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Tuscany Countryside Bike Tour

Bike through the "Green Heart" of Italy in Umbria and Tuscany

Tour Duration

5 Days / 4 Nights

Trip Style

Classic Guided, Discover

Activity Level

Level 3

Hotel Level

Explorer

Bikes

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

View details

Starting from

$2,399.00 per person

See dates

Discover two of Italy's top cycling destinations: lush Umbria, renowned for its fine olive oil, and the noble Montepulciano wine region.

Traverse two of Italy's most scenic regions—Umbria and Tuscany—on this captivating bike tour. Let us take you along serene country roads to discover their enchanting medieval towns. Begin your adventure in Umbria, Italy's "Green Heart," pedaling through rolling hills, vineyards, and olive groves. Immerse yourself in the charm of Umbria's hilltop towns like Bevagna, Montefalco, and Assisi, each showcasing the region's vibrant culture and artistic heritage. As you journey to southern Tuscany, witness the transformation into a picturesque landscape of bountiful fields and elegant farmhouses framed by cypress trees. Starting from Montepulciano, a renowned wine region, explore captivating hilltop towns and uncover the ancient tradition of winemaking. Let the sun-drenched scenery be your backdrop as you discover Tuscany's incredible cycling, delectable cuisine, and world-class wines. Also see our Tuscany Bike Tour » and our Tuscany Wine Country Bike Tour »

Trip Wows
  • Soak up the medieval ambience and ancient traditions in the quintessential hilltop towns of Pienza and Cortona

  • Indulge in the olive oil and wine tastings in Tuscany and Umbria, where the best quality is produced

  • Bike through timeless towns and enchanting farms nestled in Umbria’s rolling landscape, Italy’s "Green Heart"

  • Discover the medieval town of Assisi, a UNESCO World Heritage Site and home of St. Francis

  • Enjoy gracious boutique hotels with distinct regional flavor, boasting their own wineries

Vast rolling hills in Tuscany's Val d'Orcia

The rolling hills, vineyards, and medieval villages in Val d'Orcia

Renaissance landscapes of Val d'Orcia

This vast, undulating valley is a UNESCO World Heritage site. You'll quickly fall in love with this idyllic rural landscape much admired and painted by Renaissance artists.


What Guests are Saying
A group of people posing in front of a Tuscany landscape

This bike tour takes you to two stunningly beautiful regions of Italy. Umbria, often underestimated, showcases a vibrant local culture, unique artistic heritage, and untouched natural beauty. Southern Tuscany, with its picturesque landscapes painted with earthy and warm tones, has a mesmerizing allure. Come and discover for yourself this authentic Italian paradise that has stolen my heart away.

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Susy Maddalon, Trip Designer

Sara and Angelo our guides are phenomenal humans and amazing guides – they ensured we enjoyed the trip of a lifetime! We were already very loyal to Trek on the bicycle side, and now Trek Travel will be our go-to cycling trip provider! Everything was perfect and they both worked very hard to provide a very special experience.

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Liz A., Trek Travel Guest

Two Cyclists riding by the camera in Tuscany, Italy

We couldn’t have loved it more! From the expert guides to spectacular bikes, this was definitely a trip of a lifetime! We were referred by friends for this trip and it exceeded our expectations. Thanks Trek Travel!

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Linda S., Trek Travel Guest

A female cyclist in Tuscany, Italy

This is my 5th Trek Travel Trip. With every trip, I say, “Wow, this is the best trip yet!” I’ve encouraged quite a few friends to try Trek Travel and they too are now repeat customers. The trip itineraries are perfect. The cycling amazingly beautiful and perfectly (did I really just say that?) challenging. But please know, your guides make these trips. I’m not sure how they are chosen; what the interview process is. But you nail it every time.

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Allie Z., Trek Travel Guest


Great Ride

Borgo Tre Rose to Pienza Loop

Pedal quiet roads through rolling hills and vineyards around Montepulciano, with sweeping views of ploughed fields and cypress-lined lanes, leading up to the Renaissance charm of Pienza.


Dates & Pricing

Book early for the best price

  • Guaranteed

  • Join Waitlist

  • Private

  • Limited Availability


Itinerary
Activity Information

Hotels
pool side view at the Valle di Assisi Resort and Spa
hotel room at the Valle di Assisi Resort and Spa
plated ravioli at the Valle di Assisi Resort and Spa
dining area at the Valle di Assisi restaurant with a view of surrounding hills
indoor pool at the Valle di Assisi Resort and Spa
fly over view of the Hotel Valle di Assisi Resort and Spa
Santa Maria degli Angeli, Umbria - Italy
Valle di Assisi Resort & Spa
Explorer

A country resort surrounded by 60 hectares of unspoiled Umbrian countryside including olive groves and vineyards, Valle di Assisi Spa Hotel is the perfect blend of all the things Umbria has to offer. Set at the foot of Mount Subasio, a short distance from the town of Assisi, the hotel features a terrace overlooking Assisi, an outdoor pool, a wellness centre and a golf course. The property produces its own olive oil, wine, and balsamic vinegar.

...

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beautiful hotel room with terracotta floor at the Borgo Tre Rose hotel
pool surrounded by stunning landscape
Hotel room and balcony at the Borgo Tre Rose
Wine cellar
outdoor terrace at the Borgo Tre Rose
outside flyover view of the Borgo Tre Rose
Valiano di Montepulciano , Tuscany - Italy
Borgo Tre Rose
Explorer

The breathtaking landscape of the Val di Chiana hills is the setting for Borgo Tre Rose, an antique medieval hamlet perfectly preserved and converted into a charming country hotel perched on the top of a hill in the Montepulciano region and surrounded by the vineyards of a winemaking estate.

...

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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 water bottles to keep
  • Cinch sack day bag to keep
  • Garmin Edge 1030 GPS computer with pre-loaded routes
  • Bontrager saddle*
  • Bontrager helmet*
  • Choice of Shimano SPD-SL road style pedals, Shimano SPD mountain style pedals, caged, or flat pedals*
  • *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.
  • Bontrager front and rear Flare R lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
A collage of cycling gear guests will use on a Trek Travel Ride Camp, Discover, or Self-Guided 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 begins from 1:00 PM and dinner from 8:00 PM. Dinner can also last two or more hours, allowing time to enjoy the delicious cuisine of the area at a leisurely pace.
  • Biking in the region: We want to make sure you have a comfortable and enjoyable experience on this trip, so it’s important to note that while we strive to find quiet, paved secondary roads, there may be some occasional traffic when entering and exiting towns. It is important to stay vigilant while taking in the views of this beautiful region.

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 (75F-90F/24C-32C) and evening temperatures 10-15 degrees cooler. A jacket or wrap will be useful in the evening. Summers are warmer with warm daytime temperatures (80F-95F/27C-34C). Rain is always a possibility, however, so be prepared with wet-weather gear in order to best enjoy your cycling 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 Discover trip, we recommend $150-$200 per guest.

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.

Don’t see exactly what you are looking for 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 Explorer and Luxury hotels. Rest assured, no matter which hotel level 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).

Hiking: 1-3 hours of hiking. Up to 5 mi (8 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).

Hiking: 2-4 hours of hiking. 4-8 mi (6-12 km). Up to 1,500 ft (450 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).

Hiking: 3-5 hours of hiking. 6-10 mi (9-16 km). Up to 2,000 ft (600 m).

Level 4:

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

Gravel: 4+ hours of riding. 30-50 mi (45-80 km). Up to 4,000 ft (1,200 m).

Hiking: 4+ hours of hiking. 7-15 mi (11-24 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 - Discover:

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