Tuscany’s charming countryside beckons visitors to explore its timeless treasures. This immersive day tour from Florence promises an unforgettable journey through the region’s medieval gems. Travelers will discover the architectural splendor of Siena’s iconic cathedral, stroll the picturesque streets of San Gimignano, and indulge in the renowned culinary and viticultural traditions of Chianti. Led by an expert guide, the intimate group experience offers a seamless way to uncover the essence of this captivating corner of Italy. But what secrets might these historic towns hold, and what unexpected delights await along the way?
Key Points

- Immersive day tour from Florence to the Tuscan countryside, including visits to the medieval towns of Siena and San Gimignano.
- Guided walking tours of Siena’s stunning cathedral and the charming, UNESCO-listed village of San Gimignano.
- Gourmet lunch and wine tasting at a family-run farm in the Chianti region, showcasing the region’s culinary delights.
- Comprehensive overview of Tuscan history, architecture, and cuisine, led by an expert English-speaking guide.
- Intimate group experience limited to 14 people or fewer, ensuring a personalized and unforgettable journey through the Tuscan landscape.
Tour Overview

This immersive day tour whisks visitors from Florence into the picturesque Tuscan countryside, offering an intimate group experience limited to 14 people or fewer guided by an expert English-speaking professional.
The tour provides a rundown of the region, stopping at the remarkably well-preserved medieval town of Siena, the UNESCO-listed storybook village of San Gimignano, and the gourmet paradise of Chianti.
Along the way, guests can enjoy expertly guided walking tours, a delectable seasonal lunch, and wine tastings at a family-run farm.
With a designated professional driver providing safe transport, this tour delivers a seamless and unforgettable journey through the heart of Tuscany.
Ready to swirl and sip more? More wine adventures we love in Florence
Destination Highlights
The tour’s destination highlights include the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race.
Plus, visitors will explore the UNESCO World Heritage-listed storybook village of San Gimignano, renowned for its iconic skyline of medieval towers.
Lastly, the tour delves into the gourmet paradise of Chianti, where guests can indulge in a seasonal lunch and wine tastings at a family-run farm.
These three distinct destinations offer a rich tapestry of Tuscan culture, history, and culinary delights, providing a truly immersive experience for travelers seeking to discover the essence of this captivating region.
Siena: Magnificent Cathedral and Palio

Siena’s magnificent cathedral stands as a testament to the town’s rich history, its striking white and green marble façade visible from afar. Within its walls, visitors can marvel at the intricate Gothic architecture and ornate interiors, including the renowned Piccolomini Library adorned with stunning frescoes. But Siena’s most famous tradition is the Palio, a thrilling horse race held twice a year in the town’s iconic shell-shaped Piazza del Campo. Jockeys representing the city’s 17 contrade, or neighborhoods, compete in a no-holds-barred race around the piazza, captivating spectators with their speed, skill, and passion.
| Siena Cathedral | Palio Horse Race |
|---|---|
| Gothic Architecture | Twice Yearly Event |
| Striking Façade | 17 Neighborhood Teams |
| Piccolomini Library | Intense Competition |
San Gimignano: Storybook Village

A captivating UNESCO World Heritage site, San Gimignano’s iconic skyline of towering medieval stone keeps stands as a testament to the town’s illustrious past.
Wandering through its narrow, winding streets, visitors are transported back in time, marveling at the beautifully preserved architecture and the charming piazzas.
The town’s 14 remaining medieval towers, once symbols of wealthy families’ power and status, now offer panoramic views of the rolling Tuscan hills.
San Gimignano’s quaint, picturesque nature makes it a highlight of the day trip, with ample opportunities to sample local delicacies and the renowned Vernaccia white wine.
It’s easy to see why this storybook village is considered one of the must-see destinations in the Tuscan countryside.
Chianti: Gourmet Lunch and Wine

After exploring the medieval splendor of Siena and the storybook village of San Gimignano, the tour takes guests to the gourmet paradise of Chianti, where they’ll savor a seasonal, locally-sourced lunch paired with expertly selected wines at a family-run farm. The farm’s warm hospitality and idyllic setting provide the perfect backdrop for a true taste of Tuscan life. Guests will enjoy a multi-course feast featuring regional specialties, from handmade pasta to locally-sourced meats and vegetables. The wine tasting showcases the renowned Chianti varietals, with knowledgeable staff on hand to guide guests through the flavors and nuances of each vintage.
| Course | Wine Pairing | Ingredients |
|---|---|---|
| Handmade Pasta | Chianti Classico | Flour, Eggs, Tomatoes, Basil |
| Grilled Meats | Rosso di Montalcino | Beef, Pork, Seasonal Vegetables |
| Tiramisu | Vin Santo | Mascarpone, Espresso, Cocoa |
Here are more great tours and experiences we've reviewed in Florence
- Siena and San Gimignano: Small-Group Tour With Lunch From Florence
- Explore Chianti on Vespa: Tour, Guide & Lunch From Florence
- Chianti Wineries Tour With Tuscan Lunch and San Gimignano
- Essence of Chianti Small Group Tour With Lunch and Tastings From Florence
- Tuscany Day Trip From Florence: Siena, San Gimignano, Pisa and Lunch at a Winery
- Cooking Class and Lunch at a Tuscan Farmhouse With Local Market Tour From Florence
Included Activities

The tour includes expertly guided walking tours of the remarkably well-preserved medieval town of Siena and the storybook UNESCO World Heritage site of San Gimignano.
In Siena, you’ll stroll through the captivating streets and learn about its magnificent cathedral and the famous Palio horse race.
Then, in San Gimignano, you’ll wander the charming alleys and admire the town’s iconic towers that have earned it world-renowned status.
The day also includes a gourmet lunch and wine tasting at a family-run farm in the Chianti region, where you’ll savor local delicacies paired with the area’s renowned vintages.
It’s a well-rounded experience that showcases the best of Tuscany’s history, architecture, and culinary excellence.
Logistics

The tour meets at Piazza della Repubblica in Florence, with a start time of 8:30 AM. Small luxury minivans are used to transport guests to the city centers, as the tour is not wheelchair accessible.
| Meeting Point | Start Time | Accessibility |
|---|---|---|
| Piazza della Repubblica, Florence | 8:30 AM | Not wheelchair accessible |
The minivans offer a comfortable and efficient way to navigate the Tuscan countryside, allowing the group to fully enjoy the picturesque landscapes. This logistical approach ensures a seamless and enjoyable experience throughout the day’s activities.
Cancellation Policy

Cancellations up to 24 hours before the experience are eligible for a full refund. This flexible policy ensures that customers can book with confidence, knowing they won’t be penalized for last-minute changes in their plans.
The tour operator understands that unexpected events can arise, and they want to accommodate their guests as best they can. By offering this generous cancellation window, they’re demonstrating their commitment to providing a smooth and stress-free experience.
Customers can rest assured that their investment is protected, and they can focus on enjoying the incredible sights and flavors of Tuscany without worrying about potential financial losses. The cancellation policy is a thoughtful touch that adds to the appeal of this immersive tour.
Frequently Asked Questions
Do I Need to Bring My Own Water/Snacks for the Tour?
The tour includes a gourmet lunch and wine tasting, so you don’t need to bring your own water or snacks. You can simply enjoy the provided food and beverages during the day.
What Is the Dress Code for the Tour?
The tour has a casual dress code. Guests should wear comfortable walking shoes and dress for the weather, as the majority of the day is spent outdoors exploring the countryside. Formal attire is not required.
Can I Take Photos During the Guided Walking Tours?
Absolutely, guests are encouraged to take photos during the guided walking tours. The expert English-speaking guides will provide commentary and allow ample time for participants to capture the remarkable medieval architecture and scenic landscapes of Siena and San Gimignano.
Is There an Option to Extend the Tour Duration?
Yes, there is an option to extend the tour duration. According to the information provided, the standard tour is a full-day excursion, but customers can choose to customize their experience by adding extra time or activities to the itinerary.
Can I Request a Vegetarian or Gluten-Free Lunch?
Yes, the tour provider can accommodate vegetarian or gluten-free dietary needs for the included lunch. Travelers simply need to specify their dietary requirements when booking the tour. The provider will ensure a suitable meal is provided.
Recap
This immersive Tuscan tour offers an unparalleled opportunity to discover the region’s enchanting medieval towns, renowned culinary traditions, and renowned wineries.
Seamlessly blending iconic landmarks, charming streets, and exceptional local experiences, it’s a must for anyone seeking to truly enjoy the essence of Tuscany.
With an expert guide, intimate group size, and hassle-free logistics, this day trip provides an unforgettable journey through the picturesque Tuscan countryside.
More Lunch Experiences in Florence
- Florence: Accademia, Cathedral & Walking Tour with Lunch
- From Florence: Cooking Class & Lunch at Tuscan Farmhouse
- Tuscany: E-Bike Tour from Florence with Lunch
- Florence: Horse ride 3h and Wine Tasting&Lunch at a castle
- Florence Wine Tour with Traditional Lunch, Private Winery
- Florence: Pisa and Florence Day Trip with Lunch
More Wine Tours in Florence
- Florence: Great Chianti Wine and Olive Oil Trail with Lunch
- Private Tuscan Dinner and Wine Tasting from Florence
- Wine Tasting Experience in Florence city centre
- Florence: Chianti Classico Wine Region PRIVATE Tasting Trip
- ROMANTIC WINE TOUR FOR 2 – Wine Tour in Chianti (Tuscany)
- From Florence: Tuscany Wine & Food Tour with Guide
More Tour Reviews in Florence
Not for you? Here's more things to do in Florence we have recnetly reviewed
- Half-Day Tour from Florence: Chianti Colors & Flavors
- WONDERFUL TUSCANY: Siena, San Gimignano & Chianti Wine Tour
- Tuscany: Siena, San Gimignano and Chianti Wine Tour
- Historic Markets Food Tour and Cooking Class
- Michelangelo and Santa Croce Private Tour
- Florence: Custom Jewelry Making Experience
- Florence Sunset Tour: Silent Disco & Aperol Spritz
- Uffizi gallery: private guided tour priority ticket
- Siena Half-Day Tour from Florence
- The Tuscan Jewels: Private Full-Day Tour From Florence
- Small-Group Uffizi Museum and Leonardo Da Vinci Highlights
- Tuscany Florence day trip with Vinery Lunch from Rome
