Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
Traveler rating
4.9/5
Based on 24,500 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 $109 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 24,500 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 (24,500)
- Duration
- 12 hours
- From
- $109 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 trip from Florence.
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
Classic Tour
Classic Tour: Siena, San Gimignano, Pisa and a Chianti winery with lunch and wine tasting included - TOUR IS ONLY IN ENGLISH!!!!
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
Semi-Independent Option
Semi-independent experience with more free time. Does not include winery stop, lunch, and Siena Cathedral entry.
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!!
With Leaning Tower Tickets
Classic Tour with pre-booked tickets to climb the Leaning Tower in Pisa - 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 24,366 traveler reviews. Written by us, not quoted from reviewers.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Traveler reviews
24,366 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.
Book it! Great full day tour.
A wonderful day trip! Staff was friendly and knowable and it was nice to sit in a comfortable air conditioned bus between stops. Siena has become one of my favorite cities in Italy. I wish we had more time to explore on our own.
via Viator
Amazing Day!!!
Wonderful day-Sienna was my fav! Meal was amazing. Miri was over the top sweet, helpful and knowledgeable!!!
via Viator
The meat of our trip
WalkAbout is a great way to see the rural country side and interface with local farmers, hunters and vendors. Manolo was great and the driver was quite skilled with getting the bus around. Manolo isn't shy when it comes to safety and information. Intelligent knowledgeable answers on related topics that weren't covered in the presentation showed a true depth of knowledge about the tours places. We stayed in Italy for a week and this tour was definately the highlight of our stay.
via Viator
Tuscan sun
Manolo and gasparre were great. Manolo was a great host and gasparre was very polite and kind. The best two people
via Viator
Highlight of our time in...
Highlight of our time in Tuscany. Very well planned and every sight is a treat for the eyes. Lovely tour and Christian was a fabulous guide.
via Viator
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
- $109 to $185
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 8,575
- Verdict
- 90+ Club
Who runs this experience
Operated by Walkabout Florence Tours, who run 10 experiences we rank across 1 city, with an average Outty Ranking of 84.5 and 6 in the 90+ Club.
See everything Walkabout Florence Tours runsWhy 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 $109 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 24,500 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 8,575 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 -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. 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.
What is included in Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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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; and In-vehicle air conditioning. Not included: Gratuities; Hotel pickup and drop-off; and Food and drinks, unless specified. Always check the voucher for the final list before you travel.
Where is the meeting point for Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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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 is not included, so plan your own transport and arrive 15 minutes early.
What languages is Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; Infants are required to sit on an adult’s lap; and Due to uneven surfaces, we cannot accept anyone with walking difficulties or using a wheel. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
What do travelers say about Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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Across 24,500 reviews averaging 4.9 out of 5, recurring themes include the guide, food and drink, knowledge and storytelling. Travelers single out the guide as the reason the experience works.
What booking options are available for Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
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There are 5 options to choose from, including Classic Tour, Semi Private Tour (MAX 8), Semi-Independent Option, Tour NO Siena Cathedral entry. Prices and start times differ by option, so compare them on the booking screen.
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