Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
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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.
Traveler rating
4.9/5
Based on 23,607 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery worth booking?
Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery is a 12-hour experience in Florence, Italy, from $90 per person. It scores 92 out of 100 on the Outty Ranking, which we label “90+ Club”, based on a 4.9/5 rating across 23,607 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing. It sits in the Outty 90+ Club, the top tier of everything we rank.
- Outty Ranking
- 92 / 100
- Rating
- 4.9/5 (23,607)
- Duration
- 12 hours
- From
- $90 per person
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach
What you get
About this experience
Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence.
What's included
Included
- Hearty farmhouse lunch with 4 wine tastings (for selected options only)
- Siena Cathedral entrance fee (for selected options only)
- Free time to explore the towns at your own pace
- Professional English speaking tour guide with you for the whole day
- In-vehicle air conditioning
- Guided walking tour of Siena with local city guide
Not included
- Gratuities
- Hotel pickup and drop-off
- Food and drinks, unless specified
What you'll see and do
Siena
Leaving Florence behind, the journey begins with a scenic drive through the rolling Tuscan countryside until the skyline of Siena appears, a perfectly preserved medieval city perched atop three hills. Known for its warm-toned brick buildings and Gothic character, Siena offers an immediate sense of stepping back in time.
90 minutes here
Piazza Salimbeni
Upon arrival, a short walk leads to Piazza Salimbeni, a refined and quieter square framed by elegant palaces. At its center stands a statue of Sallustio Bandini, surrounded by the historic headquarters of one of the oldest banks in the world, giving the square a distinctly noble and intellectual atmosphere.
20 minutes here
Contrada della Torre
As the tour continues, you’ll be introduced to the unique concept of the “contrade,” Siena’s historic districts. Each contrada has its own emblem, traditions, and fierce identity, all of which come to life during the famous Palio horse race. Walking through these neighborhoods reveals flags, fountains, and symbols that tell stories of centuries-old rivalries and pride.
20 minutes here
Piazza del Campo
The heart of Siena reveals itself in Piazza del Campo, a vast shell-shaped square that gently slopes toward the Palazzo Pubblico. This is the stage for the Palio and one of the most unique public spaces in Europe, where locals and visitors alike gather to relax and soak in the atmosphere.
20 minutes here
Duomo di Siena
The route then leads uphill to the magnificent Duomo di Siena, a masterpiece of Italian Gothic architecture. Its striking black-and-white marble façade and richly decorated interior—featuring intricate floors, sculptures, and works by masters like Michelangelo—make it one of the most breathtaking churches in Italy.
30 minutes here
Fattoria Poggio Alloro
Next, we visit an organic, family-run wine estate—one of the true highlights of the day. Here, you’ll enjoy a relaxed and informal tasting experience, sampling regional wines such as Chianti, Vernaccia, and the traditional Tuscan dessert wine, Vin Santo. This is followed by a generous lunch featuring authentic local flavors, all served with sweeping views over the surrounding countryside. It’s the perfect moment to unwind, connect with fellow travelers, and savor fresh, organic farm produce, including homemade pasta, artisanal cured meats like prosciutto and salami, local cheeses, a crisp garden salad, and classic Tuscan biscotti.
120 minutes here
San Gimignano
Leaving the winery, the journey continues through vineyards and olive groves to San Gimignano, often called the “Medieval Manhattan” for its skyline of ancient towers. This UNESCO-listed hill town offers a striking contrast with its vertical silhouettes rising above the countryside.
90 minutes here
Piazza Della Cisterna
Entering the town, you’ll find yourself in Piazza della Cisterna, a triangular square named after the well at its center. Surrounded by towers and medieval houses, it’s a picturesque and lively spot, perfect for pausing and taking in the timeless ambiance.
20 minutes here
Piazza del Duomo
A few steps away lies Piazza del Duomo, the town’s religious and civic center. Here, the Collegiate Church stands opposite the Palazzo Comunale, creating a harmonious space that reflects the balance of power in medieval life.
20 minutes here
Rocca of Montestaffoli
The visit continues to the Rocca di Montestaffoli, a fortress offering panoramic views over the surrounding countryside. From this vantage point, the rolling hills, vineyards, and distant villages create a quintessential Tuscan landscape.
20 minutes here
Pisa
In the afternoon, the itinerary heads west toward Pisa, a historic maritime republic known worldwide for its architectural treasures. The city’s atmosphere blends academic energy—thanks to its university—with centuries of history.
75 minutes here
Piazza dei Miracoli
Arriving in Pisa, you’ll step into the remarkable Piazza dei Miracoli, a vast green space where some of Italy’s most celebrated monuments stand in striking harmony. This UNESCO World Heritage Site showcases an extraordinary collection of Romanesque architecture.
30 minutes here
Leaning Tower of Pisa
The visit naturally culminates at the iconic Leaning Tower, Pisa’s most famous landmark. Instantly recognizable for its distinctive tilt, this elegant white-marble bell tower has fascinated visitors for centuries. Whether admired from afar or up close, it provides the perfect opportunity for memorable photos and a fitting finale to a day rich in history, culture, and unforgettable landscapes.
30 minutes here
Florence
You will be dropped off in Florence at around 8.30pm with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
75 minutes here
Where it starts and ends
Meeting point
Florence
Check-in: 7.45am - Your guide will be holding a WALKABOUT TOURS sign, right by the taxi stand at Santa Maria Novella train station across from the outside McDonald's
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Check-in: 7.45am - Your guide will be holding a WALKABOUT TOURS sign, right by the taxi stand at Santa Maria Novella train station across from the outside McDonald's
Options you can book
Semi Private Tour (MAX 8)
Enjoy the exclusivity of a private tour without the private price tag—English only, Tuscany’s must-see highlights, no crowds
With Leaning Tower Tickets
Classic Tour with pre-booked tickets to climb the Leaning Tower in Pisa - TOUR IS ONLY IN ENGLISH!!!!!
Semi-Independent Option
Semi-independent experience with more free time. Does not include winery stop, lunch, and Siena Cathedral entry.
Classic Tour
Classic Tour: Siena, San Gimignano, Pisa and a Chianti winery with lunch and wine tasting included - TOUR IS ONLY IN ENGLISH!!!!
Tour NO Siena Cathedral entry
Tour NO Siena Cathedral entry : This does not include tickets to enter the Cathedral in Siena. Unlike other multilingual tours, our tour is ONLY in ENGLISH!!
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Walkabout Florence Tours
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Travelers should have at least a moderate level of physical fitness
- Due to uneven surfaces, we cannot accept anyone with walking difficulties or using a wheelchair
- Vegetarian option is available, but we regret that gluten free or other alternative dietary requirements cannot be catered for
- It is recommended to book any rail travel from Florence after 9pm to allow time for any traffic delays on your return journey
- When the Duomo of Siena is closed for religious services, Palazzo delle Papesse will be visited instead
- Operates in all weather conditions, please dress appropriately
- Please note: For the Leaning Tower of Pisa children under the age of 8 are not admitted. Children between 8 and 12 years old must be accompanied by an adult and held by the hand at all times while you are in the Leaning Tower of Pisa. Teenagers between 13 and 18 years old must be accompanied by an adult while you are in the Leaning Tower of Pisa
- Classic Tour option includes the visit to Pisa but not the ticket to climb the Leaning Tower
- With Leaning Tower Tickets option also include the tickets to climb on the Leaning Tower in Pisa.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 23,646 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Good for families
3 mentionsReviewers traveling with kids report it landed well with their group.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
23,646 verified traveler reviews for Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery. Ratings and reviews provided by Viator and Tripadvisor.
Great experience
We had a family group of 8, with one being a senior who had a harder time walking. Our guide Manolo did a wonderful job of getting them an alternative for the harder part of the trip. Manolo (tour guide) did a fantastic job of explaining everything along the tour and was very knowledgeable, friendly and helpful. Ali (driver) did a wonderful job and was very good at getting in and out of tight spots.
via Tripadvisor
Great Experience
Manolo and Allie (bus driver) awesome duo. It is a long day trip but they make it great and get to see so much in 1 day.
via Tripadvisor
Trip was great and Adela...
Trip was great and Adela was the best! Take your walking shoes! You get a little of everything on this trip.
via Viator
An Unforgettable Day in Tuscany with Mirela
Our Tuscany tour with Mirela was absolutely amazing and truly one of the highlights of our trip to Florence! If you are visiting Florence, I would highly recommend adding this tour to your itinerary — Tuscany is a must-see! We loved every part of the day. Walking through the charming narrow streets of Siena, visiting the beautiful cathedrals, and taking in the incredible atmosphere was unforgettable. Lunch at the winery was absolutely to die for, especially with the breathtaking views of the Tuscan countryside. We also had so much fun taking the classic funny pictures with the Leaning Tower of Pisa! And, of course, San Gimignano was a highlight — getting to try what is said to be some of the best gelato in the world was the perfect way to finish the experience. Mirela was a fantastic guide and made the entire day so enjoyable and memorable. Her knowledge, warmth, and enthusiasm really made a difference, and we felt very well taken care of throughout the tour. We are so grateful to Mirela for giving our family such a wonderful day filled with beautiful places, great food, history, laughter, and unforgettable memories. Absolutely a 5-star experience!
via Viator
Excellent
Miri was extremely knowledgeable and we had a great day out
via Tripadvisor
Good to know
- Duration
- 12 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $90 to $345
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 8,262
- Verdict
- 90+ Club
Why this scores 92
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery cost?
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Prices start at $90 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 Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery take?
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Plan for about 12 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 Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery worth it?
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It holds an Outty Ranking of 92 out of 100, which we label "90+ Club". That score blends traveler sentiment (4.9/5 across 23,607 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Florence, and how flexible the cancellation terms are. Scoring 90 or above puts it in the Outty 90+ Club, the top tier of everything we rank.
Can I cancel or reschedule Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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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 Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 12-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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Around 8,262 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 12-hour experience runs outdoors or after sunset.
Where does Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery 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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