Tuscany’s Chianti Region

Posted in Chianti, Tuscany and Umbria, Culinary & Wine Tours, Italy, Italy Popular Walks, Trips


  • Visit Tuscany’s authentic Chianti region with an idyllic terrain of vineyards, lush woods, quaint farmhouses, fabulous wineries, interesting churches, and Etruscan ruins.
  • Delight in fabulous views over small wine estates and wooded hills.
  • Meander through medieval and renaissance villages
  • Reawaken your sense with perfect pizza and sumptuous gelato.
  • Discover Pienza, the perfect mix of architecture, food and trasdition.
  • Explore the small hamlet of Chianti with picture perfect towns like Greve and Castelini in Chianti
  • Breath the timeless character of medieval Montalcino and Montepulciano.
  • Savor authentic Tuscan food and wine.

Departure dates

May 6, 2020
October 20, 2020

*Personalized departures available. Use our concierge service to plan based on your dates of travel and preferred hotels. Choose your dates and let us do the rest.

Trip Length 6 days/5 nights
Start/Finish Florence/Florence
Walk Rating Moderate
Included All breakfasts, 2 dinners, 2 lunches, land transfers, wine tasting.
Hotels Country Casual
Price starting at: €2,995
Single Supplement €550


This itinerary can be priced for luxury accommodations upon request.


After a short drive from Florence, we will stop in Greve for a discovery walk of this charming town. A welcome lunch at Paola’s is a perfect way to decompress and take in the environment. If you begin your trip on a Saturday you can enjoy the the weekly market filled with typical produce and lively town action. After lunch we’ll taste sip fabulous Chianti wines, famous throughout the world. Transfer to your hotel and relax before a welcome dinner of local Tuscan fare.

Accommodations: Albergo del Chianti (or similar property) (L, Welcome D)


Following an Italian breakfast, walk along the vignemaggio overlooked by the one time resident of La Jaconda, better known as the Mona Lisa. We’ll take along a picnic lunch and find the perfect spot to enjoy the amazing vistas that surround the valley and that have been immortalized in Renaissance art. Dinner is on your own tonight and our guide is happy to steer you in the right direction or join you if you wish.

The Walk: 8 km. /5 miles
Accommodations: Albergo del Chianti (or similar property) (B, PicL)


This morning transfer to Radda and enjoy specialty food of local salamis and other delicacies. Discover  shops as you meander through the alleys of this typical Chianti town. If time and energy permits, we’ll add a guided walk in the surrounding vineyards.

The walk: 3.4km./2 miles

Accommodations: Albergo del Chianti (or similar property) (B)


Today we visit Castello di Brolio and the surrounding area. This medieval castle has been the seat of Barone di Ricasole since the 12th century. The estate still produces excellent wines. Later, if time permits, we’ll learn about the distillation of grappa, followed by a tasting of the final produce it you dare. Transfer to Castellina in Chianti. For dinner, we’ll dine like locals at a simple trattoria.

The walk: 14 kms. / 9 miles
Accommodations: Hotel San Leonino (or similar property) (B, D)


clip_image006Enjoy a guided tour of Sienna, one of the best preserved Medieval towns in Italy. Lunch on your own today at one of the many restaurants. We suggest an outdoor trattoria where you can people watch and delight in the architecture. We return to Castellina in Chianti with enough time to freshen up before our farewell dinner.

The walk: Variable
Accommodations: Hotel San Leonino (or similar property) (B, D)


After breakfast we say our goodbyes and transfer by car back to the Florence train station where you can continue on your journey or let us help you plan an extension trip.(B)

Additional days in Florence can be arranged. Extra charges apply. Extensions to Florence include transportation to Florence from San Gimignano.

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

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, taxes, consumer protection (OPC).

B= breakfast included, L=lunch included, PicL=picnic lunch included, D=Dinner included
All bookings through Voyages GAMSPS Travel, Quebec Licensee.

* Personalized Departure Dates: All trips can be customized to your dates. Supplemental charges may apply. This itinerary is also available using luxury hotels. Prices are based on your hotel selection.