Explore the charming towns of Siena and San Gimignano on this comprehensive day tour from Florence. Wander through Siena’s historic center, admiring the stunning Piazza del Campo and impressive Cathedral. Then, savor a delightful 3-course lunch paired with wine tastings at a renowned Chianti winery. Finish your day by discovering the iconic medieval towers of San Gimignano, a true highlight of Tuscany’s rich cultural heritage. This tour offers a well-rounded experience, immersing you in the region’s captivating sights, flavors, and history.
Key Points

- A 9-hour excursion from Florence that visits the historic towns of Siena and San Gimignano, with a guided tour of Siena and a winery lunch and tasting.
- The tour includes round-trip transportation, a guided tour of Siena’s architecture and heritage, and 2 hours of free time for shopping and dining in Siena.
- The winery visit features a 3-course meal paired with 4 different Tuscan wines, providing an immersive introduction to the region’s renowned viticulture.
- San Gimignano, a UNESCO World Heritage Site, is explored for 1.5 hours, allowing visitors to experience its charming medieval ambiance and iconic skyline of towering stone-built towers.
- The tour allows for cancellation up to 24 hours in advance for a full refund, offering flexibility for participants.
Tour Overview

The Siena & San Gimignano Tour with Wine & Lunch is a 9-hour excursion that departs from Piazzale Montelungo in Florence, Italy.
A 9-hour excursion departing from Piazzale Montelungo in Florence, Italy to explore the historic towns of Siena and San Gimignano.
Priced from $81.61 per person, the tour includes round-trip transportation on an air-conditioned coach and visits to the historic towns of Siena and San Gimignano.
In Siena, guests enjoy a guided tour and free time, while in the Chianti region, they experience a wine tasting and 3-course lunch at an organic winery.
The tour also offers 1.5 hours of free time in San Gimignano.
Cancellations can be made up to 24 hours in advance for a full refund.
Here are more experiences we've reviewed in Florence
Exploring Siena

After departing from Florence, the tour takes visitors to the historic city of Siena.
The guided tour provides insights into Siena’s stunning architecture and medieval heritage. Visitors explore the Piazza del Campo, the famous shell-shaped town square, and admire the ornate Siena Cathedral. They learn about the Palio, Siena’s renowned horse race that’s held twice a year.
With 2 hours of free time, travelers can wander the narrow streets, browse local shops, and sample regional delicacies.
Whether it’s marveling at the unique cityscape or immersing in Sienese culture, this part of the tour offers an enriching experience.
Chianti Winery Lunch and Tasting

Next, the tour moves into the renowned Chianti wine region. Here, guests visit an organic winery for a 105-minute lunch and tasting experience. Diners savor a 3-course meal expertly paired with 4 different Tuscan wines. This provides an immersive introduction to the region’s renowned viticulture.
| Wine | Tasting Notes |
| — | — |
| Chianti Classico | Bright red fruit, balanced acidity |
| Rosso di Montalcino | Rich, full-bodied with notes of plum |
| Super Tuscan | Complex, velvety texture with bold flavors |
| Vin Santo | Sweet, syrupy dessert wine with nutty notes |
The winery lunch offers travelers a chance to deepen their appreciation for Tuscany’s celebrated culinary and wine culture.
Discovering San Gimignano

Departing the winery, the tour then ventures to the medieval town of San Gimignano.
Travelers are treated to 1.5 hours of free time to explore this UNESCO World Heritage Site. Renowned for its iconic skyline of towering medieval stone-built towers, San Gimignano offers a glimpse into Italy’s past.
Visitors can wander the narrow streets, visit the historic piazza, and admire the architecture and views. The tour provides an opportunity to discover San Gimignano’s charming ambiance and understand why it’s often called the "Manhattan of the Middle Ages."
This picturesque hilltop town completes the day’s culture in Tuscany.
More Great Tours NearbyTransportation and Logistics

The tour begins with round-trip transportation from Florence on an air-conditioned coach.
This comfortable ride whisks guests to the medieval towns of Siena and San Gimignano.
Upon arrival in Siena, guests will enjoy a guided tour led by an expert local guide. After the tour, they’ll have 2 hours of free time to explore the city on their own.
Next, the coach takes the group to an organic winery in the Chianti region for a 105-minute lunch and wine tasting experience.
The final stop is San Gimignano, where guests have 1.5 hours to roam the historic streets.
Ready for another glass? Here are more wine experiences we've reviewed in Florence
- Small-Group Wine Tasting Experience in the Tuscan Countryside
- Tuscany Day Trip From Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- Full Day Tour to Val Dorcia and Gladiators Fields With Wines
- Wine Safaris: off Road Tuscany Wine Tours and Lunch From Florence
- Tuscany Bike Tours Through the Chianti Hills With Wine Tasting
- Florence Sunset Food & Wine Tour With Eating Europe
Accessibility and Recommendations

This tour may not be suitable for individuals with mobility impairments or wheelchair users. Strollers and large bags aren’t allowed on the coach.
However, the tour provides useful recommendations to ensure a comfortable experience. Visitors should wear comfortable shoes and bring a sun hat, sunscreen, and water.
Wear comfortable shoes and bring sun protection and hydration for a pleasant tour experience.
Dietary restrictions can be accommodated if notified at booking, and vegetarian options are available.
From November to March, the Siena guided tour is replaced with self-exploration, allowing travelers to discover the city at their own pace.
Customer Testimonials

According to customer reviews, the Siena & San Gimignano Tour has an impressive overall rating of 4.6 out of 5 stars based on 95 reviews.
Travelers praised the knowledgeable, fun, and clear guides, such as Tabatha, Juliano, and Renata. Reviewers also highlighted the comfortable transportation and excellent value for money.
As one satisfied customer from India noted, the tour provided an "informative and fun experience."
Another UK-based reviewer appreciated the "informative winery lunch." An Australian traveler recommended the tour, citing the knowledgeable guide and smaller group size as key highlights.
Booking and Cancellation Policy

Customers can book the Siena & San Gimignano Tour from the provided starting point in Florence, Italy. The tour is priced at $81.61 per person and is likely to sell out, so booking in advance is recommended.
The cancellation policy is flexible, allowing for free cancellation up to 24 hours prior to the tour for a full refund.
Key booking details:
-
Duration: 9 hours
-
Guided tours in Siena available from April to October
-
Accessibility: Not suitable for those with mobility issues
-
Dietary restrictions can be accommodated with advance notice
Ask Away

How Much Walking Is Involved on the Tour?
The tour involves a moderate amount of walking, with guided tours in Siena and free time in San Gimignano. Comfortable shoes are recommended, and the tour may not be suitable for those with mobility impairments or wheelchair users.
Can We Take Photos During the Wine Tasting?
Yes, you can take photos during the wine tasting portion of the tour. The tour allows ample time for participants to capture photos and enjoy the scenic winery setting while tasting the Tuscan wines.
Is There an Option to Extend the Stay in San Gimignano?
The tour provides 1.5 hours of free time in San Gimignano, but there’s no option to extend the stay. Travelers who want more time can opt to explore San Gimignano independently before or after the tour.
Do We Have Free Time to Explore Siena on Our Own?
The tour provides 2 hours of free time in Siena, allowing you to explore the city on your own. This self-guided exploration is a good opportunity to discover Siena’s historic sights and attractions at your own pace.
Can We Bring Any Souvenirs or Purchases Back on the Bus?
Yes, participants can bring any souvenirs or purchases back on the bus. The tour includes a comfortable coach for transportation, and there’s ample space to store any items acquired during the free time in Siena and San Gimignano.
Final Words
The From Florence: Siena & San Gimignano Tour With Wine & Lunch offers a captivating exploration of Tuscany’s historic towns, gourmet experiences, and stunning vistas. Travelers can enjoy the medieval charm of Siena and San Gimignano, complemented by a delightful winery lunch and wine tasting. This comprehensive tour provides an efficient and enriching way to experience the heart of Tuscany’s cultural and culinary heritage.
You can check availability for your dates here:More Guided Tours in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Florence Old City Street Food Tour and Guided Sightseeing
- Santa Maria del Fiore Cathedral tickets and Audio guide
- Florence: Uffizi Gallery Tickets with Optional audio guide
- Florence: Highlights Walking Tour with Expert Guide
- Florence: 2.5 hour Audio Guided Walking Tour led by Host
More Tours in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
- Florence Medici Bike Tour Cycle Through History and Power
More Tour Reviews in Florence
- Florence: Cathedral Duomo Tour with Local Guide
- Fiesole E-Bike Tour with Olive Oil Tasting or Pool & Chill
- Florence: Tuscan Cheese and Wine Tasting Experience
- Florence walking Tour: Music Headphones & Aperol Spritz
- Walking Tour: Florence Noir and Its Secrets
- Florence Old City Street Food Tour and Guided Sightseeing
Still browsing? Here are more Florence experiences we've covered recently
- What Are The Best 2-Hour Tours In Florence? Our Top 3 Picks
- Our Picks For The 13 Best Wine Tours In Florence
- The 12 Most Popular Workshops & Classes In Florence
- The 11 Best Dining Experiences In Florence
- 14 Best Tours In Florence
- Florence’s 10 Best Dinner Experiences (With Prices & Reviews)
- 14 Best Walking Tours In Florence (With Prices)
- Florence’s 3 Best Hiking And Trekking Tours
- 7 Must-Try Private Driver Services In Florence
- Florence’s 14 Top Food Tours
- 14 Of The Best Photography Experiences In Florence
- Our Picks For The 13 Best Pasta Experiences In Florence
