Exploring the medieval marvels of Tuscany from Rome is an enriching day trip. The Siena and San Gimignano Day Tour takes visitors to these captivating hilltop towns, showcasing their iconic architecture and offering local wine tastings. With private transportation and an English-speaking driver, the tour provides a seamless journey through Italy’s history and culture. Whether you’re drawn to Siena’s stunning cathedral or San Gimignano’s famous towers, this experience promises an unforgettable glimpse into the region’s timeless allure.
Key Points

- Explore the medieval marvels of Siena, including the iconic striped cathedral and the unique fan-shaped Piazza del Campo.
- Discover the charming town of San Gimignano, known for its well-preserved medieval towers and opportunity to taste local Vernaccia wines.
- Enjoy a private, air-conditioned vehicle with an English-speaking driver for a comfortable and seamless journey from Rome.
- Indulge in a delicious local lunch as part of the tour package, with all admission tickets and gratuities included.
- Benefit from the expertise of private licensed guides who provide insightful commentary throughout the day.
Tour Highlights

The tour begins with a visit to the historic city of Siena, known for its stunning medieval architecture and the iconic striped cathedral.
Here, guests can explore the winding streets and lively Piazza del Campo, the site of the famous Palio horse race.
Next, the tour heads to the charming town of San Gimignano, famous for its well-preserved towers that provide panoramic views of the surrounding Tuscan countryside.
Guests can enjoy a local wine tasting and sample the region’s delicious cuisine during an included lunch.
Throughout the day, an English-speaking driver offers information and assistance to ensure a comfortable and seamless experience.
Looking for more options in Rome? We've reviewed plenty of other experiences.
Siena: Medieval Marvels

As guests step into the historic city of Siena, they’re immediately captivated by its well-preserved medieval architecture and the iconic striped cathedral that dominates the skyline. Wandering through the narrow, winding streets, they discover the Piazza del Campo, a unique fan-shaped public square that hosts the famous Palio horse race twice a year. The city’s rich history comes alive through its stunning Duomo, with its intricate marble facade and interiors adorned with exquisite frescoes and sculptures. To further enjoy Siena’s medieval charm, guests can visit the Palazzo Pubblico and climb the towering Torre del Mangia.
| Key Sights | Highlights |
|---|---|
| Piazza del Campo | Iconic fan-shaped public square |
| Siena Cathedral | Striped marble exterior and interior masterpieces |
| Palazzo Pubblico | Seat of Siena’s government with impressive architecture |
| Torre del Mangia | Towering bell tower offering panoramic city views |
San Gimignano: Towers and Tastings
Departing Siena, guests journey to the enchanting hilltop town of San Gimignano, renowned for its stunning skyline of medieval towers.
Wandering the charming streets, visitors marvel at the well-preserved architecture and have the opportunity to sample local Vernaccia wines.
Climbing the Rocca, the highest tower, rewards guests with panoramic vistas of the lush, rolling Tuscan countryside.
The tour includes a wine tasting at a family-owned vineyard, where guests learn about the region’s winemaking traditions.
With free time to explore the town’s artisan shops and cafes, the San Gimignano experience immerses visitors in the timeless allure of this historic hilltop haven.
Transportation and Comfort

Guests are transported in a private, air-conditioned vehicle throughout the day, ensuring a comfortable and relaxing journey.
Pickup is provided from their custom accommodation in Rome. An English-speaking driver offers information and support during the tour.
The tour is wheelchair accessible and stroller-friendly, catering to the needs of all guests.
This level of personalized transportation and service allows guests to focus on enjoying the historical sights and stunning landscapes of Siena and San Gimignano without the hassle of navigating public transit or driving themselves.
Tour Inclusions

The tour includes private licensed guides who provide expert commentary and insights throughout the day.
Admission tickets to all sites are included, ensuring hassle-free access. Guests can enjoy a delicious lunch as part of the package, with gratuities and courtesy services provided.
The tour offers convenience and value, with a wide range of inclusions that cater to the needs of travelers.
Whether exploring the medieval charm of Siena or admiring the panoramic views from San Gimignano’s towers, the tour offers a comprehensive and seamless experience.
- Rome: Colosseum, Roman Forum and Palatine Hill Fully Guided Tour
- Pompeii Day Trip From Rome With Mount Vesuvius or Positano Option
- Skip-the-Line Group Tour of the Vatican, Sistine Chapel & St. Peters Basilica
- Pizza Cooking Class in Rome – Near Piazza Navona
- Cooking Class in the Heart of Rome: Pizza and Tiramisu Making
- Pasta Cooking Class in Rome – Fettuccine Class in Piazza Navona
Booking Information

The price for this private tour starts from €374.50 per person, with the exact cost varying based on the size of the group. Travelers can reserve their spot now and pay later, providing flexibility. All bookings come with free cancellation up to 24 hours before the experience starts, and confirmation is received at the time of booking.
| Booking Details | |||
|---|---|---|---|
| Price | €374.50 per person | Group Size | Varies |
| Cancellation | Free up to 24 hours | Confirmation | At time of booking |
| Payment | Reserve now, pay later |
Customer Experiences

Travelers have consistently highlighted the patience and accommodating nature of the drivers, contributing to fantastic experiences.
Guests praise the ability to customize tours, including last-minute winery tastings and lunch arrangements tailored to individual preferences.
Reviewers emphasize the seamless logistics, with the driver providing helpful information and support throughout the journey.
The tour’s 5.0 rating and 100% recommendation rate from previous travelers further underscores the exceptional customer experience.
Why Choose This Tour

With a 5.0 rating and 100% recommendation rate, this tour offers an exceptional experience that sets it apart.
The tour’s value is evident in its inclusions – private transportation, licensed guides, site entries, and lunch. Travelers also appreciate the flexibility to customize the experience, whether it’s a last-minute winery visit or arranging a suitable lunch.
The tour’s accessibility, from wheelchair-friendly options to English-speaking drivers, ensures a comfortable and hassle-free journey.
Whether you’re seeking historical exploration, picturesque landscapes, or local wine tastings, this Siena and San Gimignano day tour is an unparalleled choice.
Frequently Asked Questions
Can I Customize the Tour Itinerary?
Yes, the tour allows for customization. The description notes guests can make last-minute adjustments, such as adding winery tastings or modifying lunch arrangements, to personalize the itinerary and enhance their experience.
How Long Will the Tour Last?
The full-day private tour typically lasts around 8-10 hours, providing ample time to explore the medieval towns of Siena and San Gimignano, including a wine tasting and panoramic views. The tour’s duration allows for a comprehensive experience.
What Type of Vehicle Will Be Used for Transport?
The tour includes private transportation in an air-conditioned vehicle. Guests are picked up from their accommodation in Rome and transported comfortably throughout the day by an English-speaking driver.
Is Wi-Fi Available in the Vehicle?
The vehicle used for transport on this tour includes Wi-Fi, allowing passengers to stay connected during the journey. This feature enhances the overall comfort and convenience of the private transportation provided.
Can the Tour Be Booked for a Single Traveler?
The tour can be booked for a single traveler. The price per person varies based on the group size, so a solo traveler would pay the higher individual rate compared to a larger group.
The Sum Up
The Siena and San Gimignano Day Tour from Rome offers an unparalleled opportunity to explore Tuscany’s medieval wonders. Travelers can enjoy the captivating architecture, lively piazzas, and renowned wine tastings of these historic towns, all while enjoying the convenience of private transportation and an English-speaking driver. This tour provides a seamless and memorable journey through Italy’s rich cultural heritage.
More Lunch Experiences in Rome
- Florence & Tuscany Day Tour from Rome with Wine Tasting & Lunch
- Classic Half-Day Wine Tour in Frascati with Lunch
- Rome: Bracciano Castle Visit, Cornetti Class, & Farm Lunch
- From Rome: Tuscany & Siena with Wine Tasting and Lunch
- Turano Lake: full day trip with Hike, Castle, Tour and Lunch
- ROME: Truffle Hunting and Lunch with Truffle Dishes
More Cooking Classes in Rome
More Tour Reviews in Rome
Still browsing? Here are more Rome experiences we've covered recently
- 13 Fantastic Wine Tours In Rome
- 14 Top Private Driver Services In Rome (With Reviews & Prices)
- Which Rome Shore Excursions To Choose? Our Best 6 Picks
- The 14 Most Popular City Tours In Rome
- Which Rome Tours & Experiences To Choose? We Rank The 14 Best
- 14 Must-Try Cruises And Boat Tours In Rome
- Discover 14 Great Tours In Rome
- 12 Best Walking Tours In Rome (With Reviews & Prices)
- 14 Of The Best Shopping & Market Tours In Rome
- The Top 13 Rome Workshops & Classes
- 14 Must-Try Lunch Experiences In Rome
- Our 14 Favorite Rome Motorbike And Scooter Rentals
