Tuscany Biking
- Spin on Tuscany’s most gentle byways in the Val di Chiana (the van is always close by for a lift)
- Iconic hill towns of Pienza and Montepulciano
- Savor the relaxed Tuscan way of life thanks to well-planned shorter routes on easier terrain
- A culinary lesson with longtime Backroads friend Viviana
- Sample prized Vino Nobile di Montepulciano
Easy Biking South of Siena
Who’s to say which is right? Riding off into the Tuscan sunset after an amazing daylong ride, or sipping a Brunello into the sunset in a Cortona café. That’s Tuscany. Mile after mile of vistas, villages, scenery and flavors. How you experience it should be your choice. Less mileage, more time to explore. Bike to your heart’s content, then leave time to smell the sunflowers, marvel at the Renaissance towns, savor the cappuccinos, and sample the region’s delicacies. Take your cues from the pace of countryside life - Tuscany is best enjoyed slowly.
Days 1-2 Well-planned shorter routes on easier terrain (and a lift always handy) 
An 18th-century villa sets the scene for a picnic lunch of typical Tuscan fare Soak up postcard-perfect views of Val di Chiana In the historic hill town of Cortona, immortalized by Frances Mayes’ Under the Tuscan Sun, behold majestic architecture during a guided walk.
Days 3-4 The iconic hill town of Montepulciano, with glorious Renaissance buildings Bike past quaint farmhouses en route to the atmospheric fortified village of Castiglione del Lago, set on a promontory on Lake Trasimeno in Umbria A fourth-generation vintner invites us to his family’s cantina for a tasting of the local lifeblood, a wine esteemed through the centuries by the likes of Voltaire and Thomas Jefferson Spin leisurely through a classic southern Tuscan landscape of rolling fields, cypress-lined roads and quiet hamlets.
Days 5-6 Celebrate the relaxed Tuscan way of life Pedal past vineyards to adored Pienza, one of the region’s architectural gems Sample locally made pecorino cheese, admire exquisite ceramics, wander down medieval streets and gaze over the Val d’Orcia Feel like shifting gears? Opt to hike through forests of oak, broom and cypress above Montefollonico.
Guests Reviews About This Trip
For us it was a truly amazing and educational experience. Loved the physical challenge, loved the cultural interactions and loved the way that the Backroads team made it appear effortless and that we were the only riders on the road, the only customers at the hotels and restaurants. A joy, every minute of it.
This trip was wonderful! Our leaders were fabulous, the cycling was just challenging enough. The hotels were very comfortable, and the service was excellent. And the countryside was so incredibly beautiful - the food, the people - something I will remember for a very long time.- San Marcos, CA
The leaders, the varied activities, the van support, the collective personality of the group made this my most special Backroads trip.- Phoenix, AZ
Premiere Inns*
Hotel Villa Marsili
Cortona (1 night) This elegant 14th-century palazzo rests within Cortona’s Etruscan walls and offers outstanding views of the Val di Chiana.
Villa Petrischio
Farneta (2 nights) Set on a quiet hill, this 18th-century villa is surrounded by hundred-year-old cypress and pine trees and overlooks the Val di Chiana. (pool)
Relais La Chiusa
Montefollonico (2 nights) A charming country inn described by Hideaway Report as a "family-run stone manor that looks across to the medieval hill town of Montepulciano."
* Casual Inn
Puglia Biking
Italy's Sun-Drenched Adriatic Coast
Classic:
Singles+Solos:
Tuscany Biking
Timeless Landscapes & Renaissance Treasures
Classic:
Singles+Solos:
This Trip Is Rated Level 1-3
Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of
interests and fitness levels. We know your pace may vary from one
day to the next-and your traveling companion's may differ somewhat
from yours. So we present a range of mileage options, and each
day you decide exactly what and how much you want to do.
| Activity Level | Average Time | Road Bike Average | Mountain Bike Average* | Walk & Hike Average |
|---|---|---|---|---|
| Level 1 | 2-3 hours | 10-20 miles | 10-15 miles | 2-5 miles |
| Level 2 | 2-4 hours | 21-30 miles | 16-20 miles | 5-7 miles |
| Level 3 | 3-5 hours | 31-40 miles | 21-25 miles | 7-9 miles |
| Level 4 | 4-6 hours | 41-55 miles | 26-30 miles | 9-11 miles |
| Level 5 | 5-7+ hours | 56-75+ miles | 31+ miles | 11-13+ miles |
*Mountain bikes are used in locations where the best riding is on a combination of dirt and paved roads. View trip locations
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 2 Route Options Available
- 16, 18 miles
- 90 - 680 feet elevation gain
Day 2
- Levels 1 to 2 2 Route Options Available
- 18, 26 miles
- 500 - 780 feet elevation gain
- Guided Walk 2 hours
Day 3
- Levels 1 to 3 4 Route Options Available
- 14, 17, 27, 37 miles
- 140 - 920 feet elevation gain
Day 4
- Levels 1 to 3 4 Route Options Available
- 11, 15, 23, 35 miles
- 200 - 2460 feet elevation gain
Day 5
- Levels 1 to 4 4 Route Options Available
- 11, 21, 33, 42 miles
- 450 - 2430 feet elevation gain
Day 6
- Level 1 2 Route Options Available
- 7, 13 miles
- 210 - 1100 feet elevation gain
- or Walking 2.4 miles
- 420 feet elevation gain
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For 33 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. See our award-winning Europe Italy biking tours, Europe Italy walking and hiking tours and Europe Italy multisport tours.
