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Route Rating Level 1 to Level 4

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Premiere Inns
  • From $4,198
    To $4,398 pp dbl. occ.
  • (+$1,350 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 1 lunch and 1 dinner.

PERFECT FOR A PRIVATE TRIP
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Cancellation Policy

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Meet / Depart

Florence, Italy

Special Interest

Cooking, Culture & History, Fine Wine & Cuisine, Horseback Ride, Romance &/or Honeymoon, Swim

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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 Walking Vacations

Tuscany Walking

Ancient Footpaths North of Siena

Walk with us in Tuscany and experience the essence of Italy—vineyards and cypress-lined lanes, dramatically perched hill towns, valleys bathed in golden sunlight, celebrated wines, mouthwatering cuisine, unforgettable Renaissance art and architecture and a warm and welcoming people. Make your way along footpaths strung along wide-open hillsides and ramble through picturesque villages that color the landscape. At day’s end, settle into some of Tuscany’s most charming hotels and savor hearty local cuisine and wines. Benvenuti in Toscana!

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Days 1-2 Radda in Chianti

Meet in Florence Hike a shaded and mostly level trail to the ancient ridgetop village of Radda in Chianti Explore medieval passageways and learn about this historic town—the center of Chianti Classico wine production—on a guided tour A local wine expert joins us for a tasting of Chianti Classico wines Follow centuries-old footpaths through vineyards in the Chianti hills, perhaps sampling local vintages in an enoteca (wine cellar) along the way Arrive in charming Volpaia, a village-turned-winery known for its fine vintages On a beautiful garden terrace with views of Radda in Chianti, enjoy a repast of regional specialities.

Days 3-4 Gaiole in Chianti

Setting your sights on Gaiole, walk to the tiny fortified hamlet of Vertine, perched well off the beaten path  Learn the finer points of piatti tipici toscani, typical Tuscan dishes, at Toscana Mia cooking school Stroll the strade bianche (unpaved trails) of Gaiole, past ancient vineyards and gnarled olive trees At the 11th-century Castello di Monteluco, feast on local delicacies at a grand picnic.

Days 5-6 Candeli

Stroll along wooded paths to the well-regarded wine- and olive oil–producing estate of Badia a Coltibuono Discover the nuances of fine Tuscan olive oils and honey at a tasting with Coltibuono’s resident expert From the countryside outside of Florence, take in views of this grand city.

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

Our leaders were fabulous. The itinerary and experiences could not have been better—I can't say enough to praise this trip! Having spent a lot of time in Chianti previously, I still learned, saw and experienced new things in unusual ways. My two friends with whom I traveled feel exactly the same way. It was perfect.
Marilyn R.—Scarsdale, NY

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For more than 29 years, Backroads has been perfecting the art of active travel. We are the Tuscany tour experts. For walking tours and hiking tours in Europe Italy, trust our in-depth connections. To see all our Europe Italy walking tours and hiking tours click here. For our selection of award-winning Europe Italy biking tours click here. For our selection of award-winning Europe Italy multisport tours click here.

Tuscany Walking

DISTINCTIVE ESTATES : Premiere Inns

Palazzo Leopoldo

Radda in Chianti (2 nights): This charming estate has undergone careful restoration while maintaining the refined style of Tuscan nobility, and offers spectacular views of the countryside.

Castello di Tornano

Gaiole in Chianti (2 nights): Surrounded by vineyards and with valley views, this medieval castle features spacious and comfortable guest rooms, a swimming pool built in the ancient moat and a top-notch restaurant.

Villa la Massa

Candeli (1 night): Located just outside of Florence, this Leading Small Hotels of the World member is a Renaissance villa featuring lavishly appointed guest rooms, a swimming pool, a well-stocked wine cellar, and a superb restaurant.

Tuscany Walking Tuscany Walking

Castello di Tornano

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View the Classic Casual Inns Itineraries.

Tuscany Walking

Route Rating

Daily Mileage Options & Cumulative Elevation Gain

Day 1
  • Level 1 1 Route Option Available
  • 2.8 miles
  • 0 - 500 feet elevation gain
Day 2
  • Levels 1 to 3 3 Route Options Available
  • 2.4, 4, 7.4 miles
  • 500 - 2000 feet elevation gain
  • Walking Tour of Radda 1 hour
Day 3
  • Levels 1 to 2 2 Route Options Available
  • 4.5, 5.7 miles
  • 0 - 500 feet elevation gain
Day 4
  • Levels 2 to 4 2 Route Options Available
  • 6.3, 10.8 miles
  • 1000 - 2500 feet elevation gain
Day 5
  • Levels 1 to 2  2 Route Options Available
  • 3, 5.2 miles
  • 0 - 1000 feet elevation gain
Day 6
  • Level 1 1 Route Option Available
  • 2.2 miles
  • 0 - 1000 feet elevation gain
Tuscany Walking Tuscany Walking

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