Exploring the enchanting Tuscan countryside is a must-do for any visitor to Florence. This captivating full-day tour offers the chance to discover the charming towns of Siena, Cortona, and Montepulciano, as well as the stunning Val D’Orcia region. From medieval landmarks to renowned wineries, there’s something to delight every traveler. Whether you’re seeking history, culture, or simply breathtaking scenery, this intimate experience is sure to leave a lasting impression.

Contents show

Key Points

This full-day tour from Florence showcases the historic towns of Cortona, Montepulciano, and Siena, with a scenic drive through the UNESCO-recognized Val D’Orcia.
Visitors will have the opportunity to explore the quaint, picturesque streets and architecture of Cortona, made famous by the novel "Under the Tuscan Sun."
In Montepulciano, the tour includes a guided wine tasting in a 14th-century cellar, highlighting the region’s renowned Vino Nobile wine.
The scenic drive through the Val D’Orcia provides breathtaking views of the undulating hills, cypress trees, and charming farmhouses that define the region’s landscape.
The tour culminates in Siena, where visitors can discover the medieval charm of the city’s narrow streets and visit iconic sites like the Piazza del Campo and Siena Cathedral.

You can check availability for your dates here:

Tour Overview

This full-day tour from Florence takes visitors through the captivating landscapes of Tuscany, exploring the historic towns of Siena, Montepulciano, Cortona, and the scenic Val d’Orcia.

The tour lasts 9-11 hours and is limited to 8 participants, led by an English-speaking guide. Prices range from $239.38 to $215.44 per person, with the option to book flexibly and cancel up to 24 hours in advance.

Highlights include a visit to a local farm, wine tastings, and ample time to discover the medieval charm of each destination.

Looking for more options in Florence? We've reviewed plenty of other experiences.

Visiting Cortona

Why is Cortona a highlight of this Tuscany tour? The quaint hilltop town of Cortona, made famous by the book and film "Under the Tuscan Sun," offers a charming glimpse into authentic Italian life.

Visitors will stroll Cortona’s narrow streets, popping into artisan shops and cafes. The town’s medieval architecture and Etruscan ruins provide a captivating backdrop.

Guests can also enjoy stunning views overlooking the valley below. With an hour allotted, there’s ample time to soak up Cortona’s ambiance and browse its unique local offerings, making this stop a memorable part of the Tuscany experience.

Exploring Montepulciano

After exploring the charming town of Cortona, the tour proceeds to the historic hilltop village of Montepulciano, renowned for its association with the "Twilight Saga: New Moon." This 1.5-hour stop allows visitors to enjoy the medieval atmosphere of the town, strolling its narrow streets lined with Renaissance palaces and admiring the impressive Duomo. Highlights include a guided wine tasting in a 14th-century cellar, where guests can sample the town’s renowned Vino Nobile di Montepulciano.

| Reason to Visit | | |

|————-|—|—|

| "Twilight Saga: New Moon" | Renaissance Palaces | 14th-Century Wine Cellar |

| Medieval Atmosphere | Impressive Duomo | Vino Nobile di Montepulciano |

Scenic Drive Through Val D’orcia

Leaving the historic hilltop town of Montepulciano, the tour embarks on a scenic drive through the breathtaking landscape of Val d’Orcia.

This UNESCO World Heritage site is renowned for its undulating hills, cypress trees, and picturesque farmhouses. Along the way, guests soak in the quintessential Tuscan vistas, stopping for photo opportunities to capture the region’s natural beauty.

The route winds through small medieval villages, offering a glimpse into the local way of life. This leisurely drive sets the stage for the final destination – the medieval city of Siena, where the tour continues its exploration of Tuscany’s cultural riches.

More Great Tours Nearby

Discovering the Medieval Charm of Siena

Having completed the scenic drive through the picturesque Val d’Orcia, the tour arrives at the medieval city of Siena.

Strolling through Siena’s narrow streets, visitors discover the city’s medieval charm. The tour explores Siena’s famous Piazza del Campo, known for its distinctive shell-shape and twice-yearly horse race, the Palio.

Tourists can admire the impressive Siena Cathedral, a masterpiece of Italian Gothic architecture. The tour also visits lesser-known sites like the Basilica of San Domenico and the Baptistery of San Giovanni.

With its well-preserved historic center, Siena offers a glimpse into Italy’s past, as featured in films like "Letters to Juliet" and "Stealing Beauty."

There's plenty more to explore in Florence

Tasting Local Delicacies

As the tour moves on, guests have the opportunity to savor the local delicacies at a typical Tuscan farm.

They’ll sample cured meats, bruschetta, and wines made from the farm’s own ingredients. This intimate encounter allows them to experience the authentic flavors of the region.

The farm visit provides a glimpse into the daily life and traditions of Tuscany, as guests engage with the passionate owners.

After indulging in the farm’s bounty, the tour continues to the medieval town of Montepulciano, known for its renowned 14th-century cellars and acclaimed Vino Nobile wines.

Practical Information

The tour provides flexible booking options, allowing guests to reserve their spot and pay later.

With free cancellation up to 24 hours in advance, travelers can plan with confidence.

The tour departs from Porta Romana in Florence at 8:00 AM, making it easy to join.

While the experience isn’t suitable for pregnant women or those with mobility issues, the provider offers a private option if the minimum of 3 participants isn’t met.

Comfortable shoes are recommended, and dietary needs should be communicated in advance.

Frequently Asked Questions

Can I Request a Private Tour for My Group?

Yes, the tour offers a private option if the minimum of 3 participants is not met. Customers can reserve the private tour and enjoy a personalized experience with just their group.

Do I Need to Bring My Own Snacks and Water?

You don’t need to bring your own snacks and water. The tour includes food and wine tastings at a local farm and 13th-century cellar, so you’ll be well-fed throughout the day.

Are There Any Restroom Stops During the Tour?

Yes, the tour includes scheduled restroom stops during the day. Participants can use the facilities at the local farms, wineries, and towns visited along the route throughout the full-day excursion.

Can I Bring My Pet on the Tour?

Unfortunately, pets are not allowed on this tour. The tour provider’s policy prohibits bringing animals due to safety and comfort considerations for all participants. Only service animals are permitted.

What Is the Cancellation Policy for This Tour?

The cancellation policy allows for free cancellation up to 24 hours in advance. Customers can reserve now and pay later, providing flexible booking options.

The Sum Up

This captivating Tuscan tour from Florence offers a delightful blend of medieval towns, picturesque landscapes, and wine tasting. Discover the charms of Siena, Cortona, and Montepulciano, while savoring the scenic drive through the stunning Val D’Orcia. With personalized attention and unforgettable experiences, this tour is a must-do for anyone seeking an immersive exploration of Tuscany’s cultural and culinary treasures.