Siena and San Gimignano Tour from Florence - Exploring Monteriggioni: The Tuscan Fortress

Siena and San Gimignano Tour from Florence

Explore Siena, San Gimignano, and Monteriggioni on a private, guided day trip from Florence featuring historic sites, scenic drives, and personalized experiences.

Discover the beauty of Tuscany in just one day with the Siena and San Gimignano Tour from Florence. Priced at $1,127.49 per group (up to 8 people), this private excursion offers a comfortable, personalized way to see three iconic Tuscan towns. The tour lasts approximately 8 to 9 hours, includes hotel pickup and drop-off, and features round-trip private transportation with WiFi onboard. Given its high 5.0/5 rating from 17 reviews, it clearly appeals to those seeking an intimate, flexible experience with knowledgeable guides like Francesco, who is praised for his expertise and engaging storytelling.

This tour is perfect for travelers who want to explore Tuscany’s authentic towns at their own pace without waiting for others. It combines scenic drives through rolling hills with stops at Monteriggioni, Siena, and San Gimignano, making it an efficient way to cover multiple highlights in a single day.

Key Points

Siena and San Gimignano Tour from Florence - Key Points

  • Private tour with exclusive transportation and personalized attention
  • Visit three historic Tuscan towns: Monteriggioni, Siena, and San Gimignano
  • Includes hotel pickup and drop-off for convenience
  • Flexible itinerary with free time for photos, shopping, and gelato
  • Onboard WiFi enhances the experience during scenic drives
  • Total duration of approximately 8-9 hours, ideal for a full-day adventure

Pickup and Transportation in Tuscany

Siena and San Gimignano Tour from Florence - Pickup and Transportation in Tuscany

The tour begins with hotel pickup, ensuring a hassle-free start from your Florence accommodation. You then travel comfortably in an air-conditioned private vehicle, inclusive of WiFi for sharing photos or browsing during the scenic drive across Tuscany. The round-trip transportation means there’s no need to worry about navigating or parking in busy towns, which can be a challenge during peak seasons.

The private nature of the tour allows for a relaxed pace and flexibility, such as stopping at any point for photos or to enjoy the views. This setup suits travelers who prefer an intimate experience and direct interaction with their guide, rather than a large group.

Exploring Monteriggioni: The Tuscan Fortress

Siena and San Gimignano Tour from Florence - Exploring Monteriggioni: The Tuscan Fortress

The itinerary kicks off at Monteriggioni, a fully intact fortress set in the Tuscan countryside. This 45-minute stop offers a chance to walk around the medieval walls, take in the impressive stone architecture, and enjoy a delicious cappuccino at local cafes. The admission is free, making it an easy, low-pressure introduction to Tuscany’s historic defenses.

Monteriggioni’s walls seem frozen in time, providing a picture-perfect setting for photos and a quick taste of medieval life. With its well-preserved structure, it appeals to history enthusiasts and scenery seekers alike. The short stop means you have ample time to soak in sights and atmosphere without feeling rushed.

Siena’s Piazza del Duomo and Its Architectural Marvels

The tour continues to Siena, where the first highlight is the Piazza del Duomo, a stunning Cathedral Square. You’ll have about one hour here for pictures and exploring the exterior monuments. Entrance tickets for the Siena Cathedral are purchased on the spot, giving you flexibility in planning your visit.

The Piazza del Campo follows, a uniquely shaped square famous for hosting the Palio, a historic horse race drawing crowds from around the world. This one-hour stop showcases Siena’s distinctive architecture and lively atmosphere, offering a genuine sense of local culture. The square’s shell shape, combined with its medieval brickwork, makes it a memorable sight—perfect for photos and soaking in the town’s vibrant vibe.

San Gimignano’s Medieval Skyline and Local Delights

Siena and San Gimignano Tour from Florence - San Gimignano’s Medieval Skyline and Local Delights

Next, the group moves to San Gimignano, a medieval village renowned for its 14 towers. This hour-long stop provides ample time to stroll through the cobblestone streets, shop for local crafts, and indulge in gelato. The town’s skyline is instantly recognizable, and its well-preserved towers offer sweeping views of the Tuscan landscape.

San Gimignano’s unique architecture and atmosphere make it a highlight for those interested in history, architecture, and authentic local experiences. The free time allows for a leisurely exploration of the town’s shops and scenic viewpoints.

Scenic Drive Through Tuscany’s Rolling Hills

Siena and San Gimignano Tour from Florence - Scenic Drive Through Tuscany’s Rolling Hills

Throughout the day, the tour offers about an hour of driving through Tuscany’s iconic landscapes. Surrounded by rolling hills and picturesque scenery, travelers can enjoy the views from the comfort of the vehicle or pause for photos at any point. The flexibility to stop at any moment makes this part of the experience especially pleasurable.

This drive encapsulates the essence of Tuscany: vast, peaceful landscapes dotted with vineyards, olive groves, and charming farmhouses. It’s an excellent opportunity to relax and take in the serene countryside.

The Expertise of Guides Like Francesco

Siena and San Gimignano Tour from Florence - The Expertise of Guides Like Francesco

Reviews highlight the knowledgeable guides, especially Francesco, whose expertise and engaging storytelling bring the trip to life. He adds a personal touch, even making reservations for lunch, exemplifying attentive service. Travelers appreciate how his stories make the towns’ history and culture more vivid and memorable.

The guides are praised for their ability to explain local sites clearly and with enthusiasm, making the experience more enriching. Their familiarity with the area ensures that you get the most out of each stop without feeling rushed.

Inclusions and Practical Details

Siena and San Gimignano Tour from Florence - Inclusions and Practical Details

This private tour includes all taxes, fees, and handling charges, with the major costs like attractions’ entrance tickets not included. The hotel pickup and drop-off are included, removing the stress of finding meeting points. The air-conditioned vehicle and WiFi onboard add comfort and convenience.

The tour is suitable for most travelers, but since some stops involve walking on cobblestone streets, comfortable footwear is advised. The non-refundable policy means plans should be confirmed with confidence, as cancellations are not possible once booked.

Who Will Love This Tour?

Siena and San Gimignano Tour from Florence - Who Will Love This Tour?

This private tour appeals most to those who value customized attention and flexibility. It is ideal for small groups or families seeking a personalized day through Tuscany’s highlights. History buffs, architecture fans, and anyone eager to experience Italy without the hassle of large crowds will find this tour particularly satisfying.

The intimate setting, combined with expert guidance and scenic drives, offers a comprehensive yet relaxed way to enjoy Tuscany’s most iconic towns in a single day.

Final Thoughts on the Siena and San Gimignano Tour

This private day trip from Florence offers a well-balanced mix of sightseeing, culture, and scenic relaxation. The high praise for guides like Francesco confirms that personalized service and expert storytelling enrich the experience. The stops at Monteriggioni, Siena, and San Gimignano are carefully chosen to showcase Tuscany’s diverse charm—from medieval fortresses to lively piazzas and skyline-defining towers.

The cost of $1,127.49 per group reflects the private and tailored nature of the tour. It’s a worthwhile investment for those who prefer a more exclusive, flexible experience with the convenience of door-to-door service and onboard amenities like WiFi.

While it does not include attraction tickets, the flexible approach allows travelers to prioritize what they want to explore further at each stop. This tour suits those seeking a personalized, scenic, and culturally rich day in Tuscany, delivered by knowledgeable guides and comfortable transportation.

Ready to Book?

Siena and San Gimignano Tour from Florence



5.0

(17)

100% 5-star

“Francesco was amazing! From the start, he expressed his knowledge about Tuscany. He added Monteriggioni to the itinerary and even made a reservatio…”

— Aryane B, Jun 2025

Frequently Asked Questions

What is included in the tour price?
All taxes, fees, handling charges, hotel pickup and drop-off, private transportation, air conditioning, and onboard WiFi are included.

Are attraction tickets included?
No, tickets for attractions like the Siena Cathedral are purchased on the spot.

How long is the tour?
The tour lasts approximately 8 to 9 hours, providing a full day of exploration.

Is this tour suitable for children or people with mobility concerns?
Most travelers can participate, but walking on cobblestone streets may require comfortable footwear and mobility considerations.

Can I customize the stops or timing?
As a private tour, flexibility is possible, and stops can be adjusted slightly to suit your preferences.

Is there WiFi onboard?
Yes, the vehicle offers WiFi for sharing photos and staying connected during the scenic drives.

What is the guide’s role?
Guides like Francesco offer in-depth commentary, storytelling, and assistance, enhancing the experience with their local expertise.

How far in advance should I book?
Most bookings are made around 42 days in advance, but availability may vary.

What is the cancellation policy?
This experience is non-refundable, so confirm your plans carefully before booking.

Who is the tour provider?
The tour is operated by Limo Service in Italy, contactable at +393466233326 or [email protected].