Things to Do
Lago Trasimeno
Lakeside Relaxation (40 min away) Spend a peaceful afternoon by the water—rent bikes, hop on a ferry to Isola Maggiore, or simply enjoy a long lunch lakeside in Passignano sul Trasimeno.
Terme Antica Querciolaia
Spas & Thermal Baths – Soak & Unwind (40 mins away) Tuscany is dotted with natural hot springs. Check out Terme di Rapolano or Bagno Vignoni for a restorative spa day in a picturesque setting.
Montepulciano
Wine Tasting & Hilltop Views (45 min away) Famous for its Vino Nobile and medieval charm, Montepulciano is the perfect spot for a relaxed day of wine tasting, strolling through narrow lanes, and soaking in panoramic views of the Val d'Orcia.
Perugia
Art, Chocolate & Umbrian Culture (1 hr from Cortona) A vibrant hilltop city with a rich Etruscan history, Perugia offers a perfect blend of medieval charm and lively culture. Explore ancient city gates, stroll through the elegant Corso Vannucci, and admire Renaissance masterpieces at the Galleria Nazionale dell’Umbria. Don’t miss a taste of the city’s famous Baci chocolates!
Arezzo
Antique Markets & Hidden Gems (45 min away) Less touristy and full of charm, Arezzo offers art, cathedrals, and a fantastic antique market (first Sunday of each month). Don’t miss the frescoes by Piero della Francesca in the Basilica of San Francesco.
Pienza
Pecorino & Postcards (1 hr away) This UNESCO World Heritage town is known for its Renaissance beauty and delicious pecorino cheese. Wander through romantic streets and grab a lunch with views that look like a painting.
Spello
Flower-Filled Streets & Peaceful Strolls (1 hr 15 min from Cortona) Often called one of the most beautiful villages in Italy, Spello is a hidden gem known for its winding stone streets, colorful flower displays, and quiet, romantic atmosphere. This medieval town is perfect for a slow afternoon—browse local art galleries, sip wine at a sidewalk café, and admire ancient Roman arches tucked into everyday life.
Assisi
Sacred Beauty & Timeless Charm (1.5 hrs from Cortona) This enchanting hill town is the birthplace of St. Francis and home to the stunning Basilica di San Francesco, a UNESCO World Heritage Site adorned with frescoes by Giotto. Assisi is perfect for a peaceful day of history, spirituality, and sweeping views over the Umbrian countryside.
Siena
Medieval Magic & Piazza del Campo (1.5 hrs away) Step into another time in Siena, home of the Palio horse race and stunning Gothic architecture. Climb the Torre del Mangia for a breathtaking view, then enjoy a cappuccino in the iconic Piazza del Campo.
Radda in Chianti
Chianti Region – Scenic Drives & Sips (1.5 hrs away) Take a slow, winding drive through vineyard-covered hills in Chianti. Stop at family-run wineries for tastings, and maybe even bring back a bottle (or two) to enjoy at the villa.