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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

Rider Level

3

Hotel Level

Ultimate luxury

Bikes

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 Tuscany with us, where every detail is tailored to perfection.

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 this region has to offer. Enjoy the revered wines and heartfelt hospitality of the Mascheroni Stianti family, our friends at Castello di Volpaia. 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, epitomes of luxury, where we see to it that every detail ensures your comfort, from the first light of a fiery sunrise to the evening's last sip of Chianti. 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

Enjoying delicious wines at an exclusive visit to Castello di Volpaia

Experience an exquisite wine tasting and paired lunch at Castello di Volpaia

The Mascheroni Stianti family personally welcomes you for a spectacular wine-paired lunch in their villa. Taste the finest vintages and enjoy 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

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

  • Guaranteed

  • Join Waitlist

  • Private

  • Limited Availability


Itinerary
Rider Information

Hotels
Hotel Variation Castel Monastero guest room
Hotel Variation Castel Monastero exterior
Hotel Castel Monastero pool
Hotel Variation Castel Monastero guest room
Hotel Variation Castel Monastero exterior
Castel Monastero d'Ombrone, Italy
Castel Monastero
Ultimate Luxury The Leading Hotels of the World Collection

Castel Monastero is a beautifully restored medieval village and monastery that is nestled among Chianti vineyards and chestnut forests. This truly luxurious Tuscan retreat exudes a feeling of simple refinement and pure elegance. Tantalize your tastebuds at one of their two gourmet restaurants and don’t forget to stop in at the wine bar to sample the most famous labels of Tuscan wines. At the harmonious Renaissance spa, you will enjoy a haven of 5-star service and attention to detail.

...

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Belmond Castello di Casole hotel pool
Belmond Castello di Casole hotel exterior
Belmond Castello di Casole hotel terracce
Belmond Castello di Casole hotel guest room
Belmond Castello di Casole hotel exterior
Casole D'elsa, Italy
Belmond Castello di Casole
Ultimate Luxury

Part of the exclusive Belmond group and ranked the #1 Resort in Europe by Travel + Leisure magazine, 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 latest Trek Domane is the best way to enjoy the ride. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes and electronic shifting. This new bike is lighter than ever before, and carbon wheels come standard on every bike. The road-smoothing IsoSpeed technology lets you ride as long as you want with less fatigue. The bike you ride on a biking vacation matters. That is why we provide the newest and best bikes in the business.

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Verve+ electric assist lowstep bike E-Bike
Trek Electric-Assist Verve+

Fun from the first pedal stroke, our e-bikes give you the boost you want to venture further on your bike tour. With its low-step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain, with energy to spare.

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

Take the tailwind with you and leave your limits behind on the Domane+ SLR 7. With a groundbreaking ratio of ultra-lightweight design and electric assist, the Domane+ has everything you love in a road bike, with the extra boost to take you farther than ever before. This performance e-road bike will assist you on the climbs and enable you to venture further on your cycling vacation. So go ahead—take the long way. With Domane+ SLR 7, there’s always room for more distance, more speed, 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. Please contact a Trip Consultant to check availability.

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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 bottles to keep
  • Cinch sack day bag to keep
  • Bontrager saddle
  • Bontrager helmet
  • Bontrager front and rear Flare R lights
  • Garmin Edge 1030 GPS computer with pre-loaded routes
  • Shimano SPD-SL road style pedals, Shimano SPD mountain style pedals, caged, or flat pedals
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • 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:

  • Dining 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 (°F) 52.0° 55.0° 61.0° 67.0° 77.0° 84.0° 90.0° 90.0° 80.0° 71.0° 60.0° 52.0°
High (°C) 11.1° 12.8° 16.1° 19.4° 25.0° 28.9° 32.2° 32.2° 26.7° 21.7° 15.6° 11.1°
Low (°F) 37.0° 37.0° 42.0° 48.0° 55.0° 62.0° 66.0° 66.0° 60.0° 53.0° 45.0° 38.0°
Low (°C) 2.8° 2.8° 5.6° 8.9° 12.8° 16.7° 18.9° 18.9° 15.6° 11.7° 7.2° 3.3°
Rain (in) 0.93° 0.91° 0.72° 1.93° 1.16° 0.97° 0.24° 0.48° 1.08° 1.95° 2.02° 1.45°
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. 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 bike tour. We want to make it as easy as possible to do so and below you’ll find our timeline.

Have a question? Just give us a call, 866-464-8735.
Read our Cancellation Policy

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


Guaranteed Trips

Our trips are guaranteed to run once we have one confirmed booking on the trip. Click here to view our full guarantee policy.

Trek Travel reserves the right to cancel trips with zero guests, therefore you must book with Trek Travel before making travel arrangements for the trip. We are not responsible for travel arrangements made prior to confirming your Trek Travel Trip. Select trips are not guaranteed.

Sold Out/Waitlist

This trip is currently sold out, but you may be added to the waitlist in the case of availability.

Limited Availability

If a date is marked with Limited Availability, there are few spots left to book. We will secure additional rooms from our hotels before confirming your reservation.

Looking to travel with a small group? Ask our trip consultants about private trips and learn more.

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 - Discovor:

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.

Self-Guided

Enjoy a bike tour on your schedule with just your chosen travel companions.

Private

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.

Luxury:

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.

Explorer

These handpicked hotels provide relaxation and fun in a casual and comfortable environment. Delicious cuisine and great service mix perfectly for a memorable stay.

Combined

On select cycling vacations, you’ll stay at a mix of hotel levels, from Explorer to Luxury to Ultimate Luxury. Rest assured, no matter which level of hotel 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).

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).

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).

Level 4:

Road: 4+ hours of riding. 40-70 mi (60-110 km). Up to 8,000 ft (2,400 m).

Gravel: 3-5 hours of riding. 30-50 mi (45-80 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 - Discovor:

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.

Self-Guided

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