PRIVATE TRANSFER: from Assisi to Florence with stops in Cortona & Montepulciano

Assisi , Italy

PRIVATE TRANSFER: from Assisi to Florence with stops in Cortona & Montepulciano

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About this experience

Explore the enchanting cities of Cortona and Montepulciano during your transfer from Assisi (or Perugia) to Florence with our experienced driver and uncover the hidden gems of Tuscany! Immerse yourself in a full-day trip through the iconic landscape of rolling hills, cypress-lined avenues, and medieval hilltop towns, while enjoying delightful wines.

We will pick you up at your location.

Our first stop is Cortona, a picturesque Etruscan town at 600 meters above sea level, offering stunning views of the valley and Lake Trasimeno. Cortona is also famous as the setting of the beloved film Under the Tuscan Sun.
For lunch, our driver will recommend a place for you to eat.
Next, we’ll visit Montepulciano, where we'll explore the city and visit two Historic Cellars. See colossal oak barrels holding Vino Nobile di Montepulciano DOCG, followed by a wine tasting and explanation of its unique characteristics.
In the afternoon, we will drop you off in Florence at your destination.

Available options

PRIVATE TRANSFER: from Assisi to Florence with stops in Cortona & Montepulciano

Pickup included

What's included

Bottled water

Local expert driver and tour leader

Visit two historic cellars and 2 wine tastings included: Red wine of Montepulciano, Nobile Wine of Montepulciano, Super Tuscan and Brunello of Montalcino.

Air-conditioned vehicle

Detailed itinerary

Stop 1 Pass by

Our professional driver will pick you up directly from your hotel, B&B, or private apartment and take you on a scenic drive through the rolling hills between Umbria and Tuscany.
Along the way, we’ll pass near the beautiful Trasimeno Lake — a stop can be arranged upon request. Surrounded by lush greenery, reeds, and graceful white water lilies, Trasimeno Lake is a true natural paradise, home to wild ducks, cormorants, kites, and kingfishers — the perfect spot to enjoy a peaceful break and stunning views.

First Stop: Cortona – Free Visit
Discover Cortona, the main cultural and artistic center of the Val di Chiana after Arezzo. Founded by the Etruscans (original name Curtun), the town still preserves impressive remains from its ancient past. Cortona boasts a rich artistic heritage, with connections to great Renaissance masters such as Luca Signorelli and Beato Angelico, as well as Pietro da Cortona from the Baroque period.

Before your self-guided walking tour, your English-speaking driver will provide you with the main directions and tips to help you explore the town at your own pace.

The charming streets, panoramic views, and timeless atmosphere of Cortona also inspired the famous movie “Under the Tuscan Sun.”
Just outside the town, you’ll visit the peaceful Hermitage of San Francesco – Le Celle, a spiritual retreat surrounded by nature and history.

Second Stop: Montepulciano – Free Visit and Wine Tasting
Enjoy a stop in Montepulciano, a beautiful medieval hilltop town famous for its wines and authentic Tuscan charm. Known for its pork, pecorino cheese, handmade “pici” pasta, lentils, and honey, Montepulciano is celebrated worldwide for Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano.
Your English-speaking driver will accompany you to the historic wineries, providing directions and tips for a self-guided walking tour of the town. In the ancient underground cellars, a qualified winemaker will show you the impressive oak barrels where the famous wines are aged.
After the visit, enjoy a guided wine tasting of the estate’s top wines, with insights into their unique characteristics.
If you wish, your driver will recommend great local restaurants for a traditional Tuscan lunch.
At the end of your visit, we will depart from Montepulciano and head to Florence, arriving after about 1 hour and 30 minutes of scenic driving.

What's not included

During the tour our driver will show you excellent places to have a tuscan lunch.

Everything not found under the heading inclusions is excluded

Available languages

Guide guide

EN FR ES

Reviews breakdown

Viator 5.0

1 reviews

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Important information

Specialized infant seats are available

Infants and small children can ride in a pram or stroller

Suitable for all physical fitness levels

Wheelchair accessible

About Assisi

Assisi is a picturesque medieval town in the Umbria region of Italy, nestled in the hills of the Apennine Mountains. It is renowned as the birthplace of St. Francis, the patron saint of animals and the environment, and is home to stunning religious architecture, including the iconic Basilica of San Francesco. The town's charm lies in its well-preserved medieval streets, vibrant art scene, and the serene atmosphere that permeates its historic center.

Top Attractions

Basilica of San Francesco

The Basilica of San Francesco is a UNESCO World Heritage Site and one of the most important religious sites in Italy. It consists of two churches, an upper and lower basilica, adorned with stunning frescoes by Giotto and Cimabue.

Religious/Historical 1-2 hours Free (donations welcome)

Basilica of Santa Chiara

This basilica is dedicated to St. Clare, a contemporary of St. Francis. It features a beautiful rose window and a simple, elegant interior with a large crucifix attributed to St. Francis.

Religious/Historical 30 minutes to 1 hour Free (donations welcome)

Rocca Maggiore

This medieval fortress offers panoramic views of Assisi and the surrounding countryside. The fortress was built by the Germans in the 12th century and later used by various rulers, including the Papal States.

Historical 1 hour €4

Temple of Minerva

This ancient Roman temple, built in the 1st century BC, is one of the best-preserved Roman buildings in Italy. It was later converted into a church and now serves as a significant historical landmark.

Historical/Architectural 30 minutes Free (donations welcome)

Eremo delle Carceri

This hermitage is located in the woods above Assisi and is believed to be where St. Francis and his followers retreated for prayer and meditation. It offers a peaceful and spiritual atmosphere amidst beautiful natural surroundings.

Religious/Nature 1-2 hours (including the hike) Free (donations welcome)

Must-Try Local Dishes

Truffle Pasta

A classic Umbrian dish made with fresh pasta and shaved black truffles, often served with a simple tomato or cream sauce

Main Course Contains gluten (pasta), can be made vegetarian

Wild Boar Stew (Cinghiale in Umido)

A rich and flavorful stew made with wild boar, tomatoes, onions, and herbs, often served with polenta or crusty bread

Main Course Contains meat, can be made gluten-free with appropriate sides

Olive All'Ascolana

Large green olives stuffed with a mixture of meat, breadcrumbs, and herbs, then fried until crispy

Appetizer Contains meat and gluten, not suitable for vegetarians or those with gluten allergies

Torta al Testo

A traditional Umbrian flatbread made with flour, water, and salt, often served with cured meats, cheeses, or vegetables

Main Course Contains gluten, can be made vegetarian

Popular Activities

Hiking in the surrounding mountains Rock climbing Mountain biking Wine tasting Spa treatments Strolling through the historic center Visiting museums and art galleries Attending local festivals and events

Best Time to Visit

May to September

This is the warmest and most popular time to visit Assisi, with pleasant weather ideal for exploring the town and its surrounding countryside. The town is lively with tourists and cultural events.

18°C to 30°C 64°F to 86°F

Practical Information

Language

Official: Italian
Widely spoken: English, French, German, Spanish
English: Moderately spoken in tourist areas, limited in more remote locations

Currency

Euro (EUR)

Time Zone

GMT+1 (Central European Time, CET), GMT+2 (Central European Summer Time, CEST) during daylight saving time

Electricity

230VV, 50HzHz

Safety Information

Overall Safety Rating: Generally safe

Assisi is generally a safe destination for travelers, with low crime rates and a welcoming atmosphere. However, as with any destination, it's important to be aware of your surroundings and take basic precautions to ensure a safe and enjoyable trip.

Important Precautions:

• Be aware of your surroundings, especially in crowded areas
• Keep valuables secure and out of sight
• Use licensed taxis or public transportation

Getting there

By air

Perugia San Francesco d'Assisi Airport • 15 km from Assisi
Rome Ciampino Airport • 200 km from Assisi

By train

Assisi Station

By bus

Assisi Bus Terminal

Getting around

Public transport

The bus system is efficient and affordable, with frequent services connecting major points of interest. Buses are a convenient way to get around, especially for those staying in the town center.

Taxis

Available • Apps: MyTaxi

Rentals

Car, Bike, Scooter

Neighborhoods

Borgo di San Pietro Piazza del Comune San Francesco

Day trips

Spoleto

30 km from Assisi • Half day to full day

Spoleto is a charming medieval town known for its well-preserved architecture, rich history, and vibrant cultural scene. It hosts the annual Festival dei Due Mondi, a renowned arts festival featuring opera, theater, and music.

Montefalco

20 km from Assisi • Half day to full day

Montefalco is a picturesque hilltop town known for its stunning views, rich history, and excellent wine. It is the birthplace of the Sagrantino grape, and the town is home to several renowned wineries.

Gubbio

40 km from Assisi • Full day

Gubbio is a beautiful medieval town nestled in the Apennine Mountains, known for its well-preserved architecture, rich history, and stunning natural surroundings. It is also famous for its annual Palio della Balestra, a historic crossbow competition.

Festivals

Calendimaggio • Late April to early May Assisi International Festival • July to August Feast of St. Francis • October 4th

Pro tips

Visit the Basilica of San Francesco early in the morning or late in the afternoon to avoid crowds and enjoy a more peaceful experience
Explore the town's medieval streets and hidden alleys to discover local shops, art galleries, and charming cafes
Try local specialties like truffle pasta, wild boar stew, and olive all'ascolana for a true taste of Umbrian cuisine
Take a day trip to nearby towns and cities like Spoleto, Montefalco, or Gubbio to explore the region's rich history and cultural heritage
Attend local festivals and events, such as the Calendimaggio or the Assisi International Festival, for a unique and unforgettable experience