Cortona Holidays

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Things to do in and around Cortona

Cortona is ideal for a romantic getaway, offering stunning scenery and outdoor adventures. Explore popular activities such as indulging in spa treatments, enjoying local theatre performances, and embarking on custom tours. Don't miss the chance to discover charming tourist destinations and take delightful day trips, making the most of your time in this enchanting Tuscan town.

Shopping

Cortona offers delightful shopping experiences, with the Valdichiana Outlet Village nearby, featuring a mix of brands and entertainment vibes. If you're up for a drive, RI Crea RE and Maioliche Nulli, located 21 and 46.7km away respectively, provide unique gifts and souvenirs for a perfect memento of your visit.

Recreation

Experience luxury at Tennis Club Castiglionese, where you can indulge in tennis surrounded by stunning countryside. For a cultural evening, enjoy a performance at the romantic Signorelli Theatre. If you're a golf enthusiast, the scenic Golf Club Valdichiana offers a perfect outdoor retreat just 14.5km away.

Adventure

Embark on Hannibal's Journey, a captivating hiking trail located 8.0km from Cortona, offering stunning outdoor scenery and adventure vibes. For adrenaline enthusiasts, the Magione Racetrack, 25.7km away, provides thrilling motor racing experiences. Families can enjoy the fun at Tavernelle Aquatic Park, situated 32.2km from Cortona.

Nightlife

Cortona's nightlife offers a charming atmosphere with quaint bars and vibrant music. Enjoy a glass of local wine at Bar Milla in the town centre, or dance to live music at La Saletta, where the energy keeps you entertained all night long.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Cortona

Cortona, a charming Italian town in Tuscany, offers a perfect blend of romance, outdoor activities, and picturesque scenery. Visitors can explore its captivating churches, lively piazzas, and serene lakes, catering to those seeking cultural enrichment and vibrant city experiences. With numerous attractions to discover, Cortona promises a delightful getaway for those eager to immerse themselves in the enchanting beauty of this historic town.

  • Isola Maggiore: A charming island located 14.5km from Cortona, Isola Maggiore offers a serene escape with its beautiful outdoor spaces and beach vibes. Stroll along the picturesque shores, enjoy local cuisine, and immerse yourself in the tranquil atmosphere of this enchanting island.
  • Palazzo Comunale: Situated in the heart of Cortona, the Palazzo Comunale is a historic palace that embodies the rich culture of the region. Admire its stunning architecture, explore the galleries, and take in the vibrant local art scene that brings the building to life.
  • Lake Trasimeno: Just 17.7km from Cortona, Lake Trasimeno captivates with its romantic scenery and outdoor activities. Enjoy leisurely walks along the lakeshores, indulge in water sports, or relax on the beach while soaking up the breathtaking views.

Best time to go to Cortona

The best time to visit Cortona can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Cortona falls in July, when visitor numbers are slightly high and weather is sunny with no rain. The coolest average temperature in Cortona falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.2°F (4.0°C)Light RainMostly CloudySlightly LowSlightly Low
February41.2°F (5.1°C)Light RainMostly SunnySlightly LowSlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnySlightly HighAverage
May59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageSlightly High
July74.8°F (23.8°C)No RainSunnySlightly HighSlightly High
August74.5°F (23.6°C)No RainSunnySlightly HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
December41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Cortona

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Cortona.
  • Consider traveling to Cortona during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Cortona

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR
S$923
19 Oct - 20 Oct
includes taxes & fees
Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
S$517
11 Oct - 12 Oct
includes taxes & fees
10/10 Exceptional! (332 reviews)
"I cannot say enough great things about our stay at the Monastery. The property is gorgeous and clean, the staff were beyond helpful and the food was incredible! The spa baths were also so relaxing. We did not want to leave this hotel. I’d like to specifically call out Frederico with the glasses, ..."

Reviewed on 17 Sept, 2026

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR
S$634
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (143 reviews)
"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact ..."

Reviewed on 10 Sept, 2026

Il Falconiere - Relais e Chateaux
See all 1,185 properties in Cortona
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Cortona attractions

Villa Bramasole

9.2/10 (20 reviews)
Made famous by "Under the Tuscan Sun," Villa Bramasole showcases classic Tuscan architecture. Admire this private residence from the road during a scenic walk through Cortona's charming countryside.
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Piazza della Repubblica

9.4/10 (95 reviews)
Piazza della Repubblica pulses as Cortona's medieval heart, framed by the Palazzo Comunale and its clock tower. Savour authentic Tuscan cuisine at outdoor cafés while absorbing panoramic countryside views.
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Cortona Cathedral

9.4/10 (77 reviews)
This Romanesque-Renaissance cathedral stands on ancient Roman temple remains, showcasing elegant portals and slender columns. Inside, experience serenity while admiring panoramic views of the Tuscan countryside.
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Santa Margherita Basilica

9.2/10 (30 reviews)
Perched high above Cortona, this Gothic-Baroque basilica houses Saint Margaret's remains, the town's patron saint. Visitors can admire the silver urn and enjoy sweeping Tuscan countryside views.
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Santa Maria Nuova

8.8/10 (5 reviews)
This Renaissance masterpiece by Giorgio Vasari features a striking central dome and Greek cross plan just outside Cortona's walls. Enjoy the serene atmosphere while taking in panoramic views of the Tuscan countryside.
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Fortress of Girifalco

8.8/10 (25 reviews)
You can find out about the history of Cortona with a trip to Fortress of Girifalco. You can enjoy the wineries while in the area.
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Palazzo Comunale

9.2/10 (44 reviews)
Palazzo Comunale is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theatre.
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Signorelli Theatre

9.2/10 (14 reviews)
You can enjoy a show at Signorelli Theatre on your trip to Cortona. Discover the area's countryside and monuments.
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What to do in Cortona

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

S$124
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Horseback riding through the vineyards in Montepulciano Tuscany

Horseback riding through the vineyards in Montepulciano Tuscany

S$119
per adult
Horseback riding through the vineyards in Montepulciano Tuscany
Horseback riding in the hills of Montepulciano in Tuscany

Horseback riding in the hills of Montepulciano in Tuscany

S$118
per adult
Horseback riding in the hills of Montepulciano in Tuscany
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Frequently asked questions

How much does a Cortona holiday package cost?
You'll find cheap prices on Expedia for your Cortona break. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Cortona costs.
What are the cheapest months to go to Cortona?
If you'd like to snag a cheap Cortona holiday package, consider travelling in December, January and February. You're likely to find better prices on airfares and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Cortona?
With around 3 days, you'll have enough time to enjoy popular neighbourhoods like Cortona Old Town and Sodo during your Cortona holiday. Be sure to also add Palazzo Comunale and Museum of the Etruscan Academy to your must-see list. Searching for more adventures? Consider exploring outside of Cortona on tours and day trips.
Is it worth booking a holiday package to Cortona?
Popular for its views, dining and walking trails, a Cortona holiday is a hit with all kinds of visitors. Be sure to check out top sights like Villa Bramasole and Piazza della Repubblica, and consider renting a set of wheels for day trips to discover even more.
How to find the best Cortona package deals?
Start your search for a Cortona package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Cortona package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cortona escape underway.
Is it cheaper to book a Cortona holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customise your Cortona trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Cortona?
If you're considering an impromptu Cortona holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Cortona?
  1. Choose when to go: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Cortona.
  2. Budget wisely: Besides the price of your stay, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Cortona.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Cortona. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: Once you've nailed down your dates and duration, book the right Cortona holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.