Sample Itinerary

Below is a sample itinerary for our Tuscan tour and is subject to change. Tour includes: 7 days accommodations, pick up and drop off from Florence airport, all meals except dinners, 6 winery tours, cooking class & ground transportation during tour. If you are interested in joining our tour, please email us at for pricing and specific itinerary details.

TUSCANY  - Chianti, Chianti Classico, Montalcino, and San Gimignano. Experience the wines of Chianti, Brunello, Vernaccia di San Gimignano and more, along with the wonderful local food.

Day 1:  Arrival and check-in at accommodations near San Gimignano by 4pm. Meet and greet reception at the villa followed by our first event;  a winery tour and tasting at a local Vernaccia producer near San Gimignano. Cheese &amp charcuterie will be served during the tasting. For dinner we will dine at an exceptional Osteria in the heart of the village.   

Day 2: Breakfast at villa. We travel to the Chianti Classico region to one of the oldest family-owned winery & properties in Tuscany. This family property dates back several hundred years and produces world-class wines in addition to goat cheese, olive oil & fruit trees. After tour of the grounds and tasting, we will have a picnic lunch on the winery grounds, weather permitting. That evening we will prepare a multi-course family mean at the villa. Ground transportation, tour and all meals inclusive.   

Day 3:  Breakfast at pasticceria in San Gimignano. Our winery excursion takes us to the area of Montevarchi to visit a very small, family-owned organic winery that produces Chianti wines. Though their facility is the smallest operation along our tour, the winemaker is charming and his wines are of outstanding quality. Following the tasting, we'll enjoy a lunch of local delicacies in their home. One the way back we will stop in Siena, one of the most historic towns in Tuscany and experience the breathtaking view from the famous Piazza del Campo. After, we'll sip wine and have dinner at a popular wine bar. Ground transportation, tour, and all meals inclusive. 

Day 4:  Breakfast at pasticceria in San Gimignano. We head out early to the famous Montalcino region. We will visit the oldest producer of Brunello di Montalcino wine. Located near Montalcino in a small commune where several levels of their newly renovated winery have been built directly in to the hillside. We'll break for lunch at a beautiful osteria where we will we enjoy an amazing meal al fresco (weather permitting). Next we will visit a second Montalcino producer; a newer estate that is already gaining recognition for their state-of-the-art facility and exceptional quality. We will finish the day with dinner at a lovely Osteria in the Saint Agostino piazza in San Gimignano All ground transportation and meals included.   

Day 5:  Breakfast at villa. We will be taking a break from our road trips by spending the afternoon at a local cooking school. Our day will be spent learning how to prepare classic Tuscan dishes at a family operated agriturismo. After each course is prepared our group will get to enjoy our handiwork as we eat our dishes along with the typical wines of the region. Ground transportation, cooking class and lunch inclusive. Guests are free to dine on their own this evening. Dinner not included.   

Day 6:  Breakfast at pasticceria in San Gimignano. We return to the Chianti Classico region for a private tour & tasting at one of Chiantis most highly regarded wineries. Our guide will take us through the family's beautiful castle gardens & private cellar. You will get to experience the story of how a small family winery has become a world-class producer of exceptional wines in just 30 years. We will have a multi-course lunch at the winery especially designed for their wines. That evening guests will have the opportunity to dine on their own in town. Ground transportation, tour and all meals inclusive. Dinner not included.   

Day 7:  Breakfast at villa. For our last day together, we will take a scenic drive to the famous commune of Volterra, known for its Neolithic history and Etruscan walls. We will explore the village and take in its sites with a leisure walk. There will be time for guests to browse in the many shops and we'll have a light lunch in the town center. For our last evening and dinner together in San Gimignano we will celebrate at one of the best ristoranti in the area with a beautiful multi-course meal. Ground transportation, tour, and dinner all-inclusive. 

Day 8: Breakfast at villa. Checkout of villa by 10am. Transportation provided back to Florence airport.