Chianti countryside and wines

Posted in Chianti, Tuscany and Umbria, Italy, Italy Popular Walks, Trips


  • Walk with our local expert guide through the cobbled streets of the Tuscan hill towns and off-the-beaten tourist path.
  • Sip a glass of Brunello or Chianti wines.
  • Taste freshly pressed olive oil.
  • Enjoy hearty Tuscan cuisine, wineries, and specialty food tastings (plan includes all breakfasts, two lunches, and three dinners).
  • Daily walks among the quintessential Chianti vineyards.
  • Some trips offer an optional pre-breakfast yoga warm-up.

Enjoy a sojourn in the heart of Chianti, away from the crowded hustle of Florence. Along little used trails and backroads, you arrive at hilltop towns with lovely views over the small wine estates and the wooded hills. Stop to sample the wines and enjoy authentic, delicious Tuscan feasts. There are castles to explore, some of them hosting highly regarded wineries, others abandoned among the forests, as well as country churches shyly hiding some remarkable art. This is the authentic Chianti, which few know about: an idyllic terrain of vineyards and lush woods, sprinkled with quaint farmhouses and quiet villas.

Group Departure dates

 April 21, 2020, May 19, 2020, October 21, 2020

Custom departure dates available.
*Custom departure dates are based on your travel schedule and can start any day of the week, group departures as noted. Contact our concierge service for more information.

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, OPC (consumer protection).
Hotels See options below.
Price Starting at $3,079 US
Single Supplement $750



Our local guide(s) pick you up in Florence, and it is just a short drive to our first walk into Chianti’s countryside, just south of Florence. Our orientation walk through the vineyards starts the trip off right. We’ll partake in a wine tasting at one of the local estates. There is time to freshen up at your hotel before a welcome dinner. Stress gone!

The walk: 6 kms. /3.8 miles
Accommodations: Choose between our country casual, first class, or deluxe hotels.
Options include: Fattoria Valle, Hotel San Niccolo, and Villa Le Barone. (Wine tasting, D)


Our day begins with an Italian buffet breakfast followed by a visit to Greve, Chianti’s central market town. After exploring the village’s unique funnel-shaped piazza, lined with interesting shops, you walk into the hills above Greve, passing through the fortified village of Montefioralle. If time permits, there is a visit to a local olive press along with olive oil tastings.

The walk: 8 kms. /5 miles)
Accommodations: Choose between our country casual, first class, or deluxe hotels. (B, L)


Today you walk south of Radda to the tiny village of San Leo. In the afternoon, you visit the imposing Castello di Brolio, where the recipe for Chianti was originally invented. Our guide will return you to Radda and help you find the perfect spot for dinner.

The walk: 7.2 kms. /4.5 miles
Accommodations: Choose between our country casual, first class, or deluxe hotels. (B)


We drive up cypress-lined roads to get to the centre of Lamole, our starting point for today. Begin at the village of Lamole and follow centuries-old farm tracks through chestnut woods and pastures to the summit of Monte San Michele, which at 892m is the highest point in Chianti, with wonderful panoramas of the surrounding countryside.

The walk: 12 kms. / 9 miles
Accommodations: Choose between our country casual, first class, or deluxe hotels. (B, L)


You begin the day with a walk in the area of Volpaia, a fortified village of medieval origin, built around an 11th century castle. Your walk takes you past quaint hamlets with fantastic panoramic vies of the countryside. You’ll walk past chapels hidden among the surrounding forests in what was considered piaoneer territory between the Sienese and Florentine borders. In the afternoon, you enjoy a tasting of local specialty foods amidst the perfect Tuscan countryside. We say our good byes with a quintessential Tuscan meal.

The walk: 8 kms. /5 miles
Accommodations: Choose between our country casual, first class, or deluxe hotels. One option Villa San Paolo. (B, D)


Our guide takes you on an early morning walk before your transfer 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, 5 nights hotel stay, hotel taxes and hotel gratuities, all breakfasts, 2 dinners, one lunch, guided walks in Greve, Radda, guided walks on country footpaths, wine tasting at the home of the original Chianti vineyards, specialty food tasting, luggage transfers, consumer protection.

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 GAM-SPS Travel Inc, Quebec Licensee.


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


Hotel Type Preferred Hotel Price per Person
Country Casual Fattoria Valle $3,179 US
Deluxe Hotel San Niccolo $3,729 US
First Class Villa Le Barone $4,069 US
Luxury and Uber Luxury Upon request Priced upon request
Single Supplement