From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape
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September 2026
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Adults
Age 13 and over
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Age 12 and under
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Non-refundable booking. Same price on Viator, Outty earns a commission.
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Quick answer
Is From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape worth booking?
From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape is a 7-hour experience in Florence, Italy, from $450 per person. It scores 39 out of 100 on the Outty Ranking, which we label “Worth a Look”. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 39 / 100
- Rating
- Not yet rated
- Duration
- 7 hours
- From
- $450 per person
Escape the crowds and experience the best of Tuscany with this private shore excursion from Livorno or Florence. Travel in comfort from your ship or hotel with a private driver and enjoy a small-group walking tour of San
What you get
- Private transportation
- Guida privata
About this experience
Escape the crowds and experience the best of Tuscany with this private shore excursion from Livorno or Florence. Travel in comfort from your ship or hotel with a private driver and enjoy a small-group walking tour of San Gimignano, led by a local expert. Discover medieval towers, artisan shops, and breathtaking views in this UNESCO-listed town. Enhance your day with an optional wine tasting and Tuscan lunch at a renowned Super Tuscan winery, where you’ll sample Vernaccia di San Gimignano and other local labels in an authentic countryside setting. After lunch, continue to Siena, one of Tuscany’s most enchanting cities. Enjoy free time to explore Piazza del Campo, admire the Siena Cathedral from outside, and stroll the historic streets at your own pace. This flexible experience can be tailored to your cruise schedule, with guaranteed on-time return. Perfect for travelers seeking a mix of history, beauty, and flavor in a single day.
What's included
Included
- Private transportation
- Guida privata
Not included
- Wine tasting and Lunch
- Museum Tickets
What you'll see and do
Florence
Scenic Drive from Florence to San Gimignano The tour begins with a relaxing and comfortable ride from Florence in a private air-conditioned VAN. You’ll be accompanied by an English-speaking local guide who will share stories, fun facts, and insights about Tuscany along the way. As you drive through the stunning Tuscan countryside, you’ll follow part of the historic Chianti wine road, passing olive groves, vineyards, cypress trees, and stone villages. Enjoy the landscape, take pictures, and if you'd like, listen to some classic Italian music to set the mood for your day. This journey is more than just a transfer — it’s your first taste of authentic Tuscany. Pick-up can also be arranged from the port of Livorno upon request.
70 minutes here
San Gimignano
Arriving in the iconic hilltop town of San Gimignano, you'll take a guided walking tour through its historic streets, famous for their medieval towers and unforgettable views. Your guide will lead you through the town’s highlights: • Piazza della Cisterna • Piazza del Duomo • Palazzo Comunale & Torre Grossa (inside and outside) • Collegiata di Santa Maria Assunta After the tour, enjoy some free time to wander the charming streets and try a world-famous gelato at Gelateria Dondoli, multiple-time winner of the Gelato World Cup.
75 minutes here
San Gimignano
Wine Tasting & Tuscan Lunch at a Local Winery To complete your Tuscan experience, you’ll visit a traditional, family-run winery nestled in the countryside. Here, you'll enjoy a guided wine tasting of several locally produced labels, accompanied by a typical Tuscan lunch with seasonal dishes, local olive oil, and freshly baked bread. It’s the perfect way to relax, taste the essence of the region, and immerse yourself in its food and wine culture — all in a warm, authentic setting.
150 minutes here
Siena
After lunch and the wine tasting at the winery, you'll continue on to Siena, one of the most enchanting cities in Tuscany. The scenic drive takes about one hour and brings you deep into the heart of the Sienese countryside. Upon arrival, your driver will show you a convenient meeting point and then give you free time to explore the city at your own pace. Stroll through the medieval streets, visit the famous Piazza del Campo, home of the Palio horse race, admire the stunning Siena Cathedral from the outside, or treat yourself to a traditional sweet like ricciarelli or panforte. Siena offers breathtaking views, timeless charm, and the chance to discover its historic districts on your own.
50 minutes here
Florence
After a memorable day immersed in the beauty, flavors, and history of Tuscany, sit back and relax on the comfortable drive back to Florence. Enjoy the scenic countryside one last time as your guide wraps up the day with a few final insights or lets you unwind in peace.
70 minutes here
Where it starts and ends
Meeting point
Florence
In front of the Santa Maria Novella station in Florence.
Hotel pickup
Pickup is available for selected locations.
Ends at
In front of the Santa Maria Novella station in Florence.
Before you book
- Cancellation
- All sales are final. No refund is available for cancellations.
- Languages
- ru, en, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 travelers per booking
- Operated by
- Untracked Italy
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
Photos
Good to know
- Duration
- 7 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- 16+
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Available for selected locations
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 39
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape cost?
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Prices start at $450 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape take?
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Plan for about 7 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.
Is From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape worth it?
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It holds an Outty Ranking of 39 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape?
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No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape suitable for kids and families?
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The operator sets a minimum age of 16. Older children generally do well here, and families should factor in the 7-hour running time when deciding.
How far in advance should I book From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 7-hour experience runs outdoors or after sunset.
Where does From Siena to San Gimignano: Hilltop Towns & Wine Tasting Escape start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Florence?
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On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Florence?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Florence?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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