Tuscany Biking
Please Note: This trip is currently only available as a Private Trip. Looking for a similar trip? See Tuscany Biking: North of Siena, Slovenia/Italy Biking, Puglia Biking, and Piedmont Biking. Or call 800-462-2848 to speak with a Trip Consultant.
In the Heart of Tuscany
If you dream of experiencing the full spectrum of Tuscany in a single vacation, this sensational eight-day cycling journey may be the perfect trip for you. The itinerary showcases the region's diversity and highlights some of its most prized possessions - including those signature hills! Visit the beloved hill towns of Cortona and Pienza, and ride past the famed vineyards and peaceful woodlands of Chianti. Behold the wide-open landscapes of southern Tuscany and explore the streets of Montepulciano and Montalcino, where the incomparable Vino Nobile and Brunello wines were born. Off your bike, discover unforgettable Renaissance art and architecture, and refuel with hearty cuisine. Join us for the best Tuscany has to offer.
Days 1-2 curina
Meet in Siena 
Spin past world-famous vineyards in the heart of the Chianti wine region Treat yourself to the perfect cappuccino or refreshing gelato in such renowned towns as Radda and Castellina Check out Castellina's old ramparts, fortress and arcaded walkway.
Day 3 cortona
Pedal rolling terrain in the captivating Val di Chiana, renowned for its prized Chianina cattle Shop for unique handicrafts in the historic hill town of Cortona.
Days 4-5 rocca d'orcia
Head through a landscape of rolling hills, farmland and quaint villages into the Val d'Orcia Visit medieval Montepulciano and discover hidden piazzas, a welcoming enoteca and the Tempio di San Biagio pilgrimage church Ride through a classic Tuscan tableau of cypress trees, pines and olive groves to the famous monastery of Monte Oliveto Maggiore In the ancient village of Bagno Vignoni, see a Roman bath favored by members of the Medici family A side trip leads to Pienza, one of Tuscany's Renaissance gems Tackle the challenging ride to Montalcino.
Days 6-8 Sovana
Enter Tuscany's Maremma region 
Bike to the sleepy hamlet of Sovana, known for its rich Etruscan heritage Visit the fairy-tale village of Pitigliano, where high tufa cliffs tower above bright green valleys Soak in the therapeutic waters of Saturnia Hot Springs, used for centuries by the Etruscans and the Romans Shuttle to Orvieto.
A GRACIOUS WELCOME: Casual Inns
Villa Curina (2 nights): This Renaissance villa welcomes us with traditional and modern décor, a large pool and tennis court.
Hotel San Michele (1 night): Enjoy a night in the heart of town at this beautifully restored 13th-century manor house.
Hotel San Simeone (2 nights): At this splendidly restored gem, bask in an atmosphere of style and elegance in a magnificent hilltop location overlooking the Val d'Orcia.
Sovana Hotel & Resort (2 nights): This inviting hotel offers elegantly furnished rooms, exposed-beam ceilings and terra-cotta tile floors.
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Levels 1 to 2 2 Route Options Available
- 15, 24 miles
- 1000 - 1500 feet elevation gain
Day 2
- Levels 3 to 5 3 Route Options Available
- 30, 51, 61 miles
- 1500 - 4000 feet elevation gain
Day 3
- Levels 1 to 4 3 Route Options Available
- 19, 39, 43 miles
- 500 - 2000 feet elevation gain
Day 4
- Levels 2 to 4 4 Route Options Available
- 25, 39, 42, 45 miles
- 1000 - 3000 feet elevation gain
Day 5
- Levels 2 to 4 3 Route Options Available
- 26, 35, 51 miles
- 1000 - 3500 feet elevation gain
Day 6
- Levels 2 to 5 3 Route Options Available
- 26, 51, 58 miles
- 1500 - 3000 feet elevation gain
Day 7
- Levels 2 to 4 2 Route Options Available
- 30, 47 miles
- 2000 - 3000 feet elevation gain
Day 8
- Conclusion of Trip
Trips 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 | Average Distance | |
|---|---|---|---|
| Biking | Walking & Hiking | ||
| Level 1 | 2-3 hours | 10-20 mile | 2-5 miles |
| Level 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| Level 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| Level 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| Level 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |
Guest Trip Reviews
If you love challenging climbs, outstanding vistas, great food and insights into local art and history this has got to be an almost perfect vacation. I admit I was almost in tears as I made my final descent back to my hotel on the last day. Great leaders and great fun.- Komoka, ON
The trip was by far the best vacation we have ever been on. Every aspect of the trip exceeded our expectation from the accommodations, to the quality of the leaders to the bike routes! It was the best biking we have ever done in our lives! It is not a matter of "if" we do a Backroads trip in the future, but "when" we can work it into our schedule!- Durango, CO
The region and location of the hotels and resorts were perfect! It was everything I dreamed it would be.- Batesville, IN