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Route Rating Level 2 to Level 5

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TRIP NOTES

All meals included except 2 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/Arezzo, Italy

Special Interest

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

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Southern Tuscany Biking

Tuscany Biking

South of Siena

This trip is currently only available as a Private Trip. Looking for a similar trip? See Tuscany Biking, Tuscany Easy Biking, Piedmont Biking, Puglia Biking, and Italy/Slovenia Biking. Or call 800-462-2848 to speak with a Trip Consultant.

You'll quickly understand the allure of southern Tuscany as you pedal between villages so intimate, you will experience the sounds and aromas of pranzo (the midday meal) as it's being prepared inside Italian homes. While there are plenty of hills to climb, your efforts will be well rewarded. After spinning through rolling vineyards, past undulating wheat fields and over chalky white hills by day, savor pecorino cheese, homemade pasta, fruity olive oils, celebrated Brunello di Montalcino wines and the warmth of Italian hospitality each evening.

You are viewing the Classic Premiere Inns version of this trip.
View the Classic Casual Inns Itineraries.

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Days 1-2 San Casciano dei Bagni

Meet in Siena Enjoy a delicious picnic lunch of Tuscan specialties at a local organic farm and agriturismo, then warm up with a pleasant rolling ride in the countryside  Pedal to Montalcino through vineyards yielding southern Tuscany's prestigious Brunello di Montalcino wine.

Day 3 Pienza

Follow country lanes to the quaint village of Castelmuzio In Pienza, one of Tuscany's Renaissance gems, marvel at architectural masterpieces and shop for ceramics For dinner, savor such Tuscan favorites as panzanella, pappardelle al sugo and acquacotta.

Days 4-6 Farneta

In medieval Montepulciano, Tuscany's highest hilltop town, discover hidden piazzas, visit the famous Tempio di San Biagio pilgrimage church and perhaps taste Vino Nobile di Montepulciano Pedal through the Val di Chiana, where Chianina cows graze contentedly  Climb to the postcard-perfect Etruscan village of Cortona for a guided walking tour of its ancient town center, gaining insight into its storied past Bike along picturesque roads of the Val di Chiana to Lago Trasimeno, the country's fourth-largest lake and a favorite vacation spot of Italians.

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

This truly was a remarkable, memorable trip. I feel that biking allowed us to truly experience Italy in an intimate way. We met people on the roadside picking mushrooms...we could see Tuscany, feel Tuscany, and smell Tuscany!
Marianne Kaluza - Sammamish, WA

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

MEDIEVAL MASTERPIECES: Premiere Inns

Relais Il Chiostro di Pienza

Pienza (1 night): Originally a 15th-century convent, this hotel is situated in the heart of town and offers tastefully furnished guest rooms and a pool.

Fonteverde Natural Spa Resort

San Casciano dei Bagni (2 nights): With an atmosphere reminiscent of an ancient Tuscan villa, this Leading Small Hotels of the World member features a luxurious spa and wellness center and boasts stunning views of the Val d'Orcia.

Villa Petrischio

Farneta (2 nights): Set on a quiet hill, this lovely four-star hotel, nestled in pine trees, was built in the 18th century for the Lombardi counts who wanted to be close to the Abazzia Farneta.

Tuscany Biking Tuscany Biking

Relais Il Chiostro di Pienza

You are viewing the Classic Premiere Inns version of this trip.
View the Classic Casual Inns Itineraries.

Tuscany Biking

Route Rating

Daily Mileage Options & Cumulative Elevation Gain

Day 1
  • Level 1   1 Route Option Available
  • 12 miles
  • 1000 feet elevation gain
Day 2
  • Levels 2 to 5  3 Route Options Available
  • 21, 42, 85 miles
  • 2500 - 7500 feet elevation gain
Day 3
  • Levels 2 to 4 3 Route Options Available
  • 24, 41, 54 miles
  • 1600 - 4800 feet elevation gain
Day 4
  • Levels 2 to 4  2 Route Options Available
  • 29, 43 miles
  • 1800 - 2300 feet elevation gain
Day 5
  • Levels 2 to 5  4 Route Options Available
  • 21, 44, 51, 66 miles
  • 800 - 2500 feet elevation gain
Day 6
  • Level 2 1 Route Option Available
  • 21 miles
  • 700 feet elevation gain

Please note: Terrain in Tuscany is hilly and the routes can be more challenging than the mileage suggests.

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