Private Tuscan Tour from Florence: Siena, Pisa, San Gimignano

Three hilltop towns, one private driver, stops whenever the view demands it.

A full-day private tour from Florence visits Siena, Pisa and San Gimignano with hotel pickup and drop-off, a professional driver fluent in English or Spanish, and the flexibility to shape the itinerary as you go. Siena Cathedral entry is included. Leaning Tower entry is optional. The driver handles all navigation and timing so you explore at your own pace without arranging transport between towns.

Step-by-step itinerary

Stops and time spent at each

1. Pubblico Palace1h
2. Mangia Tower30m
3. Siena Cathedral30m
4. Leaning Tower of Pisa30m
5. Pisa Cathedral30m

Private tour of Siena, San Gimignano, Pisa

• Pickup from Florence accommodation
• Drive through Tuscan countryside to Siena
• Explore Siena near the Cathedral
• Visit Piazza del Campo and enjoy a cappuccino
• View Torre del Mangia from outside
• Enter and tour Siena Cathedral
• Drive to San Gimignano with photo stops
• Explore San Gimignano town and viewpoint
• Visit Piazza della Cisterna and grab gelato
• Discover San Gimignano Cathedral interior
• Drive to Pisa
• Climb Leaning Tower of Pisa (optional)
• Visit Pisa Cathedral
• Shop for souvenirs in Pisa
• Return drive to Florence accommodation

The experience

You're picked up at your Florence hotel in a Mercedes with air conditioning and free WiFi, then driven through Tuscan countryside dotted with vineyards and hilltop towns for about an hour to Siena. The driver drops you near the Cathedral and you have two hours to wander: Piazza del Campo, where the annual palio horse race happens, is the natural gathering point, and the Cathedral itself is included in the tour price. Inside you'll see 56 marble mosaic floor scenes, Renaissance frescoes and the Piccolomini Library. Torre del Mangia, the clock tower rising above the piazza and the third tallest in Italy, stands nearby if you want to climb it (entry separate).

After Siena, the drive to San Gimignano takes you through some of the most photographed countryside in Italy, and your driver will stop whenever you ask. San Gimignano sits on a hilltop with thirteen medieval towers still standing, earning it the nickname medieval Manhattan. You get an hour to explore the town, walk through Piazza della Cisterna and its Cathedral, grab gelato, and take in the views. The itinerary is yours to shape: the driver knows the towns and adjusts based on what interests you.

The final leg is Pisa, about an hour away. The Leaning Tower and Pisa Cathedral sit in the same piazza. The Cathedral is often overlooked but it's a masterpiece of Pisan Romanesque architecture with Giovanni Pisano's pulpit and golden ceilings inside. If you've chosen the Leaning Tower option, you can climb to the top for views across the city rooftops. After exploring, your driver takes you back to Florence, a one-hour return journey. The whole day runs ten hours, and you're dropped at your hotel.

What’s included

• Hotel pickup and drop-off from Florence in a luxury Mercedes.
• air conditioning and free WiFi on board.
• professional driver commentary in English or Spanish.
• entry to Siena Cathedral.
• bottled water.
• independent sightseeing time in Siena, San Gimignano and Pisa.
• photo stops along the Tuscan countryside.
• flexible itinerary you design with your driver.
• dedicated office support to customize the experience before and after the tour.

Options for this experience

5 options

Tour for private groups, conducted in Spanish08:00, 08:30 and 09:00Includes pickup

Private tour conducted in ItalianGuide in English or Spanish · Available from 2 Jan 2027Includes pickup

Private tour given in English08:00, 08:30 and 09:00Includes pickup

See 2 more options

Tour in English including the Leaning Tower08:00, 08:30 and 09:00Leaning Tower ticket: Enhance your visit by adding skip-the-line tickets to the Leaning Tower of Pisa. Pickup is included.

Tour in Spanish that includes the Leaning Tower08:00, 08:30 and 09:00Leaning Tower tickets: Enhance your visit by adding skip-the-line tickets to the Leaning Tower. Pickup is included.

You pick the guide language when booking.

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

Before you book

Days and timesEvery dayDepartures at 08:00, 08:30 and 09:00

Book up to2d before

GroupPrivate

Live guideEnglish and Spanish

Meeting point and pickupHotel pickup included.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 14 days ago

Good to know

Moderate physical effortStroller-friendlyInfant seats availablePublic transport nearbyNot recommended with heart problemsNot recommended with back problemsInfants must sit on laps

Operated by Ciao Florence Tours Srl

Is this one for you?Book this tour if you're arriving in Florence and want a full day of Tuscan towns without renting a car or navigating between them. The driver handles all the logistics and timing, so you step out and explore at your own pace. Choose the Leaning Tower option if climbing it is on your list. Skip it if you'd rather spend the time in the towns themselves or save the entry fee.

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Top questions

What languages is the tour guided in?

Live guide in English and Spanish.

What's included in the tour price and what costs extra?

Hotel pickup and drop-off from Florence, the Mercedes with air conditioning and WiFi, driver commentary in your chosen language, bottled water, and entry to Siena Cathedral are all included. The Leaning Tower in Pisa is optional. You add it at checkout if you want to climb it. Lunch is not included, so you'll eat at your own pace in the towns. Torre del Mangia in Siena also has a separate entry fee if you want to climb it.

Can I choose which towns to visit, or is the itinerary fixed?

The itinerary is flexible. You design it with your driver. He's at your full disposal and will adjust stops and timing based on what you want to see. You can spend more time in one town and less in another, or ask him to stop for photos along the drive through the countryside.

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

Siena gets about two hours of free exploration time, and San Gimignano gets an hour. Pisa's timing depends on whether you climb the Leaning Tower and how long you spend in the Cathedral. Your driver will guide the pace and let you know when it's time to move to the next stop.

Is this tour suitable for families with young children?

Yes. Infants can ride in a pram or stroller, and specialized infant seats are available if needed. The tour involves walking through town centers at your own pace, so you control the intensity. The Mercedes is air-conditioned and comfortable for long drives.

What happens if I arrive late or want to start at a different time?

Your dedicated office support is available before the tour to customize timing and pickup. Contact them to arrange a start time that works for your arrival or schedule.