Exploring the picturesque landscapes of Tuscany can be a delightful experience. This semi-private day trip from Florence offers a chance to discover the charming towns of Siena, Monteriggioni, and San Gimignano, as well as the renowned Chianti wine region. Visitors can expect an intimate tour with personalized attention, a traditional Tuscan lunch, and the opportunity to savor the renowned local wines and olive oils. Whether you’re a first-time visitor or a seasoned traveler, this curated excursion promises to immerse you in the beauty and flavors of this captivating region.
Key Points

- This is a day trip from Florence to the historic cities of Siena, Monteriggioni, and San Gimignano, as well as the scenic Chianti wine region.
- The tour offers personalized attention with a small group size of up to 8 travelers.
- Highlights include an orientation walk in Siena, a stop in Monteriggioni, free time in San Gimignano, and a wine and olive oil tasting at a local winery.
- The tour includes an authentic Tuscan lunch with dishes like lasagna, Ribollita soup, and Cantuccini biscuits.
- The tour starts and ends at a meeting point in Florence, with detailed information provided for participants.
Tour Overview

This day trip from Florence provides visitors with the opportunity to explore the historic towns of Siena, Monteriggioni, and San Gimignano, as well as the renowned Chianti wine region.
It is an ideal excursion for first-time visitors looking to cover multiple highlights in a limited time. The small group size, with a maximum of 8 travelers, ensures personalized attention from the guide.
Travelers can expect an orientation walk in Siena, a short stop in Monteriggioni, leisure time in San Gimignano, and a scenic drive through the Chianti countryside, culminating in a wine and olive oil tasting at a local winery.
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Highlights of the Itinerary

The day trip begins with an orientation walk through the historic center of Siena, allowing visitors to get their bearings and admire the city’s magnificent architecture. Travelers then make a short visit to the well-preserved medieval town of Monteriggioni, before spending an hour exploring the UNESCO-listed San Gimignano, famous for its iconic skyline of towers. The scenic drive through the Chianti wine region culminates in a tasting at a local winery, where guests sample a variety of Tuscan wines and extra virgin olive oils, complemented by an authentic regional lunch.
| Itinerary Highlights | |
|---|---|
| Siena Orientation Walk | Monteriggioni Visit |
| San Gimignano Exploration | Chianti Wine Tasting |
| Tuscan Lunch | Wine & Olive Oil Sampling |
Authentic Tuscan Lunch and Tastings

As part of the day trip, travelers are treated to an authentic Tuscan lunch that showcases the region’s rich culinary heritage.
The lunch includes:
- Antipasti Toscani, a selection of bruschetta, pecorino cheese, and Tuscan cured meats.
- Lasagna infused with the earthy flavors of truffle oil.
- A traditional Ribollita soup, a hearty blend of vegetables and bread.
The meal concludes with Cantuccini, the classic Tuscan almond biscuits.
Dietary options are available upon request, allowing guests to savor the flavors of Tuscany while accommodating their dietary needs.
Meeting Point and Logistics

The meeting point for this tour is Parcheggio Oltrarno, located in Piazza della Calza, Florence.
Guests are recommended to arrive at 8:45 am, as the tour departs promptly at 9:00 am. The tour ends back at the original meeting point.
This tour is not wheelchair accessible but is located near public transportation.
Participants should plan their travel accordingly to arrive on time and be prepared for the day’s activities.
Detailed meeting and departure information is provided to ensure a smooth start to the tour experience.
Traveler Feedback and Ratings

Feedback from previous travelers highlights the overall positive experience of this tour. The tour boasts an impressive 4.8 average rating based on 52 reviews.
Key highlights from traveler feedback include:
- Flexibility and knowledgeable guides who provide personalized attention in the small group setting.
- Enjoyable experiences, from the scenic Chianti drive to the wine and olive oil tastings.
- Some critiques mentioned van comfort and age diversity within the group tours, though these seem to be minor concerns.
With free cancellation available and a price of $263.98 per person, this tour appears to offer an excellent value for first-time visitors to Tuscany.
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Flexibility and Personalized Attention

Flexibility and personalized attention emerge as key highlights of this Tuscany tour.
With a maximum of 8 travelers, the small group setting allows for a more intimate and customized experience. The tour guides are attuned to the needs and interests of each guest, ensuring a tailored itinerary.
Whether it’s accommodating dietary restrictions or allowing for independent exploration, the tour demonstrates a commitment to flexibility. This attention to detail and personalization sets the experience apart, catering to the diverse preferences of first-time visitors to the region.
The intimate group size fosters a sense of exclusivity and allows for meaningful interactions throughout the day.
Exploring Siena, Monteriggioni, and San Gimignano

Siena, a historic medieval city, serves as the first stop on this captivating tour. Visitors embark on an orientation walk, seeing the city’s rich history and charming architecture.
The tour then continues to Monteriggioni, a well-preserved walled town with:
- Stunning medieval ramparts.
- A strategic location overlooking the Chianti countryside.
- A chance to explore the quaint streets and piazzas.
Finally, the journey leads to San Gimignano, renowned for its striking skyline of towering medieval stone buildings. Guests have an hour to wander at their own pace, discovering the town’s unique character and local artisanal offerings.
Scenic Drive Through the Chianti Wine Region

After exploring the historic towns of Siena and San Gimignano, the tour delves into the picturesque Chianti wine region.
Guests enjoy a scenic drive through the rolling hills blanketed with vineyards and olive groves. The guide provides commentary on the Chianti wine production and history of the area.
The highlight is a visit to a local winery where guests partake in a tasting of 7 Chianti wines and 3 extra virgin olive oils. They also sample 50-year-old balsamic vinegar, learning about the cultivation and production of these Tuscan specialties.
This immersive experience showcases the rich culinary heritage of the region.
Frequently Asked Questions
Is There Free Time Allotted for Shopping or Independent Exploration?
Yes, the tour includes free time for independent exploration in Siena and San Gimignano, allowing travelers to shop, sightsee, or dine at their own pace during the day trip.
What Is the Group Size Ratio of Guide to Travelers?
The tour has a maximum group size of 8 travelers, ensuring a small group setting with personalized attention from the guide. The guide-to-traveler ratio is not explicitly stated, but the small group size suggests a favorable ratio for a personalized experience.
Can the Tour Be Customized to Accommodate Specific Dietary Needs?
The tour accommodates dietary restrictions upon request, including vegetarian, vegan, and gluten-free options for the included Tuscan lunch and wine and olive oil tasting. Guests can communicate their needs at the time of booking.
Are Headsets Provided for Better Audibility During the Tour?
The tour provides headsets for better audibility during the guided portions. This ensures travelers can clearly hear the guide’s commentary throughout the day, enhancing the overall experience. Dietary requests can also be accommodated upon advance notice.
Is There an Option to Extend the Tour Duration for Additional Activities?
The tour does not offer an option to extend the duration. However, if travelers wish to add more activities, they can consider booking an entirely separate tour with a longer itinerary or inquire about customized options with the tour provider.
The Sum Up
This semi-private tour from Florence offers an exceptional opportunity to experience the stunning Tuscan countryside, historic towns, and world-renowned wine region. Highlights include an orientation walk in Siena, a stop in Monteriggioni, exploration of San Gimignano’s iconic towers, and a delightful wine and olive oil tasting paired with a traditional Tuscan lunch, creating an unforgettable culinary experience.
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