
From Florence: Siena & San Gimignano Private Day Trip
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
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Quick answer
Is From Florence: Siena & San Gimignano Private Day Trip worth booking?
From Florence: Siena & San Gimignano Private Day Trip is a 8-hour experience in Florence, Italy, from $159 per person. It scores 55 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 55 / 100
- Rating
- Not yet rated
- Duration
- 8 hours
- From
- $159 per person
Begin your private day trip with hotel pickup in Florence by a friendly, English-speaking driver in a comfortable, air-conditioned vehicle. Travel through Tuscany’s scenic hills to explore two iconic destinations. First,
What you get
- Hotel pickup and drop-off
- Fuel and Tolls
- Water
- On-board WiFi
- Hotel or custom pickup and drop-off
- Professional English-speaking local driver/informal guide
About this experience
Begin your private day trip with hotel pickup in Florence by a friendly, English-speaking driver in a comfortable, air-conditioned vehicle. Travel through Tuscany’s scenic hills to explore two iconic destinations. First, visit Siena, known for its medieval streets, Piazza del Campo, and Gothic cathedral. Then, enjoy an optional lunch and wine tasting at a local vineyard nestled among the rolling countryside. Continue to San Gimignano, a UNESCO-listed hilltop town famed for its medieval towers, charming streets, and stunning views. This fully customizable tour lets you adjust stops and timing. End the day with a relaxing ride back to Florence, filled with memories of Tuscany’s beauty and flavor.
What's included
Included
- Hotel pickup and drop-off
- Fuel and Tolls
- Water
- On-board WiFi
- Hotel or custom pickup and drop-off
- Professional English-speaking local driver/informal guide
- All taxes and handling charges
Not included
- Meals and beverages
- Tips and Gratuities
- Licensed guides available to accompany you inside the attractions
What you'll see and do
Florence
Your Welcome driver will pick you up from your accommodation in Florence, at a convenient time of your choice.
120 minutes here
Siena
Siena is a charming Tuscan city known for its medieval architecture and the lively Piazza del Campo.
120 minutes here
Local Winery. A delightful lunch at a charming winery (costs not included in tour price).
120 minutes here
San Gimignano
San Gimignano is a hilltop town famed for its medieval towers and well-preserved historic center.
120 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 travelers per booking
- Operated by
- Welcome Pickups
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- For 1-3 people: A comfortable sedan will be assigned to your group.
- For 4-7 people: A spacious minivan will be assigned to your group.
- Throughout your ride, our drivers serve as informal local guides—sharing stories, history, and local tips at every stop. Please note that drivers are not permitted to enter museums or archaeological areas, but they’ll ensure you make the most of your visit with suggestions and background information before you explore on your own.
- Some stops on your itinerary may be closed on the date of travel due to public holidays, maintenance or special events. We recommend verifying opening hours on the attraction’s official website or contacting us before your tour. If a stop is unexpectedly closed, we will try to offer a suitable alternative.
Photos






Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $159 to $988
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 55
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
From Florence: Siena & San Gimignano Private Day Trip: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does From Florence: Siena & San Gimignano Private Day Trip cost?
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Prices start at $159 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 Florence: Siena & San Gimignano Private Day Trip take?
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Plan for about 8 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 Florence: Siena & San Gimignano Private Day Trip worth it?
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It holds an Outty Ranking of 55 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 last minute in Florence, and how flexible the cancellation terms are.
Can I cancel or reschedule From Florence: Siena & San Gimignano Private Day Trip?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is From Florence: Siena & San Gimignano Private Day Trip suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book From Florence: Siena & San Gimignano Private Day Trip?
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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 8-hour experience runs outdoors or after sunset.
Where does From Florence: Siena & San Gimignano Private Day Trip 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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