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Tuscany Wine Country Bike Tour

Wine, castles, and quintessential luxury in Chianti.

Tour Duration

6D / 5N

Trip Style

Reserve, Classic Guided

Activity Level


Hotel Level

Ultimate luxury


Trek Domane SL 7
Trek Electric-Assist Verve+
Trek Electric-Assist Domane+ SLR 7

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Starting from

$7,299.00 per person

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If you’ve imagined your perfect luxury bike tour in Italy, then you’ve envisioned traveling to the heart of Tuscany with us.

Experience the essence of Italian joy—allegria—in Tuscany, a sentiment woven into every aspect of this region. From the lush olive groves to the sun-kissed vineyards, we’ve explored every corner to bring you the best cycling this region has to offer. Enjoy the revered wines and heartfelt hospitality of the Mascheroni Stianti family, our friends at Castello di Volpaia in Chianti. Delight in Michelin-starred Tuscan cuisine and learn the art of pizza-making with our favorite expert pizzaiolo. Rest each night in secluded, historic hotels that are epitomes of luxury. We see to it that every detail is tailored to perfection, ensuring your comfort from the first light of a fiery sunrise to the evening's last sip of Chianti Classico. This tour is more than the ultimate bike and wine adventure; it’s an exploration into the heart of joy.

Trip Wows
  • Toast the day from Travel + Leisure’s #1 European hotel resort Belmond Castello di Casole

  • Enjoy your spectacular 5-star hotel Castel Monastero — A medieval hamlet that has been transformed into the ultimate in luxury properties.

  • 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 at a gourmet lunch paired with an 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

A group toasting at dinner in Tuscany, Italy

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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Melissa, Trek Travel Guest

Three people sharing a cheers in a vineyard

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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Kiwi Nat, New Zealand

Group inside a huge wine barrel

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 O's, Chicago, IL

Two Cyclists riding by the camera in Tuscany, Italy

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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Ron, Texas

A group of people saying cheers with their Aperol Spritzes

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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Bernie, DC Area

Two people on ebikes cycling past cypress trees

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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Mary, Appleton, WI

Group of cyclists with wine glasses

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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Bud L. Dallas, TX

Cyclist riding by vineyards

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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Dates & Pricing

Book early for the best price

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