Private Tour of San Gimignano & Siena

Discover Tuscany on a Private Day Trip from Florence

This private tour of San Gimignano and Siena offers a seamless way to experience two of Italy’s most captivating towns in just one day. Priced at $1,292.28 per group for up to 8 people, it provides an intimate, personalized experience with a licensed local guide, air-conditioned vehicle, and hassle-free transportation from Florence. The tour lasts approximately 9 hours, making it ideal for those who want to explore without rushing, and it has a perfect 5.0/5 rating from 23 reviews.

What sets this tour apart is the private format, which guarantees tailored attention and flexible pacing. It’s especially suited for groups seeking a comfortable, guided day to Tuscany’s highlights, including free time for shopping in San Gimignano and a delicious lunch with wine tastings. The only potential limitation is the additional cost for lunch and tastings, which are not included in the base price.

Key Points

• Private, guided day trip from Florence to San Gimignano and Siena
• Up to 8 guests per group for a personalized experience
• Includes transportation, guide, and free time at each stop
• Lunch and wine tastings available nearby San Gimignano (own expense)
• Focus on medieval architecture, scenic views, and local artisan shops
• Highly rated with perfect reviews emphasizing knowledgeable guides

Starting the Day: Pickup and Transportation from Florence

The tour begins promptly at 8:00am, with pickup included from your location near Florence or at a designated meeting point. Once aboard the air-conditioned private vehicle, travelers enjoy a comfortable 45-minute drive through Tuscany’s classic landscape—rolling hills, vineyards, and olive groves set the perfect scene for what’s to come. The small group size ensures an intimate atmosphere, with just your group and the guide.

This setup guarantees a smooth start to the day, avoiding the hassle of public transportation or crowded tours, and allows flexibility in timing and stops. The private transportation ensures a personalized journey tailored to your interests and pace.

Exploring San Gimignano’s Medieval Skyline

San Gimignano is known for its 13th-century towers, which symbolized the town’s thriving merchant prosperity. The guided visit lasts about 1 hour, during which the licensed local guide shares insights about the town’s history and architecture. You’ll walk through Cisterna Square, admire the Duomo, and appreciate the medieval walls that encircle this hilltop settlement.

After the guided portion, guests have free time to explore the many artisan shops. This is a great chance to pick up local linen, pottery, olive oil, or wine. The town’s scenic views make it perfect for photos, and the narrow streets are ideal for a leisurely stroll. Many visitors find the towers particularly impressive, offering a glimpse into the town’s past wealth.

Wine Tasting and Lunch Near San Gimignano

A highlight of the tour is a visit to a nearby winery, where guests enjoy a tour of the vineyards and cellars. While lunch and wine tastings are not included in the tour price, they are highly recommended and can be arranged at your own expense. Expect to sample at least 5 different wines and extra virgin olive oils, perfectly complementing the regional flavors.

This stop provides an authentic taste of Tuscany’s winemaking tradition, with the scenic vineyard views adding to the experience. The lunch typically features local dishes that celebrate the region’s cuisine, making the day both flavorful and visually appealing.

Discovering Siena’s Gothic Charm

After exploring San Gimignano, the group boards the vehicle for a 45-minute drive to Siena. The town’s medieval streets lead to Santo Domenico Church, famed for its relics of Santa Catarina da Siena, a prominent figure in Italian history. The guide shares stories of the town’s Palio horse race, with a stop at the shell-shaped Campo Square, where the lively atmosphere reflects Siena’s spirited traditions.

Guests then visit the Palazzo Pubblico, where external views reveal stunning Gothic architecture. The tour also includes an inside visit to the Cathedral of Siena, regarded as one of Italy’s most beautiful Gothic churches. Its intricate façade and impressive interior decor highlight Siena’s artistic richness.

The Artistic and Architectural Highlights of Siena

The Cathedral of Siena is a masterpiece of Gothic design, with its black and white striped marble façade and stunning interior artworks. Visitors have the opportunity to admire the floor mosaics, chapels, and sistine-like frescoes. The guide’s commentary enhances understanding of Siena’s artistic heritage and historical significance.

The external visit of the Palazzo Pubblico offers a chance to marvel at Siena’s medieval civic architecture and town hall square. This area remains a hub of local life and events, especially during the Palio festival, which the guide explains in detail.

Practical Details and Additional Costs

This private tour includes transport, a licensed guide, and air conditioning for comfort throughout the day. However, lunch and tastings are not included in the base price, and travelers should budget separately for these experiences. The meeting point is flexible, with pickup offered near Florence, simplifying logistics.

The tour operates with free cancellation if canceled at least 24 hours in advance, providing peace of mind. The total duration of around 9 hours makes it suitable for those with a full day to dedicate to exploring Tuscany’s highlights.

Why Choose This Private Tour?

What makes this tour particularly appealing is its personalized nature, with a small group and dedicated guide. The testimonials praise guides like Paola and Giuseppe for their knowledgeable storytelling and friendly approach, which enrich the experience. Travelers often comment on the stunning views, artistic sites, and local wine tastings as standout features.

The private format also means you can customize the experience, spend more time at your favorite spots, or ask questions freely. It’s ideal for groups of up to 8, ensuring a relaxed, intimate day that balances guided sightseeing with free exploration.

Who Will Most Enjoy This Tour?

This experience suits history buffs, art lovers, and wine enthusiasts eager to explore Tuscany’s cultural gems comfortably and privately. It’s also perfect for small groups or families wanting a flexible, guided day with expert insights. Those wanting a stress-free day without worrying about transportation or navigating unfamiliar towns** will find this tour highly valuable.

However, travelers should plan for additional costs for lunch and tastings and be prepared for some walking in historic town centers.

Final Thoughts on the San Gimignano & Siena Private Tour

This private day trip from Florence offers a balanced blend of guided sightseeing, free time, and local tastings. The expert guides and personalized approach stand out as key strengths, making it a reliable choice for anyone wanting to experience Tuscany’s medieval towns with comfort and depth.

While lunch and wine tastings are not included in the base price, they are easily arranged nearby, adding to the overall value. The tour’s flexibility, small-group intimacy, and attention to detail make it a solid option for those seeking an authentic, hassle-free exploration of Tuscany’s historic centers.

Frequently Asked Questions

Is pickup included in the tour?
Yes, pickup is offered near Florence, making it convenient to start your day without extra transportation arrangements.

How long does the tour last?
The entire experience lasts approximately 9 hours, from departure to return.

What is included in the tour price?
The price covers private transportation, a licensed local guide, and air-conditioned vehicle. Lunch and tastings are not included but can be arranged separately.

Can I cancel this tour?
Yes, there is free cancellation if you cancel at least 24 hours in advance.

Is this tour suitable for all ages?
Most travelers can participate; however, some walking is involved in the historic towns, so plan accordingly.

How many people are in each group?
Up to 8 guests per group, ensuring an intimate experience.

Are entrance fees included?
No, entrance fees to sites like the cathedral are not included in the tour.

Who are the guides?
Guides like Paola and Giuseppe are praised for their knowledge and friendly manner, making the experience engaging and informative.

What makes this tour stand out?
The private format, personalized attention, and the opportunity to enjoy scenic views, artistic sites, and local wines in a single day.

Can I customize the experience?
As a private tour, it offers flexibility, allowing you to focus more on your interests where possible.