PRIVATE Transfer from Siena to Assisi with stops in Montepulciano and Cortona

(or Viceversa)

Overview

Experience Tuscany’s Hidden Treasures: Transfer from Siena to Assisi with Stops in Montepulciano and Cortona

Discover the best of Tuscany’s iconic beauty during your private transfer from Siena to Assisi, accompanied by our knowledgeable local driver. Travel through the enchanting landscapes of rolling hills, cypress-lined roads, golden sunflower fields, and medieval hilltop villages that make this region unforgettable. Along the way, we’ll take you on a journey through the famous Val d’Orcia, a UNESCO World Heritage Site celebrated for its postcard-perfect scenery and its appearance in films like Gladiator.

This unique transfer includes two captivating stops:

1. Montepulciano: A Medieval Gem and Wine Lover’s Paradise 🍷🏰

Our first stop is the medieval town of Montepulciano, renowned for its rich history, wine culture, and breathtaking views of the Tuscan countryside. Wander through its atmospheric streets, lined with ancient buildings and artisan shops, and discover its hidden treasures.

Underground Cellars: Explore the ancient wine cellars carved deep into tuff stone, complete with vaulted brick ceilings. These historical spaces tell the story of Montepulciano’s winemaking tradition.
Nobile di Montepulciano Wine: Enjoy a guided wine tasting featuring 6 exceptional Tuscan wines, paired with a delicious traditional lunch. An expert sommelier will share insights into the unique characteristics and history of each wine.
Stunning Views: Don’t miss the chance to take in the panoramic views from the town’s high vantage points, overlooking vineyards, olive groves, and rolling hills.

2. Cortona: The Enchanting Etruscan Town 🏛️🌅

Next, we visit Cortona, a charming and historic walled town steeped in Etruscan heritage. Known for its inspiring beauty, Cortona offers a magical mix of art, history, and stunning views.

Panoramic Views: From the town’s elevated position, enjoy breathtaking vistas of Lake Trasimeno and the surrounding valley.
Etruscan Legacy: Stroll through Cortona’s narrow, cobblestone streets and discover its Etruscan walls and historic landmarks, which date back over 2,000 years.
Under the Tuscan Sun: Fans of the beloved film will recognize Cortona as the setting for Under the Tuscan Sun, a movie that captures the town’s timeless charm and romantic atmosphere.

Arrival in Assisi ✨⛪

After your unforgettable exploration of Tuscany, we’ll drive you to Assisi, where you’ll arrive at your hotel, B&B, or private apartment. Assisi, the hometown of St. Francis, awaits with its spiritual beauty and tranquil ambiance.

This transfer is more than a ride—it’s a chance to immerse yourself in the secret heart of Tuscany, filled with culture, history, and flavors that will stay with you forever.

What's Included

Air-conditioned vehicle
6 Wine tastings (Nobile of Montepulciano, Super Tuscan, Extra virgin olive oil and more..)
3 Course Lunch & wine tasting in historic winery
Bottled water
Local expert driver

Please Note

Traveler pickup is guaranteed
Our english speaking Driver will pick you up at your location
Welcome sign always PEK TUSCANY IN LIMO + your name.
Transfer aboard our 8 Seats Mercedes Minivan or similar Minivan

What To Expect: Itinerary

Stop At: Montepulciano, Visit Lunch and Wine tasting 🍇 🍝🍷

Our driver will pick you up from your hotel, B&B, or private apartment and take you on a scenic journey through the rolling hills of Tuscany. Enjoy a picturesque trip along the famous wine route, featured in the movie Gladiator.

The first stop is Montepulciano, a town known for its exceptional food and wines. You’ll first visit Piazza Grande, the stunning main square surrounded by beautiful Renaissance buildings. Then, you’ll explore the town’s charming streets before heading to the incredible underground cellars, known as the “Underground Wonders.” Here, a qualified guide will lead you through vast oak barrels that age the renowned Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC.

At the end of the tour, indulge in a traditional Tuscan lunch, featuring local specialties such as prosciutto, salami, pecorino cheese, bruschetta, and “pici” pasta. You’ll also enjoy a sweet typical dessert and a tasting of six wines, including Nobile, Super Tuscan, and Brunello, with an expert explanation of each wine’s characteristics.

The menu includes:

Appetizer: A selection of cured meats such as prosciutto and salami, paired with local cheeses like pecorino, and served with freshly made bruschetta drizzled with local olive oil.
First Course: A hearty first course of “pici” pasta, a traditional Tuscan pasta similar to thick spaghetti, often served with a rich, savory sauce.
Tuscan sweet: A typical Tuscan dessert, such as a traditional ricciarelli (almond cookies) or cantucci with vin santo, a sweet dessert wine.
Wine Tasting: Six wines to sample, including the famous Nobile di Montepulciano DOCG, Super Tuscan wines, and the renowned Brunello di Montalcino, along with an expert explanation of their unique characteristics and production methods.

This delightful meal offers a true taste of Tuscany, perfectly paired with the region’s exceptional wines.

Duration: 3 hour

Stop At: Cortona🏛️🌅

Next, we’ll head to the charming town of Cortona.

Cortona, a jewel of Tuscany perched on a hilltop in the Val di Chiana, is a town that exudes history, art, and charm at every turn. With origins dating back to the Etruscans, Cortona retains a wealth of ancient walls and archaeological remains, offering a glimpse into its storied past. Known as “Curtun” during the Etruscan era, the town also flourished in the Renaissance and Baroque periods, leaving behind a legacy of architectural and artistic treasures.

Start your visit at Piazza della Repubblica, the heart of the town, where the Palazzo Comunale stands proudly with its elegant clock tower. From there, explore the nearby Piazza Signorelli, home to the majestic Teatro Signorelli, a cultural hub since the 19th century. Don’t miss the Diocesan Museum, which houses masterpieces by artists such as Luca Signorelli and Beato Angelico, including the renowned Annunciation.

A short stroll brings you to the Basilica of Santa Margherita, perched at the highest point of Cortona. This serene church offers breathtaking views of the valley and Lake Trasimeno, as well as a spiritual connection to the town’s patron saint, St. Margaret of Cortona. Nearby, the Eremo Le Celle, a hermitage founded by St. Francis of Assisi, provides a tranquil escape surrounded by nature.

Cortona also holds a special place in modern culture thanks to the beloved film Under the Tuscan Sun. Many scenes were shot in the town, capturing its picturesque streets, stone houses, and sweeping Tuscan vistas. Visitors can retrace the steps of the film’s protagonist, Frances, and immerse themselves in the town’s enchanting atmosphere.

Whether you’re drawn by its history, its art, or its cinematic allure, Cortona is a destination that promises to captivate and inspire.

Duration: 1:30 hour

Pass By: Lake Trasimeno

During the transfer, we will pass by the picturesque Lake Trasimeno. Nestled in the green heart of Umbria, Lake Trasimeno is a serene natural paradise surrounded by reeds and dotted with beautiful white water lilies. The lake is home to a variety of wildlife, including wild ducks, cormorants, and kingfishers. After this peaceful detour, we will continue to Assisi, where we will drop you off at your hotel, B&B, or private apartment, concluding a memorable day of exploration.

Additional Info

Confirmation will be received at time of booking
Wheelchair accessible
Stroller accessible
Infant seats available
Most travelers can participate
This is a private tour/activity. Only your group will participate

Please Note:

Inform us about any food allergies or intollerances you might have in advance during your booking procedure.