Take In Sweeping Tuscan Views and Indulge in Local Cuisine and Wine

Your first stop today passes winding roads through the medieval town of Cortona to the 13-century Convent Le Celle. Tucked away in a trickling gorge wrapped in thick vegetation, this place oozes peace and tranquility.
It is not hard to see why St. Francis and his followers retreated to this area to do religious work.
The convent is one of the absolute must-visit attractions in Cortona. Standing still in time, it is set in a beautiful setting with lovely views
Opening hours: 07:00-19:00

On the highest point of Cortona, you find the 16th-century Fortezza del Girifalco overlooking the town. The views are spectacular, but it is well worth visiting the castle itself too.
The castle was built on top of ruins of other castles that stood there before, from Etruscan, Roman, and medieval structures.
Inside, you can enjoy temporary exhibitions, walk around the castle, and maze at the sweeping views of Cortona and the surrounding countryside.
You can park right outside the castle.

Park at Parcheggio Piazza Mazzini, just a 10-minute walk from the restaurant and the historic center.
Fett'Unta Bistrot Fiaschetteria is an enchanting restaurant serving typical Tuscan food from antipasti and pasta to meat. Especially the pasta dishes are amazing!
The ones that are not driving can enjoy a nice glass of Tuscan wine with the food. In the summer months, they have outside tables too.
Opening hours for lunch: Thursday-Tuesday: 12:00-15:00 Wednesday: Closed You can visit their Facebook page here
If you travel on a Wednesday, another wonderful restaurant nearby is the Trattoria Toscana which is open for lunch on Wednesdays between 12:00 and 14:30.

Only a short walk from the restaurant you will find the Etruscan Museum, one of the absolute highlights of Cortona. The museum houses a large collection of Etruscan archaeological finds from the area. It is an excellent place to learn more about pre-Roman culture in Tuscany.
To this day, excavations are ongoing, and new artifacts are being uncovered.
When you visit, you should download the audio guide app on your phone to get the most out of your visit. It is available in English and Italian.
Opening hours: 1st of April to 31st of October: 10:00-19:00 1st of November to 31th of March: 10:00-17:00
You can visit the museum's official website here (only available in Italian)

Continue your journey to Perugia where you will check in at Al Giardino Di Alice, a super cute bed and breakfast with a lovely garden.
Call them up-front to let them know you need parking and to inform them about your arrival time. There is free, private parking about a 5-minutes walk from the hotel.
After you check in and leave your car and luggage, it is time to see the old town which is right next to the accommodation.

Walk down to the old town and visit the cathedral, dedicated to Saint Lawrence that was martyred in Rome in 258. The modest church has understood several rebuilds and restoration works over the centuries since the original structure was raised in the 9th century on top of an ancient Etruscan forum.
Perugia Cathedral is situated on the ancient Piazza IV Novembre where you will also find other attractions worth seeing, like Palazzo dei Priori and the Fontana Maggiore fountain.
Closing time: 19:00

Also situated on the Piazza IV Novembre, visit the Palazzo dei Priori next. This is not only one of the most important landmarks in Perugia, it is also home to Galleria Nazionale dell’ Umbria which features more than 3000 pieces of art, like paintings and sculptures. Particularly the vibrant frescos that cover the ceiling and walls in the Sala dei Notari are worth mentioning.
Closing time: 19:00

End today's sightseeing with a visit to the National Archaeological Museum of Umbria. The museum, situated in a 13th-century Dominican monastery, showcases a large collection of Etruscan and Roman finds, mainly from Umbria.
The tour of the museum goes pretty fast considering most information is only written in Italian, but it is worth visiting nonetheless.
Opening hours: Tuesday-Sunday 08:30-19:30. Note! Closed on Mondays, so if you happen to be there on a Monday, you can shuffle tomorrow morning's itinerary to fit it in if you want to explore the museum (highly recommended!)

Take your time walking to the restaurant and take in the enchanting streets of the historic center as it does not open until 20:00.
Ristorante Dal Mi' Cocco serves tasty set menus for an economical price. The house wine is also amazing and since you are not driving tonight, it is a perfect opportunity to share a nice bottle.
Opening hours for dinner: Tuesday-Sunday 20:00-22:00 Mondays closed.
You can check out their Facebook page here
If you happen to be there on a Monday, head to Osteria a Priori which is a wonderful alternative. It is open for dinner Monday-Sunday 19:30-22:00 and closed on Sundays. Check out their website here for more information.

If you want, you can walk around the old town or go for a drink before heading back to the hotel. However, keep in mind that tomorrow is an early start.