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Featured Hotel: Castello di Casole

Here, you’re royalty. Welcome to the Timbers Resort ranked the #1 Resort in Europe by Travel + Leisure magazine, Castello di Casole.

A beautifully restored castle dating back to the 10th century and set on a stunning 4,200-acre private estate, Castello di Casole is a guest and guide favorite. This five-star boutique hotel boasts a destination spa, gourmet and relaxed dining, and exquisite suite accommodations that effortlessly combine the old world Tuscan charm of its storied past with modern luxuries of today.

Trek Travel Castillo di Casole Tuscany Cycling Vacations

The Restoration

Castillo di Casole and its surrounding villas were restored using traditional methods and reclaimed materials found throughout the estate, preserving its rich history.

Maintaining the Land

In the 1800’s the estate played host to over 30 farms rich in wheat, olives, grapes and livestock. Now, you can vacation among 100 acres of organic vineyards and olive groves.


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Serenity Now

Rejuvenate after a day in the saddle at the Essere Spa. This space was formerly the estate’s wine cellar, and its barrel-vaulted ceilings and expansive views of the valley are a sight to behold. Choose from a full treatment menu inspired by local ingredients and featuring a collection of Etruscan, traditional and modern therapies. Or unwind at your own pace in one of the many pools or steam rooms.

A Culinary Oasis

Whether you dine at the cozy Pazzia, the ever inviting Bar Visconti or the unforgettable Tosca, you can expect rustic dishes in the Italian tradition infused with a bit of the unexpected. Handmade pasta, fresh organic vegetables and local fish and game are paired with wines from the best wineries in Italy to bring to life recipes that will “stir the soul”.


Trek Travel Castillo di Casole Tuscany Cycling Vacations


Indulge your senses in the rolling hills of Tuscany

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There’s Always the Van

When I got on the plane to Italy in October 2006 for our Trek Travel Tuscany trip, I knew nothing about the van. A week later, the van was to become one of my favorite things about a Trek Travel trip.

Words by Deb Dingwall, Trek Travel Guest

We landed in Florence and spent the next couple of days exploring the city before hopping on a bus and heading out to the Tuscan countryside with our fellow Trek Travel guests. What I remember most about that first day was standing astride my bike in the Val d’Orcia, gazing up at the lovely hilltop town of Pienza, and thinking, “How beautiful but what the hell have I gotten myself into?” You need to understand that I grew up in Lincoln, Nebraska (Go Big Red!) and was very comfortable with a relatively flat landscape of the Midwest. And while I had spent plenty of time skiing in Colorado as I was growing up, that was downhill. Grudgingly, I clipped in and started to slowly ascend towards the town, my husband Adam alongside me.
Trek Travel Tuscany Bike Tour
Our Trek Travel guide, Dave Edwards, rode up next to us and noticed I was struggling. “Just put it in your easiest gear and pedal slowly” he said. I wasn’t about to break out my, “Don’t tell me what to do” attitude at this early in the game, so I did as Dave suggested and Adam and I made our way up to the town. From the walls of Pienza we gazed across the valley and a shot of reality hit me, each and every town seemed to be at the top of a hill. From our vantage point we could see enough hilltop towns to make my heart sink a bit, and I wondered how the rest of the trip was going to be. I was very convinced I would never let Adam talk me into another one of these vacations.

That night we enjoy an amazing Italian four-course feast with plenty of wine. Dave stopped by our table during dinner to ask how the first day went. Admittedly I was a bit down, and I told him the elevation for the rest of the week looked daunting as it wasn’t quite what I had expected. “Simple,” Dave said, “there’s always the van. You don’t want to ride up the hill, just let us know and we’ll boost you to the top in the van. It’s your vacation.”

“There’s always the van” became my new mantra, and one that I’ve shared in numerous conversations about Trek Travel. It is my vacation and if part of what I want on vacation is relief from some of the cycling challenges that are an awesome part of every Trek trip, I’m allowed to jump in the van. I’ve been known to do that for a boost up a steep hill, a rest after lunch for a bit, or at the beginning of the day if I’m not quite feeling up to the start.
Trek Travel Supported Bike Tours
I’ve boosted up climbs in Tuscany, France, Vermont, California, Oregon, and the San Juan Islands just to name a few. My reluctance about that first climb up to Pienza disappeared with the realization that the van was there to enhance my, and any Trek Travel guest’s, experience.

Adam did talk me into another trip, and another, and another. This July we will take our 11th trip with Trek Travel, this time to the California Wine Country. I’ve grown to enjoy the riding–and even the climbing–so much more than I did on that first trip. But ever since my childhood days skiing in Colorado, the downhills have always been, and always will be, a love of mine. And if you ever have the chance to descend into Bend off of Mount Bachelor, do it.

A Trek Travel vacation is so much more than cycling. It’s food and wine, conversation and amazing scenery. It’s the bike and the guides. And sometimes, it’s the van.
Trek Travel Oregon Crater Lake Bike Tour

A Foodie’s Tour of Italy

I grew up around the table. Weekly dinners at my grandmother’s were part of the family routine and while us kids were allowed to run off and play after the meal, the adults would linger for hours, retelling family stories, discussing world events, and enjoying one more glass of wine.

Words by Katherine Usher, Sales and Guest Services Manager
Dine at Tenuta San Pietro hotel in Italy on Trek Travel's Cinque Terre bike tour

Now as an adult, I treasure each moment spent at the table. Although the company changes–friends and family, old and new–there is always something special about lingering around the table.

Our new Cinque Terre vacation is a foodie’s dream, offering many unique culinary experiences and opportunities to gather around a table with new friends. This past September I had the privilege of being a guest on this trip, and while the riding and hiking are spectacular, my lasting memory is one of robust flavors that linger on your palate long after the table is cleared.
Stay in Lucca, Italy on Trek Travel's Cinque Terre cycling vacation
The trip starts in Tuscany, nestled in the hills above the sought-after town of Lucca. The grades of these “rollers” are no joke but the traditional Toscana cuisine that awaits is worth the ride. The first hotel of the trip, Tenuta San Pietro, boasts its own vineyard, olive grove, and vegetable garden and Chef Guido Lotti is not shy to craft a Mediterranean menu directly from the land.
Experience the meals of Chef Guido Lotti at Tenuta San Pietro on Trek Travel's Cinque Terre bike tour
As the trip moves toward Cinque Terre and the region of Liguria, you start to notice the cuisine change as drastically as the landscape. The menus of handmade pastas, garden fresh tomatoes and aromatic herbs now feature sardines, squid, anchovies, and whatever the sea is generous to provide that morning. Perhaps the taste I savored most, however, is the Italian Riviera’s renowned artisanal pesto.

The shared experiences of riding through the unspoiled countryside and hiking the rugged hills of Cinque Terre’s five historic villages are certainly highlights, but the time spent gathered around the table is truly something special. The flavors are memorable and even more unforgettable are the stories behind them. From the young up-and-coming chef in San Pietro who is willing to take risks with his menu, to the woman who learned how to roll pasta from her grandmother and would never dare to change her ways, the stories behind the meals bring the experience to life.
Eat fresh seafood on Trek Travel's Cinque Terre bike tour

Il Gallo Nero

The Black Rooster marks some of the greatest wines in the world.

It is easy to see why Tuscany remains one of our most popular trips. I moved to Italy some 12 years ago to immerse myself in this magic, and have determined that cycling through this region is the ideal way to learn about the place.

On a bike, we leave other tourists behind and get to experience places as they have remained for thousands of years. The epicenter of Tuscany – flanked by Florence to the North and Siena to the South – for its wine, wild boar, small, winding roads and forested hilltops. In the center of Chianti is the ideal, 9th century one-strip hilltop wonder of cobblestones enotecas and cafés known as Radda in Chianti. Ride up to the entrance of Radda in the morning and you’ll find Fabrizio Ferrucci, owner of Bar Dante making panini for the hungry denizens who flock to his café for local treats. Fabrizio will assure you that while Radda is not perfect, it is pretty close.

Visit Tuscany on a Trek Travel bike trip

Radda is so ideal, in fact, that the two warring city-countries of Florence and Siena have fought over it for centuries. Legend has it that late in the 12th century, these two archenemies finally decided to end their bloody land-feud peaceably. By parliamentary agreement, at the first crow of their respective roosters on the appointed day, one knight from Florence, and one knight from Siena would depart on horseback down the road the connects the two cities. At the precise point the two knights meet on their journey, the line would be drawn to divide the Province of Florence from the Province of Siena.

While Siena chose to fatten and spoil a fine, plump rooster, the Florentines were far more devious. They selected a lean, black rooster and locked it in a windowless dungeon without food or water. When the date arrived, the rooster’s hyper-sensitive retinas led him to crow his heart out, giving the Florentine knight a dramatic head start. He reached all the way to Fonterutoli, a territory of Castellina, before he met the Sienese knight. And so they established the border at Castellina, a mere 19 kilometers from Siena’s walled city.

To this day, the internationally recognized symbol of Chianti is a silhouette of Il Gallo Nero, The Black Rooster. It marks some of the greatest wines in the world, and cyclists wear the jersey with pride. Next time you find yourself in Radda, ask Fabrizio about his story. He just may fill you in on some more history of this remarkable area that we are fortunate to ride our bikes through. The rest of the learning comes from the air flowing in your face while you spin down the winding roads, the same roads the two knights thundered down all those years ago.

By Jacob Young, a guide for Trek Travel

Visit Tuscany on a Trek Travel bike trip

Experience a Trip to Tuscany for yourself»

This is Happy Hour

At any given time or place around the world, there is a group of travelers finishing their day’s ride. They have a euphoria, a sense of tired accomplishment.

The ride included exploring a cobbled-street village in Provence, or experiencing an authentic cappuccino in a Tuscan cafe, or tasting a wine high up over the Napa Valley. The elation carries into conversations with new-found friends, often around a Trek Travel trailer, about the day’s adventure.

This is happy hour.

It can linger for hours into the setting sun with guides, travelers, and cyclists enjoying the company of one another, reveling in the stories at hand.

Read more in our storybook»

Culinary Delight

A great meal is about more than the food on your plate. A perfect atmosphere makes any meal taste richer, effortless company makes it more fulfilling, and the right beverage helps it go down easily. A wave of nostalgia always sweeps over us as we sit down to our first meal at home. We crave the flavors and the environments of far away places. Though Healdsburg and Tuscany may top our list, we know that our next vacation will bring new tastes to savor, new friends to laugh with, and new landscapes to adore.

Healdsburg, CA by Meagan Coates

I sat down at my desk after returning from a weeklong bike trip in California’s wine country with a request to write a piece on my favorite North American restaurant and I have found it nearly impossible to pick a clear winner. Napa and Sonoma biking trips with Trek Travel

My first inclination is Charlie Palmer’s Dry Creek Kitchen in Healdsburg—an obvious choice as they receive so many nods in the culinary world with their fresh, local and seasonal food that is perfectly paired with a supremely local wine list and formal but non-stuffy service. Diners enjoy fresh caught fish, local duck and an array of farm-fresh vegetables in a hip and beautiful dining room with expansive ceilings and large windows.

Our Trek Travel groups even have the unique opportunity to dine in the intimate wine library off the hotel lobby after spending a day on the bike and an afternoon at the pool or spa on property. We cap it off with decadent desserts like the chocolate tart with pear sauce or the variety of fresh sorbets served in an old-fashioned soda jerk style container.

california-wine-country-weekend-02-1600x670However, I would be remiss not to mention other Healdsburg haunts like my new favorite—The Shed—located just off the square behind Hotel Healdsburg. Area farmers showcase their handmade products and provide the makings of super hydrating “shrub” drinks at the fermentation bar. I sampled the strawberry, carrot and kumquat but ultimately loved the blood orange best.

Or, just steps away are other amazing restaurants such as Willi’s Seafood, Ravenous, Bistro Ralph, Barndiva and countless others. Savor a craft cocktail at h2’s Spoon Bar (like the cucumber martini!) or just stroll around Healdsburg and you are sure to find something that suits even the most discerning palates. After visiting restaurants in every corner of the world, Healdsburg is definitely the best kept secret for foodie’s looking to travel in North America.

Tuscany, Italy by Kari Kruckow

But close your eyes and take a 6,000-mile journey across the Atlantic. Rolling green hills lined with cypress trees, sun kissed vines, slow food and delicious wines…oh and Roberto. Welcome to Tuscany!

Last week I was able to cycle through this beautiful region and experience its culture. The way Trek Travel invites you to be a local for 6 days on a Trek Bike is amazing. Cycling was the biggest highlight for me on this trip, but food was not far from the top.

I encourage you to grab a little something to munch on…I promise you will get hungry as I tell you about my favorite lunch spot on this trip: da Roberto, Taverna in Montisi.

Roberto made us all feel at home as soon as we rolled in on our bikes. He is a countryside cuciniere (cook), whose only claim is to feed himself and guests honestly. Roberto is a true joy and lives to feed people at his table. His mantra is to wake up every morning happy and build a space of peace, balance and harmony to offer to people that dine at his Taverna, which ties perfectly to the experience that you have cycling through Tuscany.

Aside from the comfort and ambiance, the food prepared was as honest, delicious, and as inspiring as the hilltops that overlook the Tuscan valley. The three-course meal was not a surprise on this Trek Travel trip, being as every meal and break on the bike offered plenty of fuel for the calories burned that day.

Tuscany LuxuryRoberto started off the lunch with a unique bean and carrot salad. It goes without saying, but the beans sourced from a local farmer, the carrots grown in his garden behind the restaurant. Food aside, one of the best “accents” to the menu was Roberto’s story behind each dish, his amicability is contagious with every guest that comes into his “home.” Next was the homemade pasta with a true Italian Ragu sauce, to coin a phrase, “mama, mia!” The lunch ended with three dessert options, my favorite was the panna cotta with berries. It provided just enough guilt and enough fulfillment to encourage the balance of the gorgeous ride that afternoon.

Roberto is proud of his food by identifying flavors by gathering fresh, local ingredients, protecting the value of biodiversity, and visiting farms for fresh cheeses and to certify the quality of his meal.

Roberto’s lunch experience was enriching on all levels and what made for a perfect afternoon was the short bike ride to a beautiful accommodation, which felt like an estate and offered a very relaxing evening.

What can I say, Tuscany is tasteful in so many ways. And it is certainly my favorite culinary delight in Europe.

A Moment in Italy, by Bob Joy

Trek Travel president Tania Burke recently explained why she thinks Tuscany is the best place to take an Italy bike tour. I couldn’t agree more. Tuscany combines amazing scenery, outstanding food and wine, and some of the world’s friendliest people. One can tour Tuscany by bus, or see it in a car, but the only way to really experience it is on a bike.

Let’s start with scenery. On a bike, you don’t just view the landscape, you feel it. In your calves and thighs, of course, but you also become aware of the breezes, can savor the aromas of flowers in bloom or bread just coming out of the oven in the village paneterria, and can hear the laughter of children kicking a soccer ball or the peal of a church bell in the distance. You aren’t just an observer of the landscape, you are connected to it in a way that the typical tourist never is.

Maybe it’s the effort that cycling takes that makes the food and wine taste so much better. Or maybe it’s the guilt-free knowledge that you are burning off the calories just as fast as you are taking them on. How wonderful it is to indulge in pasta and wine for a week and not put on any weight!

Traveling by bike is a great way to connect with people, too. On a 2009 trip with Trek Travel our group started the day at Lido di Camaiore on the coast just north of Pisa. We climbed up a series of hills as we headed east and were rewarded by ever more dramatic views of the Ligurian Sea. We stopped in a little village at the crest of a ridge to check our maps and regroup. I noticed that the older gentleman sitting on a stone bench seemed to be eyeing us curiously. He motioned for me to join him, but as I did he saw the sweat pouring off my body and made a big deal about shifting to the far end of the bench, clearly conveying the notion that I was untouchable. On impulse, I slid right next to him. His reaction was captured in this photo. Despite the differences in culture, age, and language, we made a human connection that afternoon. It was just another Trek Travel moment, but the memory will last a lifetime.

Why Tania Picks Tuscany…

I have been lucky enough to collectively spend 2 years in Tuscany guiding and researching new trips, and when people ask what my favorite TT trip is, although hard to choose I pick Tuscany.  It really lives up to its reputation. Great wine, food, people, hotels, picturesque cypress lined drives, riding.  For me not one of those items stands out on it’s own.  It’s the blend of all these simple things that make it special; moments like watching the sunset over the Chianti hills, tasting wild boar ragu, watching the old men chat in the parks, the scent of Pecorino cheese wafting out of the stores in Pienza, taking a photo of the loan cypress tree on the top of a hill, tasting Brunello di Montalcino – in Montalcino, riding on some of the smoothest black topped roads through small villages, eating vine ripe tomatoes with just olive oil and salt. I could go on forever.  I would live in Italy again if the opportunity arose but for now I just feel lucky to have spent the time there that I did. If you love to travel and bike – don’t miss Tuscany!


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