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Tuscany Countryside Bike Tour

Biking through Tuscany and Umbria, the “Green Heart” of Italy

Book now to guarantee the best prices and your preferred dates before September 27th!

Discover two of Italy's great cycling destinations: verdant Umbria, famous for its olive oil, and the charming Montepulciano wine country. 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. Journeying 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. Book your trip with confidence »
Tuscany Countryside Bike Tour
$1999 Per Person
5 Days & 4 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Hotel Level: ?
From $1999 per person View All Details
Trip Wows
Soak up the medieval ambience and ancient traditions of charming hilltop towns
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
Watch the Experience
Tuscany Countryside Bike Tour
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.
-Susy Maddalon, Trip Designer

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price is guaranteed.
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Single Occupancy from: +$399
May 27 – May 31 
$2199 / Person, Double Occupancy Book this date
Jun 9 – Jun 13 
$2099 / Person, Double Occupancy Book this date
Jun 16 – Jun 20 
$1999 / Person, Double Occupancy Book this date
Jun 23 – Jun 27 
$1999 / Person, Double Occupancy / Domane+ is not available on this date Book this date
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Welcome to the start of your Tuscany Countryside bike adventure! Meet your Trek Travel guides at the Assisi Train Station at 11:00 AM. A quick 5-minute shuttle ride takes you to your hotel near Assisi, a peaceful property surrounded by vineyards, olive groves, and fruit trees. After a short round of introductions, get fitted to your Trek bicycle and enjoy a casual buffet-style lunch at the hotel. Begin your first scenic ride and, as you familiarise yourself with your bike, explore the quiet roads up to Pieve San Nicolò. Take in the breathtaking views from the top before descending to Assisi to return to the hotel. In the evening, gather with your fellow travelers for an Italian aperitif on the hotel terrace, followed by a gourmet dinner featuring Umbrian specialties and estate wines. And get ready for more exciting cycling adventures ahead!

Valle di Assisi to Pieve San Nicolò Loop
Approximately 22 mi | 36 km and 2,190 ft | 670 m


Valle di Assisi Resort & Spa

Included Meals:

Lunch | Social Hour | Dinner

Today's route takes you through the beautiful Val'Umbra, Umbria's largest and most prolific valley, rich with vineyards and olive groves. A leisurely ride leads you to Bevagna, a celebrated town with two of Italy's oldest Romanesque churches in its central cobblestone piazza. Wander the narrow streets and enjoy its enotecas and art galleries. Then gear up for a rewarding climb to reach the hilltop town of Montefalco, synonymous with world-renowned Sagrantino wine. Enjoy a well-earned lunch of your choice in this picture-postcard town characterized by its warren of narrow, cobbled streets within its ancient walls. Afterward, relish a pleasant flat section of your ride before ascending to Assisi. You'll take in the panoramic views of this magical medieval town before heading back to the hotel for a relaxing afternoon by the pool. This evening is yours to explore the cobbled streets of medieval Assisi. Enjoy dinner of your choice at one of the many small bistros. Be sure to visit Assisi's celebrated Basilica of Saint Francis, a UNESCO World Heritage Site.

Today's Ride:

Bevagna to Montefalco to Assisi Loop
Approximately 42 mi | 68 km and 2,520 ft | 769 m

Avid Option:

Bevagna to Montefalco to Assisi Loop with Eremo climb
Approximately 48 mi | 78 km and 3,100 ft | 950 m


Valle di Assisi Resort & Spa

Included Meals:


After your morning cappuccino, prepare to say arrivederci to Umbria. Pedal along quiet secondary roads, winding through rolling hills, olive groves, rich vineyards, and wide valleys. Midway into the ride your guides will be ready with your packed sandwich for the day and a van full of ride snacks and drinks to keep you fueled! Your destination is Passignano, a charming village on the northern shore of Lake Trasimeno. Enjoy the views of the lake, the largest in Umbria and home to wild ducks, cormorants, and more. From here, choose to join the van or continue riding the last 20 kilometers all the way to our lovely country hotel, perched on a hilltop amidst picturesque vineyards. Spend the afternoon relaxing by the pool or strolling through the estate. You'll spend this evening in Montepulciano, a fascinating Tuscan town famous worldwide for its exquisite wine, Vino Nobile di Montepulciano. Tonight is yours to find the perfect dinner in this historic town, armed with the best recommendations from your guides.

Today's Ride:

Valle di Assisi to Passignano with Shuttle to Borgo Tre Rose
Approximately 39 mi | 63 km and 2,320 ft | 710 m

Avid Option:

Valle di Assisi to Borgo Tre Rose
Approximately 51 mi | 83 km and 2,980 ft | 910 m


Borgo Tre Rose

Included Meals:

Breakfast | Lunch

Prepare for a fantastic day ahead as you pedal along quiet country roads, with unobstructed views of vast ploughed and sown lands stretching over gentle hills that seamlessly blend with the horizon. These captivating vistas are accentuated by the presence of rows of majestic cypress trees. The consistently rolling terrain unveils three captivating climbs, leading you to the charming hilltop towns of Montefollonico, Pienza, and Montepulciano. This renowned region is celebrated for its exceptional extra virgin olive oil and of course its world-famous wines. Prepare to be mesmerized by breathtaking panoramas that resemble masterpieces paintings. This evening we'll raise a toast to our unforgettable Tuscany bike tour during a visit to the hotel's cellar, followed by a delightful wine tasting featuring the estate's own exquisite wines. Indulge in a sensational dinner at the hotel's restaurant, where you will be treated to an array of local specialties, creating a perfect finale to our remarkable Italian adventure.

Today's Ride:

Borgo Tre Rose to Pienza to Montepulciano Loop
Approximately 42 mi | 69 km and 4,000 ft | 1,235 m

Avid Option:

Borgo Tre Rose to Pienza to Monticchiello to Montepulciano Loop
Approximately 47 mi | 77 km and 4,950 ft | 1,517 m


Borgo Tre Rose

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Rise early this morning for one last spin on the gently rolling hills as you say buongiorno to the locals working in the fields. Our destination? Cortona, distinctively perched high on a hill on the eastern slope of the Valdichiana. Arrive in the Piazza della Repubblica, the main square, and observe its unique shape before pedaling back to the hotel. We will bid our farewells, and at 11:00 AM, you’ll depart by private shuttle for the Terontola/Cortona train station, arriving at approximately 11:30 am, in time to catch connecting trains to either Florence or Rome.

Today's Ride:

Borgo Tre Rose to Cortona Loop
Approximately 24 mi | 39 km and 1,660 ft | 507 m

Included Meals:



hotel image

Valle di Assisi Resort & Spa

Santa Maria degli Angeli, Italy

Explorer Accommodation | 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, only 2.5 mi from 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.
hotel image

Borgo Tre Rose

Montepulciano, Italy

Explorer Accommodation | 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 and surrounded by the vineyards of a winemaking estate, just a few steps from Montepulciano and Cortona.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Domane SL 7

Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane is the best way to enjoy the ride. Trek Bikes has launched the all-new Trek Domane and now you can ride it on our trips. 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. Learn More


Trek Electric-Assist Domane+ SLR 7

Take the tailwind with you and leave your limits behind on the all-new Domane+ SLR 7. With a groundbreaking ratio of ultra-lightweight design and electric assist, Domane+ SLR 7 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 help you on the climbs, hang with the fast group, and 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. Learn More


Trek Electric-Assist Verve+

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. Learn More


  • Four nights of accommodation at a single handpicked hotel
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, three lunches, and two dinners
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+, available in a limited quantity
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), front and rear Bontrager Flare R lights, a Bontrager saddle, and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A digital photo album of your trip


  • Upgrade your ride to the Trek Electric-Assist Domane+ SLR 7 (+$399, subject to availability)
  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this trip, we recommend $100-$150 per guest. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or our staff can help 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. 
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

55 kilometers / 33 miles
275 kilometers / 169 miles
778 meters / 2,538 feet
3,891 meters / 12,690 feet
Riding in Umbria and Southern Tuscany is highlighted by dream-like vistas and quiet, winding roads thanks to the beautifully rolling hills. Many of the towns sit atop hills and although the roads are not steep, the ascents are often upwards of five kilometers long. The roads are consistently rolling with few flat stretches and are commonly narrow. However, the locals are accustomed to sharing the quiet roads with cyclists and are alert to our presence. Our Tuscany Countryside Bike Tour is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider. Type 4+ Riders will enjoy the extra mileage the avid route options offer.
On most Trek Travel trips, we offer non-riding suggestions for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these suggestions may need to be scheduled before your trip. Expenses and related transportation to these activities are not included in the trip price. Some non-riding options on the Tuscany Countryside bike trip are:
  • Enjoy the pool at both properties
  • Explore the medieval town of Assisi and the Renaissance town of Montepulciano
  • Delight in olive oil and wine tastings
  • Relax at the Spa at the hotel Valle di Assisi
  • Arrange your own cooking class at the hotel Borgo Tre Rose

See itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our "Today’s Ride" options.

Travel Details

How to Get There

Florence Airport (FLR)
11:00 AM
Assisi Train Station, Italy

Say Farewell

Rome Fiumicino (FCO)
11:30 AM
Terontola/Cortona Train Station, Italy


We suggest that you arrive at least one day prior to the start of your Tuscany Countryside bike tour, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays.

We recommend that you fly into the Florence Airport (FLR). The airport is about three miles from the center of Florence. You can take a taxi (approximately 20 euros) directly to Santa Novella train station, or a bus which departs hourly. There are frequent direct rains from Firenze S.M. Novella to Assisi and the ride takes two and a half hours. We recommend you purchase your ticket in advance on the Trenitalia website at www.trenitalia.it or at a Biglietteria office or from ticket machines available at the train station. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform.

You can also fly into Rome and take a train to Assisi. From Rome’s Fiumicino Airport (FCO), you may take a direct train to Rome’s central station, Roma Termini. Follow the “Stazione/Railway Station” signs. There are frequent direct trains from Roma Termini to Assisi and the ride takes about two hours. Tickets can be purchased on the Trenitalia website at www.trenitalia.it or at a Biglietteria office or from ticket machines available at the train station. All tickets must be validated before getting on the train: do this by stamping your ticket at the yellow boxes near the platform.

Your Trek Travel guides will meet you at the Assisi train station at 11:00 AM on the first day of the trip. Please wait here to meet your Trek Travel guide, who will be visible and dressed in Trek Travel attire. Together you'll shuttle 5 minutes to the hotel Valle di Assisi, your home for the next two days. Here you will be welcomed by a casual buffet-style lunch while your guides fit and familiarize your group with your Trek bike for the week. Please have your first day's cycling clothes easily accessible, separate from your luggage, to facilitate the bike fitting and ride. After a brief orientation and a safety talk, saddle up to begin the day's ride through the Umbrian countryside.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip starts with their names and contact details. If you cannot reach them, please call our first hotel, Valle di Assisi (+39 075 804 4580) and leave a message with your expected arrival time and contact details. You may take a taxi from Assisi to to the first night’s hotel for approximately 20 euros.

View our pre hotel recommendations


You will say farewell to your guides at 11:00 AM at the Borgo Tre Rose in Montepulciano. You’ll depart by private shuttle for the Terontola/Cortona train station, arriving at around 11:30 AM. It is a small train station but trains connect to Florence and Rome and to many European destinations. Please, do not reserve a seat prior to 12:00 PM, allowing adequate connection time for any ongoing travel or possible traffic delays. Train schedules, fares and bookings can be made on the Trenitalia website at www.trenitalia.it, or www.fs-on-line.com, for other European destinations. From Roma Termini train station we suggest you take a direct express train (about 30 minutes ride) to the Fiumicino airport in Rome (FCO). Please do not schedule a flight prior to 5:00 PM.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

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. Packing List

Before and After Your Trip


Before: Florence, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and strolling beside the Arno. Along with the Duomo and Ponte Vecchio, the Uffizi gallery, a pillar of the Renaissance and Medici eras, merits a visit. Michelangelo's David in the Galleria dell'Accademia is not to be missed. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra euros and pre-book your tickets—this will enable you to bypass long lines of visitors at the entrances. We recommend the following accommodations for your pre-trip hotel:


After: Rome, Italy

Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abounds as well. The Coliseum, the Forum, Vatican City, and the Pantheon are some of the must-see attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine. We recommend the following accommodations for your post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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