Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - Wine Tasting at a Renowned Chianti Winery

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme

Experience Tuscany’s highlights on a small-group day trip from Montecatini Terme, visiting San Gimignano, Siena, and Chianti with wine tastings and expert guides.

The Siena, San Gimignano, and Chianti Wine Small Group Tour from Montecatini Terme offers a full-day exploration of some of Tuscany’s most beloved towns for $184.61 per person. Spanning approximately 10 hours, this tour combines scenic drives, guided visits, and tastings, making it a practical choice for those who want to see Tuscany without the hassle of organizing transport or multiple bookings.

The tour departs from Viale Giuseppe Verdi at 8:45 AM and includes transport by air-conditioned bus or minivan, a guided wine tasting, and tastings of bruschetta, pecorino cheese, and extra-virgin olive oil. With a high satisfaction rating of 4.7 out of 5 from 45 reviews and 96% recommending the experience, it’s clear many travelers find this tour offers good value and memorable moments.

While the tour does not include Siena’s local guide (which costs an additional €25), the tour leader provides a wealth of historical and cultural insights, often praised for their knowledge and friendly demeanor. The small group size—capped at 25 participants—ensures a more intimate experience, with plenty of opportunities for questions and personal attention.

Key Points

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - Key Points

  • Full-day trip exploring San Gimignano, Siena, and Chianti from Montecatini Terme
  • Price of $184.61 includes transport, guided wine tasting, and local tastings
  • Approximately 10 hours from departure to return
  • Small group size enhances comfort and interaction
  • Highlights include medieval towers, Piazza del Campo, and Chianti wine estate
  • Optional Siena guide available for €25 on the day

Starting Point and Schedule of the Tour

The adventure begins at Viale Giuseppe Verdi in Montecatini Terme promptly at 8:45 AM. The tour stays consistent, returning to the same meeting point at the end of the day, making logistics straightforward. The timing allows for a leisurely yet structured exploration of each location, with enough free time to soak in the atmosphere and enjoy the local tastes.

Discovering San Gimignano’s Medieval Skyline

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - Discovering San Gimignano’s Medieval Skyline

San Gimignano is the first major stop, famous for its medieval towers that dominate the skyline. Travelers get about 1 hour and 30 minutes to wander these ancient streets, admire the stone towers, and browse ceramic shops. A highlight is the chance to savour the best gelato at the very spot where the film “Tea with Mussolini” was shot.

Visitors can also opt to visit the local museum, which features a replica of a 14th-century tower, offering deeper insight into the town’s history. The town’s lively atmosphere and picturesque setting make it a favorite for photo opportunities and leisurely exploration.

Wine Tasting at a Renowned Chianti Winery

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - Wine Tasting at a Renowned Chianti Winery

Between the medieval towns, the tour visits a famous Chianti wine cellar where a guided sampling takes place. The winemaker introduces the group to Vernaccia, a Chianti white wine, as well as the classic Chianti DOCG. These are paired with bruschettas and pecorino cheese, making for a delightful experience of local flavors.

This tasting session lasts about 1 hour and 30 minutes, providing a relaxed setting to learn about wine production and enjoy some of Tuscany’s best offerings. The estate’s setting offers scenic views of vineyards and rolling hills, adding to the appeal.

Exploring Siena’s Historic Center and Piazza del Campo

The journey continues to Siena, a medieval hilltop town built among scenic hills. Here, the tour leader guides visitors through narrow medieval streets to reach Piazza del Campo, one of Europe’s most remarkable squares with a shell-shaped design. The square is the site of the famous Palio di Siena horse race and is surrounded by colorful buildings.

Visitors are given around 3 hours to explore independently. While the guided tour of Siena requires an additional €25, the free time allows for visiting Siena Cathedral, an architectural masterpiece with monumental significance. The square itself offers excellent photo opportunities and a chance to soak in the lively atmosphere.

Transport and Group Size Benefits

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - Transport and Group Size Benefits

The air-conditioned bus or minivan provides smooth and comfortable travel between towns, removing the stress of driving or navigating public transport. The small group setup—capped at 25 travelers—means that the experience feels more personal, with guides able to focus on individual questions and interests. This setup also allows for more flexible pacing and spontaneous stops.

The Rich Tasting Experience in Chianti

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - The Rich Tasting Experience in Chianti

The Chianti wine estate visit is a highlight, often praised for its quality of wine, cheeses, and olive oils. Tastings include bruschettas with pecorino cheese and extra-virgin olive oil, showcasing authentic Tuscan flavors. Visitors appreciate the opportunity to learn about wine and food pairing directly from the winemaker, often described as knowledgeable and engaging.

The Role of the Tour Guide

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme - The Role of the Tour Guide

The tour leader is frequently praised for their expertise, professionalism, and friendliness. Reviews consistently mention Valerie or Valeria as outstanding guides who go out of their way to find special spots, provide umbrellas in case of rain, and answer questions thoroughly. Their engaging storytelling enhances the experience and makes the day more memorable.

Accessibility and Physical Requirements

While the tour involves walking on uneven surfaces, it’s not recommended for travelers with walking difficulties. The physicality required is moderate, mostly involving standing and strolling through towns. Travelers should have moderate physical fitness to fully enjoy the experience.

Flexibility and Cancellation Policy

Booking is flexible with free cancellation available up to 24 hours prior. This makes the tour a low-risk option for those uncertain about their plans. The minimum participant number is not specified, but if the threshold isn’t met, a full refund or alternative date is offered.

Who Will Love This Tour

This experience suits history and wine enthusiasts who enjoy small-group personalized visits. It’s ideal for those seeking a comprehensive day trip with scenic views, cultural highlights, and authentic tastings. It also appeals to travelers who prefer organized logistics and guided commentary without the stress of planning.

Limitations to Consider

The Siena guide is an optional add-on, which requires €25 paid on the day. Some participants wish for more time in San Gimignano, and the tour sequence (visiting San Gimignano first, Siena second) may not match everyone’s preferred order.

Siena, San Gimignano, and Chianti: A Practical Tuscany Day Trip

This small-group tour offers a well-rounded glimpse of Tuscany’s iconic towns, scenic landscapes, and culinary delights. Its value lies in the combination of guided visits, tastings, and scenic drives that weave together history, culture, and flavor.

The expert guides are a key strength, often praised for their knowledgeability and personable approach. The small group size ensures a more relaxed and engaging experience. However, the additional fee for Siena’s local guide might be a consideration for those who want a more in-depth tour of Siena’s treasures.

For those who want a convenient, well-paced tour with authentic tastings and picturesque stops, this experience fits confidently into a day dedicated to Tuscany’s classic sights. It’s especially suitable for first-time visitors or anyone looking for a stress-free way to explore the region’s highlights.

✨ Book This Experience

Siena, San Gimignano and Chianti Wine Small Group from Montecatini Terme



4.5

(45 reviews)

82% 5-star

“Excellent tour. Our tour guide Valerie was outstanding. She was very knowledgeable, professional and just a nice person. Towards the end of our tou…”

— Robert B, Featured

Frequently Asked Questions

Does the tour include hotel pickup?
No, the tour starts at Viale Giuseppe Verdi in Montecatini Terme.

Can I cancel the tour?
Yes, free cancellation is available up to 24 hours before the start time.

Is the Siena guide included?
No, the local Siena guide costs an additional €25 and is paid on the day.

What is the tour duration?
The tour lasts approximately 10 hours from departure to return.

What is included in the price?
The price covers transport, guided Chianti wine tasting, bruschettas, pecorino cheese, and olive oil tastings.

Are there any accessibility concerns?
The tour involves uneven surfaces and is not recommended for those with walking difficulties.

What makes this tour special?
The combination of scenic towns, small-group intimacy, authentic food and wine tastings, and expert guides makes it a memorable Tuscany experience.

Can children participate?
Yes, children under 18 are free of charge for tastings but should be aware of the minimum drinking age of 18.

What is the recommended booking window?
Most bookings are made 67 days in advance, but the tour remains flexible with last-minute options available.

What are the main highlights?
San Gimignano’s medieval towers, Piazza del Campo in Siena, and the Chianti wine estate are the tour’s standout features.