If you’ve imagined your perfect luxury bike tour in Italy, then you’ve envisioned traveling to the heart of Tuscany's wine country with us.
Experience Italian joy—allegria—in Tuscany, woven into every aspect of this luxurious bike tour in Chianti. From lush olive groves to sun-kissed vineyards, we bring you the best cycling this region offers. Enjoy revered wines and heartfelt hospitality at Castello di Volpaia, hosted by our friends, the Mascheroni Stianti family. Delight in Michelin-starred Tuscan cuisine and learn pizza-making with an expert pizzaiolo. Rest in secluded, historic luxury hotels. Every detail is tailored to perfection, from the first light of a fiery sunrise to the evening's last sip of Chianti Classico. This wine country cycling tour is more than the ultimate bike and wine adventure; it’s an exploration into the heart of joy.
Trip Wows
Toast the day at Belmond Castello di Casole, awarded the Two Key recognition in the inaugural 2024 Michelin Guide hotel ratings
Enjoy your spectacular 5-star hotel nestled in the heart of Chianti, transformed from a historic building into the ultimate luxury property
Visit San Gimignano, where you’ll be met with vibrant colors, sights, and sounds of the open-air market
Experience an intimate gathering with the Mascheroni Stianti family, enjoying a gourmet lunch and exquisite wine tasting at their hidden estate, Castello di Volpaia
Take part in a private pizza-making class and sip local wines with perfect dessert pairings
Savor the finest vintages at a private visit to Castello di Volpaia
Enjoy a wine tasting and gourmet lunch at Castello di Volpaia
The Mascheroni Stianti family welcomes you for an exquisite wine-paired lunch in their villa, with an exclusive visit of the castle’s cellars and olive oil press.
What Guests are Saying
Another spectacular adventure! After an incredible trip to Napa with Trek Travel, we were excited to explore yet another amazing area with you. Tuscany was absolutely awesome, and we are already debating where we should go with Trek Travel next. Thanks for all that you do – we can’t imagine anyone doing it better.
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Whichever the season, Tuscany is always beautiful. Intimate dining experiences, private tours, and exceptional hotels are just some of what makes this such a special trip. Be prepared for some climbing, the views are the best enjoyed at the top! Afterwards relax in the hotel spa then glam up for splendid dinners complete with local wine pairings. This is a trip I always look forward to!
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All expectations were exceeded. The sights, the tastes, the people... all spectacular. The tone was set by our guides, who immediately put us at ease when we felt apprehensive about our ability to keep up with the group. It was obvious that a lot of attention went into planning every detail of the trip, which made our experience relaxing and wondrous.
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The itinerary, accommodations, food, and restaurant selections were all super. Guides were great. This was our 7th trip with Trek Travel...that should say all you need to know.
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All around awesome —we enjoyed everything!!! The riding was great. The food was awesome. Our guides were absolutely fantastic. We enjoyed the pizza making, the country lunch and the lunch at the residence, the tour of Siena. The places that we stayed were first class. It was a totally awesome vacation.
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The trip was wonderful. I was a little anxious before we left since my biking skills are not at the same level as my husband's, but the e-bike made all the difference...It's super easy to use! I was also pleased with the routes we biked - great roads and the motor vehicles know to be cautious of bikers. The accommodations were top rate and so was the food. Our guides were fantastic and kept the trip moving smoothly. The people of Italy were kind and welcoming. Can’t wait until our next Italy trip!
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Can't say enough great things about the guides, the itinerary, the organization, the bikes, and the accommodations. This trip was long overdue for us and exceeded all our expectations.... We will travel with Trek Travel again to be sure.
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Great Ride
Gaiole in Chianti to Villa a Sesta Loop
Experience Great Ride #6 on our List of Great Global Rides. Perfect ribbons of road carving through the hillsides, dotted with quaint villages, olive groves, and vineyards for as far as the eye can see.
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