Tuscany Biking
Easy Biking South of Siena
Who's to say which is right? Riding off into the Tuscan sunset after an amazing day-long ride, or sipping espresso 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. Well, this is your espresso choice. Less mileage, more time to explore. And if you ask host, friend and chef Viviana Beccarelli, Tuscany is best enjoyed slowly. And you'll have plenty of time to ask her - she's having you over for supper.
- Spin on Tuscany's most gentle byways in the Val di Chiana (the van is always close by for a lift)
- 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
- Iconic hill towns of Pienza and Montepulciano
The Day-to-Day Itinerary
Days 1-2 Well-planned shorter routes on easier terrain (and a lift always at hand) 
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.
Day 3 Learn the secrets of Tuscan cooking and sample prized Vino Nobile at an exclusive culinary lesson with our longtime friend Viviana Bike past quaint farmhouses en route to the atmospheric fortified village of Castiglione del Lago, set on a promontory on Lake Trasimeno in Umbria.
Day 4 The iconic hill town of Montepulciano, with glorious Renaissance buildings 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 regions's architectural gems Sample locally made pecorino cheese, admire exquisite ceramics, wander down medieval streets and gaze over the Val d'Orcia On foot, explore the forests of oak, broom and cypress above Montefollonico.
- Premiere Inns: These lodgings possess both elegance and authentic regional flair.
- Casual Inns: These lodgings are comfortable and appropriate to the area with such characteristics as authenticity, scenic settings and proximity to our activities.
- Deluxe Family Camping: We set up the tents (and take them down), handle every camp chore and perform culinary magic.
Other Trips You Might Like:
Loire Valley Biking Turkey Biking Tuscany WalkingOther Italy Trips
Look at what other guests are saying 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.More about this Trip All Guest Reviews
For 32 years, Backroads has been perfecting the art of active travel. We are the tour experts. To see all our biking tours click here. For our selection of award-winning walking and hiking tours click here. For our selection of award-winning multisport tours click here.
Tuscany Biking
Premiere Inns*
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.
Relais Alla Corte del Sole
Petrignano del Lago (2 nights) An elegantly appointed 16th-century estate built on the grounds of a 14th-century monastic village. A Small Luxury Hotels of the World member. (pool)
Relais La Chiusa
Montefollonico (2 nights) A charming country inn described by the Hideaway Report as a "family-run stone manor that looks across to the medieval hill town of Montepulciano."
* Casual Inn
Tuscany Biking
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 | Biking Average | Walking Average |
|---|---|---|---|
| 1 | 2-3 hours | 10-20 miles | 2-5 miles |
| 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |
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
- 12, 28 miles
- 320 - 730 feet elevation gain
- Walking Tour of Cortona 2 hours
Day 3
- Levels 1 to 3 2 Route Options Available
- 19, 34 miles
- 490 - 850 feet elevation gain
Day 4
- Level 1 3 Route Options Available
- 9, 17, 20 miles
- 540 - 1760 feet elevation gain
Day 5
- Levels 1 to 2 2 Route Options Available
- 11, 21 miles
- 800 - 1780 feet elevation gain
Day 6
- Level 1 3 Route Options Available
- Biking 7, 13 miles
- 210 - 1100 feet elevation gain
- Walking 2.4 miles
- 420 feet elevation gain