Fall 2025 Itinerary

First Week

Second Week

Thursday, October 23

• Depart the US for your transatlantic flight to Europe

Friday, October 24

• Arrive at Florence Peretola Airport (FLR)
• Transfer provided to Florence hotel
• Lunch provided for those that arrive in Florence early
• Relax at the hotel or enjoy a private guided tour of the city
• Dinner at Osteria ‘dell Enoteca at 7:30 escorted by your private guide

Saturday, October 25

• Breakfast provided at the hotel
• Transfer to Vintage Cars
• Vintage Italian car tour – Discover the Tuscan hills while driving an original vintage Italian classic!
• Drive to Lunch in Lamole in the Chianti Classico hills.
• Return to Florence
• Stop by Piazzale Michelangelo for an overview of the city of Florence
• Departure for Villa Giuncheto
• Welcome dinner at the Villa prepared by our own private chef featuring the wines of Antolini presented by Luca Marchiani.

Sunday, October 26

• Breakfast at 8:30
• Depart for Casa alle Vacche – A family-owned, small winery known for producing award winning wines from native Tuscan grape varietals.
• Tour the vineyards and cellars of Casa alle Vacche.
• Lunch with Andrea Ciappi, winemaker, at the Casa alle Vacche Trattoria.
• After visiting Casa alle Vacche, we depart to visit San Gimignano – Called the “Manhattan of Tuscany” due to the 13 medieval towers still standing today. Enjoy a private guided tour of the city.
• Dinner at the Villa prepared by our own private chef featuring the wines of Casa alle Vacche.

Monday, October 27

• Breakfast at 8:30.
• Depart for Marzocco di Poppiano Winery at 9:30 – Home of Chiantis from the Colli Fiorentini area of Tuscany.
• Tour the vineyards and cellars of Marzocco di Poppiano.
• Lunch at Marzocco with Roberta Chini and Maurizio Mazzantini, owners and winemakers of Marzocco di Poppiano.
• Dinner at the Villa prepared by our chef featuring the wines of Marzocco di Poppiano.

Tuesday. October 28

• Breakfast at 8:30.
• Depart for Siena at 9:30.
• Private guided tour of Siena including the Duomo with an optional visit to the attic known as the “Gate to Heaven” – One of the most dramatic cathedrals in Italy known for its artifacts and statues by Bernini. (***Please note that the “Gate To Heaven” requires ascending and descending a spiral staircase with over 150 steps***)
• Piazza IL Campo – Home of the famous Palio horse race that is run in July and August each year and one of the best piazzas in all of Italy.
• Lunch in Siena.
• Shopping in the Medieval Town (2500 years old).
• Dinner in Siena

Wednesday, October 29

• Breakfast at 8:30
• Depart for Montalcino at 9:30
• Morning in Montalcino – The medieval town of Montalcino is known for wine and honey. Enjoy shopping or site-seeing in this wine focused town
• Depart for Querce Bettina.
• Private tour of vineyards and cellar of Querce Bettina – Producer of artisanal Brunello and Rosso di Montalcino by the husband-and-wife team of Roberto Moretti and Sandra Barenghi.
• Lunch with the producer
• Dinner at the Villa prepared by our own private chef featuring the wines of Querce Bettina. 

Thursday, October 30

• Breakfast at 8:30
• Depart for San Gimignano
• Gelateria Dondoli (gelato class) – The 2-time World Champion gelato maker teaches us how to make 2 different types of gelato in our private class
• Quick lunch
• Spend the afternoon shopping on your own
• Return to Villa Giuncheto and dress for dinner
• Depart Villa Giuncheto at 6:30 for L’Assinello, an inventive 1-star Michelin restaurant located in the heart of Chianti               

Friday, October 31

• Breakfast at 8:30               
• Morning at leisure
• Enjoy a massage (150 euro/hour additional fee) if desired
• Roam the grounds of this 80-acre estate.
• Lunch at the Villa prepared by our own private chef featuring the wines of Fongaro.
• Afternoon cooking class at the Villa under the tutelage of our wonderful chef, Cristina.
• Eat what you have prepared paired with the wines of Fattoria Ambra, one of only 12 producers in the Carmignano area of Tuscany.

Saturday, November 1

• Breakfast at 8:30
• Checkout of Villa at 9:30
• Transfer to Hilton Metropol in Florence
• Additional time in Florence if desired on your own
• Dinner in Florence at IL Nugolo

Sunday, November 2

• Transfer to Florence airport for your departure back to the US