Chianti Classic

Posted in Chianti, Tuscany and Umbria, Italy, Italy, Trips, Women's Destinations


  • Walk with our local expert guide through the cobbled streets of the Tuscan hill towns of Pienza, Montalcino, Montepulciano, and Montichiello.
  • Sip a glass of Brunello or Chianti wines. Taste freshly pressed olive oil.
  • Enjoy authentic Tuscan cuisine (plan includes all breakfasts, two lunches, and three dinners).
  • Visit the local market in Greve.
  • For group departures we can offer a pre morning yoga stretch class.

Departure dates

September 22, 2014
October 5, 2014
May 5, 2015

*Personalized departure dates available.

Trip Length 6 days/5 nights
Start/Finish Florence/Florence
Walk Rating Moderate
Included All breakfasts, two lunches, three dinners, full time guide, land transfers, wine tasting, olive oil tasting.
Hotels Deluxe
Price $3,590US
Single Supplement $705US



Our local guide(s) pick you up in Florence, and it is just a short drive to our first walk along Chianti’s white roads. We stroll past towering cypress trees to the market in Greve. Shop at the market stalls and enjoy the typical action of an Italian town square. Share a welcome lunch at a trattoria specially chosen by our guide for its authenticity. We return by local bus to our accommodations for the evening. In the late afternoon, begin a new walk through the vineyards to the town of Panzano.

The Walk: 2 times 6 kms. /3.8 miles
Accommodations: Villa le Barone (or similar property) (L, D)


Our day begins with an Italian buffet breakfast followed by visits to the town of Radda, one of Chianti’s most interesting historical spots, and the small hamlet of Volpaia. Following lunch, the walk continues to the Castello d’Albola where we visit the cellars and enjoy a tasting of the genuine Chianti Classico. Included in today’s activities is a visit to a local olive press along with olive oil tastings.

The walk : 14 kms. /9 miles)
Accommodations: Villa le Barone (or similar property) (B, D)


A short transfer brings us to the Renaissance town of Pienza. Today we walk through the fertile valleys of the beautiful Val D’Orcia past cypress trees and vineyards linking Pienza to Montichiello.

The walk: 7.2 kms. /4.5 miles
Accomodations: Il Chiostro, Pienza (or similar property) (B, D)


Walk from Montalcino through cool forests and one of the best wine-producing regions in Italy. Visit the 12th-century Romanesque structure of the Abbey of Sant’Antimo. Before dinner, enjoy a wine tasting of the exclusive Brunello wines.

The walk: 9 to 14 kms. /5.5 to 9 miles
Accomodations: Il Chiostro or equivalent (B, L)


Begin with an early morning walk around Bagno Vignoni, the famous hot springs of the Medici family. Following lunch, transfer by car to Montepulciano, famous for its Vino Nobile. Stop at Contucci, one of the oldest wineries in the region. A farewell dinner is planned at Il Chiostro.

The walk: 14 kms. /9 miles
Accomodations: Il Chiostro or equivalent (B, D)


Our guide takes you on an early morning walk around the town of Siena before transferring to Florence.

The walk: Variable
Accommodations: (B)

Additional days in Florence can be arranged, or ask about our cooking course in Gaoile. Extra charges apply.

INCLUDED: Pick up and drop off in Florence, full time guide for each day, hotel, hotel taxes and gratuities, all breakfasts, all dinners, one lunch, guided walks in Siena, guided walks on country footpaths, wine tasting, specialty food tasting, luggage transfers, FICAV contribution.

NOT INCLUDED: Airfares, airport taxes, travel insurance (mandatory), pre and post trip arrangements, personal purchases, mini-bar services, alcohol unless specifically included, gratuities for guide and driver.

B= breakfast included, L=lunch included, PicL=picnic lunch included, D=Dinner included
All bookings through Garth Allen Marksted Travel, Quebec Licensee.

* Personalized Departure Dates: We can customize any of our trips to begin on a date that is convenient to you. Supplemental charges may apply. We can also offer this itinerary with luxury hotels. Prices are based on your hotel selection.