3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns

Early booking recommended
an old building on top of a hill with houses
Show all photos

Escape the city and immerse yourself in the timeless beauty of Tuscany on a fully private, 3-day journey through rolling hills, historic villages, and unforgettable food and wine. Starting from Florence, your personal driver-guide will take you through the heart of Tuscany. You'll visit San Gimignano, Siena, Montepulciano, and the Chianti wine region. Enjoy exclusive tastings at family-owned wineries, admire Renaissance art, and relax each evening in hand-picked boutique countryside hotels.

This tour is curated for travelers who want to slow down, connect with authentic Italy, and enjoy VIP treatment from start to finish. Highlights:

Private driver-guide throughout the tour

Visits to San Gimignano, Siena, Montepulciano & more

Wine tastings in Chianti and Montalcino (Brunello!)

Time to explore, shop, and dine in historic piazzas

Option to include truffle hunting or cooking class

What's included

  • Private transportation
  • Lunch
  • Air-conditioned vehicle
  • Private Guide

Languages spoken by guide

Russian
English
Italian

Additional information

Infants are required to sit on an adult’s lap

Suitable for all physical fitness levels

We pick up all the travelers. The guide will wait you at your hotel reception

Not wheelchair accessible

Please bring your ticket with you to the attraction.

Frequently asked questions




Tell us how we’re doing and what we can improve

Tickets and prices