Discover the enchanting charm of Tuscany on a semiprivate day trip from Rome. This small-group tour takes you to the UNESCO-listed medieval centers of Siena and San Gimignano, where you’ll explore historic landmarks and indulge in a winery visit to sample the renowned Vernaccia di San Gimignano white wine. With an English and Italian-speaking guide leading the way, you’ll enjoy a personalized experience that showcases the best of these picturesque Tuscan towns. But the true allure of this journey lies in the stories yet to be uncovered.
About Your Stay

- Visit the UNESCO World Heritage sites of Siena and San Gimignano on a day trip from Rome.
- Explore the medieval architecture, culture, and history of these picturesque Tuscan towns.
- Enjoy a wine tasting of the renowned Vernaccia di San Gimignano white wine paired with local appetizers.
- Small-group tour limited to 14 participants with a live guide in English and Italian.
- Complimentary transportation by air-conditioned minivan with pickup and drop-off services.
Tour Overview

The article provides an overview of a day trip from Rome to the medieval towns of Siena and San Gimignano.
It’s a small-group tour limited to 14 participants, with a live guide available in English and Italian. The tour lasts 1 day and is priced at $436.89 per person.
Free cancellation is allowed up to 24 hours in advance for a full refund.
The itinerary highlights include exploring the UNESCO-listed towns, tasting Vernaccia wine in San Gimignano, visiting a local winery for Chianti tasting, and wandering the historic center of Siena.
Here are more experiences we've reviewed in Rome
Exploring Siena

As visitors explore Siena, they’ll discover a city that has meticulously preserved its medieval character.
The historic center, a UNESCO World Heritage site, features Gothic architecture, winding streets, and the magnificent Piazza del Campo, home to the iconic Mangia Tower. Visitors can wander through the lively square, admiring the intricate details of the surrounding buildings.
Siena is also renowned for its vibrant culture, with the biannual Palio horse race drawing crowds from around the world.
Whether strolling through the city or sampling local cuisine, travelers are immersed in Siena’s rich history and traditions.
Discovering San Gimignano

After exploring the captivating medieval streets of Siena, visitors continue their journey to the charming town of San Gimignano.
This UNESCO World Heritage site is renowned for its iconic skyline of medieval towers. Visitors can stroll through the quaint alleys, admiring the remarkable architecture and local shops.
The highlight is a visit to a local winery, where they can sample the renowned Vernaccia di San Gimignano white wine and savor local delicacies.
With its well-preserved historic center and stunning vistas, San Gimignano offers a unique glimpse into Italy’s past, leaving visitors with lasting memories.
Winery Visit and Tasting
During the tour, visitors are treated to a stop at a local winery, where they’ve the opportunity to sample the renowned Vernaccia di San Gimignano white wine.
This delightful tasting is accompanied by a selection of appetizers that complement the wine’s flavor profile. Guests learn about the winemaking process and the unique terroir that gives this historic wine its distinctive character.
The tasting provides a chance to savor the fruits of the region’s winemaking traditions and gain a deeper appreciation for the local culture and cuisine.
More Great Tours NearbyHighlights of the Itinerary
This semiprivate day trip allows visitors to enjoy the enchanting medieval charm of Siena and San Gimignano, both UNESCO World Heritage sites.
In San Gimignano, travelers will wander the town’s charming streets and have the chance to taste the renowned Vernaccia wine.
The tour then heads to a local winery for a Chianti tasting paired with appetizers.
In Siena, the group will explore the historic center, including the iconic Piazza del Campo and the Mangia Tower.
Throughout the day, a knowledgeable guide provides insights into the history and culture of these picturesque Tuscan towns.
- 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
Inclusions and Exclusions

The tour includes transportation by air-conditioned minivan, a driver/guide, and tastings of local products like wine and food.
Pickup and drop-off services are also provided. However, lunch isn’t included, and gratuities are optional.
The tour is unaffected by adverse weather conditions, so travelers can enjoy the experience regardless of the weather.
Participants are advised to wear comfortable shoes and bring a camera, and cash for any additional expenses.
The excursion offers a comprehensive experience, allowing visitors to explore the medieval towns of Siena and San Gimignano, both UNESCO World Heritage sites.
Important Information
Although the meeting point for the Siena & San Gimignano Day Trip is your hotel in Rome inside the Aurelian Walls, participants are advised to wear comfortable shoes and bring a camera, as well as cash for any additional expenses.
The tour is unaffected by adverse weather conditions, so it’ll run rain or shine. Tips aren’t included in the price, so they’re optional.
With a small group limited to 14 participants, the tour offers a personalized experience led by a live guide available in English and Italian.
Customer Feedback

Customers have generally provided positive feedback on the Siena & San Gimignano Day Trip from Rome.
With an overall rating of 4.2 out of 5 based on 9 reviews, the tour has received praise for its knowledgeable and friendly tour guide and driver. Reviewers highlighted the exceptional service provided by Felice and Andrea.
However, a few customers noted scheduling issues, such as delays.
Questions About Your Stay
How Much Time Is Allotted for Each Town Visit?
The tour allots approximately 1.5-2 hours to explore each town. Visitors get to wander the medieval streets, visit key landmarks, and enjoy local wine and food tastings in both Siena and San Gimignano during the day trip.
Can We Explore the Towns on Our Own?
Travelers can explore the medieval towns on their own during the tour. The itinerary includes guided visits to key highlights, but also provides free time for independent exploration of the charming streets and local attractions.
Is There an Option to Join a Larger Group Tour?
No, there doesn’t appear to be an option to join a larger group tour. The tour is described as a "semiprivate" experience, with a small group limited to 14 participants. The tour company doesn’t seem to offer a larger group option.
Can We Request a Specific Pickup Location in Rome?
Yes, travelers can request a specific pickup location in Rome for this tour. The tour includes pick-up and drop-off service, so customers can arrange to be picked up from their hotel or another convenient location within Rome’s Aurelian Walls.
Can the Tour Be Extended to Include Additional Activities?
Yes, the tour can be extended to include additional activities. Travelers can request customizations, such as visiting other nearby towns or adding extra wine tastings, for an additional fee. The tour operator is generally flexible in accommodating such requests.
Final Verdict On This Stay
This semiprivate day trip from Rome showcases the charming medieval towns of Siena and San Gimignano, offering a personalized experience with an expert guide. Visitors can explore the UNESCO-listed Siena, admire the iconic Mangia Tower, wander through the picturesque alleys of San Gimignano, and savor the renowned Vernaccia di San Gimignano white wine at a local winery. It’s an opportunity to take in the beauty and history of Tuscany.
You can check availability for your dates here: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
