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Route Rating Level 2 to Level 4

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Premiere Inns
  • From $4,198
    To $4,298 pp dbl. occ.
  • (+$1,000 for sgl. occ.)

Reserve early for the best available price. More Info

6 DAYS, 5 NIGHTS
ROLLOVER DATES BELOW FOR SPECIFIC PRICES
2008 DATES
CLASSIC TRIPS
ROLLOVER DATES ABOVE FOR SPECIFIC PRICES
TRIP NOTES

All meals included except 2 lunches and 1 dinner.

Cancellation Policy

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Meet / Depart

Siena, Italy/Arezzo, Italy

Special Interest

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

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

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

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Southern Tuscany Biking Vacations

Tuscany Biking

South of Siena

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 wines and the warmth of Italian hospitality each evening.

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View the Classic Casual Inns Itineraries.

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Days 1-2 castelnuovo dell'abate

Meet in Siena Warm up with a pleasant ride over rolling terrain along the flank of Monte Amiata, Tuscany's highest mountain   Pedal through vineyards yielding southern Tuscany’s prestigious Brunello di Montalcino wine Tranquil roads lead past the Abbazia Monte Oliveto Maggiore, the region’s most notable monastery, and the exposed chalk hills known as biancane.  

Day 3 pienza

Visit the ancient spa town of Bagno Vignoni, where Catherine de' Medici was known to linger Follow country roads 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 contentedly graze  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, Italy’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

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Trip praise

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

For more than 29 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

Castello di Velona

Castelnuovo dell'Abate (2 nights): Set on a hill above the Val d' Orcia, this elegant Renaissance castle welcomes you with a sparkling swimming pool, antiques and broad views of the countryside.

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.

Villa Petrischio

Farneta (2 nights): Set on a quiet hill, this lovely four-star hotel, enclosed by 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 3 Route Options Available
  • 10, 12, 19 miles
  • 0 - 2000 feet elevation gain
Day 2
  • Levels 2 to 3 3 Route Options Available
  • 21, 37, 44 miles
  • 1000 - 3000 feet elevation gain
Day 3
  • Levels 2 to 4 3 Route Options Available
  • 25, 41, 54 miles
  • 2000 - 5000 feet elevation gain
Day 4
  • Levels 2 to 4  2 Route Options Available
  • 29, 43 miles
  • 1500 - 2500 feet elevation gain
Day 5
  • Levels 2 to 4 3 Route Options Available
  • 21, 44, 51 miles
  • 500 - 2500 feet elevation gain
Day 6
  • Level 1 1 Route Option Available
  • 21 miles
  • 500 - 1000 feet elevation gain
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