As we look forward to celebrating 20 years of incredible cycling vacations in 2022, we’re looking back at some of the timeless destinations we’ve been visiting since our very first season. From the awe-inspiring vistas in Glacier to the unforgettable race moments at the Tour de France, these destinations get better and better over the years.

See Where We’ve Been Traveling Since Our First Season

Tuscany Bike Tour


Rider Level: 3 (Active)

Over the years, this trip has carefully brought together the quintessential Tuscan experience, highlighting beautiful hotels, world renowned wines, and exquisite food. As our local guides and trip designers discover new, exclusive experiences in the region, this trip continues to evolve to ensure we highlight only the best of Tuscany.

Provence Bike Tour


Rider Level: 2/3 (Recreational/Active)

Travel in Provence is about discovering a slower way of life. We have uncovered all the hidden gems this region has to offer, so you can savor each bite of cuisine, chat with the locals as you walk through quaint town markets, and ride some of the most spectacular roads.

Bryce & Zion Bike Tour

Bryce & Zion

Rider Level: 3 (Active)

The rugged, stunningly beautiful landscape of southwest Utah has been capturing hearts for generations. Much like the landscapes of these beloved national parks, our trip here is always evolving to ensure you’re experiencing the best of the region.

San Juan Islands Bike Tour

San Juan Islands

Rider Level: 2 (Recreational)

With the Pacific ocean sprawling to the west, the magnificent North Cascades on the horizon, and the broad open skies above, the San Juan Islands are a timeless paradise for nature lovers, and they keep us coming back year after year.

Ireland Bike Tour


Rider Level: 3 (Active)

On our Ireland trip, enjoy great storytelling and rich traditions as we introduce you to local friends we’ve made here over the years, explore stone remains of ancient Celtic ruins, and ride through velvety pastures speckled with flocks of sheep.

Vermont Bike Tour


Rider Level: 2/3 (Recreational/Active)

There’s no better place to celebrate the brilliance of summer or the beauty of changing seasons than Vermont’s Champlain Valley and Green Mountains. That’s why this trip has been a guest favorite since the start!

California Wine Country Bike Tour

California Wine Country

Rider Level: 2/3 (Recreational/Active)

Saturate your senses in one of the world’s premier cycling regions. We have tested out the best routes, best wineries, and best hotels to plan the ultimate escape in California Wine Country.

Prague to Vienna Bike Tour

Prague to Vienna

Rider Level: 2 (Recreational)

A bicycle is truly the best way to discover the secret forests, charming Baroque palaces, and quiet cobblestone streets that keep us coming back to ride in this enchanting Bohemian wonderland.

Tour de France Bike Tours

Tour de France

Rider Level: 3/4 (Active/Avid)

This trip is as dynamic as the race itself, with new regions to explore each year and new riders to cheer for. As an Official Tour Operator for the race and Trek Segafredo, we secure the best hotels in the most spectacular locations and highlight the most exciting stages. Ride on the race course ahead of the pros, enjoy VIP access, and feel the energy of the final sprint across the finish line. It’s an adrenaline trip that keeps giving.

Pro Race Italy Bike Tours

Pro Race Italy

Rider Level: 4 (Avid)

Every year, there is something unique to experience as you savor the excitement of Italy’s largest cycling event. We love taking you to the heart of the action to experience the race’s most epic moments and stunning climbs.

Glacier National Park Bike Tour


Rider Level: 2/3 (Recreational/Active)

After riding all over the globe, Going-to-the-Sun Road keeps us coming back to Glacier over and over. Did you know it is our pick for the best ride in the world?

Then & Now

Legacy Trek Travel Trips

Not only have we continued to bring guests to some of our most beloved destinations over the years, we have also continued introducing them to new and exciting places around the globe. Just see how much our offerings have expanded in the last two decades!

Our First Season:
Legacy Trek Travel Trips
Our 2022 Season:
2022 Trek Travel Trips

Ready to Ride with Us in 2022?

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