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How to Choose Your Travel Style

person riding a bike with awesome South Dakota view in the background

With more ways to travel with us than ever before, we’re here to help you decide which style is the best for you! Whether you want a classic guided experience or something totally custom, there’s a little something for everyone.

Guided trips are a great choice for you if…

  • You like traveling with a group and meeting new people
  • You feel most comfortable riding with the support of professional guides and a van
  • You want to arrive at your trip and have all the details organized for you

Self-Guided trips are a great choice for you if…

  • You love independence and private time during your vacations
  • You’re the master of your schedule and prefer to have the flexibility to change plans as you go
  • You feel comfortable changing a flat tire and you’re comfortable with self-navigating

Private, Custom, and À la Carte are great choices for you if…

  • You want to travel exclusively with your own friends and family
  • You have a specific destination in mind that isn’t part of our current offerings
  • You want to incorporate additional elements into your trip, such as private boat rides, fishing excursions, or guided hiking experiences
  • You want us to help with specific planning details, such as providing bikes and routes

Pro Race trips are a great choice for you if…

  • You’re a cycling fan and love watching the pros battle it out in the big races
  • You’re an avid cyclist who wants to experience what it’s like to ride like the pros
  • You’re looking for a VIP experience, with behind the scenes access and premier viewing locations

Ride Camps are a great choice for you if…

  • You love big days in the saddle
  • You get more excited to ride than to go sight see
  • You want to meet other avid riders from around the country


Found your perfect way to travel? Now find your dream destination.

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The Best get Better For 2020

We’ve made some of our most popular adventures even better with some extra-special additions, moments and features. Whether it’s wine, luxury or lavish itineraries, you’ll find more of what you love, and more magic in every moment.

Join Trek Travel for a Spanish Bike Tour to Andalucia, Spain


If you’ve dreamed of Spain, you’ve dreamed of Andalucia. This is quintessential Spain. Andalucia is limestone peaks, white villages, spectacular views. It is exquisite tapas, rich olive oils, classic wines, warm hospitality and passionate music. This Andalucia is the birthplace of Spanish romance, where flamenco and a vibrant history combine to create a once-in-a-lifetime experience. Picasso called this place his home. You’ll call it amazing. Ernest Hemingway was enchanted with this region of Spain. You, too, will fall under its spell.

Join Trek Travel for a bike tour to Blackberry Mountain by Blackberry Farm

Blackberry Mountain

Framed by vast, panoramic vistas, Relais & Chateaux designated Blackberry Mountain is an immersive experience that seamlessly blends outdoor activity, wellness and thoughtful indulgence. Blackberry Mountain continues the Blackberry Farm legacy of world-renowned hospitality and unwavering appreciation for the land. With 2,800 acres of land in conservation, the Mountain preserves natural wonder and offers breathtaking views—each morning. From relaxing spa treatments to outdoor adventures, activities are vast on the Mountain and include hiking, yoga and meditation, mountain biking, craft classes and more. With 4- and 6-day options, Blackberry Mountain has something for every guest.

Join Trek Travel for a Italy Bike Tour to Cinque Terre

Cinque Terre

There is no place on Earth like the five villages of Cinque Terre. And no way to see them like this. Join us for this adventure and see for yourself. We’ll pedal a selection of rides from the dramatic mountains that dominate the Tuscan coast to the winding streets of the Italian Riviera to discover the stunning beauty of the Cinque Terre. This UNESCO World Heritage site is home to thousand-year-old villages perched on top of sheer rocky outcroppings, connected only by walking trails and a narrow-gauge 19th-century railway. Food is the showpiece of this special destination, and we’ll introduce you to some of the best and most exotic, including handmade focaccia, fresh anchovies, and the locally-sourced pesto. All at once, Cinque Terre is sure to seduce, charm and beguile you with its best.

Join Trek Travel for a Texas Ride Camp bike tour to Texas Hill Country

Texas Ride Camp

Is it too bold to say that the Texas countryside was actually made for cycling? Well, then let’s be bold, because we think the meandering roads, gentle ascents and bike-friendly rural highways of this super-sized state are begging for two wheels. For decades, Fredericksburg and the surrounding hills have been a revered training ground by anyone that has put rubber to the road. The seemingly endless asphalt around Gillespie County is perfect for Texas-sized mileage, where even short rides can easily go long as way leads on to way. Here you will ride the many roads that pros use for offseason winter miles and good, old-fashioned Southern hospitality. Texas Ride Camp has 4- and 6-day options to suit any rider’s training needs.


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You Can’t Beat Firsthand Experience

Each year we take to the field to see our trips for ourselves. Our team prides itself on being able to guide you, our guests, to the right trip—whether it be an avid climbing adventure through the Alps or a weekend trip to California Wine Country.

But all that knowledge has to come from somewhere. That’s why we make a point to send our team into the field to gain firsthand experience on a variety of trips. From the food to the rides to the accommodations, our team can provide thoughts and recommendations based on what they’ve seen for themselves.


Ashley: Trip Design Coordinator

Where did you go? Yellowstone and the Grand Tetons

Favorite ride of the trip? This is difficult…I only rode twice while I was there, but I have to say each ride was equally beautiful in their own ways. My first ride was an amazing introduction to the sights of the Tetons. My second ride was a bit more challenging with some hill climbs but incredibly worth it to see views of the mountains and wildlife.

What was your favorite trip WOW? The views – although they are always changing, they never end! From the craggy mountain peaks to the turquoise waters, it seems like this place is too good to be true. It doesn’t hurt that the wildlife isn’t too shy either–I saw countless elk, mountain sheep, and two black bears!

Would recommend this trip to guests who…? This trip is a great option for those fellow nature junkies who truly want an iconic experience in a National Park. It is a great mix of cycling the long wildlife corridor roads and hiking the more remote and special places of the parks.


Luke: Trip Consultant

Where did you go? Tuscany, Italy

Favorite ride of the trip? Day 5 San Quirico to Montalcino Loop was awesome. Loved it so much I did it twice!

What was your favorite trip WOW? Lunch on Day 4 at Da’Roberto’s.

Would recommend this trip to guests who…? Love beautiful views, appreciate good food and wine, want a few cultural experiences, and enjoy challenging riding.

Sherrie: Trip Consultant

Where did you go? Zion Long Weekend

Favorite ride of the trip? My favorite ride was on the last day from Springdale to the Temple of Sinawava. It was a super peaceful and serene ride.

What was your favorite trip WOW? Riding into Zion National Park past the Checkerboard Mesa and then hiking the Canyon Overlook Trail for some incredible views looking down onto Zion National Park.

Would recommend this trip to guests who…? Are looking for a weekend getaway and want to explore one of America’s great National Parks. This trip is for the adventurous guest who is looking to ride but also hike some throughout the weekend.


Essie: Guest Services Coordinator

Where did you go? Asheville to Brevard

Favorite ride of the trip? Day 4, had the most beautiful ride up Mount Mitchell, the highest peak east of the Mississippi River. It is a gorgeous ride with panoramic views and many lookout points. At the summit, you can see Tennessee in the distance.

What was your favorite trip WOW? We had two brewery stops on the trip, and I do not drink beer. The guides surprised me with high-quality gin and tonic, so I was able to have a drink along with everyone else!

Would recommend this trip to guests who…? Anyone who loves great views, and wants to see the beautiful Appalachian mountains.


Find your next cycling vacation.

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Sneak Peek: New Wows for 2019

We’ve gone and overhauled some of our most popular adventures with some extra-special additions, moments and features. Whether it’s wine, luxury or lavish itineraries, you’ll find more of what you love, and more magic in every moment.

Trek Travel Chile Cycling Vacations


In 2019 we’ll call the Lakes and Volcanos district of Chile home riding from the outdoor mecca of Pucon along the Lakes & Volcanoes Scenic Route to the Patagonian rain forest and onward past the majestic Osorno Volcano to your final destination on the shore of Lake Llanquihue. Want to explore Patagonia more? Hike four days in Torres del Paine as a trip add on. Plus, did you know Chile is in the Eastern time zone? So you’ll spend less time shaking jet lag and more time soaking up the scenery.
Trek Travel XC Cycling Vacations

Cross Country USA: Santa Barbara to Myrtle Beach

Back by popular demand, we’re excited to bring back our epic southern Cross Country USA trip. Ride over 3,400 miles and climb more than 137,000 feet as you make your way from Santa Barbara to Myrtle Beach in 42 days. Through the miles, you’ll take in a sunrise over the Grand Canyon, pedal portions of historic Route 66, two-step the night away listening to Nashville’s best country music and admire the views from Caesar’s Head before descending into quaint downtown Greenville.
Trek Travel Santa Barbara Cycling Vacations

Santa Barbara

Our newest addition, this hotel may be called the Californian, but is pure Santa Barbara from its trendy Funk Zone neighborhood location to its two signature restaurants. You’ll lavish in every luxurious touch, whether it’s taking a break on the rooftop pool with a panoramic view of palm trees and Pacific shoreline or treating your skin to a decadent treatment at the surreal spa.

Vermont Cycling Vacations


Vermont is full of new for 2019. You’ll meet the Castle family and learn about the variety of berries they grow and feature in their small batch Sisters of Anarchy Ice Cream. Then make some ice cream of your own. You’ll also get the chance to kayak or paddle board on Lake Champlain and settle into quintessential Vermont at Basin Harbor, managed by the Beach family for 5 generations, you’ll feel right at home as soon as you arrive.


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Go North: Alaska Beckons

From the majestic living glaciers and steep fjords of the Kenai Peninsula, north to the lonesome gravel roads of the interior outpost of Talkeetna and skyward to 20,310’ Mt. Denali, America’s last frontier is untouched and full of mystery. Here, Trip Designer Tony Ferlisi pulls back the curtain on the rugged and beautiful landscape that is Alaska.

“There’s gold, and it’s haunting and haunting;
It’s luring me on as of old;
Yet it isn’t the gold that I’m wanting
So much as just finding the gold.

It’s the great, big, broad land ‘way up yonder,
It’s the forests where silence has lease,
It’s the beauty that thrills me with wonder,
It’s the stillness that fills me with peace.”

-Robert Service, from The Spell of the Yukon

Scale acts to lend us perspective. It clarifies detail. It takes something small and magnifies it. Takes something giant and makes it tangible; brings it into our human world of understanding. Sometimes we use numbers or ideas to correlate size. Sometimes, we create physical replicas. Spin a globe in your local library or restructure a model atom in high-school chemistry class.

Trek Travel Alaska Multisport Cycling Vacation

The scale of Alaska is seemingly impossible. Rivers and their flood plains stretch laterally across valley bottoms farther than you can see from the window of an airplane. Imagine the Hudson, the Columbia, the Ohio, the Colorado, the Rio Grande all running within a few hundred miles of each other. Add those to over 9,000 other rivers and you get the idea of the number of waterways in Alaska. 3 million lakes, 100,000 glaciers, and almost 34,000 miles of coastline; more than Florida, California, Louisiana, Texas, North Carolina, Maine and Virginia… combined. Mountains tower above the landscape, piercing the clouds and consuming all horizons; the highest rising over 20,000 feet above the sea and 10 of which are higher than any peak in the lower 48 states. Overlay a map of the continental United States with a map of Alaska and its land-mass stretches from the Pacific Ocean to the Atlantic.

But none of these perspectives do justice to those who haven’t laid eyes upon this place. Recall the feeling of standing at the foot of the Empire State Building for the first time and looking up or sailing on a boat just out of sight of land. Imagine what it might be like to be awash in the emotional waves of experiences like these for days in a row, each one new and each different than the other. That is Alaska, even for those who return time and time again.

Trek Travel Alaska Multisport Cycling Vacation

After John Muir first visited Alaska in 1879, he recorded in his journal that one should “never go to Alaska as a young man because you’ll never be satisfied with any other place as long as you live…” There is truth to this thought. You’ll dream about this place: the possibilities and the impossibilities. Movies against the backs of your eyelids as you lie awake at night, teetering just beyond sleep. Wind playing tag through dense alder thickets. Afternoon sunshine casting shadows against the jagged, snow-covered towers of the Chugach. Two bald eagles perched in a snag high above a shallow creek teaming with spawning salmon. Waiting. Watching. Your nostrils twinge with the scent of a Sitka spruce stand. Fingers feel the chill of the morning dew. Ears deafened with the silence. You contemplate the size of this landscape. You meditate on its scale. You’ll wonder when, not if, you’ll journey back to the north. Back to the great big, giant mystery that is… Alaska.

Trek Travel Alaska Multisport Cycling Vacation

Make a great escape to Alaska

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Our Newfound Cycling Paradise in the UK: Scotland [Video]

Put away your golf spikes and three-iron for a moment and consider this: Scotland was actually built for bikes, too. At one of our newest destinations, we’ll ride through the Highlands where you will be treated to stunning scenery each day, along with a huge array of cultural experiences. We’ll visit and stay in castles, indulge in a tour at the Glenfiddich distillery and perhaps a microbrewery as well. But don’t let us do all the talking. We went to explore just how special Scotland is while designing our newest trip. Watch the video below, it showcases our experience best.

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Meet Our Team: Amy Davison

Amy Davison knew that practicing law wasn’t the end-all-be-all. That’s when, after a little soul-searching, she decided to take a leap and blend the things she loved the most into a career she could be passionate about.

Tell us your story. How did you end up at Trek Travel?

After several years of practicing law in Chicago, I was questioning my career choice. It took a couple of years of soul-searching and brainstorming about what should come next but ultimately, I decided to blend the things I loved most – traveling, athletic activities, cooking and learning about other cultures – into a career. I was just starting to learn about cycling at the time and found Trek Travel via a Google search. The rest is history.

Can we get a quick run-down–what does it mean to be a Trip Designer? What’s your design process?
It’s kinda like a funnel. We cast the net wide in terms of possibilities for a new trip and narrow it down by researching several key criteria…hotels, roads and scenic beauty come to mind. Once we have a general concept that we are really excited about, we start drilling into the endless details that need to be nailed down to make it the experience of a lifetime!

Tell us about your favorite trip you’ve ever designed and why.
Well, I am relatively new to the trip design department, so I have not designed many from scratch. I have to go with our new Yellowstone Tetons trip. I am enamored with the raw beauty of the Teton range, the roaming wildlife, and the amazing network of bike paths in Jackson Hole that are flat and separated from the road. This means anyone and everyone can take it all in from a bicycle – the absolute best way to see the world, in my book.

What’s your dream travel destination?

Tell us about your best travel adventure.
It’s hard to choose, but I would say trekking in the Himalaya. The mountains were stunning. The trek was challenging. The people were gracious and kind. Life became so simple.


Meet Our Team: Amy

California Wine Country, in Three Ways

Whether it’s a rich, full-bodied pinot, a crisp chardonnay, an invigorating ride through the countryside or just a romantic escape, California wine country has got it all. Which is why we offer three different styles of trips right in the Napa and Sonoma valleys. Here we’ll compare our luxury, explorer and wine weekend trips so all you have to do is ride, sip and enjoy.

Luxury  |  Explorer  |  Long Weekend

Ride along vineyards on a California Wine Country bike tour

Enjoy wine tours and tastings on a California Wine Country bike tour
Dine at Ad Hoc, Thomas Keller on a California Wine Country luxury bike tour

California Wine Country Luxury

Price: From $3,299
Rider Level: 2 | Recreational
Start | End: Healdsburg to Yountville

Hotel Healdsburg – An perfectly luxurious hotel located in the heart of downtown Healdsburg and winner of Conde Nast Traveler’s Reader’s Choice award.
Vintage Inn – A newly-renovated AAA Four Diamond boutique hotel and winner of the 2016 Conde Nast Travelers Reader’s Choice Award. Home of one of the most bountiful breakfast spreads on any Trek Travel trip.
North Block Hotel | New Hotel in 2018 – This quaint, Mediterranean-inspired property is perfectly suited for a romantic wine country getaway. Redd Wood, the hotel’s restaurant (with James Beard Award nominee and Michelin-starred Chef Richard Reddington at the helm) offers Italian-inspired cuisine.

Riding: The terrain is hilly with available shuttles and great climbing options.

Meal Highlights:
• Trek Travel signature picnic, private tour and tasting at Summit Lake vineyards
• Picnic in the Redwoods State National Reserve
• Dine at Thomas Keller’s trendy Ad Hoc restaurant in Napa
• Dine at SHED restaurant in Healdsburg

Activity Highlights:
• Visit the Armstrong Redwoods Park
Summit Lake Wine Tasting — tour a family operated small batch vineyard with the family
Dry Creek Valley Wine Tasting
• Private Olive Oil Tasting at Trattore Farms

Biggest Differences: On our California Wine Country luxury bike tour, guests will experience Napa and Sonoma Valley and its iconic countryside and legendary acclaimed wines. We will stay at luxury accommodations with five-star meals throughout the trip, including a dinner at the Napa Valley staple Ad Hoc by legendary Chef Thomas Keller.

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Stay at Indian Springs Resort and Spa on a California Wine Country bike tour
Wine tastings and tours on our California Wine Country bike tour

California Wine Country Explorer

Price: From $2,599
Rider Level: 2 | Recreational
Start | End: Calistoga to Healdsburg

Indian Springs Resort and Spa – A newly-renovated and award-winning hotel and spa with a bohemian vibe and geyser-fed pools located in Calistoga.
h2 Hotel – Located in downtown Healdsburg, this hotel is rooted in nature and fluid by design and has been recognized by Conde Nast’s Traveler’s Gold list, Travel + Leisure World’s Best Hotels and Fodor’s Top 100.

Riding: The terrain is hilly with available shuttles and great climbing options.

Meal Highlights:
• Trek Travel signature picnic at Summit Lake vineyards
• Picnic in the Redwoods State National Reserve
• Dine at Spoonbar, a trendy market-driven restaurant with reknowned craft cocktails
• Dine at Sam’s Social Club, a highly acclaimed poolside restaurant

Activity Highlights:
• Visit the Armstrong Redwoods
Summit Lake wine tasting
Velo Vino food and wine tasting and Bruschetteria food truck

Biggest Differences: On our California Wine Country explorer bike tour, we begin in Calistoga, known for mud baths and spas, then make our way to Sonoma county. This trip offers great flexibility for guests to explore additional activities in the area.

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Ride along vineyards on our California Wine Country weekend bike tour
Stay at Hotel Healdsburg on a California Wine Country luxury bike tour

California Wine Country Long Weekend

Price: From $2,499
Rider Level: 2 | Recreational
Start | End: Healdsburg

Hotel Healdsburg – A perfectly luxurious hotel located in the heart of downtown Healdsburg and winner of Conde Nast Traveler’s Reader’s Choice Aaward.

Riding: The terrain is flat to rolling and is based in Sonoma. This trip has the least amount of climbing, but there are longer route options available for those who want more riding.

Meal Highlights:
• Dine at Dry Creek Kitchen, Chef Charlie Palmer’s charming restaurant in Healdsburg
• Picnic in the Redwoods State National Reserve
• Dine at SHED restaurant in Healdsburg

Activity Highlights:
• Visit the Armstrong Redwoods
• Tasting at Hanna Winery in Russian River Valley
• Tour Ferrari-Carano vineyards in Dry Creek Valley

Biggest Differences: On our California Wine Country long-weekend bike tour, guests experience a luxury getaway to explore Sonoma at some of our favorite spots in the region in just four outstanding days. During the entire duration of your trip, you will stay in one luxurious hotel, so you can unpack and unwind.

Designing for Giants

It’s no easy feat to climb six breathtaking giants in the Italian Alps in just four days. If anyone can put the itinerary together, it’s Trip Designer, cyclist, artist and world traveler, Jessica Singerman. Her favorite place she’s been? The Italian Alps. And we can see why. Follow along to see how Jess designed our latest cycling experience, Giants of the Giro, and join us this summer for a truly epic trip. Are you up for the challenge?

Meet Jessica Singerman, Trek Travel Trip Designer

Ride the classic climbs of the Giro on our Legendary Giro Italy bike tour

How did you put this trip together? Tell us about your design process.

On Day 1, the ride up Torre di Fraele is a more gentle climb, although still challenging. It’s the perfect way to acclimate after traveling to the region and it gives people a chance to get used to their new bikes.

Over the course of the next two days, we climb Stelvio, Mortirolo, and Gavia, some of the most challenging climbs in the world. Stelvio’s iconic hairpin turns have inspired cyclists, skiers, mountaineers, and even artists and poets since the mid-19th century. Passo Stelvio is the highest mountain pass in the Giro d’Italia, and during the Giants of the Giro, we will climb it not once, but twice. We will climb the side from Bormio, veer off through Switzerland just before the summit, and then ride up the 48 hairpins from Prato allo Stelvio before descending back into Bormio.

Trek Travel Classic Climbs of the Dolomites Cycling Tour

Passo Stelvio is the highest mountain pass in the Giro d’Italia, and during the Giants of the Giro, we will climb it not once, but twice.

On Day 3, we ride both Mortirolo and Gavia. Lance Armstrong famously said that Mortirolo was the “hardest climb” he had ever ridden, and Gavia brings to mind Andy Hampsten’s grueling 1988 Giro stage win in a blizzard. The stage ended in Bormio, our base for this trip. The reason we ride these two passes on the third day is so that people can make the decision of whether to ride Mortirolo and Gavia, or to stick to Gavia instead. Mortirolo is incredibly steep, so after the two previous days of riding, people will have a good idea of whether to ride it or not.

On the last day, the Bormio 2000 climb is for those guests who want to tick off one last climb before the end of the trip! It’s a short but challenging ride.

What about the Italian Alps is so special?

The landscape is visually stunning, the people are friendly, the riding is second to none, and the food is super tasty. It’s a bicultural region, having been fought over by Austria and Italy, so there’s a lot of history and multiple languages spoken. The region has something for everyone.

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What is the “magic moment” of this trip? Is it a specific climb, the gratification of hard work, or maybe the view from the top?

The views from the top of Stelvio are unreal. Looking down and seeing the switchbacks rise up from the valley to the summit is incredibly rewarding and visually breathtaking. Because of the way the road is built, you can stop periodically along the ride from either side of the pass and see the hairpin turns stacked on top of one another.

Another amazing part of the riding here is simply how long the climbs are. There aren’t many places where we can climb for hours. I love the mental part of climbing like this. Watching your breath, finding your cadence; getting into a rhythm is so satisfying. In the midst of this effort we remind ourselves to look around us, and the breadth of the Alpine landscape is stunning. Riding here is a truly spiritual experience.

There aren’t many places where we can climb for hours. I love the mental part of climbing like this. Watching your breath, finding your cadence; getting into a rhythm is so satisfying.


Learn more about our Giants of the Giro bike tour.



It’s no wonder how the majestic Italian Alps have inspired Jessica in many of her paintings. Below she shares with us three pieces, all sparking creativity from the giants.

“During the making of these, the Italian Alps landscape was absolutely one of my inspirations.”

Oil Paintings inspired by the Italian Dolomites by Jessica Singerman

Top left: The Things I Can’t Reach 1, oil and acrylic on canvas, 40 x 40 inches, 2014
Right: Sweeping Green Blue Air, oil on canvas, 30 x 30 inches, 2014
Bottom left: How to Keep Warm, oil and acrylic on canvas, 40 x 30 inches, 2016

You can learn more about Jessica’s work on her website.

Traveling To Cuba: Need To Know

So the allure of old, American-made cars, hand-rolled cigars, and back ally Cuban music streaming into the city streets has captured your sense of adventure. We couldn’t be more excited to announce our People-to-People tour to Cuba, one of the few cycling trips available that meets the US legal requirements. We are excited to explore this culturally rich nation with you during the experience of a lifetime.

Cuba is in a unique time in history, constantly changing as a growing American tourism market emerges. With regular flights departing U.S. soil bound for Cuba and regulations loosening, now is a great time to see and experience the charm of this developing country.

If you’re interested in visiting the island but unsure how it all works, below are some tips to get you started on researching your dream cycling vacation to Cuba.

Experience vintage Cuba on a Cuba bike tour

Is it legal to travel to Cuba? What does People-to-People mean?

Technically, traveling to Cuba for a leisurely beach vacation is still illegal for Americans. Your trip must fall under one of the 12 categories of permitted travel set forth by the Treasury Department’s Office of Foreign Assets Control (OFAC). One of these categories is educational activities, including People-to-People interaction. What does this mean exactly and how will affect your travel to Cuba? It means you can travel to Cuba if you, “Maintain a full-time schedule of educational exchange activities intended to enhance contact with the Cuban people…and that will result in meaningful interaction between the traveler and individuals in Cuba.” You won’t just pedal through Cuba. You’ll spend time with locals each day in a variety of settings, whether it is sharing experiences over coffee or a mojito, visiting a local sugar plantation, or meeting with artists and authors to hear their stories. We have taken care of designing a trip that meets the legal requirements so you can enjoy an authentic and worry-free vacation.

Please take note of the Planning for your Trip section on our Cuba trip page. There is a lot more information regarding travel requirements both before and after your trip. Traveling to Cuba presents unique challenges, and we want to ensure you have the best experience possible.

Experience vintage Cuba on a Cuba bike tour

Fun and Flexible

Because Cuban tourism is just begining to develop, traveling there presents unique challenges not found in more common destinations such as Western Europe. Hotel quality can vary significantly and plans may change at the last minute. Infrastructure in Cuba is not at the same level as our other destinations and resources can be limited. We have selected the best possible hotels, which are centrally located in historic towns, instead of isolated all-inclusive resorts offered by our competitors. These allow for a more enriching cultural experience, but it means that you may forgo some of the comforts and amenities that you are used having available on other Trek Travel vacations. We are leveraging years of trip design expertise and relationships with local partners to make your trip as smooth and comfortable as possible, but we suggest bringing your sense of adventure along for this journey. After all, this is Cuba!

At Trek Travel, our internal mantra is simple: fun and flexible. It means that no matter the circumstance, our rockstar guides will handle any curveball thrown their way while always keeping our guests’ experience and safety as their main priority. On this trip, we invite you to adopt our mantra, keep an open mind, and enjoy what authentic Cuba has to offer before it is gone.

Experience vintage Cuba on a Cuba bike tour

Why go with Trek Travel to Cuba?

On our People-to-People journey to Cuba, expect to have an incredible and authentic experience while engaging with locals at every turn. Our trip designers have worked hard with local partners to ensure you get a unique view into Cuban life. You will burn plenty of energy each day as we enjoy four days of cycling between some of Cuba’s oldest colonial towns, take a walking tour in each (including the grand finale tour of La Habana Vieja), lace up your hiking boots for a day hike in the mountains, and snorkel in the warm waters of the Caribbean. Combined with educational People-to-People experiences, your vacation to Cuba is an authentic itinerary you’ll remember for the rest of your life.

Allow us to take care of the logistical hassles of traveling to Cuba. Your safety and well-being is our primary concern. You will have the full resources of Trek Travel behind your trip, including our knowledgeable trip consultants who will help you prepare, two Trek Travel guides, two local guides, and a driver once you are there.

Our Cuba People-to-People itinerary is not for everyone. But for those seeking a true adventure to a burgeoning destination, it is sure to entice. The possibilities are endless for this country and its tourism infrastructure. But with that comes change, and now is the time to experience Cuba’s rich and engaging culture at its best. We hope you will join us.

Other great resources for planning your Cuba bike tour:

General travel information from our friends at Travel + Leisure.

Health information from the CDC.

Getting ready for Cuba from Cuba Explorer.


If a date is marked as Private, it is reserved for a private group.

Looking to travel with a small group or looking for a custom date?
Call our trip consultants at 866-464-8735

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.


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.


These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.


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.

Activity Level

Level 1:

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.


Enjoy a bike tour on your schedule with just your chosen travel companions.

Single Occupancy

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