Tuscany’s rolling hills, medieval towns, and renowned wineries captivate travelers from around the world. This guided tour offers a chance to take in the region’s rich history and vibrant culture. From the iconic Piazza del Campo in Siena to the picturesque streets of San Gimignano, the journey unveils the enchanting essence of Tuscany. But the true highlight lies in the Chianti vineyards, where visitors savor the flavors of exceptional wines paired with a delightful local lunch. What secrets will this tour uncover?
Key Points

- This 6.5-hour tour explores the historic towns of Siena and San Gimignano, as well as the renowned Chianti wine region, with guided visits and tastings.
- Visitors can admire the medieval architecture and panoramic views in Siena, including the iconic Piazza del Campo and the Mangia Tower.
- The tour offers an opportunity to discover the rich winemaking heritage of Chianti, with visits to two local wineries and a light lunch with wine pairings.
- Travelers can wander the charming streets and plazas of the medieval hilltop town of San Gimignano, known for its striking skyline of towers.
- The tour includes roundtrip transportation from two locations in Florence and is available in both English and Spanish.
Tour Overview
The Tuscany: Siena, San Gimignano and Chianti Wine Tour is a 6.5-hour excursion that takes travelers through the picturesque Tuscan countryside.
Priced from $194.76 per person, the tour is offered in English and Spanish, with pickup and drop-off included from two locations in the Metropolitan City of Florence.
Highlights include a guided tour of medieval Siena, visits to two wineries for tastings and a light lunch, and free time to explore the charming town of San Gimignano.
The tour features scenic drives, wine pairings, and photography opportunities, making it a comprehensive Tuscan experience.
Ready for another glass? Here are more wine experiences we've reviewed in Florence
Exploring Siena

Siena’s medieval charm captivates visitors from the moment they set foot in the city. The guided tour takes guests through the highlights, starting with the iconic Piazza del Campo, a stunning 13th-century town square.
Visitors can then explore the:
-
Palazzo Pubblico, the grand city hall, with its striking architecture and famous Mangia Tower.
-
Torre del Mangia, a 14th-century bell tower offering panoramic views of the city.
-
Narrow cobblestone streets, lined with historic buildings and quaint shops, where travelers can soak in the authentic Tuscan atmosphere.
The comprehensive tour ensures travelers leave Siena with a deeper appreciation for its rich history and timeless beauty.
Discovering the Chianti Region

What makes the Chianti region so captivating? This renowned wine-producing area offers visitors a chance to enjoy its rich winemaking heritage.
On the tour, guests visit two local wineries, where they’ll learn about the centuries-old traditions and sample the region’s renowned Chianti wines. During the tastings, a light lunch with wine pairings provides a delightful complement to the experience.
Beyond the wineries, the scenic drives through the rolling Tuscan hills offer breathtaking views that inspire awe.
Exploring the Chianti region is a chance to savor the flavors, history, and natural beauty that make it a cherished destination.
Visiting San Gimignano
After exploring the Chianti region’s winemaking heritage, the tour next takes visitors to the captivating town of San Gimignano.
This medieval hilltop town is renowned for its striking skyline of towers and scenic views.
Visitors can:
-
Wander the charming streets and plazas, taking in the architectural wonders.
-
Browse the quaint shops and sample local delicacies.
-
Capture breathtaking sunsets from the town’s vantage points.
With free time to explore at their own pace, travelers can enjoy the unique character of San Gimignano before returning to Florence.
More Great Tours NearbyIncluded Tour Features

The tour includes several notable features, such as a visit to a winery in the Chianti region for a wine tasting and light lunch.
Travelers will also enjoy a guided tour of the medieval city of Siena, exploring landmarks like Piazza del Campo and Palazzo Pubblico.
Scenic drives between destinations offer panoramic views of the Tuscan countryside.
Plus, the tour provides free time in the picturesque town of San Gimignano, allowing for shopping and photography.
While some wines may be available for purchase, the core tour package includes a comprehensive experience showcasing the highlights of this renowned region.
- Small-Group Wine Tasting Experience in the Tuscan Countryside
- Tuscany Day Trip From Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- The Best Tour in Florence: Renaissance & Medici Tales – Guided by a STORYTELLER
- Cinque Terre Day Trip From Florence With Optional Hiking
- The Best Tour in Florence: Renaissance and Medici Tales
- Early Access Guided Uffizi Gallery Tour Skip-the-Line Small Group
Important Information for Travelers

When planning for this Tuscany wine tour, there are a few important details travelers should be aware of.
First, the tour isn’t suitable for children under 7 years old, wheelchair users, or those with mobility issues or serious back problems.
Plus, the cancellation policy allows for free cancellation up to 24 hours in advance for a full refund.
Finally, travelers should pack comfortable shoes, a sun hat, camera, sunscreen, and water to make the most of the scenic drives and outdoor activities.
Customer Reviews

Travelers’ overwhelmingly positive experiences with the Tuscany wine tour have been reflected in the 5/5 overall rating based on 1 review.
The feedback highlights the beauty of the tour and quality of wine tastings. Visitors praise the guided tour of medieval Siena, the visits to two wineries for tastings with light lunch, and the free time in the picturesque town of San Gimignano.
The scenic drives and sunset photography opportunities are also noted as highlights. The tour provides an immersive experience in the heart of Tuscany, allowing travelers to savor the region’s renowned wine and culture.
Frequently Asked Questions

Are There Any Dining Options on the Tour?
The tour includes a light lunch with wine pairings at one of the wineries visited. Travelers can also purchase extra wine during the tastings if they wish to do so.
Can I Purchase Additional Wine After the Tastings?
Yes, the tour allows you to purchase additional wine separately after the included wine tastings. The tour description states that "Extra wine available for separate purchase" is one of the exclusions.
What Is the Dress Code for the Tour?
The tour does not have a formal dress code, but comfortable shoes and sun protection are recommended. Travelers should dress for a day of sightseeing and wine tasting in a temperate climate.
How Much Walking Is Involved During the Tour?
The tour involves a moderate amount of walking. Visitors can expect to explore the medieval cities of Siena and San Gimignano on foot. However, transportation is provided between sites, reducing the overall walking distance.
Can I Extend My Stay in Tuscany After the Tour?
Yes, you can extend your stay in Tuscany after the tour. The tour provider offers flexibility, allowing you to continue exploring the region at your own pace following the conclusion of the day’s activities.
The Sum Up

This guided tour offers an immersive Tuscan experience, blending medieval charm and renowned wine tasting. Travelers can explore the historic cities of Siena and San Gimignano, savor local flavors, and indulge in the renowned Chianti wines. With a convenient round-trip from Florence, this day-long excursion provides a well-rounded introduction to the picturesque Tuscan countryside and its cultural treasures.
You can check availability for your dates here:More Workshops & Classes in Florence
- Florence: Premium Pizza & Gelato Preparation Class with Wine
- Florence: Pizza or Pasta Class with Gelato at a Tuscan Farm
- Florence: Pasta-Making Class with Dinner, Wine and… SING!
- Florence: Cocktail Making Class with Aperitivo
- Florence: Tiramisu & Pasta Making Class with Unlimited Wine
- Florence: Pasta and Tiramisu Class with Unlimited Wine
More Cooking Classes in Florence
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
