Travelers seeking a harmonious blend of history and wine exploration will find the ‘Small Group Tour: Classico Wines With Ancient Middle Age Cities’ an ideal choice. Imagine strolling through the cobblestone streets of San Gimignano, savoring the renowned Vernaccia di San Gimignano wine, and uncovering the secrets of this medieval gem.
But what hidden treasures lie in wait in the ancient city of Siena, where time seems to stand still amidst the rolling vineyards? Join this exclusive tour for an unforgettable journey through Italy’s past and present, where every sip of wine reveals a story waiting to be told.
Good To Know
- Explore historic sites in Siena and San Gimignano while indulging in Chianti wine tasting.
- Immerse in local culture and traditional Tuscan customs during the tour.
- Enjoy scenic views of the Tuscan countryside and capture the beauty with a camera.
- Blend wine indulgence with cultural heritage, discovering medieval towers and streets in the ancient cities.
Tour Overview

Set out on a captivating journey through the heart of Tuscany with a full-day private tour that delves into the rich history and flavors of San Gimignano and Siena. Tour logistics are seamless, with an air-conditioned minivan providing comfortable transport from Florence.
A highlight of this experience is the wine tasting at a local winery, where visitors can savor the renowned Chianti wine and learn about the Sangiovese grapes that make it so special. The tour allows for a maximum of 8 people per booking, ensuring an intimate and personalized experience.
After a day of exploring the picturesque countryside and charming villages, you will return to the meeting point in Florence, filled with memories of a delightful wine-filled adventure.
Interested in wine? More Florence vineyard visits we've reviewed
Itinerary Highlights

Discover the enchanting sights and flavors awaiting you on the itinerary highlights of this immersive tour through San Gimignano and Siena in Tuscany, Italy.
- Wine tasting at a local winery to savor the renowned Chianti wine
- Explore the historic sites of Siena, including the stunning Cathedral and Piazza del Campo
- Cultural exploration in San Gimignano, known for its medieval towers and charming streets
Enjoy the rich history and beauty of these ancient Middle Age cities, surrounded by scenic views of the Tuscan countryside. This itinerary promises a perfect blend of indulging in world-class wines and experiencing the cultural heritage of Italy’s past.
Inclusions and Exclusions

Guests on the tour to San Gimignano and Siena can look forward to experiencing a variety of inclusions and exclusions that enhance their exploration of these historic Tuscan destinations. The table below outlines what is included and excluded in this exciting tour:
| Inclusions | Exclusions | Wine Tasting | Local Culture |
|---|---|---|---|
| Transport by air-conditioned minivan | Meals and personal expenses | Visit to a local winery for Chianti wine tasting | Immersive experiences in Siena and San Gimignano |
| Visit to a local winery | Tips and gratuities | Guided wine tasting session | Interaction with locals and artisans |
| Opportunity to purchase local wines | Discovering traditional Tuscan customs |
This tour offers a blend of enriching inclusions like wine tasting and visits to local wineries, coupled with exclusions that allow guests the freedom to explore and savor the local culture at their own pace.
Booking Information

Upon reserving a spot on the tour to San Gimignano and Siena, travelers will receive comprehensive booking information for their upcoming Tuscan adventure. The booking process is straightforward and user-friendly, ensuring a hassle-free experience. Payment options are flexible, with the choice to pay upfront or opt for the Reserve Now and Pay Later feature, adding convenience to the planning process.
- Clear and Simple Booking Process
- Flexible Payment Options
- Reserve Now and Pay Later Feature
Travel Tips
As travelers prepare for their Tuscan adventure to San Gimignano and Siena, practical travel tips can enhance their experience and make the most of their time exploring these ancient Middle Age cities.
When packing for this trip, essentials include comfortable walking shoes for exploring cobblestone streets, a hat and sunscreen for sunny days, and a camera to capture the picturesque landscapes and historic sites.
To fully immerse in the local culture, tasting the traditional Tuscan cuisine is a must. Indulge in the region’s famous dishes like ribollita (bread soup) and pici cacio e pepe (hand-rolled pasta with cheese and pepper) at authentic eateries. Remember to try the renowned Chianti wine along the way to complement your culinary journey through Tuscany.
- Florence: Duomo Cathedral Guided Tour
- Val DOrcia: Cheese and Wine Tasting Tour From Florence
- Florence: Skip-the-Line Uffizi Small Group Tour
- From Florence: Pisa Day Tour With Leaning Tower of Pisa
- Florence: Anish Kapoor Exhibition Ticket at Palazzo Strozzi
- Florence: Accademia Gallery Tour With Skip-The-Line Tickets
Frequently Asked Questions
Are Children Allowed on the Tour?
Children are welcome on the tour, participating in child-friendly activities and enjoying tour flexibility. There are no specific age restrictions, and the group dynamics accommodate a maximum of 8 people per booking, ensuring a personalized experience.
Is There a Dress Code for the Winery Visit?
For the winery visit, guests should wear smart casual attire. This respects the winery etiquette and showcases cultural appreciation. Understanding the historical significance enriches the experience. Dress comfortably yet elegantly to honor the tradition and setting.
Can Special Dietary Restrictions Be Accommodated During the Wine Tasting?
Special dietary restrictions can be accommodated during the wine tasting. Vegetarian options, vegan alternatives, and considerations for allergies and food preferences are available. The tour ensures a delightful experience for all participants.
Is There a Restroom on the Minivan for Long Drives Between Locations?
Yes, there is a restroom on the minivan for long drives between locations, ensuring passenger comfort and convenience. Restroom breaks are strategically planned to minimize travel discomfort, offering a pleasant touring experience.
Are There Any Specific Souvenirs or Local Products Recommended to Purchase During Free Time in Siena and San Gimignano?
During free time in Siena and San Gimignano, visitors can discover local products like handmade crafts, traditional ceramics, specialty foods, and unique jewelry. These souvenirs capture the essence of Tuscany’s rich cultural heritage.
The Sum Up
Experience the magic of Tuscany on the ‘Small Group Tour: Classico Wines With Ancient Middle Age Cities.’
From savoring the flavors of Chianti wine to exploring the historic towns of San Gimignano and Siena, this tour offers a perfect blend of culture, history, and gastronomy.
With a private driver to guide you through the stunning landscapes, this journey promises an unforgettable adventure through the heart of Italy’s wine country.
Book your spot today and embark on a truly enchanting experience.
More Wine Tours in Florence
- Chianti Rufina Lunch and Wine Tasting Experience
- Tuscany & Umbria-food and wine tour: flavors of Italys heartland
- Florence Golf Cart Tour & Pasta Cooking Class with Unlimited Wine
- Florence Pasta Cooking Class with Unlimited Wine
- Florence Wine Window Private Tour
- Florence Uncorked A Journey Through Wine and Time
More Tour Reviews in Florence
- 3H Semi Private Guided Tour to Uffizi Gallery & Accademia Gallery
- From Florence: 2-Day Combo Tour to Pisa, Cinque Terre & Tuscany
- Michelangelos David & Medici Treasures Accademia Gallery Tour
- Private Day Trip from Florence to Siena and San Gimignano
- Guided Tour of Boboli Gardens: Florences Living Masterpiece
- Florence Guided Tour Accademia, Dome climb and Cathedral Museum
Looking for something different? Other Florence activities we've written about
- 3H Semi Private Guided Tour to Uffizi Gallery & Accademia Gallery
- From Florence: 2-Day Combo Tour to Pisa, Cinque Terre & Tuscany
- Michelangelos David & Medici Treasures Accademia Gallery Tour
- Private Day Trip from Florence to Siena and San Gimignano
- Guided Tour of Boboli Gardens: Florences Living Masterpiece
- Florence Guided Tour Accademia, Dome climb and Cathedral Museum
- Michelangelos David: Skip-the-Line Accademia Gallery Ticket
- Florence: Duomo Cathedral Timed Entry with Host
- Florence Duomo Tour with Dome Climb and Skip the Line Ticket
- Motorcycle tour through the secret emotions of Tuscany
- Explore Florence with Electric Mini Car Night Tour
- Florence David First Viewing & Duomo with Terrace VIP Access Tour
