Private Tour: Siena, San Gimignano and Pisa Day Trip from Florence

A private day trip from Florence offers an ideal way to explore three of Tuscany’s most iconic medieval cities: Pisa, San Gimignano, and Siena. Priced at $1,014.11 per group, this tour accommodates up to seven people, making it a comfortable and personalized experience. With a 10-hour duration, the trip includes hotel pickup and drop-off, a luxury minivan, and the knowledge of a driver familiar with the region.

What truly sets this tour apart is the private chauffeur service, allowing your group to explore at your own pace. While the cost may seem high, the exclusivity, flexibility, and the chance to visit two UNESCO World Heritage sites—Pisa and Siena—make it appealing for those seeking a tailored Tuscan adventure. Keep in mind that lunch and entrance fees are not included, so planning for meals and tickets is recommended.

Key Points

• Private, personalized experience with hotel pickup and luxury transport
• Visit three iconic cities: Pisa, San Gimignano, and Siena
• Flexible stops with options for ice cream or a farmhouse lunch in San Gimignano
• Learn from a knowledgeable driver sharing insights about Tuscany’s culture and history
• Includes UNESCO sites and historic centers, with free time at each location
• Suitable for small groups of up to seven members, ideal for families or friends

Luxury Transportation in a Private Minivan

This tour features hotel pickup in Florence and travel in a luxury minivan, ensuring comfort throughout the 10-hour day. The vehicle can seat up to seven people, making it perfect for small groups or families who prefer an intimate experience with personalized attention.

The driver acts as a guide, offering local insights, cultural tidbits, and answering questions during the ride. The fuel surcharge is included, so there are no surprises about additional costs for transportation. Since the tour is private, only your group will participate, providing an exclusive and relaxed atmosphere.

Exploring Pisa’s Piazza dei Miracoli and the Leaning Tower

The trip begins with a stop in Pisa for about an hour at the Piazza dei Miracoli, one of Italy’s most famous landmarks. The Leaning Tower of Pisa is the centerpiece, and despite the crowds, the site radiates a timeless beauty with its perspective-defying architecture.

Visitors can enjoy free time to admire the cathedral and baptistery within the square, taking photos of the iconic tower. While admission tickets to climb the tower are not included, the view from the outside offers plenty of photo opportunities and a sense of history.

San Gimignano and Its Medieval Towers

The next stop is San Gimignano, renowned for its medieval architecture and tower houses that create a stunning skyline. The historic center is compact, allowing for a walk through narrow streets, with free time to explore the medieval walls and vantage points.

In San Gimignano, visitors have about an hour to experience the town’s ambiance. You can choose to indulge in a gelato at Dondoli, famous for its ice cream shops within the city walls, or opt for a farmhouse lunch outside the town to taste authentic Tuscan flavors. This flexible option is paid on the spot, giving you control over your experience.

Siena: Medieval Majesty and Cultural Riches

The tour allocates approximately two hours in Siena, famed across Italy for its medieval architecture and vibrant street life. Key sights include the Piazza del Campo, a conch-shaped square that hosts the famous Palio di Siena horse race, and the 13th-century Siena Cathedral, showcasing stunning Gothic architecture.

Strolling through Siena’s historic streets, you’ll find numerous local shops selling gifts and local food. The time in Siena allows for sightseeing, shopping, or simply soaking in the atmosphere, with no guided tour or entrance fees included, so you’re free to explore as you like.

Flexibility in San Gimignano: Gelato or Farmhouse Lunch

One of the tour’s highlights is the choice between a sweet treat or a hearty meal. You can enjoy gelato at Dondoli, a renowned ice cream shop inside the city walls, or head just outside San Gimignano for a lunch and tasting experience at a local farm.

This flexible stop is entirely paid on-site and offers a genuine taste of Tuscan cuisine, whether you prefer delicious gelato or rustic farm fare. The one-minute stop ensures minimal disruption to your schedule, emphasizing the tour’s personalized approach.

The Role of the Private Driver as a Local Guide

Unlike typical group tours, the driver in this experience doubles as a local guide, sharing stories, insights, and curiosities about each city and region. The knowledgeable driver enhances the experience by providing contextual information about Tuscany’s history, culture, and traditions, making each stop more meaningful.

Guests appreciate how this personalized guidance adds depth to the visit, helping them understand the significance of landmarks and local customs without the need for a formal guide or additional costs.

Uncovering Tuscany’s UNESCO World Heritage Sites

This tour includes visits to two UNESCO World Heritage sites: Pisa’s Piazza dei Miracoli and Siena’s historic center. The pacing allows ample time to appreciate each site’s architecture and ambiance, without feeling rushed.

While the Leaning Tower and the Piazza del Campo are the main attractions, the free time at each location provides the flexibility to absorb the atmosphere, take photos, or browse local shops. The exclusion of entrance tickets means visitors can choose whether to access paid attractions or simply enjoy the views from outside.

Who Should Consider This Tour

This private day trip caters best to small groups seeking comfort, flexibility, and personalized service. It’s suited for families, friends, or couples who want to explore medieval Tuscany with ease, avoiding the hassle of driving or rigid schedules.

Since lunch and entrance fees are not included, those who prefer a customized experience with options for dining or entrance access will find this tour particularly appealing. It’s not ideal for travelers with mobility issues due to walking in historic city centers, but the pick-up and drop-off make logistics simple.

The Sum Up: A Convenient, Personalized Tuscan Experience

This private tour from Florence offers a relaxing way to see Pisa, San Gimignano, and Siena in one day, with the comfort of luxury transportation and the flexibility to explore at your own pace. The knowledgeable driver, acting as a local guide, provides insights that deepen the appreciation of each city’s history and culture.

While lunch and entrance tickets are additional costs, the exclusivity and customization make this tour stand out. It’s particularly suitable for small groups looking for a comfortable, tailored experience without the restrictions of large tours. For those who value personalized service and a balanced schedule, this trip offers a practical way to enjoy Tuscany’s highlights.

Frequently Asked Questions

Is this tour suitable for families?
Yes, the tour accommodates groups up to seven people, making it ideal for families or small groups seeking a personalized experience.

What is included in the price?
The hotel pickup and drop-off, private luxury minivan, bottled water, and the driver’s local guidance are included. Lunch and entrance tickets are not included.

How long is each stop?
Pisa is about one hour, San Gimignano also one hour with a flexible activity (gelato or lunch), and Siena gets around two hours for sightseeing.

Can I choose what to do in San Gimignano?
Yes, you can opt for gelato at Dondoli or a farmhouse lunch, both paid on the spot.

Are entrance fees included?
No, entrance fees to towers and museums are not included; visits are mainly external, and you can choose to enter paid attractions yourself.

What makes this tour special?
The private chauffeur, flexible stops, and the opportunity to explore UNESCO sites at your own pace make this tour both comfortable and personalized.

Is this tour accessible for people with mobility issues?
While most of the cities are pedestrian-friendly, some walking in historic areas is necessary; accessibility details are not specified.

What is the cancellation policy?
You can cancel free of charge up to 24 hours in advance for a full refund.

Who is the provider of this tour?
This experience is provided by Chianti Drivers private tours.