Overview
Enjoy this 5-Day Food & Wine-Focused Tour of Tuscany with Private Driver
Indulge in the authentic flavors and world-class wines of Tuscany on this 5-day independent tour with a private driver for a worry-free and flexible experience.
Explore the Tuscan towns of Florence, Montepulciano, San Gimignano, and Pienza, each offering unique culinary delights and wine traditions.
Upgradeable with a licensed tour guide.
Food & Wine Experiences Included:
Montepulciano
Visit a countryside wine cellar and enjoy a guided tasting paired with local specialties such as pecorino cheese, cured meats, and bruschetta. Learn about traditional winemaking.
Pienza
Known as the "City of Cheese," Pienza is famous for Pecorino Toscano — a rich sheep’s milk cheese. Enjoy a tasting and scenic drive through the Val d'Orcia countryside.
San Gimignano
Enjoy a wine tasting at a family-owned vineyard with beautiful countryside views, accompanied by local produce and handmade pasta dishes.
What's Included
- Breakfast
- Lunch
- Hotel/Airport pickup and drop-off
- Private tour
- 4 nights accommodation
- Driver
- Breakfast
- Transport by air-conditioned minivan
- Additional touring time (60EUR/hour)
- Excess luggage charges (where applicable)
- Food and drinks, unless specified
- Gratuities
- Private guide (60EUR/hour)
Meeting and Pickup
• Pickup Airport: Driver will meet you near the Meeting Point just outside baggage claim area with a sign with your name on. • Tour Ends at the same location where it started.
What To Expect
Day 1: Rome Arrival (No meals)
3 Stops
Day 2: San Gimignano and Pisa Day Trip (B)
2 Stops
Day 3: Montepulciano and Pienza (B)
2 Stops
Day 4: The Mall and Florence (B)
2 Stops
Day 5: Departure to Rome (B)
1 Stop
Additional Info
- Confirmation will be received within 48 hours of booking, subject to availability
- Suitable for all physical fitness levels
- Accommodations: standard double room; 3-star hotel
- Please note: If you would like to spend more time on the tour, you may add extra hours to the itinerary for an additional cost of 90EUR/hour. Pay in cash only direct to the driver.
- If you would like a guide, it will be an additional 90EUR/hour with a minimum of 3-hours per day. Pay in cash only direct to the driver
- Each traveler is allowed a maximum of 1 suitcase and 1 carry-on bag. Oversized or excessive luggage (e.g. surfboards, golf clubs or bikes) may have certain restrictions, please inquire with the operator prior to travel to confirm if your excess luggage is acceptable
Frequently Asked Questions (7)
Q: What is the cancellation policy for the Wine and Cooking 5 Days Under the Tuscany Sun?
Cancellation Policy
Still have questions?
We're here to help.
Activity code: C-107660P173
Traveler Photos
Additional Info
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Frequently Asked Questions (7)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
- Breakfast.
- Lunch.
- Hotel/Airport pickup and drop-off.
- Private tour.
- 4 nights accommodation.
- Driver.
- Breakfast.
- Transport by air-conditioned minivan.
- Additional touring time (60EUR/hour).
- Excess luggage charges (where applicable).
- Food and drinks, unless specified.
- Gratuities.
- Private guide (60EUR/hour).
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 Wine and Cooking 5 Days Under the Tuscany Sun is as follows:
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Wine and Cooking 5 Days Under the Tuscany Sun will be included in your confirmation email from City Sky Diving. 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
- Breakfast
- Lunch
- Hotel/Airport pickup and drop-off
- Private tour
- 4 nights accommodation
- Driver
- Breakfast
- Transport by air-conditioned minivan
- Additional touring time (60EUR/hour)
- Excess luggage charges (where applicable)
- Food and drinks, unless specified
- Gratuities
- Private guide (60EUR/hour)
Additional Info
- Confirmation will be received within 48 hours of booking, subject to availability
- Suitable for all physical fitness levels
- Accommodations: standard double room; 3-star hotel
- Please note: If you would like to spend more time on the tour, you may add extra hours to the itinerary for an additional cost of 90EUR/hour. Pay in cash only direct to the driver.
- If you would like a guide, it will be an additional 90EUR/hour with a minimum of 3-hours per day. Pay in cash only direct to the driver
- Each traveler is allowed a maximum of 1 suitcase and 1 carry-on bag. Oversized or excessive luggage (e.g. surfboards, golf clubs or bikes) may have certain restrictions, please inquire with the operator prior to travel to confirm if your excess luggage is acceptable
