Tuscany Wine Country Bike Tour

Wine, castles, and quintessential luxury in Chianti and San Gimignano

Tour Duration

6 Days / 5 Nights

Trip Style

Classic Guided, Reserve Tours

Activity Level

Level 3

Hotel Level

Ultimate luxury

Bikes

Trek Domane SL 7
Trek Electric-Assist Verve+ Gen 3
Trek Electric-Assist Domane+ SLR 7

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Starting from

$7,499.00 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'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 hand crafted 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 dinner 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

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 dinner at Castello di Volpaia

The Mascheroni Stianti family welcomes you for an exquisite wine-paired dinner in their villa, with an exclusive visit of the castle’s cellars and olive oil press.


What Guests are Saying
Two

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


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

  • Guaranteed

  • Join Waitlist

  • Private

  • Limited Availability


Itinerary
Activity Information

Hotels
Aerial view of Pieve Aldina hotel and landscape
Radda in Chianti, Italy
Pieve Aldina
Ultimate Luxury

Nestled in Chianti, Pieve Aldina embodies Tuscany’s soul with its 10th-century charm, surrounded by vineyards and olive groves. Enjoy Chef Niccolo Pini’s Tuscan cuisine in various settings, relax by the pool with countryside views, and unwind in the spa. As a member of the renowned Relais & Chateaux collection, you’ll experience luxury, history, and culinary excellence at this serene retreat.

...

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Belmond Castello di Casole hotel pool
Casole d’Elsa, Italy
Belmond Castello di Casole
Ultimate Luxury

Part of the exclusive Belmond group and awarded the Two Key recognition in the inaugural 2024 Michelin Guide hotel ratings, the superbly luxurious Castello di Casole is a beautifully restored castle set on a 4,200-acre private estate. This five-star boutique hotel boasts an incredible destination spa, both gourmet and relaxed dining, and exquisite suite accommodations that effortlessly combine Old World Tuscan charm with modern luxuries.

...

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Bikes & Gear
Ride the Best Bikes in the Industry
New in 2023 Domane SL 7 Road
Trek Domane SL 7

Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane SL 7 Gen 4 is the best on the road. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes, road-smoothing IsoSpeed technology, and electronic shifting. This new bike is lighter than ever before, and carbon wheels are standard on every Domane SL 7 bike.

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E-Bike
Trek Electric-Assist Verve+ Gen 3

Fun from the first pedal stroke, venture further on our Trek Verve+. With its low-step frame design, upright riding position, and the barely-there Bosch electric motor, the Verve+ has one goal: pure enjoyment. Designed for both comfort and adventure, get a boost up the hills when you need it with energy to spare.

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Trek Domane+ SLR bike Road
Trek Electric-Assist Domane+ SLR 7

Upgrade your experience on the Domane+ SLR 7. It has everything you love in a road bike, with the extra boost to take you farther than ever before. With an ultra-lightweight design and a whisper quiet electric assist motor, this performance e-road bike will assist you on the climbs and enable you to venture further. So go ahead—take the long way. With Domane+ SLR 7, there’s always room for more distance and more fun!
Upgrade to the Domane+ SLR 7 on this trip for $399 (3-6 day trips) or $599 (7+ day trips). Available in limited quantities. See specific trip dates for available bike options.

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Two cyclist and one rider

Trek Travel Guides

The World’s Best

From the moment you meet our guides, you'll understand the difference. You'll feel the genuine care they take to make your vacation perfect. From their expert support to sharing their favorite hidden spots, they tailor every moment to you.

Certified Guides

Additional Gear
  • Trek Travel Santini cycling jersey
  • Trek Travel luggage tag to keep
  • Trek Travel water bottle to keep
  • Cinch sack day bag to keep
  • Garmin Edge 1030 GPS computer with pre-loaded routes
  • Bontrager front and rear Flare R lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Choice of Shimano SPD-SL road style pedals, Shimano SPD mountain style pedals, caged, or flat pedals
  • Bontrager helmet
  • Bontrager saddle
  • For the most comfortable ride, we recommend you bring your own saddle. If you prefer, you can bring your own pedals and helmet on the trip and our guides will install your gear on the first day during your bike fit.
A collage of cycling gear guests will use on a Trek Travel Classic Bike Tour.

Trip Inclusions

Additional Details

Know Before You Go!

We want you to be fully prepared for your cycling vacation of a lifetime. This involves making sure that you choose the appropriate trip for you and that every aspect of your experience is flawless. Each Trek Travel trip is unique to ensure maximum enjoyment every time.

Your Trip Need to Knows:

  • When in Tuscany: Meals in the Tuscany region often start later. Lunch from 1:00 PM and dinner from 8:00 PM. Dinner can also last two or more hours, allowing time to enjoy the decadent cuisine of the area at your leisure.
  • Please note that although hotels have air conditioning, it is not as powerful as hotels in the USA and hotel rooms may be warmer than expected during the summer months.


Before and After Your Trip

Weather

Average monthly temperature and precipitation

Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
High 52.0°F· 11.1°C 55.0°F· 12.8°C 61.0°F· 16.1°C 67.0°F· 19.4°C 77.0°F· 25.0°C 84.0°F· 28.9°C 90.0°F· 32.2°C 90.0°F· 32.2°C 80.0°F· 26.7°C 71.0°F· 21.7°C 60.0°F· 15.6°C 52.0°F· 11.1°C
Low 37.0°F· 2.8°C 37.0°F· 2.8°C 42.0°F· 5.6°C 48.0°F· 8.9°C 55.0°F· 12.8°C 62.0°F· 16.7°C 66.0°F· 18.9°C 66.0°F· 18.9°C 60.0°F· 15.6°C 53.0°F· 11.7°C 45.0°F· 7.2°C 38.0°F· 3.3°C
Rain 0.93"· 2.36 cm 0.91"· 2.31 cm 0.72"· 1.83 cm 1.93"· 4.90 cm 1.16"· 2.95 cm 0.97"· 2.46 cm 0.24"· 0.61 cm 0.48"· 1.22 cm 1.08"· 2.74 cm 1.95"· 4.95 cm 2.02"· 5.13 cm 1.45"· 3.68 cm
FAQs

Spring and fall in Tuscany are usually clear and sunny, with warm daytime temperatures (75-90ºF/24-32ºC) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are hotter with higher daytime temperatures (80-95ºF/27-35ºC) and evening temperatures 10 degrees cooler. Rain is always a possibility, however, so be prepared with wet-weather gear in order to best enjoy your vacation. View our Packing List

To reserve your space on a trip, you can either call us at 866-464-8735 to speak with an expert Trip Consultant or book online any time by clicking the “BOOK THIS TRIP” icon near the upper right of each destination’s overview page.* Once you have submitted your reservation online, a Trip Consultant will contact you within one business day to answer any questions you may have and to confirm space, bike, and room availability on your desired trip. Your booking will be finalized once your no-risk deposit is paid. If you make a reservation more than 90 days prior to the trip, a $750 no risk deposit is due at the time of booking.** If you reserve your trip less than 90 days prior to the departure, the full balance is due at the time of booking. Once your booking is complete you will receive an email confirmation with important information pertaining to your trip.

*Please note that select trips cannot be booked online at this time. For those trips, please call a trip consultant at 866-464-8735.

**Deposit amounts vary for all Race, Cross Country, Special Edition, Ride Camp, Discover, and Self-Guided tours. Please confirm deposit amounts for all trips with your Trip Consultant at time of booking.

When a trip is booked, a guest confirmation email is immediately sent out. One week prior to the trip start, you’ll receive an email containing your trip start meeting location reminder and any last-minute information that you’ll need to know. You will also receive instructions to download the Ride with GPS app before your trip to provide you the day to day plan and daily route guides.

With one person booked on a date, the trip becomes guaranteed.*

In the case where trips are at one or two guests, we will contact you prior to final payment to give you the following options:

Pay a small trip fee of $500 per person for two guests or $1000 for one guest, which ensures your preferred trip date will run. If there are three or more guests before departure date, the fee will be refunded in full.

or

Switch to a different trip or different departure date. Should there be any difference in trip price between your original trip and the new one, you will be expected to pay the difference, or we will refund you accordingly.

Offer only valid if Trek Travel contacts a guest to discuss these specific options. Bike trips with fewer than three guests may operate with only one guide. The guide will support all rides with a Trek Travel van. If you would like to discuss the option of having two guides, please speak with your trip consultant.

The small trip supplement for Ride Camps is as follows – for two guests an additional $250 or for one guest an additional $500.

*Cross Country, Discover, Race, and Special Edition trips as well as a small number of select departures have a minimum guest count to guarantee. Please check with your Trip Consultant for more information.

Unforeseen events may make it necessary to cancel or modify a trip. Our Guest Services team will update you with any changes. We reserve the right to cancel departures in cases of force majeure or the failure of third parties—such as hotels—to honor their reservations, in which case all payments received to date will be refunded, which constitutes full settlement. Trek Travel is not responsible for expenses incurred in preparation for any canceled trips, such as airline tickets, or for costs that are incurred due to travel delays, flight cancellations, or illness. We strongly encourage Travel Protection for complete coverage.

We understand things happen in life and sometimes you have to cancel or change your tour.

Read our Cancellation Policy

Our Trip Consultants are available to assist and can answer your questions. Please call us at 866-464-8735.

Trek Travel recommends that you purchase a travel protection plan to help safeguard you and your travel investment against the unexpected. We offer a travel protection plan through Arch RoamRight that provides coverage for unforeseen events that could affect your ability to travel with us. Learn more about our Travel Protection

We've collaborated with a specialized travel agency committed to delivering tailored vacation planning, ensuring your entire Trek Travel journey is nothing short of unforgettable. Learn more about our Travel Services

Sharing the joy that comes with wow moments

Trek Travel guides are dedicated to making moments that last a lifetime, and we invite you to thank them with a trip gratuity. These are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this Reserve trip, we recommend $240-$300 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience.

Like everything else about your vacation, the Trek Travel team is here to make this experience easier for you. While local currency is preferred, you may also tip through the following options:

Via PayPal (please have this account set up in advance when possible) or with your guest services representative on the phone before or after the trip.

Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip.

You cannot put a price on a wow. But you can show your thanks for an exceptional experience.

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to the most common questions that don't necessarily pertain to a specific trip. See FAQs