Florence Private Day Trip: Siena, Chianti & Pisa Tour

Siena's medieval squares, Chianti vineyards, San Gimignano's towers, and Pisa's Leaning Tower in one day

A private day trip from Florence with your own English-speaking driver and air-conditioned Mercedes, visiting Siena, San Gimignano, Chianti and Pisa over 10 hours. You decide which stops matter most and how long to spend at each one. The driver handles the route and explains what you're seeing. Lunch is your choice: the driver suggests options along the way. Bottled water and WiFi are included. Entrance fees to attractions are optional and paid separately.

Step-by-step itinerary

Tuscany private day trip highlights

• Pickup from Florence accommodation
• Drive to Siena, enjoy Tuscan countryside
• Visit Siena: Piazza del Campo and cathedral
• Drive to San Gimignano, optional lunch
• Explore San Gimignano towers and shops
• Visit Pisa: Leaning Tower and cathedral
• Return to Florence accommodation

The experience

Siena is the first stop, a 1-hour drive south through rolling Tuscan hills and vineyards. Your driver picks you up from your Florence accommodation at the time you choose and spends the opening stretch explaining the day's options so you can adjust the itinerary to match what actually interests you. Once in Siena, you walk the narrow medieval streets, see Piazza del Campo (where the famous Palio horserace runs twice a year), and visit the Gothic cathedral. How long you stay is up to you.

From Siena, the route heads toward San Gimignano through Chianti wine country: about 45 minutes of driving past vineyards and cypress-lined hills. Your driver can suggest a stop for lunch (a real Tuscan meal with Chianti wine, or something quicker if you prefer), or you can push on. San Gimignano sits on a hilltop ringed by 13 medieval towers. You'll walk past the Duomo, the town hall, and specialty shops selling ceramics, leather and the local Vernaccia white wine.

Pisa comes last, roughly an hour from San Gimignano. Your driver drops you at Piazza dei Miracoli so you can see the Leaning Tower, the Cathedral, the Baptistery and the Campo Santo cemetery: one of the world's finest architectural complexes. The day ends with a relaxed 1-hour drive back to Florence. The whole outing runs 10 hours door to door, but because you're setting the stops and timing, the day feels like yours instead of a schedule you're following.

What’s included

• Private transportation in a fully equipped Mercedes with air conditioning.
• pickup from your Florence accommodation at your chosen time.
• a professional English-speaking driver who explains the route and helps you customize the day.
• bottled water and WiFi on board.
• all fees and taxes.

Before you book

Days and timesEvery day5 departure times: the first at 08:00, the last at 10:00

Book up toStart time

GroupPrivate

Live guideEnglish

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 yesterday

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearby

Operated by Prestige Rent

Is this one for you?Choose this for a private vehicle and driver who adjusts your route and pace through four towns. You control which stops matter and how long you stay.

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Top questions

What does the driver explain during the day?

Your English-speaking driver gives you an introduction to Tuscany during the opening drive to Siena and explains the different stops and options so you can customize the schedule to match your interests. He's there to answer questions about what you're seeing as you go.

Can I choose how long to spend in each town?

Yes. The driver suggests a route and timing, but you decide the exact schedule based on what matters to you. If you want to linger in Siena's squares or spend extra time in San Gimignano's shops, you adjust the day accordingly.

Is lunch included?

Lunch is not included, but your driver will suggest the best options along the way: either a genuine Tuscan meal with Chianti wine or something faster if you prefer. You choose what and where to eat.

What is Piazza del Campo used for?

Piazza del Campo in Siena hosts the Palio, a famous horserace that runs twice a year and is the most important event in the city's calendar. The square itself is one of the most recognizable medieval plazas in Italy, lined with buildings and used for the race.

Do entrance fees to attractions cost extra?

Yes. Entrance fees to Siena's cathedral, San Gimignano's sites and Pisa's monuments are optional and paid separately at each location. Your driver can explain what's worth seeing and help you decide which ones to visit.

What's included in the vehicle?

The Mercedes is air-conditioned and equipped with WiFi. Bottled water is provided. Specialized infant seats and foldable wheelchairs can be accommodated if you need them.