Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa

Options for this experience

4 options

Semi-independent experience with more free timeGuide in English · 08:00Excludes winery stop, lunch, wine tasting, and Siena Cathedral entry; more time to explore independently.

Siena, San Gimignano, Pisa without Cathedral entryGuide in English · 08:00Excludes tickets to enter Siena Cathedral; includes winery lunch and wine tasting.

Siena, San Gimignano, Pisa with winery lunchGuide in English · 08:00Includes Siena Cathedral entry, winery lunch, and wine tasting.

Siena, San Gimignano, Pisa with Leaning Tower climbGuide in English · 08:00Includes pre-booked tickets to climb the Leaning Tower in Pisa, winery lunch, and wine tasting.

You see the exact price of each option when you check availability.See dates & prices

Three medieval towns, one winery lunch, and the Leaning Tower: all in a single day from Florence

A full-day guided coach tour from Florence through Tuscany's most famous towns: Siena, San Gimignano and Pisa. You travel by air-conditioned vehicle with a professional English-speaking guide, walk through medieval squares and Gothic cathedrals, taste regional wines at an organic family winery, and eat a hearty farmhouse lunch with views over the countryside. The tour operates in all weather and returns you to Florence around 8:30pm. You can choose whether to include entry to Siena Cathedral and tickets to climb the Leaning Tower, or explore those towns at your own pace instead.

Step-by-step itinerary

Stops and time at each

1. Pubblico Palace20m
2. Siena Cathedral30m
3. Piazza dei Miracoli30m
4. Leaning Tower of Pisa30m

Tuscany day trip from Florence

• Depart Florence for Siena
• Walk to Piazza Salimbeni
• Explore Siena's contrade districts
• Visit Piazza del Campo
• Tour Duomo di Siena
• Wine tasting and lunch at winery
• Travel to San Gimignano
• Visit Piazza della Cisterna
• See Piazza del Duomo
• View from Rocca di Montestaffoli
• Drive to Pisa
• Explore Piazza dei Miracoli
• Visit Leaning Tower of Pisa
• Return to Florence

The Experience

The coach leaves Florence behind and heads into rolling Tuscan countryside, arriving in Siena as its warm-toned brick skyline comes into view. A local city guide meets you there and walks you through the contrade: Siena's historic districts, each with its own emblem and fierce identity that comes alive during the Palio horse race. You'll see the flags and fountains that mark centuries-old rivalries, then reach Piazza del Campo, the vast shell-shaped square where the Palio takes place and where locals and visitors gather. From there the route leads uphill to the Duomo di Siena, a masterpiece of Italian Gothic with a striking black-and-white marble façade and intricate floors and sculptures inside (or, if the cathedral is closed for services, you'll visit Palazzo delle Papesse instead).

Next comes the winery: an organic, family-run estate where you taste regional wines including Chianti, Vernaccia and Vin Santo, followed by a generous lunch with sweeping countryside views. The meal features homemade pasta, artisanal cured meats like prosciutto and salami, local cheeses, a crisp garden salad and classic Tuscan biscotti. This is where the pace slows and you connect with fellow travelers over food and wine before heading back to the coach.

The afternoon takes you through vineyards and olive groves to San Gimignano, the "Medieval Manhattan" for its skyline of ancient towers. You walk into Piazza della Cisterna, a triangular square named after the well at its center and ringed by towers and medieval houses, then continue to Piazza del Duomo and up to the Rocca di Montestaffoli fortress, where panoramic views stretch across rolling hills and distant villages. From there the coach heads west toward Pisa, arriving at Piazza dei Miracoli, a vast green space where some of Italy's most celebrated Romanesque monuments stand together. The day ends at the Leaning Tower: instantly recognizable for its distinctive tilt, it's the perfect finale for photos. If your option includes the ticket, you can climb it. If not, you admire it from the piazza and explore the town at your own pace. You're dropped off in Florence around 8:30pm.

What’s included

• Professional English-speaking tour guide for the entire day.
• air-conditioned coach.
• guided walking tour of Siena with a local city guide.
• hearty farmhouse lunch with four wine tastings at an organic family winery.
• free time to explore the towns at your own pace.
• Siena Cathedral entrance fee (included in selected options only).
• Leaning Tower of Pisa climbing ticket (included in selected options only).

Days and timesDaily · 08:00

AgesAges 18+ · 8 to 17 years · Under 8 — Free

Meeting point and pickupNo pickup · ends where it startsMeeting point, per the operator: “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 McDon…”

Cancellation and refundsFree cancellation up to 24h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Moderate physical levelStroller friendlyPublic transport nearbyInfants must sit on laps

Operated by Walkabout Florence Tours

Is this one for you?Pick the Leaning Tower option if you want both Siena Cathedral and tower entry included. Choose Classic or Semi-Independent if you'd rather skip either site or explore them without a guide, since the winery lunch and medieval towns stay the same.

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Top questions

Can children come?

8 to 17 years; under 8, free.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24h before the start.

What's included in the lunch at the winery?

The farmhouse lunch includes homemade pasta, artisanal cured meats like prosciutto and salami, local cheeses, a garden salad and classic Tuscan biscotti, served with four wine tastings of regional wines such as Chianti, Vernaccia and Vin Santo. A vegetarian option is available. Gluten-free and other alternative dietary requirements cannot be catered for.

Can I climb the Leaning Tower of Pisa on this tour?

Climbing the Leaning Tower is optional and depends on which option you choose at checkout. The "With Leaning Tower Tickets" option includes the ticket to climb. The "Classic Tour" option does not. Children under 8 are not admitted to climb; children 8–12 must be accompanied by an adult and held by the hand; teenagers 13–18 must be accompanied by an adult.

How much free time do I have to explore each town?

The itinerary includes free time to explore Siena, San Gimignano and Pisa at your own pace. The guided walking tour of Siena with a local city guide covers the main squares and cathedral, then you have time to wander the contrade and streets on your own before heading to the winery.

What is the Palio, and will I see it on this tour?

The Palio is a famous horse race held in Siena's Piazza del Campo, where the city's historic districts (contrade) compete fiercely. The tour walks you through the contrade neighborhoods so you see the emblems, flags and fountains that mark these centuries-old rivalries, and you visit the Piazza del Campo where the race takes place, though the race itself runs only twice a year in summer, not on every tour date.

What happens if Siena Cathedral is closed when we visit?

If the Duomo di Siena is closed for religious services, the tour visits Palazzo delle Papesse instead, so you still see a significant cultural site in the cathedral's place.

How long is the return journey to Florence, and when should I book evening travel?

The coach drops you off in Florence around 8:30pm. If you're planning to travel by train after the tour, it's recommended to book any rail travel from Florence after 9pm to allow time for any traffic delays on the return journey.