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The Best of Florence & Chianti
Art, Food and Wine Tour


Our Signature Tour is a magnificent 8 night - 9 day accompanied journey in Florence and in magical chianti and is based on double occupancy (price is per person).

The Best of Florence & Chianti


  • 8 nights lodging in charming 4 star historical accommodations in Florence & Chianti

  • Full time bi-lingual host for the duration of the tour

  • Small group (maximum 14 guests) accompanied tour with licensed guides

  • All breakfasts and either lunches or dinners daily included in carefully selected trattorias, restaurants and winery osterie

  • All land transportation in private coach

  • Privately guided city tours in Florence, Siena, San Gimignano and Pienza

  • Guided visit & entrance tickets to the Accademia  Gallery (museum) in Florence.

  • Guided country tour to the breathtaking Val d'Orcia and the Brunello di Montalcino wine region

  • Visit to cheese farm with tasting

  • Visit to Bagno Vignoni (depending on tour period)

  • Truffles Truffles Truffles... we're going to find Truffles! (November tours only)

  • Family style dinner at a Brunello di Montalcino winery

  • Five/Six (depending on tour period) winery tours with premium tastings in wineries throughout Chianti/Vernaccia and the Montalcino regions in Tuscany

  • Olive oil and balsamic tastings in wineries

  • Market visits in Florence & Greve-in-Chianti

  • One hands-on cooking class in the heart of Chianti

  • Shopping and relax time included


8 nights in charming 4-star quality historical residences, wineries/country resorts. Room configurations are standard double occupancy with Italian queen size beds. Twin beds (in double occupancy) may not be available at all locations.  Single/solo travelers (in their own rooms) will incur a surcharge of US$720 for 2022 and $750 for 2023 tours. Please note that because of the historical architecture of the properties we partner with, rooms are unique and will likely vary in size. In many instances, it is possible to up-grade standard rooms to deluxe or suites on our tours. Please inquire when booking for supplemental prices for such upgrades.


All breakfasts and most lunches and dinners included. Two meals are included daily and there will be additional meals as per itinerary.  We hand-pick all restaurants and trattorias on our tours so as to give guests the best experience possible.  Regional wines included at all dinners.


Tour begins on day one at the hotel in Florence. Taxi service is readily available upon your arrival at the Florence airport and train station, however should you desire, we are happy to arrange a private transport service using our wonderful driver Alessandro to get you to our Florence hotel (not included in tour fees).  


All transportation is supplied as per tour specific itinerary including a complimentary transfer at tour end from Chianti residence to the Florence airport and central train stations (SMN). Departure time will be at 11.00 am, if you have a flight prior to 1:30 pm we will arrange a transfer via taxi, however not complimentary. NB: If you add on days at the completion of the scheduled tour, you will NOT be able to benefit from the the complimentary transfer to the airport or train station nor to another in Florence.  Naturally we will assist you in reserving a taxi or other service so that you can get to either the airport, train station or other destination in the area.

Guided Tours

There are four private guided city tours - Florence, Siena & San Gimignano, Pienza in addition to the country tour of the Val d'Orcia to an amazing pecorino cheese farm as well the Santa Giulia winery to taste wonderful wines in the Montalcino region. Included are entrance tickets to the Accademia Gallery in Florence. Moderate walking involved on this tour. Please bring comfortable shoes that are appropriate for walking the hard stone city streets of our renaissance and medieval towns.


You will spend the afternoon in a charming setting situated in the heart of Chianti for a wonderful hands-on cooking class. You will prepare a full-course meal with the guidance and supervision of your exuberant teacher, Elena.  You will dine family style and enjoy your meal... everything prepared in class!  Menu's vary according to the season and generally include an antipasto, a main dish and dessert.  Local wines are served with dinner.

Winery Tours & Tastings

There are 5-6 winery visits with tastings on this tour.  All wineries are located in Tuscany.  You will be touring a variety of wineries from a larger commercial winery to small family owned ones. You will be visiting their cellars, their production facilities and tasting rooms.  Our winery partners on this tour will be only in Tuscany that includes the Chianti & Montalcino regions. During wine tours & tastings you will be presented between 3 and 5 different wines. Two of the six wineries will be hosting a wine lesson (Chianti 101) giving you the essentials of how the particular wines are produced, aged and brought to market.

Group Tour Size

Groups range from 10 to a maximum of 14, not too many but just enough!


Add this magnificent tour on to your scheduled food & wine tour. Visit the Amalfi & Positano page for tour details.

tips & gratuities

Our licensed tour guides and coach drivers are selected because of their expertise and people skills.  We feel it important to let them know if they are doing a great job and tips are always appreciated. We do suggest tips Euro 5-10 per day for guides and Euro 5-10 for our coach drivers.

extend your stay

Let us know if you want to arrive early or stay on after your tour.  We'll give you some great ideas and of course if you simply want to stay on and relax at one of our partner hotels or country resorts that's always a great plan.  Please inform us of your intentions when booking your tour to ensure your reservations.

Sample Itinerary

 Days 1 & 2 

The Chianti food and wine tour begins with 2 days in Florence, the birthplace of the Renaissance and home to so many infamous artists and scholars such as Galileo Galilei, Dante Alighieri, Donatello and Michelangelo. You'll spend 2 nights in a charming "old world" historical 4 star residence located just 2 minutes (by foot) from Piazza Santa Croce.  You will be just minutes from shopping, markets and cafes in the city center.


Your first day in Florence begins with a walk in the city center with your dedicated Florence guide who will be  introducing you to the wealth of Florentine nobility during the Renaissance.  Afterwards you will be escorted to a medieval Palazzo where the group will have spectacular views of the city on the roof-top terrace and enjoy  a welcome "aperitivo" (cocktail).   The evening is not yet complete as we will be dining at a wonderful Florentine Bistro that is owned by the Ferragamo family located along the Arno River.


On your 1st full day will be given a wonderful city tour led by your private guide (Veronica) who knows Florence like she knows the back of her hand. You will be walking the same streets where European royalty, world leaders and Renaissance artists walked and lived. Your tour will focus on Michelangelo and begins with a visit to the Academia Museum and will continue on towards Santa Croce along the winding cobblestone streets towards the Ponte Vecchio, along the Arno to Santa Trinita', Piazza della Signoria and will end at the central market or the "mercato centrale", San Lorenzo followed by lunch. As are all our tours and vacations, we aim for a balance of scheduled activities and free time to explore and to shop so this afternoon is yours.

Sample Itinerary

Days 3 - 7

You will be transferred on day 3 for four nights to your Chianti residence, located near Gaiole in Chianti. The residence was built over 1000 years ago as a monastery and is situated atop the "Monti del Chianti" on 800 hectares of forest, beechwood, chestnuts, olive trees and vineyards. Upon arrival, you will have time to settle in and freshen up and later in the afternoon you will meet for a tour of the property, gardens, and the ancient cellars followed by a "wine class" 101 -  Tuscan Wines led by your sommelier Victor Duque held in the historical "refettorio" or refectory of the abbey. You will be tasting a selection of the abbey's wines and followed by a magnificent group dinner in the abbey's restaurant. Your daily breakfasts are as special as is every other detail on the property, a buffet of fresh breads, cakes, cereals, quiche and fruit. You will be taking part in a hands-on cooking class that takes place in a hamlet farm-house setting not far from the abbey. You will spend a late afternoon with Elena in her kitchen preparing a typically Tuscan farm-to-table meal then, of course, you get to enjoy it!

During the course of this tour, you will visit  a minimum of 6 wineries, some large and others small and family managed but all have their unique history with exceptional wines.  You'll visit the medieval hill-top towns of Siena (followed by lunch at the neighboring winery) led by private guide in addition to the Saturday market in Greve-in-Chianti where you will lose yourself in this amazing medieval towns' centuries old market, make sure you stop at the Antica Marcelleria Falorni, one of Tuscany's oldest butcher shops.  This food & wine tour wouldn't be complete without an excursion to the Val d'Orcia and the Crete Senesi (the regions south of Siena), a UNESCO World Heritage Site.  You will be visiting a cheese producer where you will be shown how the Tuscan Pecorino cheeses are made and naturally a light lunch will be included.  You will visit the town of Pienza with  all its amazing views. You will have time to visit the city, shop and stop for a gelato before we continue our journey to Santa Giulia Winery in the Montalcino region. This winery has been owned and managed for 3 generations by our friend Gianluca and his family.  You will be tasting their Brunello di Montalcino and you will also enjoy a special family style dinner  prepared especially for our group. What a better way to experience Tuscany!

Sample Itinerary

Days 8 & 9

The last 2 nights of the tour you will be transferred to the Castello di Gabbiano, a 4-star deluxe winery located in northern Chianti. There will be a tour of the estate and the cellars followed by a tasting of their wines, olive oils and vinegars.  You will enjoy a wonderful dinner at a local trattoria.


The group will be taken to visit the city of towers (San Gimignano) where your private guide will show you some of the city's treasures, following the city tour you will be taken to a near-by winery (Poggio Aloro) for lunch and to taste more wine!  Late afternoon you'll return back to the Chianti residence and have some time to relax on the property and take advantage of the beauty that Castello di Gabbiano has to offer. The farewell dinner will take place at "Il Caviliere", the magnificent restaurant on the estate.

You will have an early transit from the Castello di Gabbiano to the Florence train station (SMN) or the city airport.

Request a Detailed Itinerary