Skip to Content

From Cortona with Love: Tuscany’s Hidden Wonders Await

If you are planning a trip to Cortona, Italy, you are in for a treat. This beautiful countryside town is a great home base for exploring the surrounding Tuscany area. With its stunning views, rich history, and delicious food, Cortona is the perfect place to unwind and immerse yourself in Italian culture. But while there is plenty to do in town, you won’t want to miss out on the many day trips available in the area.

Ariel view of village of Cotona Italy. Village is surrounded by green flat lands
Tuscany

Luckily, there are plenty of easy day trips from Cortona that will take you to some of the most beautiful and interesting places in Tuscany and Umbria. Whether you are looking to explore medieval hilltop towns, sample delicious local wines, or simply take in the stunning scenery, there is a day trip that will suit your interests. And the best part? All of these trips are just a short drive or train ride away from Cortona, making them easy to fit into your schedule. Here are our thoughts on the best day trips from Cortona.

Exploring the Heart of Tuscany

When you’re in Cortona, the heart of Tuscany is at your fingertips. The Val d’Orcia, a UNESCO World Heritage site, is a treasure trove of natural beauty. The rolling hills, cypress trees, and Tuscan sun create a picturesque landscape that has inspired artists for centuries. You can explore charming Tuscan hill towns like Pienza, Montalcino, and Montepulciano, each offering a unique blend of history, culture, and stunning vistas. There are numerous ways to get around Tuscany, but one of the most exciting is to take a guided vespa tour throughout the Tuscany hills!

Red Vespa scooter in a garden in Tuscany, Italy

Val d’Orcia: A UNESCO Treasure

In the Val d’Orcia, you are immersed in the timeless beauty of Tuscany. Take a leisurely drive through the countryside, stopping to admire the iconic landscapes that have graced countless postcards and paintings.

The region is renowned for its production of fine wines, including the esteemed Brunello di Montalcino. You can also take part in wine tasting experiences at local vineyards, gaining insight into the Chianti Classico and other renowned varietals.

Chianti Region: Wine Lovers’ Paradise

For wine enthusiasts, the nearby Chianti region is an absolute paradise. You’ll see vineyard-dotted landscapes and picturesque villages. Discover the rich heritage of Chianti Classico wines and savor the flavors of this renowned wine-producing area.

From wine tastings to scenic drives, the Chianti region offers a delightful blend of history, culture, and gastronomy. This makes it an essential stop for any wine lover visiting Cortona.

Wine bottle and two glasses of Chianti Classico wine in Tuscany Italy
Chianti Classico wine

Historic Towns and Medieval Marvels

If you’re looking for a day trip from Cortona that will transport you back in time, you’re in luck. The region is home to several historic towns and medieval marvels. Whether you’re a history buff or an architecture enthusiasts you will find it all. One of the best ways to explore all of these towns and more is to join a tour around the Tuscany region. Here are three must-visit destinations:

1) San Gimignano: City of Beautiful Towers

San Gimignano is a small town that is famous for its medieval towers. In fact, the town used to have 72 towers, but only 14 remain today. Despite this, San Gimignano is still a sight to behold. The town’s narrow streets and medieval buildings will make you feel like you’ve stepped back in time.

While you’re in San Gimignano, be sure to visit the Piazza della Cisterna. This square is surrounded by medieval buildings and is a great place to people-watch. You should also visit the Collegiate Church of Santa Maria Assunta, which is home to some beautiful frescoes.

main pizza San Gimignano with tourists walking around
San Gimignano

2) Pienza: The Ideal Renaissance Town

Pienza is a small town that was built in the Renaissance era. The town was designed by Pope Pius II, who wanted to create an ideal Renaissance town. As a result, Pienza is a UNESCO World Heritage site and is known for its beautiful architecture.

While you’re in Pienza, be sure to visit the Piazza Pio II, which is the town’s main square. Here you will be surrounded by beautiful Renaissance buildings. This is an ideal place to relax and soak up the atmosphere. You should also visit the Palazzo Piccolomini, which is a beautiful palace that was built in the 15th century.

3) Montepulciano: Steeped in Etruscan History

Montepulciano is a town that is steeped in Etruscan history. The town is located on a hilltop and is surrounded by beautiful countryside. Montepulciano is known for its wine, and there are several vineyards in the area that offer wine tastings. A great idea is to sign up for a tour where you can see numerous wineries throughout the Chianti Hills.

While you’re in Montepulciano, be sure to visit the Piazza Grande, which again, is the town’s main square. This is another spot to take in the history and architecture. You should also visit the Duomo, which is a beautiful cathedral that was built in the 16th century. The cathedral is home to some beautiful frescoes by Luca Signorelli.

main medieval piazza in Montepulciano, Italy
Montepulciano

Overall, these three historic towns are some of the best day trips from Cortona. Whether you’re interested in medieval history, Renaissance architecture, or Etruscan culture, there’s something for everyone in this beautiful region.

Natural Escapes and Outdoor Adventures

If you’re looking to escape the hustle and bustle of Cortona and immerse yourself in nature, there are plenty of options for day trips that will take you through areas of great natural beauty. Here are a few ideas to get you started:

Lake Trasimeno: A Day by the Water

Just a short drive from Cortona, Lake Trasimeno is a beautiful spot to spend a day by the water. Take a picnic and enjoy the beautiful views of the lake and surrounding hills, or rent a paddleboat or kayak to explore the lake’s many coves and inlets.

The lake is also home to several small islands, including Isola Maggiore, which is known for its beautiful olive groves and peaceful atmosphere. If you’re lucky, you might even spot some of the wild boar that roam the area.

Whether you’re looking for a relaxing day by the water or an active adventure, Lake Trasimeno is a great choice for a day trip from Cortona.

Lake Trasimeno in Tuscany Italy
Lake Trasimeno

Cultural and Religious Sites

Cortona is surrounded by picturesque towns and cities that offer great day trip opportunities. If you’re interested in exploring cultural and religious sites, there are several places you can visit.

Assisi: Following the Footsteps of St. Francis

Assisi is a beautiful hill town in the Umbria region, known for its association with St. Francis, the patron saint of Italy. The town is home to several churches and monasteries associated with St. Francis, including the Basilica of San Francesco, which houses his tomb.

The Basilica of San Francesco is a UNESCO World Heritage Site and is one of the most visited pilgrimage sites in Italy. The basilica is divided into two parts, the Upper Church and the Lower Church. The Upper Church is decorated with frescoes by renowned artists such as Cimabue and Giotto, while the Lower Church is home to the tomb of St. Francis.

Apart from the Basilica of San Francesco, you can also visit the Church of San Damiano, which is where St. Francis received his calling from God. The church is located on a hill outside the town and offers stunning views of the surrounding countryside.

To make the most of your visit to Assisi, it’s best to take a guided tour. A guided tour will help you understand the history and significance of the town and its religious sites. For an experience that is a little off-the-beaten-path, you should try the Assisi Truffle Hunting Experience.

Overall, Assisi is a must-visit destination for anyone interested in the life and teachings of St. Francis.

Basilica of St. Francis of Assisi at sunset in Italy
Basilica of St. Francis of Assisi

Convenient Transport Options for Day Trippers

When planning your day trips from Cortona, it’s important to consider your transportation, especially the most convenient transport options available. Here are some options for getting around:

Navigating by Train and Bus

If you’re looking for the easiest way to get around, public transportation is a great option. The train station in Camucia-Cortona is located just a few kilometers from Cortona and provides easy access to other destinations in Tuscany. From there, you can take a bus to your desired location. The bus station is located right next to the train station, making transfers easy.

One of the best ways to navigate Tuscany by public transportation is to purchase a Trenitalia Pass. This pass allows you to travel on any train in Tuscany for a set period of time, making it a great option for day trippers.

The Benefits of a Rental Car

Renting a car is another great option for day trippers. It provides the flexibility to travel at your own pace and explore areas that may not be accessible by public transportation. There are several car rental companies located in Cortona, making it easy to find a vehicle that meets your needs. Discover Cars is a great place to start your search for a rental.

When renting a car, it’s important to keep in mind that parking can be difficult in some areas. If you’re planning to visit a popular destination, it’s a good idea to arrive early to secure a parking spot.

Overall, both public transportation and rental cars are great options for day trippers. Consider your travel preferences and destination when deciding which option is best for you.

Leisure and Relaxation

Looking for a leisurely day? Here are some of the best places we’ve found to relax and unwind within easy reach of Cortona.

Cortona’s Local Delicacies

One of the best ways to unwind is by indulging in delicious local cuisine. Cortona is known for its traditional Tuscan fare, including hearty soups, succulent meats, and fresh pasta dishes. Be sure to try the town’s signature dish, pici al ragù di cinghiale, a thick spaghetti-like pasta served with a rich wild boar sauce. For dessert, sample the local cantucci almond biscuits, perfect for dipping in Vin Santo sweet wine.

main medieval piazza in Cortona, Italy
Cortona, Italy

Luxury and Boutique Accommodations

If you’re looking for a luxurious and relaxing day trip, consider staying at one of the many boutique or luxury hotels in the area. The Villa Marsili in Cortona is a charming 4-star hotel with elegant rooms, a beautiful garden, and a stunning rooftop terrace with panoramic views of the surrounding countryside. For a truly indulgent experience, book a room at the Relais La Corte dei Papi, a 5-star luxury hotel located just outside Cortona. This elegant villa features a spa, outdoor pool, and gourmet restaurant serving the best of Tuscan cuisine.

Whether you’re in the mood for delicious food, a boutique hotel, or a luxury retreat, the towns and countryside surrounding Cortona offer plenty of options for a leisurely and relaxing day trip.

Practical Tips for Your Day Trip

If you’re planning a day trip from Cortona, there are a few practical tips you should keep in mind to make the most of your time and ensure a smooth experience. Here are some things to consider:

Best Places to Visit

There are many great day trips to take from Cortona, but some of the best places to visit include Montepulciano, Arezzo, Assisi, and Montalcino. Each of these destinations offers something unique, from stunning architecture to delicious food and wine.

Sign for Montalcino in Italian language in Tuscany Italy

Best Things to Do

When planning your day trip, consider what you want to see and do. Some popular activities include exploring historic landmarks, visiting wineries and vineyards, and sampling local cuisine. Make a list of your must-see attractions and plan your itinerary accordingly.

How Much Time You Have

Consider how much time you have for your day trip. If you only have a few hours, you may want to stick to a nearby destination like Montepulciano or Arezzo. If you have a full day, you can explore further afield and take in more sights and experiences.

Extra Cost

Finally, be aware that some activities and experiences may come at an extra cost. For example, wine tasting at a vineyard or visiting a museum may require an entrance fee. Plan ahead and budget accordingly to avoid any surprises.

Frequently Asked Questions

What are the top destinations for a day trip from Cortona?

Cortona is a great base for exploring the surrounding areas of Tuscany and Umbria. Some of the top destinations for a day trip around Italy include the charming medieval town of Montepulciano, the picturesque hilltop town of Montalcino, and the beautiful city of Perugia.

How do you get from Cortona to Perugia for a day visit?

The easiest and most convenient way to get from Cortona to Perugia is by car. The drive takes about an hour and offers stunning views of the Umbrian countryside. If you prefer not to drive, you can take a bus or train from Cortona to Perugia, but the journey may take longer and require multiple transfers.

Can you recommend cooking classes in Tuscany for culinary day experiences?

Yes, there are several cooking classes in Tuscany that offer fun and informative culinary day experiences to make traditional Italian recipes. One of the most popular options is a Pizza and Gelato cooking class in a Tuscan Farmhouse Cook in Tuscany, Tuscan Women Cook, and Casa Bellavista. These classes typically include a visit to a local market to select fresh ingredients, hands-on cooking instruction, and a delicious meal paired with local wine.

homemade mushroom and salami pizza with cooking tools

What are the must-see places in Siena on a day trip from Cortona?

Siena is a beautiful city with many must-see places to visit on a day trip from Cortona. Some of the top attractions include the stunning Siena Cathedral, the Piazza del Campo, the Palazzo Pubblico, and the Torre del Mangia.

Which nearby lake offers a scenic day trip option from Cortona?

Lake Trasimeno is the largest lake in central Italy and offers a scenic day trip option from Cortona. Located just a short drive from Cortona, this picturesque lake is surrounded by rolling hills and charming medieval towns. Visitors can enjoy swimming, boating, and hiking, as well as delicious local cuisine at the many restaurants and cafes along the lake’s shores.

From Cortona, what are the best towns to explore in Tuscany and Umbria in one day?

There are many beautiful towns to explore in Tuscany and Umbria on a day trip from Cortona. Some of the best options include the medieval town of Assisi, the charming hilltop town of Orvieto, and the beautiful city of Florence. Each of these destinations offers unique attractions, delicious local cuisine, and stunning scenery that is sure to make your day trip unforgettable. Wishing you safe and happy travels!

//