Exploring the medieval charm of Siena and San Gimignano is a must-do day trip from Rome. This guided tour whisks travelers through the Chianti hills, immersing them in UNESCO-listed landscapes and architectural gems. Visitors can wander the historic streets, admire iconic landmarks, and savor local wines paired with a delightful meal. With comfortable transportation and an expert guide, this day excursion promises an unforgettable cultural experience. But the true highlights are yet to be discovered.
Key Points

- This full-day tour from Rome explores the UNESCO World Heritage Sites of Siena and San Gimignano, showcasing picturesque Chianti landscapes and offering a wine tasting experience.
- The tour includes hotel pickup, transportation, and free cancellation up to 24 hours in advance, making it a convenient and flexible option for travelers.
- Highlights of the tour include wandering the narrow streets of San Gimignano, visiting Piazza del Campo and the Siena Cathedral in Siena, and enjoying a delightful a la carte lunch or menu.
- The tour is wheelchair accessible, and a dress code for churches is recommended, ensuring a comfortable and inclusive experience for all travelers.
- Customers have praised the tour’s scenic beauty, historical significance, and value for money, with suggestions for improving the driver’s English proficiency noted for enhancing the overall experience.
Tour Overview

This full-day tour from Rome takes visitors to explore the medieval towns of Siena and San Gimignano in the heart of Tuscany.
Priced at $862.86 per group (up to 3 participants), the tour includes hotel pickup, transportation, and free cancellation up to 24 hours in advance.
Lasting 1 day, the itinerary highlights two UNESCO World Heritage Sites – San Gimignano and Siena – as well as scenic Chianti landscapes and wine tasting.
The tour is wheelchair accessible, and comfortable shoes are recommended, with a dress code for churches.
Based on 4 reviews, the tour receives an overall rating of 5/5.
Ready for another glass? Here are more wine experiences we've reviewed in Rome
Itinerary Highlights

The tour’s itinerary highlights two UNESCO World Heritage Sites – the medieval towns of San Gimignano and Siena.
Explore picturesque Chianti landscapes and taste renowned wines like Chianti and Vernaccia.
The tour also stops at Monteriggioni, known for its well-preserved medieval walls and towers.
Monteriggioni, renowned for its well-preserved medieval walls and towers, is a stop on the tour.
In San Gimignano, wander the narrow streets and admire the skyline of historic towers.
In Siena, visit Piazza del Campo and the Palazzo Pubblico with its iconic Torre del Mangia.
The Siena Cathedral, a prime example of Italian Romanesque-Gothic architecture, is another highlight.
The tour includes a wine tasting with a la carte lunch or menu.
Cultural Experiences

While in San Gimignano, visitors can wander the narrow streets and admire the skyline of historic towers that have made this medieval town a UNESCO World Heritage Site.
In Siena, travelers will visit the famous Piazza del Campo, home to the striking Palazzo Pubblico and its iconic Torre del Mangia.
The city’s grand Duomo is a prime example of Italian Romanesque-Gothic architecture, featuring intricate marble facades and ornate interiors.
During the tour, guests will enjoy a wine tasting paired with a delightful a la carte lunch or menu, sampling renowned local vintages like Chianti and Vernaccia.
Transportation and Accessibility

Transportation is provided throughout the tour. Participants will be picked up from their hotel or private address and transported to the various destinations in a comfortable, air-conditioned vehicle. The tour is wheelchair accessible, allowing everyone to enjoy the sights and experiences.
| Accessibility | Dress Code |
| — | — |
| Wheelchair accessible | No shorts, miniskirts, or uncovered shoulders |
| Comfortable shoes recommended | |
The tour caters to all travelers, ensuring they can explore the medieval towns of Siena and San Gimignano with ease and comfort. Participants are advised to dress appropriately for the churches, adhering to the dress code to fully enjoy the cultural experience.
More Great Tours NearbyCustomer Feedback
The tour has received overwhelmingly positive reviews from customers. Based on 4 reviews, the tour boasts an impressive 5-star rating.
Travelers praise the convenient transportation, rating it 5/5, and find the tour represents excellent value for money at 4.8/5.
Customers are particularly impressed by the scenic beauty, historical significance, and wine tasting experiences.
However, some suggest the driver’s English proficiency could be improved to enhance the overall experience.
Despite this minor feedback, the tour appears to deliver an exceptional day exploring Tuscany’s medieval gems of Siena and San Gimignano.
Hungry for more Rome flavors? We've covered these other food and drink spots
- Rome: Fully Loaded Trastevere Food Tour With Dinner and Wine
- The Award-Winning Private Food Tour of Rome: 6 or 10 Tastings
- Rome Trastevere Food Tour at Twilight With Eating Europe
- Rome Food Tour: Unlimited Tastings With Fine Wine & Barolo
- Super Fun Pasta & Gelato Cooking Class & Oil Tasting by Vatican
- Rome Walking Food Tour With Secret Food Tours
Exploring the UNESCO-Listed Towns
Visitors embark on an immersive journey through the UNESCO-listed medieval towns of Siena and San Gimignano, exploring their well-preserved architectural wonders and soaking in the captivating histories that have shaped these iconic Tuscan destinations.
In Siena, they marvel at the ornate Duomo, a pinnacle of Italian Romanesque-Gothic architecture, and wander the charming Piazza del Campo, home to the famous Palio horse race.
In San Gimignano, they discover the town’s iconic skyline of medieval towers and stroll through the quaint narrow streets, admiring the stunning panoramic vistas across the picturesque Chianti hills.
Discovering the Chianti Hills
The picturesque Chianti hills serve as the scenic backdrop for this immersive tour, offering travelers a chance to discover the rich wine-making heritage and stunning landscapes that have captivated visitors for centuries.
Along winding roads, visitors will encounter charming medieval towns like Monteriggioni, known for its well-preserved walls and towers.
During the wine tasting, guests can savor the region’s renowned Chianti and Vernaccia vintages, complemented by a delightful a la carte lunch or menu.
Savor the renowned Chianti and Vernaccia vintages, complemented by a delightful a la carte lunch or menu.
This comprehensive experience showcases the enduring allure of Tuscany’s Chianti countryside, where history, culture, and exquisite flavors converge.
Wine Tasting and Dining
As part of the immersive experience, guests can savor the region’s renowned Chianti and Vernaccia vintages during a wine tasting.
The tour includes a la carte lunch or menu paired with the wines. Travelers can expect to learn about the winemaking process and local traditions while indulging in the flavors that have made Tuscany famous.
The wine tasting complements the exploration of the medieval towns, providing a well-rounded cultural and culinary experience.
With stunning scenery and historic architecture as the backdrop, the wine tasting elevates the day tour to a truly unforgettable adventure.
The Sum Up
The Siena & San Gimignano Day Tour from Rome offers an unforgettable journey through medieval Italy. Visitors can enjoy the historic charm of these UNESCO-listed towns, explore the breathtaking Chianti landscapes, and enjoy a wine tasting with a delightful meal. With comfortable transportation and a guided experience, it’s the perfect way to discover the essence of Tuscany in a single day trip from Rome.
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
