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




Discover Tuscany's hidden gems on a 3-day private tour. Explore Chianti Road, Val D'Orcia, and historic towns like Pisa and Lucca. Experience Tuscany's beauty at your pace.
Experience Details
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 You Get
Good To Know
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
What You’ll Experience
Val D'Orcia: Nature, Food & Wine, History Full Day Private Tour (Day 1)
4 stop(s)Chianti Road, San Gimignano and Wine Tasting Half Day Private Tour (Day 2)
2 stop(s)Pisa, Lucca & Cheese Farm with wine tasting Full Day Private Tour (Day 3)
2 stop(s)Meeting & Pickup
Cancellation Policy
Cancel your booking at least 6 days before the experience start time to receive a full refund minus a 3.2% transaction fee.
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Join a hands-on masterclass in Chianti, crafting Schiacciata Toscana with a local expert. Enjoy regional wine, aperitivos, and experience Tuscan culinary traditions in a genuine setting.

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