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Route Rating Level 3 to Level 5

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TRIP NOTES

All meals included except 3 lunches and 1 dinner.

Cancellation Policy

Cancellation fees may vary based upon departure date. Please call our expert Trip Consultants at (800) GO-ACTIVE (462-2848) for more information.

Meet / Depart

Siena, Italy/Orvieto, Italy

Special Interest

Culture & History, Fine Wine & Cuisine, Geological Wonders, Romance &/or Honeymoon

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Call: 800-462-2848
or 510-527-1555
Fax: 510-527-1444
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801 Cedar St.
Berkeley, CA 94710

Business Hours:
7 days a week
from 7 a.m. to 5 p.m., Pacific Time

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Tuscany Italy Biking Vacations

Tuscany Biking

In the Heart of Tuscany

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.

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.

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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.

Route Rating What's this? Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Each offers options for more or less activity, so you can decide exactly how much you want to do day by day.

Lodging What's this? Our lodgings are divided into three different categories.

Premiere Inns:These lodgings possess both elegance and authentic regional flair.

Casual Inns:These lodgings are comfortable and appropriate to the areawith such characteristics as authenticity, scenic settings and proximity to our activities.

Deluxe Camping:We set up the tents (and take them down), handle every camp chore and perform culinary magic.

Detailed Itinerary

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.
Chris Staines - Komoka, ON

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All Guest Reviews

For 30 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. For biking tours in Europe Italy, trust our in-depth connections. To see all our Europe Italy biking tours click here. For our selection of award-winning Europe Italy walking and hiking tours click here. For our selection of award-winning Europe Italy multisport tours click here.

Tuscany Biking

A GRACIOUS WELCOME: Casual Inns

Villa Curina

Curina (2 nights): This Renaissance villa welcomes us with traditional and modern décor, a large pool and tennis court.

Hotel San Michele

Cortona (1 night): Enjoy a night in the heart of town at this beautifully restored 13th-century manor house.

Hotel San Simeone

Rocca d'Orcia (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

Sovana (2 nights): This inviting hotel offers elegantly furnished rooms, exposed-beam ceilings and terra-cotta tile floors.

Tuscany Biking Tuscany Biking

Villa Curina

Tuscany Biking

Route Rating

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
Tuscany Biking Tuscany Biking

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
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