Vineyards, medieval hill towns and slow, sunny days at a countryside villa.
Tuscany is where life is meant to be enjoyed slowly. Renaissance Florence, medieval Siena and hilltop towns like San Gimignano are surrounded by vineyards, olive groves and cypress lined roads, perfect for long lunches and glasses of Chianti at sunset.
Need to know
Best time to visit
April to June, September to October
How long to stay
7 to 10 days
Getting there
Fly into Florence or Pisa, or take the fast train from Rome.
Getting around
A rental car is the best way to explore the hills, vineyards and villages, or a private driver on wine tasting days.
Moments we'll plan for you
- Chianti wine tour: Drive through the Chianti hills for tastings at family run wineries and a long lunch among the vines.
- Siena and San Gimignano: Visit Siena's shell shaped Piazza del Campo and the medieval towers of San Gimignano.
- Val d'Orcia: Drive through the postcard landscapes of the Val d'Orcia, with stops in Montepulciano and Montalcino for their famous wines.
- Cooking and farewell: Join a cooking class at a countryside estate and enjoy a farewell dinner at your villa under the stars.
What we'll organize for you
You tell us your dreams for Tuscany, and we take care of everything in between.
- Flights and your rental car: the best connections and a comfortable car waiting for you when you land.
- Hand picked hotels: the right place and the right room, chosen around you.
- Reservations and tickets: the tables, tours and experiences that sell out, secured before you arrive.
- Support while you travel: one message to us, and we take care of any changes along the way.
The highlights
- Florence: Renaissance art, the Duomo and the Ponte Vecchio.
- Chianti: Rolling vineyards and family run wineries.
- Val d'Orcia: Cypress lined roads and postcard landscapes.
- Siena: A medieval city around the famous Piazza del Campo.
History and culture
- Palio di Siena: A thrilling bareback horse race around Siena's main square, held every summer.
- Grape harvest: In September, vineyards come alive with the harvest and local celebrations.
- Truffle season: Autumn brings truffle hunts and food fairs in the hills around San Miniato.
- Renaissance art: Florence is home to some of the world's most famous art and architecture.
Food and drink to try
Bistecca alla Fiorentina, Pici pasta, Ribollita, Chianti and Brunello.
Where to stay
Restored farmhouses
Countryside stays with homemade food, olive oil and wine.
Villas with a pool
Perfect for families or friends traveling together.
Boutique hotels in Florence
Close to the art, the cafés and the best shopping.
Combine it with
- Cinque Terre: Five colorful villages on the Ligurian coast.
- Rome: An easy fast train ride from Florence.
Let's design your trip to Tuscany
Tell us your dates and wishes in a free 15 minute call, and we take care of everything else.
Book a free call