5 Days in Cortona, Tuscany, Italy what to see and where to stay

Day 1: Welcome to Cortona – Arriving and Settling In

Upon arrival in Cortona, you'll want to find a welcoming place to stay that captures the essence of Tuscan hospitality. From charming agriturismos to luxurious villas, local accommodations in Cortona cater to diverse preferences. Begin your journey by exploring options at Search and Stay, where you can find a wide range of holiday rentals, short-term rentals, and vacation homes tailored to your needs.

After checking in, take a leisurely stroll through the historic center of Cortona, a picturesque town perched on a hillside offering panoramic views of the Val di Chiana. This is the ideal time to get your bearings, soak in the medieval charm with narrow cobblestone streets, and admire the stunning architecture. Consider visiting the Piazza della Repubblica, the central square bustling with cafes and shops, perfect for trying local treats and immersing yourself in the lively Tuscan atmosphere.

Day 2: Dive into Cortona’s Rich History and Cultural Gems

Begin your day with a visit to the Museo dell’Accademia Etrusca, home to artifacts that tell the story of Cortona’s ancient Etruscan roots. This is a must-see for history buffs and those eager to embrace local experiences that give depth to their stay. For a more panoramic outlook, hike or drive up to the Fortezza di Cortona, a historic fortress offering breathtaking vistas of the surrounding countryside—a perfect spot to take unforgettable photos and truly appreciate your holiday destination.

In the afternoon, explore the Santa Margherita Basilica, an architectural marvel blending medieval and Renaissance styles. Wander through the nearby artisanal shops selling handcrafted ceramics and textiles, which make unique souvenirs. When hunger strikes, indulge in authentic Tuscan cuisine at cozy local trattorias, savoring dishes like pici pasta, wild boar ragù, and fresh regional wines.

If you’re interested in discovering local experiences that go beyond sightseeing, consider taking a culinary tour or a wine tasting session in the area. Tuscany is world-renowned for its wines, especially Vino Nobile di Montepulciano and Chianti. To plan your local experiences, visit Tuscany Now & More for ideas on things to do that will enrich your holiday in Cortona.

Day 3: Discover the Surrounding Countryside and Hidden Gems

Rent a scooter or car to explore the rolling hills and scenic landscapes that surround Cortona. This is an ideal way to enjoy activities like visiting nearby villages such as Castiglione del Lago or exploring the beautiful Lake Trasimeno with its quaint lakeside towns. These places to stay in the lake area offer excellent options for holiday accommodation with stunning views, perfect for relaxing after a day of adventure.

Stop by local farms and vineyards to understand more about the local agritourism scene. Many farms offer guided tours and tastings, providing a unique opportunity to connect with the Tuscan entrepreneurial spirit. These experiences seamlessly combine the idea of holiday rentals with immersive local experiences that make your trip both memorable and authentic.

For outdoor enthusiasts, consider hiking or cycling along the trails that meander through olive groves and vineyards. The countryside is dotted with points of interest and scenic spots to enjoy picnics or simply take in the natural beauty. To find rentals in these picturesque areas, visit Search and Stay.

Day 4: Embrace Local Experiences and Things to Do in Tuscany

This day is dedicated to engaging with the vibrant local culture and finding fun activities around Cortona. Join a cooking class to learn how to make traditional Tuscan dishes using fresh, local ingredients. Not only is this an immersive experience, but it also gives you a chance to connect with fellow travelers who share your love for fun and authentic encounters.

When evening approaches, attend a local festival, concert, or outdoor event, which are common during the summer months. These events are lively, inclusive, and full of energy, showcasing the local traditions and vibrant social scene of Cortona. Local markets are also an excellent place to sample seasonal produce, buy handcrafted souvenirs, and mingle with residents.

Remember to include some outdoor activities like horseback riding, hot air balloon rides, or guided architectural tours, which can be booked through local providers. This variety ensures your holiday is filled with adventure and engaging experiences, letting you truly enjoy your stay in Tuscany.

Day 5: Relax and Reflect Before Departing

On your final day, unwind at your vacation rental or holiday accommodation, taking in the beautiful surroundings that make Tuscany so special. Consider a leisurely breakfast with local pastries and freshly brewed espresso before heading out for one last exploration. A walk along the city walls or a visit to a local spa can be the perfect way to relax and absorb the tranquil atmosphere.

If you have extra time, revisit your favorite spots, or seek out new local experiences to maximize your trip. Planning your next stay or vacation rental in Cortona is easy using resources like Search and Stay. With a variety of places to stay in the area, including short-term rentals and holiday accommodation options, you’ll find the perfect spot to keep the Tuscan magic alive long after your trip concludes.