Ultimate 5-Day Trip to Castiglione del Lago, Italy Itinerary

Start with a hearty breakfast at Bar Il Grillo, then head out for a morning boat ride on Lake Trasimeno. Take in the tranquil waters and surrounding scenery, and if the weather permits, visit Isola Maggiore, one of the lake's picturesque islands.

For lunch, enjoy a picnic by the lake with provisions from Montepulciano Winery Tour, Tasting, and Vineyard Picnic. Spend the afternoon exploring the charming town of Passignano sul Trasimeno, known for its lakeside promenade and the 16th-century Church of San Cristoforo.

Return to Castiglione del Lago for a delightful dinner at Ristorante Pizzeria La Torre, where you can dine al fresco and enjoy the cool lake breeze. Afterward, take a leisurely walk through the historic center, admiring the medieval architecture and the illuminated streets.

Kick off the day with a visit to the nearby town of Montepulciano. Enjoy a guided tour of the historic cellars and a wine tasting at Montepulciano Historical Cellars Guided Tour & Wine Tasting. Pair the wines with some local cheese and prosciutto.

Have a sumptuous lunch at Montepulciano Wine Tasting & Lunch in a Typical Winery, where you'll not only taste excellent wines but also indulge in a meal featuring regional specialties. Afterward, take some time to explore the charming hilltop town of Montepulciano at your own pace.

Return to Castiglione del Lago and unwind at the Chianciano Terme Sensory Spa. Enjoy the therapeutic waters and a range of spa treatments to relax and rejuvenate. For dinner, try Trattoria Pizzeria da Mimmo for some of the best wood-fired pizzas in town.

Embark on a morning excursion to the ancient city of Perugia. Take a guided walking tour of the old town, visiting the historic Piazza IV Novembre and the majestic Perugia Cathedral. Immerse yourself in the rich history and vibrant culture of this Etruscan city.

Indulge in a traditional Umbrian food experience with a guided walking tour of Perugia's culinary hotspots, including visits to local markets and artisanal food shops. Sample a variety of regional delicacies and learn about the unique flavors and ingredients of Umbrian cuisine.

Return to Castiglione del Lago and enjoy a memorable dining experience at a local's home with Montepulciano Dining Experience at a Local's Home. Savor a home-cooked meal prepared with fresh, local ingredients and engage in lively conversation with your hosts, gaining insight into the authentic lifestyle and hospitality of the region.

Begin with breakfast at Bar Il Grillo, then spend a relaxing morning exploring the charming village of Paciano. Take a self-guided tour of this well-preserved medieval village, strolling through its narrow streets and visiting its historical landmarks, including the Church of San Giuseppe.

Enjoy an organic cooking class at a farm near Paciano, Paciano Organic Cooking Class at a Farm with Lunch and Wine. Learn to prepare traditional Umbrian dishes using fresh, seasonal ingredients, and then savor the fruits of your labor with a delicious farm-to-table lunch.

Return to Castiglione del Lago and bid farewell to the picturesque Lake Trasimeno with a final dinner at Ristorante Pizzeria La Torre. Reflect on your journey as you dine on the terrace, enjoying the panoramic views and the warm hospitality of the region.