Tuscany’s timeless allure beckons travelers to explore its historic towns and savor its renowned wines. This tour from Florence offers an immersive experience, guiding visitors through the charming streets of Siena and San Gimignano before indulging in a Chianti wine tasting at a family-owned winery. From admiring the iconic Piazza del Campo to marveling at San Gimignano’s iconic skyline, this small-group excursion promises an enriching peek into the region’s cultural and culinary heritage. With personalized attention and authentic Tuscan cuisine, the tour sets the stage for an unforgettable journey that leaves one eager to discover more of Tuscany’s captivating allure.
Key Points
- Comprehensive day tour from Florence to explore the historic cities of Siena and San Gimignano, including a winery visit and Tuscan lunch in the Chianti region.
- Guided tour of Siena’s iconic Cathedral and Piazza del Campo, a UNESCO World Heritage site known for its medieval architecture and cultural heritage.
- Discover the medieval towers and well-preserved architecture of San Gimignano, earning it the nickname ‘Medieval Manhattan’.
- Enjoy a wine tasting and traditional Tuscan lunch at a family-owned winery in the Chianti region, immersing in the local food and wine culture.
- Roundtrip transportation from Florence provided, with an English-speaking guide leading the small group of 16 or fewer travelers for a personalized experience.
More tours and experiences nearby.
Tour Overview
The tour begins with a visit to the historic city of Siena, where participants can explore the iconic Siena Cathedral and the city’s picturesque main square.
Afterward, the journey continues to the charming town of San Gimignano, known as the ‘Medieval Manhattan‘ for its distinctive skyline of medieval towers.
Along the way, travelers will enjoy round-trip transportation from Florence in a comfortable, air-conditioned vehicle.
The tour is led by an English-speaking guide who provides insightful commentary throughout the day.
The maximum group size is 16, ensuring a personalized experience.
Siena Exploration
Upon arrival in Siena, the tour begins with ample time to explore the city’s historic center and iconic Siena Cathedral.
Participants can wander through the picturesque Piazza del Campo, the city’s main square and a UNESCO World Heritage site, which hosts the famous Palio horse race twice a year.
Inside the Cathedral, visitors can admire the stunning Romanesque-Gothic architecture and intricate marble floors.
The Cathedral’s façade is a masterpiece of Italian Gothic style, featuring ornate columns, arches, and intricate carvings.
Travelers can also visit the city’s medieval alleys and charming shops, seeing Siena’s rich cultural heritage and picturesque atmosphere.
San Gimignano Visit
After exploring the historic center of Siena, the tour continues to the charming medieval town of San Gimignano, known as the ‘Medieval Manhattan‘ for its distinctive skyline of towering stone structures.
Visitors will have free time to wander the narrow streets, admire the well-preserved architecture, and visit the town’s iconic medieval towers.
The group will also have the opportunity to explore the central Piazza della Cisterna, a picturesque square surrounded by historic buildings.
Throughout the visit, the guide will share insights into San Gimignano’s rich history and cultural significance.
This quaint hilltop town offers a unique glimpse into Tuscany’s medieval past, making it a highlight of the day’s itinerary.
Wine and Culinary Experience
Following the visit to San Gimignano, the tour heads to a family-owned winery in the renowned Chianti region, where guests can indulge in a wine tasting and traditional Tuscan lunch.
At the winery, travelers learn about the time-honored winemaking process and have the opportunity to sample a variety of Chianti grape varietals.
The tasting is accompanied by a mouthwatering Tuscan lunch featuring locally-sourced ingredients.
Guests savor the flavors of the region, from the robust red wines to the homemade dishes.
This immersive culinary experience provides a glimpse into the rich food and wine culture of Tuscany, leaving a lasting impression on the palate and memory.
Inclusions
The tour includes round-trip transportation from Florence in a comfortable, air-conditioned vehicle.
Guests will visit the historic city of Siena, where they can explore the iconic Siena Cathedral at their own pace (entrance ticket not included).
The journey then takes them to a renowned family-owned winery in the Chianti region, where they’ll enjoy a guided wine tour and tasting, as well as a traditional Tuscan lunch.
Finally, the tour culminates with a visit to the picturesque town of San Gimignano, known as the ‘Medieval Manhattan’ of Tuscany.
The tour is led by an English-speaking guide and is limited to a maximum of 16 travelers, ensuring a personalized experience.
Meeting and Logistics
The tour meeting point is at V.le Filippo Strozzi, 1, 50129 Firenze FI, Italy. Participants should arrive 10 minutes early and look for a representative holding a sign with The Tour Guy.
The tour starts at 9:30 am and returns to the same meeting point at the end.
Participants don’t need to worry about transportation, as round-trip transportation from Florence in an air-conditioned vehicle is included.
The tour isn’t wheelchair accessible, but infant seats are available upon request with 72 hours’ notice.
Pregnant travelers and those with lower fitness levels may want to reconsider, as the tour requires a moderate level of physical activity.
Pricing and Cancellation
The tour is priced from $109.95 per person and includes a Lowest Price Guarantee.
Customers can take advantage of free cancellation up to 24 hours before the tour starts, providing them with flexibility in their travel plans.
Booking the tour allows travelers to reserve their spot now and pay later, which can be convenient for managing finances.
The pricing is competitive, and customers can be confident they’re getting the best deal.
This tour offers an exceptional value, with round-trip transportation, a wine tasting, a traditional Tuscan lunch, and guided exploration of iconic Tuscan destinations all included in the price.
Travelers won’t want to miss out on this opportunity to experience the best of Tuscany.
Here's a few more nearby tours and experiences we think you'll like.
- Florence Pizza or Pasta Class With Gelato Making at a Tuscan Farm
- Small-Group Wine Tasting Experience in the Tuscan Countryside
- Cooking Class and Lunch at a Tuscan Farmhouse With Local Market Tour From Florence
- Chianti Safari: Tuscan Villas With Vineyards, Cheese, Wine & Lunch From Florence
- Florence Vespa Tour: Tuscan Hills and Italian Cuisine
- Uffizi Gallery Small Group Tour With Guide
Frequently Asked Questions
Can I Bring My Own Food and Drinks on the Tour?
No, travelers cannot bring their own food and drinks on the tour. The tour includes a traditional Tuscan lunch at a family-owned winery, as well as wine tastings, so bringing outside items is not permitted.
Are There Any Discounts Available for Students or Seniors?
The tour company does not offer any discounts specifically for students or seniors. However, they suggest checking their website or contacting customer service to inquire about any current promotions or sales that may be available.
Can I Extend the Tour Duration or Add Additional Stops?
While the standard tour duration and stops cannot be extended, travelers can inquire about customizing the experience to meet their needs. The tour provider may be able to accommodate special requests for an additional fee.
What Is the Dress Code for the Tour?
The tour does not have a strict dress code, but comfortable, weather-appropriate clothing and walking shoes are recommended. Guests should dress for a day of sightseeing and tasting in a casual, relaxed manner.
Are Photography and Video Recording Allowed During the Tour?
Photography and video recording are generally allowed during the tour. Guests are encouraged to capture the scenic landscapes, historic sites, and winery activities to document their experience. However, guests should be respectful and avoid disrupting the tour.
Not for you? Here's more of our most recent tour reviews happening neaby
- Florence: Firenze Card Official Museum City Pass
- Private Transfer From Florence to Venice
- 5 Mornings or 5 Afternoons Sculpture in Clay Guided Workshop
- Tour to Pisa and Lucca in English Español and Purtuguês
- Chianti Day Trip From Florence
- Florence: Uffizi Gallery Small Group With Entrance Tickets
- Florence: Uffizi and Accademia Gallery Skip-the-Line Ticket
- Private Walking Tour of Uffizi Gallery
- Florence Card and Exclusive Private Tour on Michelangelo Genius
- Explore Cinque Terre From Florence
- Private Tour to Pisa, San Gimignano and Siena From Florence
- Uffizi Gallery Small Group Tour: Discover Uplifting Masterpieces
- PISA HALF-DAY: From Florence by Minivan Including Leaning Tower Ticket
- Private Transfer From Florence City Centre to Pisa Airport
- Unique Tuscany Experience in 1 Week With the Locals
Recap
This Tuscan tour offers a captivating blend of historic cities, medieval architecture, and renowned wine tasting.
Travelers will be immersed in the cultural and culinary delights of Siena, San Gimignano, and Chianti, making it an unforgettable experience.
The small-group format ensures personalized attention, allowing visitors to deeply engage with the region’s rich heritage.
This day trip from Florence is a must-do for anyone seeking to discover the essence of Tuscany.