Thanksgiving in Italy: A Week in Florence and Chianti

More and more American families are choosing to spend Thanksgiving in Italy, and late November is a better time to visit Tuscany than most people think. The summer crowds are long gone, the hills turn copper and gold, and it is the season of the year's best food: new olive oil straight from the press, white truffles and the first tastings of the new wine. Thanksgiving falls on November 26 this year, so a week from the Saturday before to the Sunday after is easy to plan.

This guide suggests how to split the week between Florence and Chianti, what to eat and book, and three historic places to stay, all with breakfast included.

How to spend Thanksgiving week in Tuscany

Days 1–3: Florence

Start in the city while you are fresh from the flight. See Michelangelo's David at the Accademia, climb Brunelleschi's dome at the Duomo and spend a morning at the Uffizi, all with timed tickets booked in advance. In November, museums are noticeably quieter than in spring, and the evening walk across Ponte Vecchio is yours.

Days 4–7: Chianti

Pick up a rental car and drive 45 minutes south into Chianti Classico, between Florence and Siena. This is the time of the olive harvest: many estates open their mills (frantoi) so visitors can taste the bright green oil on toasted bread. Spend your days between wine cellars, medieval villages such as Radda and Castellina, and a day trip to Siena. On weekends in November, the town of San Miniato hosts its white truffle fair.

Want the full route? Our Florence, Chianti and Siena journey lays it out stage by stage.

Where and what to eat

There is no turkey on Tuscan menus, but a Thanksgiving dinner here can be memorable: ribollita and other bean soups, pappardelle with wild boar ragù, bistecca alla fiorentina, roasted chestnuts and, if you are lucky, fresh pasta with shaved white truffle.

Practical tips. Book your Thursday dinner ahead: Italians do not celebrate Thanksgiving, so restaurants run their normal schedule, but the best trattorias in Florence fill up on weekends. The Florentine steak is priced by weight, usually per 100 grams, and a one-kilogram steak serves two. A small cover charge per person (coperto) is normal. Tipping is not expected as it is in the US; leaving a few euros for good service is appreciated.

Where to stay for Thanksgiving in Tuscany

Loggiato dei Serviti – Florence

A 15th-century building on Piazza Santissima Annunziata, one of the most harmonious Renaissance squares in Florence, 150 meters from the Accademia and a short walk from the Duomo. Rooms are furnished with antiques and breakfast is included. The ideal base for your first nights, with everything within walking distance.

Borgo Vescine – Radda in Chianti

A medieval hamlet surrounded by vineyards and olive groves in the heart of Chianti Classico, now a five-star country hotel. It offers wine tastings and cooking classes on site, a restaurant, and a heated outdoor pool. Breakfast is included. A good choice if you want your Thanksgiving week to include a hands-on Tuscan cooking lesson.

Castello di Fonterutoli – Castellina in Chianti

A medieval village on the road between Castellina and Siena, home to the Mazzei family's wine estate. Rooms are spread across the historic stone houses, and guests can join guided tours of the winery. Breakfast is included. Perfect for wine lovers and for easy day trips to Siena.

Check availability for Thanksgiving week. Rooms in historic Tuscan properties are limited, and late November fills with travelers who know the season. Choose a hotel and your dates below to see live rates. You book directly with the hotel: no booking fees.

Frequently asked questions

Is November a good time to visit Italy?

Yes, for travelers who prefer food and culture to beaches. Tuscany is quieter, prices are lower than in spring, and it is the season of new olive oil and white truffles.

What is the weather like in Tuscany in late November?

Cool and changeable: daytime highs around the mid-50s °F (12–14 °C), colder nights in the hills, and some rain. Pack layers and a waterproof jacket.

Do I need a car in Chianti?

Yes. Florence is best on foot, but Chianti's villages and wineries are spread across the hills. Pick up your car when you leave the city, not before.

Plan the rest of your trip

Explore more historic hotels in Tuscany, or tell us about your trip in Plan your trip. We are a small team in the Venice area, and we help you book directly with each hotel.

Cover photo: Lauramcr92, CC BY-SA 4.0, via Wikimedia Commons