Last Updated on March 17, 2023

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Since gaining fame from the book and subsequent movie “Under the Tuscan Sun,” Cortona’s tourism has made leaps over the past few years.  But this enchanting hilltop town has much more to offer than a filmset following.

Cortona’s history goes back 2,500 years to Etruscan times.  Set in eastern Tuscany, Cortona perches proudly on a green mountainside above terraced olive groves and vineyards, with stunning views across the plain of Valdichiana, all the way down to Lake Trasimeno in Umbria.

Cortona’s position makes it a wonderful base for exploring nearby Tuscan and Umbrian towns such as Arezzo, Siena, Montepulciano, Montalcino (Brunello wine capital), Orvieto, Pienza and Perugia, all within an hour’s drive.

With its Roman and Etruscan rampart walls, steep cobblestone streets and mix of medieval and Renaissance architecture, Cortona has splendidly retained its historic charm, remaining unchanged over many centuries.

Staying in a vacation rental in Cortona’s historic center, my husband and I almost felt like one of the locals on our summer vacation to Italy. Since we stayed here twice during our six-week trip, we thought it would be fun to try two different apartments, and we really had trouble choosing a favorite since they were both amazing, not just for their comfort and convenient locations, but also for the service levels we experienced.

Finestra sul Teatro: A Cortona Vacation Rental in the City’s Historic Center

Finestra sul Teatro (window onto the theater), a second-floor, 2-bedroom apartment is right in the center of it all, just off lovely Piazza Signorelli, named for famous Italian Renaissance painter Luca Signorelli, a native of Cortona.  The piazza houses the beautiful Signorelli Theater, built in 1854, which still today regularly hosts plays and films. Cafes, bars and restaurants line the perimeter of the square, making it a great gathering spot for morning coffee, afternoon aperitivo or dinner, and often live music in the evening.

We loved being able to lean out of our window to peek at what was going on in the piazza, before heading down to dinner in the evenings.

Check out the other walkable vacation rentals we’ve stayed in and loved

Living room of Cortona vacation rental
The spacious open floorplan of Finestra sul Teatr. Photo courtesy of VRBO

Bright, light and airy, this apartment has been completely renovated to modern standards while retaining the charms of its medieval building. There are no elevators, which is standard for historic buildings such as this, but the walk up the stairs is great prep for the steep lanes of Cortona.

Once inside you can’t help feeling lifted by the aura of this home, with its high ceilings, joyful decor and charming details.  Owner Rosanna has clearly put her heart into this place. 

Everything you need is in the kitchen, including dishwasher, cooktop and refrigerator, coffeemaker and kettle. A separate laundry room with washing machine is a great convenience for longer stays, allowing you to pack light and get those clothes washed while you are out enjoying a delicious dinner in one of Cortona’s wonderful restaurants. All appliance instructions are thoughtfully included in a handy booklet in the unit. 

The apartment is air conditioned, including the two ample bedrooms. 

Finestra Main Bedroom in Cortona vacation rental
Finestra Main Bedroom. Photo by Linda Funay McCarley.

Both bedrooms have large wardrobes, with a desk in the main bedroom and a table and chairs in the second room.  We slept soundly in the main bedroom in the queen-size bed, and I used the second bedroom as my own personal dressing room!  This room can be requested with either two single beds or a double bed.

The bathroom has been cleverly designed to make great use of its space, with good-size shower, great water pressure, and counter space for toiletries.

Appartamento Il Petirosso: A Cortona Vacation Rental With a View

Petirosso View from Window of Cortona vacation rental
Petirosso View from Window. Photo by Linda Funay McCarley.

Appartamento Il Petirosso is on a quiet street in Cortona’s historic center, a pleasant 5-minute walk down to the main piazzas. This sophisticated first-floor, one-bedroom walk-up immediately envelopes you with sophisticated, designer-level décor that gives a nod to its history. The apartment’s location affords a stunning view of the valley below Cortona, with beautiful Lake Trasimeno in the distance.

High ceilings, generous windows and a high-style, open-concept kitchen and living area give this apartment a very spacious and warm feel.

The kitchen and living room of the Cortona vacation rental Petirosso
Petirosso Kitchen and Living Room. Photo by Linda Funay McCarley.

Continue to the bedroom and you will be drawn in by its soft tones, romantic ambiance and king bed.

Delight in the luxurious hot tub with frescoed “sky” ceiling and gorgeous chandelier above; you can’t help, but feel pampered.  The separate shower is a generous size and the bench and full-size dressing mirror flanked by two closets are pure bliss for those who hate living out of their suitcase.

A small powder bath off the living area gives that extra bit of convenience and privacy.

Check out the other historic properties we’ve stayed in and loved

What to do in Cortona

Via Nazionale
Via Nazionale. Photo by Linda Funay McCarley.

From either of these beautiful apartments, my favorite thing to do early each morning (after a quick espresso at the apartment) was to stroll down to Via Nazionale just as the shop owners were opening up, and delicious bakery smells permeated the cobblestone lane.

My final stop was my favorite bakery/caffe, Pasticceria Banchelli, with its cute little bistro tables outside, perfect for sipping, munching, and watching the town wake up.  I looked forward to browsing their glass case to see what today’s heavenly, home-made treats were, and fell in love with a new pastry every morning of our six days in Cortona.

Check out our full list of things to do in Cortona

Via Nazionale, Cortona’s main street for the “passegiata,” or evening stroll, is nicknamed by locals as Rugapiana, (flat wrinkle), as it is Cortona’s only flat street. This lane is great for browsing art galleries and shops and opens onto Cortona’s main square, Piazza Repubblica, where you will find the Town Hall, clearly recognizable with its clock tower and magnificent steps.

The Town Hall and the imposing Palazzo del Capitano del Popolo reign over the square alongside other elegant Renaissance buildings with their bars, shops and lovely loggias. Stop in for essentials at the little mercato, a small, family-owned grocery market offering laundry detergent to fresh vegetables. 

Take a cooking class while you’re in Cortona

For wine lovers, visit Enoteca Molesini, a local institution, where you can reserve a tasting and learn about regional wines from wine expert Marco Molesini. In addition to wine, Molesino carries a selection of quality cheeses (we enjoyed a divine Pecorino with our wine tasting), olive oil, and other local products.

Piazza with Molesini Wine Shop
Piazza with Molesini Wine Shop. Photo by Linda Funay McCarley.

Lunch and dinner options are plentiful in this Tuscan town, and while you wander the maze of alleys and lanes exploring the beautiful churches and art museums, it is fun to also scope out your next lunch or dinner spot.  Summertime visits in Cortona mean high season, and reservations are a must, especially for the more popular dinner restaurants such as Osteria del Teatro and La Loggetta. 

Cortona Osteria del Teatro Restaurant
Cortona Osteria del Teatro Restaurant. Photo by Linda Funay McCarley.

In most of Cortona’s restaurants, authentic Tuscan fare and regional wines usually feature on the menus, from pasta with Wild Boar Sauce (Chingiale), to Fiorentina steak (order by weight!), to vegetarian options. At our favorite pizza place Flufluns (named for an Estruscan God), we enjoyed their Margarita pizza so much we had it again the next day!

Chiesa San Francesco
Chiesa San Francesco. Photo by Linda Funay McCarley.

There are several churches in Cortona, and worth a visit is Chiesa San Francesco, built in 1247 as the first Franciscan church built after Assisi, and containing three relics of St. Francis. Luca Signorelli is believed to be buried in the crypt.

Head to the upper part of town and visit Chiesa di San Niccolo, a small, unassuming 15th-century church known for its unusual double-sided painting by Luca Signorelli. Ring the bell and ask the custodian to show you how he turns the painting around by operating its interesting pulley system.

Walks to the top of Cortona will be rewarded with a refreshment at friendly Caffe del Torreone, surrounded by enchanting views of the Cortona hills and offering coffee, pastries, beer and wonderfully fresh sandwiches (watch the owner slice your prosciutto ham right off the leg).

From Caffe del Torreone, a 2km walk further north will take you to Eramo Le Celle, the 13th– century hermitage founded by St. Francis, tucked into the slopes of Mt. St. Egidio. Built at the turn of a narrow valley, it is very impressive for its peaceful spirituality, inspiring quiet contemplation while taking in the magnificent panorama.

Villa Bramasole, inspiration for the book and film Under the Tuscan Sun
Villa Bramasole, inspiration for the book and film Under the Tuscan Sun. Photo by Linda Funay McCarley.

To see the famous Villa Bramasole owned by Frances Mayes, from the caffe make your way down the road on the right.  This road is lined with beautiful Cypress trees, each one planted in memory of every Cortonese lost in WW2. Continuing down this road will steer you back into town through a lovely park and scenic view.

Whether your needs and preference take you to Finestra sul Teatro or Appartamento Il Petirosso, you will be well taken care of during your stay in Cortona, surrounded by the romantic charms of this magical town. Our expectations were exceeded at both apartments, and we will most definitely be coming back, since Cortona kept a little piece of our hearts.

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  • Cherri steadman
    February 27, 2023

    Great article, very informative, could just See myself there !

    • Noreen Kompanik
      March 12, 2023

      We completely agree!