Castellini in Chianti Women’s

Posted in Italy, Italy, Italy Popular Walks, Trips, Women's Destinations


  • Visit authentic Chianti, an idyllic terrain of vineyards and lush woods, quaint farmhouses, fabulous wineries, and interesting churches, and Etruscan ruins.
  • Enjoy views over small wine estates and wooded hills.
  • Meander through medieval and renaissance villages
  • Taste the perfect pizza or savor an authentic gelato.
  • Meander through cobblestone streets and discover local shops.
  • Enjoy authentic Tuscan food and wine.

Departure dates

May 5 2015, May 29, 2015, September 21, 2015

Personalized departure dates available upon request. You choose the dates and let us do the rest.

Trip Length 6 days/5 nights
Start/Finish Chiusi/Florence
Walk Rating Easy to Moderate
Included All breakfasts, all dinners, land transfers, wine tasting.
Hotels Deluxe hotels included in pricing.
Price $3,095*
Single Supplement $450*

*All prices quoted in US dollars.


This itinerary is priced based on a walking holiday using 3 and 4 star properties. Pricing for luxury accommodations upon request.


After a short drive from Chuisi, we begin with a meet-and-greet while enjoying a simple Tuscan lunch. Next, join us for a warm-up walk between the Renaissance town of Pienza and medieval town of Montichiello or San Quirico. In the afternoon, we will explore the town of Pienza, birth place of 15th-century Pope Pius II, who commissioned the building of an ideal town based on Renaissance principles. Planned and built by architect Bernardo Rossellino in 1449, buildings are angled to show off the clear blue Tuscan skies. We walk through some stunning landscape and into the surrounding countryside. There is time on your own to wander through the cobblestone streets and visit local shops before going to Montalcino, your home for the next three nights. For dinner, we dine at a local restaurant.

The Walk: 6 km. /3.8 miles

Accommodations: Il Giglio, Montalcino (or similar property) (L,D)

Set in the heart of Montalcino, this simple country property offers stunning views of the Val D’Orcia. The hotel is within easy walking distance to the centre of town, local shops, and many cantinas which offer specialty wine-tasting.


Our day begins with an Italian buffet breakfast. Our guides will take you to local specialty shops and grocers, where we will help you choose your own picnic lunch. Our guides will explain the regional cheeses, breads and meats. Today we walk through one of the best wine-producing zones in Italy. We meander through cool forests to the Abbey of Sant’Antimo – a 12th-century Romanesque structure fashioned in large part from luminous alabaster. Following our luncheon feast, we take a short walk to the nearby village of Castelnuovo dell’Abate. During the afternoon, there is a transfer back to Pienza for an afternoon at your leisure. For dinner, our guide will help you find the perfect spot to dine in the town of Montalcino.

The walk: 14 kms. / 9 miles

Accommodations: Il Giglio, Montalcino (or similar property) (B,L)



Today we walk through fertile valleys to San Quirico or around the Bagno Vignoni area. After lunch, we transfer by car to Montepulciano, a miniature Florence famous for its Vino Nobile. We visit the Vintners’ cellars, dug deep beneath the town’s medieval quarter among ancient Etruscan tombs. Included in our tour is a visit to the cellars of the award-winning Avignonesi winery or the wineries of Contucci.

The walk: Variable

Accommodations: Il Giglio, Montalcino (or similar property) (B)


The area of Greve is featured today, with a visit to this quaint wine-market town and a walk in the nearby hills. Learn about the complex process of grappa distillation, followed by a tasting of the final product (if you dare!) at one of the area’s traditional distilleries. At the end of the day, we transfer to our new accommodations in Castellini in Chianti, There is time before dinner to relax by the pool or explore the twisting alleys of this small Tuscan town.

The walk: Variable

Accommodations: Palazzo Squarcialupi, Castellina in Chianti; or equivalent (B,D)

This converted 15th centruy Palazzo is situated in the heart of the historical center of Castellina in Chianti. Underneath the hotel, one can see the antique wine cellars that are still producing famous Chianti wines from the vineyards around the village.


Today we visit nearby San Gimignano, renowned for its medieval skyscrapers. Our guide will take you on a walking tour of this medieval town, after which you will have time to wander on your own and discover hidden alleys, local shops, and taste the best home made gelato (ice cream) in Italy. We will transfer back to Castellini for a farewell dinner.

The walk: Variable

Accommodations: Palazzo Squarcialupi, Castellini in Chianti; or equivalent (B,D)


After breakfast, our guide will take you back to Florence or assist you with a transfer to your next destination

Accommodations: (B)

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


INCLUDED: 5 nights accommodations at deluxe hotels, all breakfasts, 3 dinners, 1 lunch, wine tasting, full time certified local guide, luggage transfer, all hotels transfers, guided walking routes, hotel taxes and tips, FICAV contribution, tips and gratuities for included meals & hotels, and more.

NOT INCLUDED: Airfares, airport taxes, travel insurance (mandatory), pre and post trip arrangements, personal purchases, mini-bar services, alcohol unless specifically included, tips for the guides. Prices based on double occupancy.


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.