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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

24,380 Reviews 4.87 out of 5 stars Based on 24,380 traveler reviews collected by Cool Shore Excursions and TripAdvisor |
Recommended by 98% of reviewers
98% of reviewers gave this experience a rating of 4 or higher.
|
Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Florence, Italy
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from $92.16 per person

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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery Image 1
Tuscany in One Day Sightseeing Tour
Tuscany in One Day Sightseeing Tour
Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery Image 4
Tuscany in One Day Sightseeing Tour
Don't miss out!
On average, this is booked 11 (1) days in advance.
12 hours (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

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

  • 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
  • Gratuities
  • Hotel pickup and drop-off
  • Food and drinks, unless specified
See 3 moreSee 4 more

Meeting Location

Meeting point

Piazza della Stazione
27, 50123 Firenze FI, Italy

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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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.
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1 hour 30 minutes Admission Ticket Free

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.
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20 minutes Admission Ticket Free

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.
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20 minutes Admission Ticket Free

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.
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20 minutes Admission Ticket Free

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.
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30 minutes Admission Ticket Free

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.
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2 hours Admission Ticket Free

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.
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1 hour 30 minutes Admission Ticket Free

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.
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20 minutes Admission Ticket Free

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.
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20 minutes Admission Ticket Free

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.
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20 minutes Admission Ticket Free

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.
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1 hour 15 minutes Admission Ticket Free

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.
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30 minutes Admission Ticket Free

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.
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30 minutes Admission Ticket Free

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.
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1 hour 15 minutes Admission Ticket Free

Show 13 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
  • 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

Frequently Asked Questions (8)

Q: What is the cancellation policy for the Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-5070TUSCANY

Traveler Photos

Reviews

4.87
24,380 reviews

Average 4.87 out of 5 stars based on 24,376 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

5 stars
21,964
4 stars
1,943
3 stars
322
2 stars
96
1 star
51
Don't miss out!
On average, this is booked 11 (1) days in advance.
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Frequently Asked Questions (8)

Activity name

The answers provided below were previously given in response to questions from Cool Shore Excursions customers.

Filter by:

Q: What is the cancellation policy for the Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CET).
  • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Apr 2025
Q: What's included in the price?
A:
The following is 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.
  • Air-conditioned vehicle.
  • Guided walking tour of Siena with local city guide.
  • Professional English speaking tour guide with you for the whole day.
The following is NOT included:
  • Gratuities.
  • Hotel pickup and drop-off.
  • Food and drinks, unless specified.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If 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 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery is as follows:

  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery will be included in your confirmation email from Cool Shore Excursions. 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 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once 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 2026

What's Included

Activity name

  • 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
  • Air-conditioned vehicle
  • Guided walking tour of Siena with local city guide
  • Professional English speaking tour guide with you for the whole day
  • Gratuities
  • Hotel pickup and drop-off
  • Food and drinks, unless specified

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Public transportation options are available nearby
  • Travelers should have at least a moderate level of physical fitness
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap
  • 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.
  • This tour/activity will have a maximum of 40 travelers

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