This full-day tour from Florence promises an immersive exploration of Tuscany’s captivating towns and landscapes. Visitors will discover the medieval charms of Siena, the acclaimed wines of Montepulciano, and the picturesque hilltop town of Cortona. With a guided visit to a 13th-century cellar for wine and cheese tasting, and a light lunch at a local winery, the tour provides an authentic taste of Tuscany’s rich cultural heritage. Whether you’re a history buff, a wine enthusiast, or simply seeking to be enchanted by the region’s timeless beauty, this experience won’t disappoint. But there’s more to uncover about this captivating journey through the heart of Tuscany.
Key Points
- Explore the medieval town of Siena, a UNESCO World Heritage site, and marvel at its well-preserved historic center.
- Visit the picturesque hilltop town of Cortona, featured in the movie ‘Under the Tuscan Sun,’ and enjoy the stunning views.
- Savor the renowned Montepulciano DOCG wine and local cheeses during a tasting in a 13th-century cellar.
- Indulge in a light lunch at a local winery, accompanied by additional Montepulciano wine tastings.
- Discover the Val d’Orcia region, accessible from Florence via a private 8-seater mini van, known for its breathtaking landscapes.
Tour Overview

This full-day tour allows visitors to explore the charming Tuscan towns of Siena, Montepulciano, Cortona, and the Val d’Orcia region, accessible from Florence via a private 8-seater mini van.
The tour lasts 9-11 hours and highlights locations featured in popular films like Gladiator, Under the Tuscan Sun, and Letters to Juliet.
Participants will savor a wine and cheese tasting in a 13th-century cellar, enjoy a light lunch with wine tasting at a local winery, and have free time to wander the picturesque towns at their own pace.
A knowledgeable tour leader provides local insights and information throughout the day.
The tour isn’t suitable for those with mobility issues, and dietary needs should be communicated in advance.
You can also read our reviews of more tours and experiences in Florence.
Itinerary

The tour begins with a visit to the medieval town of Siena, where participants can explore the city’s iconic sights.
After Siena, the group travels to Montepulciano, known for its renowned Montepulciano DOCG wine. Here, they’ll enjoy a wine and cheese tasting in a 13th-century cellar, followed by a light lunch at a local winery with additional wine tasting.
The final stop is the picturesque hilltop town of Cortona, where participants can wander at their own pace and take in the breathtaking views.
Throughout the day, the tour leader provides local insights and information to enhance the overall experience.
Highlights of the Tour

The tour offers several highlights that showcase the best of Tuscany’s medieval towns and idyllic countryside. Visitors can marvel at Siena’s remarkably well-preserved historic center, a UNESCO World Heritage Site known for its striking cathedral and Piazza del Campo.
In Montepulciano, they’ll enjoy a wine tasting and light lunch at a local winery, sampling the renowned Montepulciano DOCG wine.
The picturesque hilltop town of Cortona, featured in movies like ‘Under the Tuscan Sun,’ provides ample opportunity for exploration and photography.
Throughout the day, the tour leader shares local insights and information, ensuring travelers get the most out of this immersive Tuscan experience.
Wine and Cheese Tasting

A highlight of the tour is the wine and cheese tasting at a 13th century cellar in Montepulciano. Visitors can sample the renowned Montepulciano DOCG wine and pair it with local cheeses in this historic setting.
The tasting takes place at a family-owned winery, giving guests an authentic taste of Tuscan winemaking and cuisine. During the tasting, the knowledgeable staff educate participants about the region’s winemaking traditions and the unique flavors of the Montepulciano grape.
This experience provides a delightful opportunity to savor the rich cultural heritage of Tuscany through its world-class wines and artisanal cheeses, all in a picturesque and atmospheric 13th century cellar.
More Great Tours NearbyLight Lunch at a Winery

After the wine tasting, participants enjoy a light lunch at a local winery, where they can savor the flavors of Tuscany. The lunch showcases regional dishes and is accompanied by additional tastings of the Montepulciano DOCG wine.
This experience provides an opportunity for guests to enjoy the culinary traditions of the area while surrounded by the picturesque vineyards and historic winery setting.
The lunch menu may feature a selection of local cheeses, cured meats, fresh bread, and seasonal vegetables.
Guests can enjoy a glass of the renowned Montepulciano wine while taking in the serene winery atmosphere.
The light meal allows participants to recharge before continuing their exploration of the Tuscan towns.
Servers provide insights into the winery’s history and the traditions behind the regional specialties.
This lunch stop offers a perfect blend of food, wine, and scenery, embodying the essence of Tuscany.
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Exploring the Towns

Following the light lunch at the local winery, guests can now explore the charming Tuscan towns on the itinerary.
Siena, a medieval gem, offers a chance to wander its picturesque streets and admire the stunning Duomo cathedral.
Montepulciano, known for its renowned DOCG wine, allows visitors to stroll its historic center and sample the region’s world-class vintages.
The hilltop town of Cortona, featured in several popular films, captivates with its ancient architecture and panoramic vistas over the Val d’Orcia valley.
Guests can enjoy the rich history, culture, and flavors of these quintessential Tuscan destinations, discovering the beauty that has inspired artists and writers for centuries.
Tour Leader’s Insights

Throughout the tour, the knowledgeable tour leader provides guests with invaluable insights into the history, culture, and local traditions of the Tuscan destinations visited. Their expertise brings the stories of these charming towns to life, captivating the audience:
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Painting a vivid picture of Siena’s medieval legacy and the famous Palio horse race
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Explaining the winemaking traditions and unique terroir of Montepulciano’s celebrated DOCG wines
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Highlighting the artistic and architectural wonders of the picturesque hilltop town of Cortona
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Sharing personal anecdotes and little-known facts that bring the Val d’Orcia region to life
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Offering insider tips on the best local eateries, shops, and hidden gems to explore during free time
Booking and Logistics

To book the tour, customers can reserve their spot and pay later. The meeting point may vary depending on the option selected, so participants should check the details of their booking. The tour is not suitable for those with mobility impairments, and guests are encouraged to inform the provider of any dietary needs.
| Booking Details | |
|---|---|
| Price | From $237.88 per person |
| Reservation | Reserve now and pay later |
| Cancellation | Free cancellation up to 24 hours in advance |
The tour offers a full-day exploration of Tuscan towns, including Siena, Montepulciano, Cortona, and the Val d’Orcia, with highlights from popular films. Guests can enjoy wine and cheese tastings, a light lunch, and free time to explore the towns at their leisure.
Frequently Asked Questions

Can the Tour Accommodate Vegetarian or Vegan Dietary Needs?
Yes, the tour provider can accommodate vegetarian and vegan dietary needs. Participants must inform the provider of any dietary requirements when booking the tour.
Is There an Option to Extend the Tour Duration?
Yes, the tour operator offers an optional extended tour that lasts 11-13 hours. This extended option allows more time to explore the picturesque Tuscan towns and visit additional sites along the way.
Can the Tour Pick up From Locations Outside the Designated Meeting Point?
The tour provider can accommodate pickups from locations outside the designated meeting point, but this may incur an additional fee. Participants should inquire about this option when booking to ensure proper arrangements can be made.
What Is the Maximum Group Size for This Tour?
The tour is conducted in a private 8-seater mini van, so the maximum group size is 8 participants. The tour provider does not accommodate larger groups for this day trip to Tuscan towns.
Are There Any Discounted Rates Available for Children or Seniors?
The tour provider offers discounted rates for children under 12 and seniors over 65. Specific pricing details can be found when booking the tour. Travelers should inquire about any age-based discounts at the time of reservation.
From Florence: Siena, Cortona, Montepulciano & the Val D’orcia
Recap
This full-day tour from Florence offers an immersive exploration of Tuscany’s charming towns and cultural heritage.
Visitors can savor the region’s renowned wines and cuisine, marvel at its stunning architecture and landscapes, and gain insider insights from an expert guide.
Whether you’re a first-time or seasoned traveler, this tour promises an authentic Tuscan experience you won’t soon forget.
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