s boot.” With picturesque beaches and quiet roads lined by majestic olive trees, Puglia is a hidden gem for cyclists.
3. Norway: A Nordic Wonderland of Fjords and Mountains
For those seeking a true Nordic adventure, Norway offers a pristine wilderness of fjords, mountains, and glaciers best to explore on two wheels. Our Norway bike tour will take you on a thrilling cycling journey through this majestic country, where every turn reveals a new postcard-worthy vista. Pedal through stunning landscapes as you encounter breathtaking sights that will leave you awestruck. Ride the legendary Sognefjellet National Tourist Route, witness the size and power of the Jostedalsbreen glacier, and take in the turquoise blue waters of the Lustrafjord.
4. France: Cycling through Wine Country
France is a haven for cycling enthusiasts, offering diverse landscapes and riding experiences that cater to all levels of riders. Our Provence tour takes cyclists through lavender fields, vineyards, and charming villages while indulging in local cuisine and wine. Our Alps tour offers challenging mountain climbs and stunning alpine scenery, including the famous Alpe d’Huez, with opportunities to rest and explore the local culture. And for true cycling enthusiasts, the Tour de France tour provides the chance to ride along the same roads as the pros, experiencing the excitement and history of this legendary race.
5. Spain: Experience a sun-drenched Spain bike tour
Spain is a country that captures the hearts of travelers with its rich history, vibrant culture, and stunning landscapes. Our Andalucia bike tour takes you on a journey through the dynamic region of southern Spain, known for its flamenco music, stunning Moorish architecture, and delicious tapas. Pedal through olive groves, vineyards, and rolling hills, and immerse yourself in the rich cultural heritage of this unique region. Our Costa Brava tour is perfect if coastal landscapes are more your style. This picturesque region on the northeastern coast of Spain is known for its rugged cliffs, sandy beaches, and crystal-clear waters. Pedal along the stunning coastline, passing through medieval villages, and enjoy breathtaking views of the Mediterranean Sea. Our Mallorca Island tour is the perfect choice for those seeking a true island paradise offering a thrilling biking experience on the largest Balearic Islands. Known for its dramatic mountain landscapes, stunning beaches, and charming villages, you can cycle through the UNESCO World Heritage-listed Serra de Tramuntana mountain range, with its winding roads and breathtaking vistas.
Get Ready to Pedal into Adventure in 2024! Sign up for our early access list to be the first to know about new destinations in 2024.
Bluegrass. Bourbon. Horse Country. Experience the understated beauty of Kentucky Bourbon Country in this day-by-day photo guide taken by our talented guest, Bob Joy.
Day 1: Ride the Legacy Trail and explore downtown Lexington:
Take your first pedal strokes through horse country on the Legacy Trail Bike Path. You’ll wind your way past the Kentucky Horse Park and into rolling fields of beautiful horse farms. Your ride ends at Evans Orchard Cider Mill, where you’ll shuttle back to Lexington to walk around downtown to do some exploring before joining your group in the bar at Lockbox for a fun social hour and dinner.
Day 2: Tour MeadowCreek Farm and enjoy a tour and bourbon tasting at Limestone Branch Distillery:
Start your day at MeadowCreek Farm, just outside the town of Lebanon. The farm is home to several impeccably pedigreed horses with impressive wins on their resumes and you will have the chance for some up-close views of these amazing creatures! After the tour, your guides will shuttle you to Limestone Branch Distillery. Ride a loop through the hills around Lebanon on quiet country roads before enjoying a tasty picnic lunch. After lunch, you’ll get a guided tour of the distillery and a bourbon tasting.
Day 3: Explore Shaker Village and take a guided hayride tour:
Today you’ll explore the many offerings of the Shaker Village area. The morning’s ride will take you northwest, on roads through open farmland in the Salt River watershed. Upon your return to the village, the rest of the afternoon is yours to spend as you like. Choose to ride a bit more, to the small town of Burgin, or set out on a hike through the Preserve which features over 30 miles of trail through native prairies, woodlands, fields, and canebrakes. Or you may opt to take one of the many tours offered daily to learn about the Shakers who lived here around the turn of the nineteenth century. In the late afternoon, you will join your travel companions for a drink and narrated hayride, which will introduce you to the rich history of the village.
Day 4: Ride to Versailles, visit Woodford Reserve, and arrive at the Kentucky Castle:
Ride alongside the Kentucky River and through several of its tributary drainages on the morning ride as you cross unique bridges and pass through forests and small farms. When you arrive in downtown Versailles, you’ll have a number of fresh and delicious lunch options to choose from. Then hop back on your bike for a short ride to Woodford Reserve Distillery, one of Kentucky’s oldest and most highly acclaimed distilleries.
Day 5: Tour Castle & Key Distillery, enjoy lunch overlooking Glenn’s Creek, and toast your week at the Kentucky Castle
You’ll start your day riding your way to Castle & Key, a small boutique distillery that has recently undergone a careful restoration. The distillery was built in In 1887 by legendary distiller Colonel Edmund Haynes Taylor, Jr. and features a castle, a classical springhouse, and sunken gardens. On a guided walk through the property, you’ll learn about the owners’ from-scratch process of distilling spirits. Enjoy a tasting of their craft then head just down the road to The Stave for lunch. Here, a menu of modern twists on favorite Kentucky dishes awaits while you relax on the patio that overlooks Glenn’s Creek.
Day 6: Cycle past the immaculate grounds of the Keeneland Race Track:
Enjoy one final spin through the green pastures of the storied grounds of the Keeneland Race Track, listed on the National Register of Historic Places and once voted the #1 thoroughbred racetrack in North America.
Many thanks to our guest, Bob Joy, for contributing the photos for this post!
See the the Kentucky Bourbon Country trip
Now it is winter. From the kitchen table where I am writing, snow covers the perennial and vegetable gardens and the apple tree’s graceful limbs are sketched against the pale gray sky. I see fox tracks wandering down to the horse chestnut tree. Birds are busy at the sunflower feeders and the four-sided suet cage attracts downy woodpeckers and both red-breasted and white-breasted nuthatches. Cavorting chickadees are everywhere. The birds splotches of color are pleasing in the monochromatic wash of our habitat.
The notion of pedaling a bike amidst 97 degrees and punishing headwinds through Badlands NP seems so distantly foreign. But it really did happen!
21 cyclists plus 5 guides, have them move from place to place in concert every day and oh, by the way, ride a bike for 3800+ miles over hill and dale no matter the weather? It’s a social experiment bar none. Better than that it was the human condition showing itself in every kind of encounter. With eyes wide open I observed how my fellow P2P’ers and I handled fatigue, heat, rain, wind, 16 century/century+ days, a different bed every night, bicycle malfunctions, laundry obligations, gut grief, saddle sores, humdrum paltry breakfasts at too many Holiday Inn Express lodgings and muling luggage to a room every night only to lug it back to the luggage trailer every morning.
Some days smiles were harder to come by. Did we pedal anyway? Yup.
The collective nature of our task over-rode the daily setbacks or frustrations that stymied all of us at one point or another. Extending grace to another who was having a frustrating or tough day helped smoothed their road. I can remember Guide Blake matter of factly saying somewhere in the middle of Wyoming to someone who was complaining about the blasting heat and wind, “We signed up to ride across the country which means we are going to encounter all kinds of weather.”
It all worked out due to having 5 superlative humans as our guides and because 21 out of 21 of us were determined to rely on our persistence no matter what. The unsung virtue.The quiet ability to keep going when all around you events seem to conspire to create hardship just for you. The pressing daunting heat, the head winds, the hills, the hill that always came when I was sure I had no more to give. Somehow I always had something more to pull out of myself. Persistence. Belief.
To a cyclist we knew the ineluctable truth: we had to pedal those bikes for so many many miles to get where we wanted to go. The endlessness of South Dakota and her ferocious unrelenting heat sucked some joy out of each of us at some point. It became a game for Sandy and me to wonder how long it would be until we’d see a sliver of shade. Oh, there it was at lunch one day. Each day we woke up and oriented ourselves eastward. Each day Sandy would say to me as we rode along, “I could do this all day!” To which I would respond, “Lucky for you, let’s keep going!”
There’s an unexplainable thing inside me that is wired to find joy in the doing of a venture like this one. Each day I was eager to ride. Each day I was engaged. Each day was it’s own distinct experience with a new route to explore and to know that at the end of my effort a warm meal and a bed were waiting. Whether cycling alone or with others, I liked taking big gulps of what was all around me absorbing it all for more energy. I noted every grasshopper that leaped up and brushed my shins, each crumpled on the road butterfly, the creases in the rock formations, the osprey and eagles, the roadside chicory that I spied all the way in every state all the way until Vermont. I could never look away from the disfigured remnants of so many alluring creatures and my heart cracked each time. It still does as I remember the stilled wildlife.
To know that these strengths are still part of me is a pleasing comfort. For years and years I found joy in the training necessary to be an elite middle distance runner. I was able to conjure that same joy for the 8.5 months I trained for P2P and then, most importantly, find it again for the journeying days across the country.
My will? Iron strong. My heart? Powerful and honed. My mind? Always engaged in the doing in front of me.
Energy begets energy. Being around people who are faucets and not drains makes an endeavor sing. I gravitated towards those who were buoyant and could see the shade when there was none, who could bend into the biting winds and not say a word and see the sun when it rained (only 3 days of that, we were so very lucky). One of my favorite memories was seeing Ian one late afternoon as he barged into our hotel lobby in the middle of nowhere. He looked at me since I was the first person he encountered upon getting off his bike and he thundered, “Those last 20 miles were HORRIBLE.” I couldn’t help laughing.
Completing P2P has left me with a cornucopia of memories and experiences that will remain rich and real. So what’s ahead? The roads will find me in Solvang, Greenville and Mallorca on TT Ride Camp weeks. Vermont’s gravel roads will be on my docket in July. Autumn beckons with TT Ride Across Italy and the stunning Ride the Ridges 100K in Cabot, VT. Looking further ahead has me eyeing the TT Pyrenees Sea to Sea trip for 2024.
Training is my daily truth. It’s powered all the more by knowing I’ve got P2P quietly riding in my back pocket. A touchstone that abides. A reminder that I’ve got plenty to give. A reminder to say, “Why not?”
You’ve heard plenty from me by now. If you are considering joining this marvelously challenging and beautiful trip I’ll leave you with this: Believe, believe, believe.
Finally, I asked a few of my fellow P2P adventurers to share why they joined this audacious idea of a trip. If you find yourself nodding your head and thinking “I could do this” while reading their comments then you know what to do. Sign up!
Thanks for reading.
Lynn Jennings
Why did you decide to ride Cross Country USA?
Pat: “Why Not?!!!” Having completed 25 marathons, 40 plus ½ marathons, 15 Half and 2 full Ironman, and canoed in the Boundary Waters, this was the next big adventure on my laundry list (aka Bucket List) of things I really wanted (and needed) to do… and what better time than now. So, when I knew could wrangle 50 days away in the summer/fall of 2022 from work; and my hubby who was very willing to hold down the fort and take care of our 2 dogs and who was extremely supportive and encouraging me to go for it… “Why Not!!!” I never looked back and I am so very glad I embraced my “Why Not” along with my 20 other P2P riders. And the best part of it all for me is that WE ALL MADE IT.
Mike: At my retirement party I announced to my colleagues that I would be riding across the country with Trek Travel. I joked that this trip was the most difficult physical challenge I could think of that didn’t involve a death zone and bottled oxygen. I was excited to place a capstone on my athletic career and as a non-directed kidney donor, I wanted to inspire potential donors and allay their concerns. But those weren’t the only reasons. Over the course of my career, I’ve flown millions of miles, crisscrossing the county, peering out the window and wondering what it’s like down there. I’ve been especially intrigued by the west – looking down at the irrigated crop circles, like emerald islands in a sea of brown connected by two lane roads leading from one grain silo to the next. I wanted to ride those roads, cruise through those small towns and do it in the most visceral way possible, from the seat of a bike.
Jacque: As I neared my 60th birthday I was feeling inspired to do something big and adventurous. The beauty of life is its fragility, so while I have it I want to use it. I had an idea that I wanted to stretch my boundaries and engage in a process that pushed beyond what I thought was possible. When I first started dreaming of cycling across the country I wasn’t even a serious rider, however an encouraging voice from a fellow female rider and Trek Travel guide was the inspiration I needed to take the leap and start training. The flow we can all experience when we dig into the well of power within us to keep pushing through long rides is the biggest reason why I stayed the course. I rode across the southern route of the US and was hooked on the feeling of fortitude and resilience to get up and go every morning again and again and again. This second ride across the northern US I was seeking a sense of solidarity with my fellow riders through the demanding terrain. My passion to keep pedaling was fueled by a belief in myself, appreciation for my body and its capacity to carry me, and connection with the riders around me.
Sandy: I was fascinated with the idea of powering myself across this continent on my own two wheels. I am always amazed by the beautiful diversity in our land, and seeing it from a bike is different than from a car. It is a totally different experience! The changes in the topography of the land each day, like from the Columbia River Gorge to the wheat fields of Oregon. From the plains of South Dakota to the lush cool cliffs of Deadwood South Dakota. On a bike, there is more interaction with the locals as you ride by, both are more likely to greet each other and have a brief conversation. Or as in Wisconsin the shy wave of the Amish children walking on the side of the road as we rode next to them. There is also the sound of water as you ride next to a stream, lake or river. I will never forget the smell of pine in the air as we rode along the Clearwater river all day, the wheat blowing in the air with fine bits of it all over the road in eastern Oregon and the constant chirping of the prairie dogs in the Badlands.
There is also the challenge mentally, not just physically to be able to face every daily challenge. I knew this would be part of the trip and the challenge, but I didn’t appreciate the full extent of it until it was over. It is one of the things I look back on and feel a sense of accomplishment. The constant heat in South Dakota, the threat of headwinds, rain, bad breakfasts, detours on the route, a bike malfunction, a lumpy bed or noisy room air conditioner. I’ll always remember knowing that we faced every challenge with a happy spirit with guides who helped us solve the daily puzzle.
Carlin: Riding my bike across the country was a notion that stemmed from a conversation with a young man in a Friday morning boot camp at the Gym. He is/was a member of the royal family of the UAE – they figured out that he was gay and was sent to Switzerland for high school and to the US for college with gentle hints not to return. He is now a successful business man and is married to a physician. In our conversation he told me that his husband rode cross country in his college-med school “gap year”. He did it the hard way with paniers and camping but I resolved that I too would do the crossing. I trained hard and attempted to sign up in 2021 to find out that the trip was full. Thus I signed up for 2022, trained like hell, and had the absolute time of my life.
I expected a major physical challenge and was hoping at 64 years of age that I could rise to the challenge. It turned out that I was rewarded with new friendships that have continued after the conclusion of the ride and I got a chance to see the country and the beauty that can never be understood by driving or a fly over with a plane.
At the completion of the ride – I wished that I could continue to ride a century daily but life – being what it is – has had other plans. That said – I was able to bring joy to others by sharing my trip with hundreds of followers and have memories that I will treasure for the rest of my life. It is said that when life ends – you regret the things that you DON’T do not the things you do. I am 100% sure that this axiom is correct.
International Women’s Day is an important time to recognize the incredible achievements of women across the globe. We are proud to be a company that empowers and celebrates women in the cycling industry and we want to highlight some of the women who make Trek Travel special.
We are proud to have 40 of our 103 guides as amazing women. These women lead trips across North America and Europe and provide support, expertise, and incredible hospitality to our guests. Part of our guide training program is making sure every guide is a Trek certified bike mechanic, meaning we have over 40 female certified bike mechanics on the team. This is just one of the great ways that we are contributing to making this male-dominated industry more inclusive. Our guides also include 3 former women cycling pros on our Trek Travel team, who add a wealth of knowledge and experience to our bike tours.
Teaching and supporting the next generation of women is also an important aspect of many of our employees. One of our guides, Sarah Edwards, teaches young girls how to mountain bike in her free time. We have also had guides start organizations, such as Little Bellas, that focuses on building confidence and team work, and gets young girls into cycling. One of our Trip Designers, Rebecca Falls, volunteers for Little Bellas in her free time as is helping to create an inclusive environment in the outdoor industry.
In addition to our guides, we are proud to be a woman-owned company, led by our President Tania Burke. Tania has led Trek Travel for over 20 years and has created a culture of empowerment and equality in the industry. Tania was recently featured in WisBusiness, where she talks about mentoring her employees. “focusing on leadership skills developed by Jim Collins, author of numerous management books, including “Good to Great”.”, read the full article here. In our office, 38 of our 64 staff members are women that make up a variety of different departments.
We are proud to have so many amazing women on our Trek Travel team, from our guides to our office staff. Happy International Women’s Day!
Each year a lucky few get the unique opportunity to experience the Etape du Tour and ride a full stage of the Tour de France mere days before the pros tackle the very same route.
The 2023 edition of the Etape du Tour takes place in the Chablais Alps. The route encompasses Stage 14 of the Tour de France, spanning 94 miles and involving a challenging elevation gain of 13,450 feet. Participants will conquer three Category-1 climbs including the Col de Cou, Col du Feu, and Col de la Ramaz, with the toughest climb, the Hors Categorie Col de Joux Plane, saved for the end. This year’s race promises to be exciting, and the beautiful surroundings only add to the experience.
Leading up to the race, you’ll have the chance to explore the area and test your legs on some of the featured climbs in the region.
You’ll ride through beautiful mountain villages and past stunning landscapes. Your guides will support you every step of the way, providing you with water, snacks, rest opportunities, and Tour-de-France-style cheers.
On the day of the race you’ll take your place among thousands of other riders who are all there to chase history together. Our support team will be available at private rest stops to provide you with both encouragement and nourishment. These private rest stops will keep you fueled and out of the long lines of the official race stops. The race takes you through some of the most beautiful mountain passes in the region, including the Col de Saxel, Cols de Cou, du Feu, and Jambas. After your ride, your guides will welcome you to relax and recover at our exclusive post-ride celebration!
With stunning landscapes, challenging climbs, and world-class support, you’ll experience what it’s like to be a pro cyclist for a day. Don’t miss this opportunity to challenge yourself and create unforgettable memories.
As we gear up for the upcoming travel season in 2023, our team of skilled guides is eager to hit the road again. To get us all in the mood, we wanted to reflect on some of the most stunning moments captured in 2022, as voted on by our dedicated guides and office team.
Best Co-Guide Photo: Martin Coyle
Martin took an outstanding picture while exploring Glacier National Park with his fellow co-guides. The breathtaking scenery of the park provided ample opportunities for capturing great photos, but this one in particular stood out among the rest.
Best Picnic Photo: Megan Waldbillig
Nothing beats a picnic in a National Park after a day of biking and hiking, and our guides wholeheartedly agree! Megan went above and beyond by not only creating a delicious spread for her guests, but also capturing a photo that deserves recognition as the best picnic of the year.
Best Activity Photo: Laura Lefranc
Every trip features unique experiences and adventures that guests will remember forever. While in Norway last year, Laura took a great photo while the group was hiking to the stunning Feigefosse waterfall.
Best Group Photo: Stefano Lingua
Our trips are all about making memories and capturing the fun. One of the highlights is always the group photo! Stefano snapped a winner with this shot in the Dolomites – a real crowd-pleaser!
Best Rider Photo: Laura Lefranc
The breathtaking scenery of Provence is a photographer’s dream come true! Laura captured the magic with this amazing shot of a guest cycling through the Gorges de la Nesque.
Best North American Photo: Jonathan Hershberger
Utah’s Bryce and Zion National Park boast a one-of-a-kind landscape unique to the American Southwest. It’s no wonder why it was named the best photo in North America!
Best European Photo: Stefano Lingua
Stefano nailed it again with another amazing shot in the Dolomites. This fantastic photo was voted the best European photo by our guides!
Most Epic Photo: Nick Bouzianis
Nick got an amazing bird’s-eye view and snapped this epic aerial photo as the seasons were changing in Vermont.
Photo of the year: Giorgio Cordini
Giorgio snapped the photo of the year in the incredible setting of the Dolomites! The image perfectly captures the grandeur of the region, and shows off Giorgio’s talent for capturing such a striking image.
Valentine’s Day is a time for being with the people you love, and what better way to celebrate it than to share a heartwarming story of two lovebirds, Francis and Sara, who experienced the proposal of a lifetime.
Toronto natives, Francis and Sara, share a big passion for cycling and it’s something that has brought them closer together as a couple. Back in April of 2022, they decided to book a Trek Travel trip to sunny Arizona for November, so they could get out of the colder temps of Canada. In September, the idea of proposing to Sara on the trip popped into Francis’ mind, “After we started planning this trip, I decided that I was going to propose.” He said. So he bought the ring and reached out to Emily, their Trip Consultant, for help in planning the perfect proposal. Emily connected Francis with one of the guides, Jen, and together, they came up with a plan that would make Sara have no inkling that something special was about to happen.
“So from there, it became this huge thing where everyone was super excited and very helpful.” He said, “Jen and I were chatting and right away she sort of came out with a list of five suggestions. Some were on-bike ideas and some were off-bike, and through a couple of e-mails back and forth with guides’ Bev, Jen, and Dave, they got right to it.” The group started finding the best spots to propose along the route and would send photos back to Francis to get his input. “They even had sort of a mock proposal with Dave and Bev so I could get a sense of what it could look like. After seeing that, I thought it was perfect!”
It was finally time to head to Arizona. Francis and Sara arrived at CIVANA Wellness Resort and Spa on Monday, with the proposal planned for later in the week on Thursday. Over the next few days, Francis and the guides plotted out the details of how they were going to get Sara to the lookout point where the proposal was going to take place. “We came up with this plan where Dave would pull over one of the vans to the side of the road, saying that he was gesturing at a turnoff point, but that just happened to be where this lookout point was as well. Then earlier in the day I would tell Sara that something was wrong with my pedals so we could pull over and walk around while Dave “fixed” my bike. Bev would also be there with her camera and would suggest an awesome spot to take some photos because I know that Sara loves taking photos.” Francis would then lead her to the spot where the guides did the mock proposal and would get down on one knee.
Thursday morning rolled around and Francis could feel butterflies in his stomach. “I was having some anxiety about where I was going to put the ring box. It’s too bulky to put in the back of my jersey because Sara can see it. Then a couple of people sort of overheard me talking with one of the guides, and they all got excited and promised to keep quiet.” The ride started and the perfect plan sprang into action. “I had this mental countdown clock in my head because I knew what mile the pullover was going to be. So the whole ride became this countdown mile by mile until, oh my gosh, this is where it’s going to happen.”
Francis and Sara saw Dave in the distance and pulled off so he could “fix” Francis’ bike. Then with Bev’s suggestion, they began walking to the spot. “The walk was not that far, but maybe like 50 yards, and Sara was saying “Why do we have to go this far? There are so many other cactuses over here. I don’t understand. Can we just take a photo here?” I kept thinking that we have to keep going.” They quickly arrived at the spot. “It’s one of these things where the rest of it is a bit of a blur. I’m sure I blabbered out some nice words that expressed my love for Sara, then I got down on a knee.”
Sara was happily shocked and didn’t expect a thing all day. “It was all a very, very big surprise, even right up until the moment it was happening.” Sara said, “Like the whole story about how Dave wouldn’t have been parked there normally to mark the turnoff, so that was just a part of the ruse. Bev also just happened to be there with her big camera. I mean she’s just hanging out, taking pictures, because that’s what she does. So the moment he got down on one knee, I had no idea what was happening. There was a flutter of intuition that sat in me, but it was just a little flutter. I didn’t think it was happening on a Thursday in the middle of a bike ride, so I didn’t expect that at all!”
Then the newly engaged couple hopped back on their bikes and pedaled to the next rest stop. On their way in, Francis and Sara were met with another surprise as guides and fellow guests greeted them with champagne, cake, and a lot of cheering. “The rest of our group, who we only knew for four days became our little family.” She said, “It was such a unique thing to share with them, and they found it so special to be a part of it.”
Celebrations continued later that day and the rest of the trip. “Earlier on the trip,” Francis said, “I reached out to CIVANA and
told them about my engagement plans.” That night was a group dinner and Francis wanted to celebrate with their new friends while also doing something special for Sara. “The hotel recommended a local flower shop and let me call ahead so they could put a little arrangement together. Then they set up a table just for two. They also had a couple bottles of bubbly waiting for us, so that was a great way to celebrate the occasion afterward. The whole week was amazing. We had the best time, and the level of service that we experienced was so incredible. Dave and Jen were the champions of this whole experience. I couldn’t have done it without them!”
Looking back on the whole trip, Francis and Sara were delighted with how the proposal worked out. They said that, “The weekend before the trip, we spent two nights at the Grand Canyon and that’s a pretty spectacular place to propose.” Sara said, “Francis told me after the proposal that he was so anxious to get it over with so that he didn’t have to keep it a secret. If he had the ring on him at the Grand Canyon, he probably would have proposed right there.” Francis was relieved that he waited one more week, he said, “I was very glad that I didn’t propose there because it would have been spectacular, but it couldn’t have been more perfect than the way we had planned it.”
When they got back from Arizona they had one more surprise waiting for them. “Tania Burke sent us beautiful orchids and a nice card.” Sara said, “The resort also sent us a beautiful card, and all these thoughtful gifts meant a lot to us!” Francis and Sara have plans on visiting Mallorca this fall with Trek Travel to experience cycling by the Mediterranean Sea. As for the wedding, these travelers have a destination wedding in mind. “We’re going to have a wedding next January, probably in the Dominican. We were teasing after the proposal that [the other guests] were all invited to the wedding, and we hopefully will be able to plan a trip reunion sometime soon.”
Whether it be bikes, travel, or anything else, it’s the shared experiences that make love even stronger. “I think when it comes to biking,” Francis says, “it’s a constant reminder that you can do hard things when you push yourself. It’s probably cheesy, but it has strengthened our relationship together. All for the love of something that’s fun and feels good.”
We are delighted to be a part of Francis and Sara’s engagement and hope that their future is filled with love, happiness, and bicycles. Watch the video made by guest, Patrick O’Connor, who captured some moments from this special day.
Whether you’re celebrating a special milestone, rekindling the romance, or just seeking a romantic escape, our tours offer the perfect balance of adventure, luxury, and romance. Check out some of our most romantic destinations that are sure to sweep you and your loved one off your feet.
Combining luxurious accommodations with an inspiring array of acclaimed restaurants, Mallorca has a reputation as one of Europe’s premier destinations. With crystal-clear waters, stunning beaches, and a lush Mediterranean landscape, it’s no wonder why this beautiful island is considered one of the world’s most romantic destinations.
Get ready to bask in the breathtaking scenery of the southwest and take your vacation to the next level! This luxury getaway offers the perfect blend of relaxation and adventure, emphasizing health and wellness. Enjoy exploring one of the most biodiverse deserts and unwind at the luxurious CIVANA Wellness Resort, rated as one of the World’s Best Destination Spas. You’ll return from this romantic vacation feeling refreshed and rejuvenated.
Step into the fairytale setting of Slovenia: marvel at the region’s historic castles, and witness the beauty of Slovenia’s crystal-clear lakes, including the famous Lake Bled. Get ready to fall in love with breathtaking landscapes and rich cultural heritage.
This sun-soaked region boasts rolling hills, charming villages, and renowned vineyards that make for the ultimate romantic getaway. Immerse yourself in the local culture and take in the breathtaking views while you explore the vineyards on a leisurely bike ride. To top it off, you’ll be staying at the luxurious Harmon Guest House, the premier hotel in Healdsburg, where you and your loved one can relax in ultimate comfort.
The heart of Spanish romance, Andalucia boasts a rich history, vibrant culture, and stunning natural beauty. As our expert guides lead the way through this romantic region, you’ll discover hidden villages, historic landmarks, and breathtaking landscapes. For all rider levels alike, Andalucia is sure to steal the heart of any active traveler.
Days 42-46: Cazenovia, NY -> Portland, ME. 3,368 total miles and 134,138 ft of total elevation.
Day 42: Cazenovia, New York Five days left in this “Crazy 47 day ‘see the country weight loss program’ trip” as one of my fellow cyclists dubbed our endeavor.
A day off the bike is a treat in that one re-discovers the joys of walking. How refreshing to stroll the one main street in Cazenovia, find a coffee shop, sit on the porch, enjoy late September warmth while sipping an artisanal hot chocolate. realize one’s weary cycling fanny does not like the hard metal chair, chat up Rae and Brent as they showed up for coffee and then perambulate with Silk back to the Brewster Inn. A triumph all the way round. I’ve missed walking.
Silk was a lawyer for a few hours, I re-organized my kit so that I could more easily find what would be needed for a few more rainy days, followed that up with a 90 minute nap and before we knew it we were walking to dinner to the Brae Loch Inn with Pat and Sandy where live Celtic music was on offer.
The mac and cheese, salmon, burgers and salads were fine enough and Sandy, Pat, Ian, Silk and I made our way back to the deserted Brewster Inn’s gift shop with its magnificently stocked ice cream freezer loaded with pints of various flavors from a local concern. We chose a few pints to share, scored some spoons and bowls from the kitchen and had the Inn’s big pub room to ourselves as we dug in.
Today’s themes:
The prospect of rain.
The prospect of serious hills post-lunch.
Riding the day after a rest day isn’t some grand reprieve from fatigue.
When will the rain hit?
Doubt I was the only one with these four themes running through my head. Oh yeah, I’ll add a fifth to make it an even quintet: what combinations of kit should I wear if the rain doesn’t hit until the afternoon?
This morning at breakfast it was all about, “What are you wearing?” The avid meteorologists-in-training were consistently saying the same things to whomever would listen, “It will rain but not until after lunch.” The glowering skies in Cazenovia were giving way to blue and rosy hues so our morning groups launched under promising conditions.
Final consensus: rain pants over tights or go without rain pants.
There’s no denying rain pants on a bike are amateur hour looking and yet considerably helpful when one is talking about endless miles with soaking wet tights. Cold weather means tights are de rigueur and a cold rain means rain pants are a smart choice over those tights.
So Silk, Sandy and I started out with rain pants wondering if they were the right thing. After our brief lunch stop at mile 55 with Sandy checking the hourly forecast, we realized we were sitting in the cat bird seat. We’d be encountering rain within just a few miles after lunch. No need to scurry around to a van, find one’s bag, pull out rain pants and don while hopping around hoping one’s bike shoes and booties would make it through the lower leg opening of the rain pants.
First pro tip: buy rain pants with a very long lower leg zipper.
Second pro tip: put a ziplock baggie around one’s cycling shoes using knife or manicure scissors (Sandy!) to cut holes for cleats to fit through.Don booties. Shoes stay dry!
After a brief and happy meet-up with sculling training partner Ken at the lunch stop, we three set out to conquer the soon to come hills and cope with the rain. Happily the brilliant orange and red leaves, bronzed ferns, and shining in autumn garb cat tails were striking with the pigeon gray skies all around. The rain came down, we powered up the hills and flew on the descents getting wetter by the minute but with dry feet and legs. Silk and I had a couple of fun push me/pull you uphill duels. Sandy enjoys the way the hill melts away as she watches us tussle.
All in all the 92 miles slid by and we were triumphant upon our near to 2pm arrival to the Irondequoit Inn in Piseco. We were the 3rd, 4th and 5th to arrive and it was quite something watching sodden, cold and tired cyclists come stumbling in over the next hour. Persistence personified.
Poor Ian was underdressed and his bright pink hands were curled into claws when he staggered in. Hot showers and a cozy wood stove soon put everything to rights. As Ron noted in his journal, “This was a nice ride until it wasn’t.” Cold rain enveloped him the last 25 miles to the Inn. He said the rain served to highlight his one poor choice in clothing; he didn’t bring gloves for cold, wet weather.
More rain tomorrow as we migrate to Ticonderoga. After that we will have sun and autumn colors in VT and NH. Four days of cycling remain.
Day 43: Piseco, New York Morning at the Irondequoit Inn dawned still, freshly washed and with pink promising skies. My frequent checks of the hourly conditions in Piseco and Ticonderoga meant it was a bifurcated day in terms of clothing. With temps in high 50’s and pink skies at 7:30 am then showers and dropping temps showing throughout the day. The perennial question, “what to wear?” predominated. Wearing the yellow Showers Pass jacket meant hotting up and sweating. No rain jacket at all would be ill considered.
I bent to the task of assembling two day bags: one for rest stop 1 and one for lunch. That way I could strip down to a dry base layer and don or doff the appropriate jacket, rain pants along with helmet cover and beanie as rain became imminent. I started with light Rapha rain topper and tights. No rain pants. No beanie.
The morning was an autumn aficionado’s delight: brightening skies, damp roads, leaves on fire, no wind, sparkling rivers and brooks, glistening grasses. Sandy and I rode as a duo today and as we swung along we both felt the power of the day. Not a day to be gotten through. An 85 mile, 4000 foot day to savor. So it might rain? We were ready.
Highway 8 took us a long way today and it was a winding, low traffic, excellent tar colorful flyway. The roads pulled us onward. We climbed and dropped, we went around corners with maple and sumac reds popping. The oranges and yellows layered evenly all around. We were riding through a silent watercolor. When the sun came out spraying her light through the trees our small slice of the world shone. Photos can’t capture what we were riding through. Taking it all in every mile of the day proved to be the only way.
We crossed the Sacandaga and Hudson rivers today. Guide Brian was staged on the former to snap our pics as we rolled through.
Lunch was a brief affair punctuated by pulling on rain pants, helmet cover and exchanging my brick colored Rapha jacket for the blazing yellow Showers Pass topper. After checking the hourly weather again it was obvious we’d be riding right into the rain. Took us but a few miles and then we were pelted. Sandy called to me, “I’m fine with this! I love it!” That set our tone and we buoyantly powered our way for the next few hours before crossing into Ticonderoga.
With 2.85 miles to go we came across the Wind Chill Factory. Sandy was alerted by Pat that as we approached Ticonderoga there would be a noted ice cream joint. We were wet and cold. Did we stop? Yup! Was it good? Absolutely! Another organizing principle on P2P was the pursuit and chase for ice cream in whatever towns we found ourselves in. The usual suspects of Pat, Sandy, Silk and me plus easy recruits Ian and Jacque and a few stray others meant we had some seriously memorable treats as we progressed across the US of A.
Sandy and I shoved off with a sugar buzz, descended into town, looped around the small roundabout entering town while admiring the stunning Liberty monument and found our way to the Best Western. As we closed in I realized anew that VT would be just minutes away tomorrow and the end of the trip was happening right now.
The day ended on a wonderful high. My long time PDX bestie Heather grew up 20 miles north of Ticonderoga. She left Hartford where she is now living and drove up to surprise me at the Best Western. Thanks to TT’s exhaustive P2P website, she knew what hotel I’d be at. Given all the P2P reports I’d been sending out along the way she had a pretty good idea of how long I’d be out on the road and about when I’d be pulling into the Best Western.
Wow. Big sign. With me thinking, “What? Heather?!” A kismet surprise that had me grinning. Heather housesat for my sweet Portland, OR house and wonderful kitty Petey one summer and autumn when I was in VT. She made a paper “Good luck Mom” sign and Petey sat near it to send me good tidings for my Head of the Charles race. A memory that always makes me happy.
Heather hung out and kept Sandy and me company as we monitored laundry and stretched on the upstairs hall carpet plus she stayed for dinner. After dinner Sandy, Pat and I piled into her Mini Cooper and she drove us to the Wind Chill (Heather knew all about the Wind Chill from her nearby growing up years) so Pat and she could get some ice cream. Pat had a tough day. Her iPhone came off her handlebars and she didn’t realize it until some miles later. Guide Brian who was at rest stop 1 circled back in the minivan and spent 90 minutes driving the first 17 miles of our route looking for it and coming up empty. Gallant effort. Ice cream helped soothe Pat’s tension and left us all smiling.
Day 44: Ticonderoga, New York The chilly seven minute Lake Champlain ferry crossing from Ticonderoga over to VT got our day started. With a quick stop at the Welcome to Vermont sign we lit out for Hanover. Silk stopped for some photos early on and I just kept going and going.
I rode solo all day, bypassed lunch and the rest stops other than to refill water at rest stop 2 and was in a happy groove, I was appreciating the silence and my ability to look around and see everything without having to engage with anyone else all day long. I felt fantastic powering up Brandon Gap and let it all unspool from there. The 88 miles flashed by and with 5600 feet of climbing I was bent to the task with concentration and effort.
Lovely Hanover with its inviting Hanover Inn was our night’s lodging. Once arrived I went for a long walk over to the Connecticut River to see the gorgeous Dartmouth boathouse, across campus down to the familiar track and then back to the Green enjoying a hot chocolate while watching the students traipse past. With two days remaining I felt the push and pull of knowing the finish was so near.
Tomorrow our penultimate ride will take us up and over the Kancamagus Highway and also Bear Notch. Lots of miles, lots of elevation.
Day 45: Hanover, New Hampshire The Hanover Inn was a sumptuous and elegant overnight respite and we woke to river valley ground fog, thick and cold as thieves. Happily our fore and aft blinking lights can cut through the densest fog so we felt safe heading out. It was also 34 degrees.
Our day ahead? 7500 feet of elevation as we cut through the White Mountains via the Kanc. It was destined to be a century day because Silk and I decided to add on the extra 3 miles. The sun was going to be shining. We were willing. Why not?
Kit choice today: purple Rapha winter jacket, arm warmers underneath, leg warmers, shoe booties, beanie under helmet and winter technical lobster claw cycling gloves (so shifting could happen). Plus a buff around my neck. Brrrrrrrrr.
Sooner or later once the real climbing started it became a sweat management morning: Unzipping my jacket on the climbs, zipping back up on the rip roaring descents. Soon enough the sun burnt off the fog and I doffed the beanie, the arm warmers and the winter riding jacket. Went with the brick colored topper coat and soon that was also bundled into my jersey pocket.
We flew in and out of lunch in less than ten minutes and were the first to start tackling the climb up the Kanc. Silk and I know every wrinkle of that climb having trained on it too many times to remember and it’s a long slog. 10 miles, I think. Then the zippity 6 mile descent before the up and over of sinuous and alluring Bear Notch with its delicious I never want it to end descent. Combined with the earlier up and over Route 18 in the Moosilauke area meant we really earned it today. There are some diabolical minds in the trip planning department at TT. Amy Davison I’m looking at you! Big time elevation today. A fitting earn the stripes wind down effort near the end.
Silk and I arrived in North Conway and the Comfort Inn with plenty of daylight to spare. A treat!
Agog at the concept: tomorrow is our last route to tackle. Unbeknownst to Ron, the idea was floated by Mike and we all agreed: Ron will be the one to lead us into Crescent Beach. Gobs of friends and family are sure to be there to ring cowbells and cheer us in.
Day 46: North Conway, New Hampshire -> Portland, Maine Today was a whirlwind of color, excitement and flurries of activity.
I had two technical issues with my bike at the start in North Conway which needed Guide Brian’s mechanical skills. I had to hold off while our group went on ahead. Guide Brian bent to the task of sorting out my gearing and the electronics and he got me on the road in record time.
I was so looking forward to riding with Sandy, Ian and Pat but time was precious today and off they went. Silk and I rode with Guides Brent and Rae and we reveled in the 68 mile jaunt absorbing the dazzling colors in Baldwin particularly as we approached Portland. By the time the four of us whirred into Scarborough there was just enough time for Silk to grab a few slices of pizza lunch while I changed into dry kit. Now near the coast the slightly warmer temps meant shedding leg warmers and heavier jackets.
With Ron leading our razzle dazzle group we formed a serpentine line behind him as we rolled the final few miles from Scarborough to Crescent Beach State Park. Bruce came by with his GoPro and we all one by one saluted, waved, smiled and fist pumped our moods.
Ron pushed and pulled us and we loved it. Our last ride. 21 of us strong. He had a tear in his eye as we grouped around him and jubilantly rolled into the beach en masse to the clamor of cheering and ringing cowbells. Friends and families holding signs, smiling, waving, hugging. It was a scene.
Bike cleats and socks went flying, champagne and beers were poured, toasts were made, bikes were hoisted and we stood in the ocean with them. Guide Blake was taking photos and all around were families beaming in wonder all thinking the same thing, “They rode all the way across the country!”
The rolling waves hosted us as singly and in groups we lifted our bikes and cheered for ourselves. We finally collected into two groups and stood in the ocean: one group of our ten women (the most ever on a P2P journey) and the other of all of us together.
Portland to Portland 2022. We did it. It’s a puzzler to sort out the truth that by pedaling one day after another we rode across the USA. There’s a lesson in there somewhere and I’m catching glimpses of it.
It feels like a dream. A savage, resilient, deep, tender, beautiful, soaring, gritty, will I turn it into something dream.
Portland to Portland. Trained for, executed and now done.
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What is the Difference?
Ultimate Luxury:
Savor some of the most spectacular, 5-star properties in the world. Exuding luxury and elegance, these one-of-a-kind accommodations offer the chance to rejuvenate at award-winning spas, dine at Michelin-starred restaurants, and more.
Luxury:
Enjoy luxurious accommodations handpicked for a refined experience. From signature spa treatments to delicious local cuisine, you’ll be more than provided for; you’ll be pampered.
Explorer:
These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.
Combined:
On select cycling vacations, you’ll stay at a mix of Explorer and Luxury hotels. Rest assured, no matter which hotel level you’re at, our trip designers carefully select every accommodation.
Road: 1-3 hours of riding. Up to 25 mi (40 km). Up to 1,000 ft (300 m).
Gravel: 1-3 hours of riding. Up to 20 mi (35 km). Up to 1,000 ft (300 m).
Hiking: 1-3 hours of hiking. Up to 5 mi (8 km). Up to 1,000 ft (300 m).
Level 2:
Road: 2-4 hours of riding. 20-35 mi (35-60 km). Up to 2,500 ft (750 m).
Gravel: 2-4 hours of riding. 15-30 mi (25-45 km). Up to 2,000 ft (300 m).
Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 m).
Level 3:
Road: 3-5 hours of riding. 25-55 mi (40-85 km). Up to 4,500 ft (1,500 m).
Gravel: 3-5 hours of riding. 20-40 mi (35-60 km). Up to 3,000 ft (900 m).
Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).
Level 4:
Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).
Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).
Hiking: 4+ hours of hiking. 7-15 mi (11-24 km). Up to 4,000 ft (1,200 m).
What are your trip styles?
Classic - Reserve:
Savor the finer things as you relax in luxurious 5-star accommodations and wine, dine, and ride in some of the most unforgettable destinations around the world.
Classic - Signature:
Explore beautiful destinations by bike, enjoy extra inclusions, savor delicious local cuisine, and enjoy the perfect mix of accommodations.
Classic - Discover:
Enjoy a casual cycling vacation with fantastic routes and comfortable accommodations.
Ride Camp:
Train like the pros in some of their favorite riding destinations.
Pro Race:
See the pros in action at the biggest cycling events of the year.
Cross Country:
Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.
Self-Guided
Enjoy a bike tour on your schedule with just your chosen travel companions.
Sometimes it’s more convenient and comfortable to have your own room while on vacation. We understand and that’s why we offer a Single Occupancy option. The additional price guarantees a private room all to yourself
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