3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns
Overview
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
- Lunch
- Private transportation
- Air-conditioned vehicle
- Private Guide
Meeting and Pickup
We pick up all the travelers. The guide will wait you at your hotel reception
What To Expect
Val D'Orcia: Nature, Food & Wine, History Full Day Private Tour
4 Stops
Chianti Road, San Gimignano and Wine Tasting Half Day Private Tour
2 Stops
Pisa, Lucca & Cheese Farm with wine tasting Full Day Private Tour
2 Stops
Additional Info
- Confirmation is instant and will be received at time of booking
- Suitable for all physical fitness levels
- Infants are required to sit on an adult’s lap
Frequently Asked Questions (7)
Q: What is the cancellation policy for the 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns?
Cancellation Policy
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Activity code: C-146766P23
Traveler Photos
Reviews
Average 5.00 out of 5 stars based on 2 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (7)
The answers provided below were previously given in response to questions from Cool Shore Excursions customers.
Filter by:
- Lunch.
- Private transportation.
- Air-conditioned vehicle.
- Private Guide.
There is no minimum age for this tour, so bring your wee one along for an adventure..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns is as follows:
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for 3-Day Private Tuscany Tour from Florence: Wine & Hilltop Towns will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Lunch
- Private transportation
- Air-conditioned vehicle
- Private Guide
Additional Info
- Confirmation is instant and will be received at time of booking
- Suitable for all physical fitness levels
- Infants are required to sit on an adult’s lap
