Tuscany and Umbria Bike Tour

Cycle through Italy's green heart, exploring Umbria and the Montepulciano wine region

Trip Style

Classic Bike

Tour Duration

5 Days / 4 Nights

Activity Level

Level 3

Bikes

Trek Domane SL 7
Trek Electric-Assist Verve+ Gen 3
Trek Electric-Assist Checkpoint+ SL6 AXS

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Starting from

$3,099.00 per person

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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 Italian bike tour. Pedal along serene country roads to uncover enchanting medieval towns, vibrant culture, and timeless traditions. Begin your adventure in Umbria, Italy's "Green Heart," cycling through rolling hills, vineyards, and olive groves. Explore hilltop towns like Bevagna, Montefalco, and Assisi, where history and art come to life. As you journey into southern Tuscany, discover the breathtaking transformation into a landscape of sun-drenched fields, cypress-lined roads, and elegant farmhouses. Ride through the countryside surrounding Montepulciano and immerse yourself in Tuscany’s rich heritage, scenic beauty, and warm hospitality. 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

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

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 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

We had 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

Wow! I was blown away by the luxurious facilities and beautiful views. The spa was a perfect place to relax post-ride and a nice surprise. The food was also delicious!

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Meg, Trek Travel Guest

A group of people posing in front of a Tuscany landscape

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

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Susy Maddalon, Trip Designer

I cannot think of ANYTHING Trek Travel could have done to improve this trip. I use this word sparingly but, it was the perfect way to see Tuscany and it was the best vacation of my life!

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Gina M., 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.

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.


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. Its carbon frame with road-smoothing IsoSpeed, responsive disc brakes, and Shimano Di2 electronic shifting deliver incredible comfort without sacrificing performance. Standard carbon wheels make this bike lighter and faster than ever.

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E-Bike
Trek Electric-Assist Verve+ Gen 3

Fun from the first pedal stroke, the Trek Verve+ 3 helps you go farther with ease. Its low-step frame and upright riding position keep you comfortable, while the Bosch motor provides a natural boost up to 15 or 20 mph (region specific). Shimano hydraulic disc brakes deliver smooth, controlled stopping, so every hill and every mile feels relaxed and enjoyable.

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Electric Road
Trek Electric-Assist Checkpoint+ SL6 AXS

New in 2026! Trek’s Checkpoint+ SL6 AXS is a lightweight e-assist bike built for miles of fun. The TQ HPR60 electric-assist motor adds a quiet boost up to 15 or 28 mph (region specific), making climbs and long days easier. Carbon wheels and frame keep it quick and responsive, while 38 mm tires and IsoSpeed tech smooth rough terrain. With SRAM’s 12-speed AXS wireless shifting and disc brakes, every move is in your control.
Upgrade to the Checkpoint+ SL 6 AXS 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
  • Choice of Trek Travel Santini cycling jersey or technical t-shirt to keep
  • Trek Travel water bottle to keep
  • Cinch sack day bag to keep
  • GPS device with pre-loaded routes providing turn by turn directions
  • Trek front and rear lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Choice of Shimano SPD-SL single sided road pedals, Shimano SPD dual sided mountain pedals, or flat pedals
  • Trek helmet
  • Trek 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.
2026-CY-Mens-Full_Flatlay-Classic

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.
  • Traffic: 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, some sections will include brief stretches of traffic when entering or exiting towns. Stay alert while soaking in the scenery—this beautiful region offers plenty to take in, both on and off the road.
  • Road conditions: You may encounter rougher road surfaces, especially during the first three days while riding in Umbria, where occasional potholes and uneven pavement are part of the terrain. It’s all part of the adventure and adds to the region’s rustic character—just ride with a bit of extra awareness.
  • E-Bikes: E-bike speeds vary worldwide due to local regulations, which determine how fast you can ride with assistance. See the E-bike speed chart to see the maximum speeds allowed in each region.

Before and After Your Trip

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, Self-Guided, and select 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, 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 trip, we recommend $200-$250 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

Want to learn more about our trips? Watch our recorded Guide-Led Virtual Events—just visit our Trek Travel Youtube Channel and search for your trip.


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.

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

Hotel Differences

Trek Travel offers three hotel levels to match your style. Luxury hotels provide elegant, thoughtful touches with exceptional hospitality. Explorer hotels blend modern amenities with local charm in unique settings. Comfort hotels are casual and conveniently located near Trek Travel activities.

Activity Levels

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 Bike:

Explore beautiful destinations with a curated blend of guided activities, local cuisine, handpicked accommodations, and itineraries to suit every traveler, from laid-back adventures to luxurious escapes.

Gravel:

Venture off the beaten path to unforgettable places, with fully-supported routes that combine gravel and paved roads in classic Trek Travel style.

Cross Country:

Tackle an epic adventure that takes you point-to-point across mountains, countryside, and more.

Pro Race:

See the pros in action at the biggest cycling events of the year.

Hiking & Walking:

Step into adventure with carefully designed routes, unparalleled hospitality, and deep-routed local connections.

Ride Camp:

Train like the pros in some of their favorite riding destinations.

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