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Discover the Chianti

On this 8 day walking tour discover Florence, the cradle of the Renaissance and dig into the history of the Roman amphitheatre of Fiesole before admiring the wonderful cathedral & Piazza del Campo in Siena. Stroll the wine hills of Greve & Radda in Chianti visiting some great wineries, meeting friendly people and tasting some great food. * Great food such as salami, Florentine steak, Cantucci with vinsanto and of course... wine!

Discover the Chianti

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8 days from
$969

Itinerary  |  Pricing  |  Hotels  |  What's Included

Discover the genius behind the Chianti Classico and Gallo Nero wines by walking through the celebrating vineyards where they are produced. Nestled amidst the flourishing art cities of Florence and Siena, the Chianti region offers natural beauty and incomparable culinary treasures. Your taste buds shall dance when you savor the world famous Chianti wines and delectable homemade olive oil. Walk along cypress lined country roads and 'strade bianche', gravel roads, traversing forests of oak, beech and chestnut. As the Tuscan sun shines above and the golden Chianti countryside reflects your delight, you will feel as if you have stepped into a Renaissance painting.

Day 1: Arrive in Florence


Arrive in Florence, check-in at your hotel and start exploring this fascinating city. Take a moment to breathe in the air of the Renaissance and the sweet scent of locally-produced red wine. We suggest you to arrive early and take a city walk around the magnificent squares and by the illustrious Arno River. Today's challenge: city walk from Piazza della Signoria, 3.5 hours. Villages along the way: Florence

Day 2: Settignano & Fiesole


Travel uphill on a twenty-five minute city bus ride to the quiet village of Settignano where the walk begins. On your way, pass magnificent countryside views of cypress trees, olive groves and Renaissance villas. Stroll through the delightful, charming town of Fiesole and tour its Etruscan ruins, the Roman amphitheater and Baths and the Franciscan Monastery. Return to Florence for overnight.(B) Today's challenge: 7km; 2.5 hours; 300m climb, 100m descent Villages along the way: Settignano & Fiesole

Day 3: From Florence to Greve in Chianti


After breakfast, a private transfer will take you to Greve in Chianti, a rustic nice market village in the capital of the Chianti wine producing region. Check into your charming hotel and head over to Le Cantine di Greve Winery where you can taste more then 50 different Chianti wines. In the afternoon, walk north from the attractive main square of Greve in Chianti through the inspirational, magical landscape. Overnight accommodation. (B) Today's challenge: 10.7km; 3.5 hours; 300m climb/descent Villages along the way: Greve in Chianti

Day 4: Greve in Chianti and Panzano walk


Take a short ride on a local bus to the picturesque fortified village of Panzano, just south of Greve in Chianti, where today's walk begins. Be in awe as you walk along a ridge overlooking the famed Greve Valley and Pesa Valley, offering breathtaking views of pure elegance in the form of medieval castles, captivating hamlets, quintessential Tuscan farmhouses and cascading vineyards. Overnight in Greve in Chianti.(B.D) Today's challenge: 5.8km; 2 hours; 250m climb, 30 descent Villages along the way: Greve in Chianti and Panzano in Chianti

Day 5: From Greve in Chianti to Radda in Chianti via Monte San Michele


After breakfast, a short car transfer takes you to the highest hill in Chianti, the Monte San Michele. From Badiaccia you descend through a forested valley of century old chestnut trees and continue towards the stunning medieval hamlet of Volpaia, situated amongst vineyards and castles. Stop in for a glass of red at a fine Enoteca, wine shop, and then continue on to Radda in Chianti for overnight. (B) Today's challenge: 11.5km; 4.5 hours; 450m climb, 350m descent Villages along the way: Badiaccia, Volpaia and San Michele

Day 6: Radda in Chianti round walk


A quiet, relaxing day awaits you. Bask under the Tuscan sun and if you wish, go for a scenic walk around the old center of Radda in Chianti. Wind along the charismatic alleyways and discover the fascinating Church of San Nicolí. Treat yourself by visiting a wine cellar and tasting the wine from their celebrated local vineyards. Overnight in Radda in Chianti.(B) Today's challenge: 7km; 2.5 hours; 250m climb/descent Villages along the way: Radda in Chianti

Day 7: Radda in Chianti to Siena


After breakfast, travel by private car transfer to the marvelous city of Siena, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy. Overnight accommodation in Siena.(B) Villages along the way: Siena

Day 8: Arrivederci Siena


The trip and our services end after breakfast, however we highly recommend you to book extra nights in Siena to continue exploring the old centre, exquisite museums, lush galleries and marvelous churches. A visit to the top of the bell tower is also quite a sight. If you leave today for the airport, travel by local bus to Florence. (B)

Getting there:


Florence, Pisa and Bologna airports are flown to by both major and low cost international carriers. All three airports can be easily reached by local transport, which is affordable and offers a frequent service. From Florence airport take the direct local bus to downtown. From Pisa airport, you can take either a direct train or bus to Florence. From Bologna airport take the bus to Bologna central station, then the train to Florence. To return from Siena to Florence, the SITA-TRA.IN bus station is very close to the hotel and a bus leaves every 30 minutes. If you come with your own car, please note that the hotels we use in Florence and Siena do not have a private parking lot of their own, there are several guarded parking areas which cost approximately 20.00 Euro per day.

Optional Services:


Additional nights may be booked at any of the accommodations along the way. Airport arrival and/or departure transfers. Guided tour of Florence or Siena with a local private city guide. Cooking lessons in Florence or Siena.

Also available as an 5 day tour!


The Challenge: Easy to moderate, along strade bianche (small gravel roads), footpaths and mule tracks, cross small hamlets and some larger villages. Lodging: Small comfortable & centrally located 3 star hotels with a friendly, family run atmosphere, and authentic farm with swimming pool. Tour Departure: Daily from April 01 to October 31.

Itinerary  |  Pricing  |  Hotels  |  What's Included

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