Tuscany’s charming hilltop villages offer a captivating escape from the bustle of Florence. This day trip whisks travelers through the region’s picturesque landscapes, immersing them in the traditions and flavors that have defined this corner of Italy for centuries. From the artistic legacy of Cortona to the renowned wines of Montepulciano and Montalcino, each destination promises an immersive cultural experience. Whether you’re a seasoned explorer or first-time visitor, this tour unveils the essence of Tuscany’s timeless allure.
Key Points
- A full-day tour from Florence visiting the historic hilltop towns of Cortona, Montepulciano, and Montalcino, known for their stunning landscapes and renowned wine production.
- Guided experiences include a live ceramic demonstration in Cortona, wine tastings in Montepulciano and Montalcino, and free time to explore the charming medieval centers.
- Explore the UNESCO World Heritage Site of Val d’Orcia, renowned for its iconic cypress trees and picturesque rolling hills.
- Flexible booking options with free cancellation and English-speaking guide support throughout the day.
- Included transportation, lunch, and assistance make this an easy and convenient way to discover the highlights of southern Tuscany.
Tour Overview
This day trip from Florence provides an opportunity to explore three captivating destinations in Tuscany: Cortona, Montepulciano, and Montalcino.
The 11-hour small group experience is led by an English-speaking guide. Participants can enjoy free cancellation up to 24 hours in advance and flexible booking to pay later.
Key highlights include a live ceramic demonstration in Cortona, wine tastings in Montepulciano and Montalcino, and free time to discover the historic centers.
Transport, assistance, and lunch are included, making this a convenient and immersive way to discover the best of the Tuscan countryside.
Looking for more options in Montalcino? We've reviewed plenty of other experiences.
Destination: Cortona
Why does Cortona captivate visitors? This hilltop village boasts Etruscan roots and charming historic walls. During the tour, guests witness a live ceramic decoration demonstration showcasing the region’s traditional craftsmanship.
| Cortona Highlights |
| — | — | — | — |
| Etruscan Roots | Historic Walls | Ceramic Demonstration | Picturesque Views |
| The town dates back to the Etruscan era, offering a glimpse into ancient Tuscan history. | Stroll along the well-preserved medieval walls surrounding the town’s center. | Observe local artisans creating and decorating ceramics using traditional techniques. | Take in panoramic vistas of the surrounding countryside from Cortona’s elevated perch.
The combination of cultural heritage, artisanal experiences, and stunning vistas make Cortona a must-see destination on this Tuscan day trip.
Destination: Montepulciano
After exploring the charming Etruscan town of Cortona, the tour moves on to the Renaissance gem of Montepulciano.
Famous for its architecture, this hilltop town offers:
-
A guided tasting of Nobile di Montepulciano wine in an underground cellar
-
Free time to wander the historic center and enjoy lunch
-
Impressive Renaissance buildings and churches to admire
-
Opportunities to purchase local wines and products for worldwide delivery
-
Stunning views over the Val d’Orcia, a UNESCO World Heritage Site.
Destination: Val D’orcia
From Montepulciano, the tour ventures into the picturesque Val d’Orcia, a UNESCO World Heritage Site renowned for its rolling hills, winding roads, and iconic cypress trees.
Visitors will be captivated by the valley’s stunning landscapes, which have inspired artists and filmmakers for centuries. The region boasts a rich cultural heritage, with charming medieval towns and historic vineyards producing renowned Tuscan wines.
As the tour explores this idyllic corner of Tuscany, travelers will have the opportunity to soak in the serene atmosphere and appreciate the area’s natural beauty.
More Great Tours NearbyDestination: Montalcino
The next stop on the tour is the renowned town of Montalcino, famous worldwide for its production of the exceptional Brunello di Montalcino wine.
Visitors will have the chance to visit a local winery and taste both the acclaimed Brunello and its younger sibling, Rosso di Montalcino.
Visitors can sample the renowned Brunello and its younger sibling, Rosso di Montalcino, at a local winery.
The experience includes:
-
A guided tour of the winery’s underground cellars
-
Sampling of the region’s renowned red wines
-
Learning about the unique terroir and production methods
-
Purchasing wines for delivery back home, if desired
-
Free time to explore Montalcino’s historic streets and landmarks.
- Picnic in the Organic Vineyards of Brunello
- Montalcino: Vineyard Picnic With a Bottle of Wine
- Castiglion Fiorentino: Wine Flight & Charcuterie Board
- Montalcino: Walk of Wine Tour With Vertical Brunello Tasting
- Picnic in Vineyards With a Bottle of Rosso Di Montalcino
- Day Trip to Montalcino With Wine Tasting From Rome
Activities
Visitors have the opportunity to participate in a variety of engaging activities throughout the day trip. The highlights include wine tastings at local wineries, where they can sample the renowned Nobile di Montepulciano and Brunello wines. Plus, the group will witness a live ceramic decoration demonstration, showcasing the traditional craftsmanship of the region. During the free time in Montepulciano’s historic center, guests can explore the charming streets, browse local shops, and enjoy a leisurely lunch. This diverse array of activities allows travelers to enjoy the rich cultural heritage and culinary delights of the Tuscan countryside.
| Activity | Location | Duration |
| — | — | — |
| Wine Tasting | Montepulciano | 1 hour |
| Wine Tasting | Montalcino | 1 hour |
| Ceramic Demonstration | Cortona | 30 minutes |
| Free Time | Montepulciano | 1.5 hours |
| Lunch | Montepulciano | 1 hour |
Inclusions
This day trip includes several key inclusions to enhance the overall experience.
Visitors will be transported by an air-conditioned mini coach, with assistance available at the meeting point. A licensed tour escort will guide the small group, providing expertise and insights throughout the journey.
Visitors will be transported by an air-conditioned mini coach, with a licensed tour escort guiding the small group throughout the journey.
Wine tastings at local wineries allow guests to sample the renowned Nobile di Montepulciano and Brunello wines. Plus, the tour includes:
-
Ceramic demonstration showcasing traditional craftsmanship
-
Free time for lunch and exploration in Montepulciano’s historic center
-
Opportunities to purchase local wines and products, with worldwide delivery available
-
Lunch
Important Information
Meeting point for the tour is at the end of the ramp connecting with the railway station, identifiable by an assistant in blue clothing with Caf Tour & Travel – Gray Line logos. To make the most of the day, attendees should wear comfortable shoes and bring a camera and sunscreen. Unfortunately, the tour is not suitable for wheelchair users. The following table outlines key details:
| Important Information | | |
|———————-|——————-|——————|
| Meeting Point | Ramp near station | Assistant in blue|
| Recommendations | Comfortable shoes | Camera, sunscreen|
| Accessibility | Not wheelchair-friendly | |
The Sum Up
This day trip from Florence provides a captivating glimpse into the enchanting landscapes and cultural heritage of Tuscany. Visitors can explore the charming hilltop villages of Cortona, Montepulciano, and Montalcino, seeing the region’s renowned wine, art, and history. With guided tastings, live demonstrations, and breathtaking views, this tour offers a unique opportunity to experience the essence of Tuscany’s Val d’Orcia, a UNESCO World Heritage Site.
You can check availability for your dates here:More Food & Drink Experiences in Montalcino
- Montalcino: Vinyard Tour with Vertical Brunello Tasting
- Seggiano: Guided Tour of the Olive Grove and Food Tasting
- Montalcino: Wine Tasting and Tuscan Lunch
- MONTALCINO : Wine Tasting with Tuscan Cold Cuts and Cheese
- Montalcino: Winery Tour & Brunello Vertical Tasting
- Chianciano: Olive Mill Tour with Oil and Food Tasting
More Tours in Montalcino
- Montalcino: Vinyard Tour with Vertical Brunello Tasting
- Seggiano: Guided Tour of the Olive Grove and Food Tasting
- Tenute Silvio Nardi: wine tour of 30 years of Brunello
- Montalcino: a unique and engaging tour of the Brunello winery
- Montalcino: Winery Tour & Brunello Vertical Tasting
- Chianciano: Olive Mill Tour with Oil and Food Tasting
More Tour Reviews in Montalcino
- Montalcino: Vinyard Tour with Vertical Brunello Tasting
- Seggiano: Guided Tour of the Olive Grove and Food Tasting
- Tenute Silvio Nardi: wine tour of 30 years of Brunello
- Montalcino: Wine Tasting and Tuscan Lunch
- Montalcino: a unique and engaging tour of the Brunello winery
- MONTALCINO : Wine Tasting with Tuscan Cold Cuts and Cheese
Still browsing? Here are more Montalcino experiences we've covered recently
- Montalcino: Vinyard Tour with Vertical Brunello Tasting
- Seggiano: Guided Tour of the Olive Grove and Food Tasting
- Tenute Silvio Nardi: wine tour of 30 years of Brunello
- Montalcino: Wine Tasting and Tuscan Lunch
- Montalcino: a unique and engaging tour of the Brunello winery
- MONTALCINO : Wine Tasting with Tuscan Cold Cuts and Cheese
- Welcome to Casale del Bosco
- Montalcino: Winery Tour & Brunello Vertical Tasting
- Montalcino: exclusive vineyard picnic with wine
- Chianciano: Olive Mill Tour with Oil and Food Tasting
- Montalcino: Vineyard Picnic with Rosso di Montalcino Wine
- Exclusive Wine Lesson and Tasting near Montepulciano