Planning a weekend getaway to Cortona, Tuscany, offers an incredible blend of scenic beauty, rich history, and vibrant local culture. Whether you're seeking a peaceful holiday accommodation in a charming villa, an upscale vacation rental in the heart of the city, or a short-term rental with dedicated workspace and fast WiFi for your business needs, Cortona provides a diverse range of options to suit any traveler’s preference. As a male business traveler, finding the perfect place to stay in Cortona that combines comfort, connectivity, and convenience is essential for balancing work and leisure. This guide will outline the top things to do in Cortona this weekend, alongside tips on where to find the best holiday rentals and holiday accommodations to enhance your stay.
1. Explore the Historic Center of Cortona
A visit to Cortona's historic center is a must for any traveler. Wander through narrow cobblestone streets, admire medieval architecture, and soak in panoramic views of the Tuscan countryside. This area is bustling with quaint cafes, artisan shops, and open-air markets where you can experience authentic local flavors and crafts. For the best places to stay in the city center, consider booking a holiday rental close to Piazza della Repubblica, providing easy access to all attractions while offering a cozy retreat after a day of exploration. Use Search and Stay to find suitable accommodations in Cortona with dedicated workspaces and high-speed WiFi.
2. Visit the Etruscan Academy Museum
This museum showcases ancient Etruscan artifacts, offering insights into Tuscany's pre-Roman history. It’s a fantastic educational excursion, perfect for history buffs and culture enthusiasts alike. Post-visit, you can relax at a nearby holiday rental with modern amenities, ideal for those looking for a short term rental with amenities suited for business travelers. Many rentals offer dedicated workspaces, high-speed internet, and flexible check-in options so you can combine sightseeing with efficient remote work when needed.
3. Discover the Religious Heritage at Santa Margherita Basilica
Sitting prominently in Cortona, this basilica features stunning architecture and beautiful artworks. Visiting during your weekend trip will deepen your understanding of Tuscany’s spiritual and artistic traditions. For accommodations, look for a place to stay in close proximity so you can enjoy early mornings or late evenings at the basilica without hassle, and benefit from rentals that include kitchenette and workspace facilities for a comfortable work-life balance.
4. Embark on a Wine Tasting Tour in Tuscan Vineyards
One of the highlights of any holiday in Tuscany is tasting world-renowned wines. Local wineries surrounding Cortona such as the *Vino Nobile di Montepulciano* region provide exceptional wine experiences paired with traditional Tuscan cuisine. Many estates offer guided tours, tastings, and on-site accommodations. For business travelers, some wineries feature lodges with high-speed WiFi, so you can unwind with a glass of fine wine while catching up on work in a serene setting.
Check out additional details about local wine experiences at Visit Tuscany and Terratoscana Wineries.
5. Hiking and Outdoor Activities in the Val di Chiana
For outdoor enthusiasts, the Val di Chiana offers scenic hiking and cycling routes that showcase Tuscany's stunning landscapes. Exploring these trails can be a rejuvenating experience, with opportunities to spot local wildlife and enjoy panoramic vistas. Many rentals in the area are equipped with outdoor spaces and modern facilities suitable for a working traveler, including fast WiFi and dedicated work areas. These rentals serve as excellent bases for both adventure and productivity over the weekend.
Further information on activity options can be found at Tuscan Ambassador and Outdoor Activities in Tuscany.
6. Indulge in Local Cuisine at Trattorias and Enotecas
No trip to Tuscany is complete without savoring the regional cuisine. From traditional trattorias serving handmade pici pasta to enotecas offering local Chianti wines, you will find plenty of unique spots to indulge your palate. Many of these establishments are nestled within the city’s historic streets, making it easy to dine authentically while staying in a centrally located holiday rental. When booking accommodation, opt for places that offer a private kitchen or dining area, so you can experience local cooking yourself or entertain clients over a Tuscan wine and antipasti.
7. Attend a Cooking Class to Learn Tuscan Recipes
Participate in a hands-on cooking class led by local chefs to learn how to prepare Tuscan specialties such as ribollita, bistecca alla fiorentina, and cantucci with Vin Santo. These classes can often be booked as part of a local experience package and are ideal for travelers wanting an immersive cultural activity. Staying in a holiday apartment with a fully equipped kitchen will allow you to practice your skills and enjoy your culinary creations in the comfort of your temporary home.
8. Explore Cortona’s Art Galleries and Studios
Feast your eyes on contemporary and classical artworks by visiting local galleries and artist studios around Cortona. This cultural immersion adds depth to your holiday experience and offers inspiration, whether for leisure or professional creativity. Many galleries are located within walking distance of your holiday rentals in the city center, making spontaneous visits easy. Ensure your accommodation provides a quiet workspace and reliable WiFi for moments when you want to research art techniques or share your experiences online during your stay.
9. Take a Day Trip to Lake Trasimeno
This picturesque lake, one of the largest in Italy, offers activities such as boat rides, lakeside walks, and visits to charming lakeside towns. Spending a day by Lake Trasimeno is an ideal way to relax and enjoy Tuscany’s natural beauty. For a seamless experience, choose a vacation rental close to the lake with facilities suitable for working travelers—fast WiFi, comfortable workspaces, and easy check-in options. This flexibility ensures your weekend combines both leisure and work commitments effectively.
10. Shopping for Local Crafts and Souvenirs
Before wrapping up your weekend in Cortona, take time to browse artisan shops offering handcrafted jewelry, ceramics, textiles, and local food products. Shopping in the city’s boutiques provides a tangible connection to Tuscany’s artistic tradition. Many holiday rentals have ample space to store your purchases, plus amenities that enable you to relax and reflect on your trip. With the convenience of online booking via Search and Stay, you can secure a place to stay in Cortona with all the comforts needed for your business and leisure travel.
Whether you’re here to explore Tuscany’s rich history, indulge in its gastronomic delights, or balance work with leisure, Cortona offers an ideal destination for your weekend escape. With a variety of holiday accommodations ranging from luxury villas to cozy apartments, you can find the perfect place to stay in Cortona that meets your needs for connectivity, comfort, and convenience. Plan ahead to ensure you have access to the best activities, local experiences, and places to stay in this stunning Tuscan town for an unforgettable weekend.