Historic stone clock tower and buildings in a European town square with person walking and stairs on the right.

CORTONA INSIDER TIPS

These Cortona Insider Tips have been carefully curated through years of firsthand experience living in and exploring Cortona, with the goal of helping our guests enjoy the very best the town has to offer.

Our dedicated team is always available to assist!

Cortona, Italy

Cortona Parking map
Cozy dimly lit alley with a small round table, chairs, and candles, leading to a rustic building entrance.

FAQS:

  • Cortona is located in southern Tuscany, about 2.5 hours north of Rome and 90 minutes south of Florence, directly in the middle of Italy.

  • Cortona is easy to access from both airports, with Florence being slightly closer. Rome is about 3+ hours by train or car, and Florence is about 2+ hours by train or car. Florence is a smaller airport while Rome is a large international airport. We recommend that you make your selection by the city that works best for your specific travel needs and preferences.

  • The best season in Cortona depends on what type of experience you would like to have. Do you enjoy warm summer months, temperate spring and fall months, or winter weather? The busiest times are April through October.

  • Visas may be required starting in 2026 to enter Europe. The visa is called an ETIAS visa. Additional details can be found on their website here. You will also require a passport. Please be sure that your passport is valid for at least 6 months beyond your planned date of departure.

  • You can get to Cortona by train, rental car, or private taxi. When you book your stay, we will send you Cortona arrival instructions.

  • You can absolutely exchange money before you arrive in Italy if that is your preference. However, withdrawing cash from local ATMs is also a convenient and widely used option. Just be sure to notify your bank before your departure. Many businesses also accept credit cards.

  • You will need to arrange a special international plan for texting and phone service before arriving in Italy. We strongly encourage you to bring a smartphone with an active international plan in the event of an emergency or an unforeseen delay in your arrival to Cortona.

  • Italy operates on a 220-volt electrical system. You will need simple plug adapters for items such as laptops, cameras, and phone chargers.

    For higher-powered items like hair dryers, curling or straightening irons, and electric shavers, you will need a voltage converter or transformer to convert the electrical current safely. You can purchase adapters HERE on Amazon.

  • In Cortona, as in many towns throughout Italy, a local tourist tax (imposta di soggiorno) is charged to overnight visitors. This municipal tax is set by the town and is collected per person, per night, for a limited number of nights. The funds support local tourism services, including the maintenance of historic sites, public spaces, and visitor infrastructure. The tax is separate from your accommodation cost and is typically paid directly at check-in or check-out in cash.

  • Tipping in Italy is not required in the same way it is in the United States, as service charges are often included. That said, Italians are accustomed to American travelers tipping, and gratuities are always welcomed and appreciated for good service. A 15–20% tip is considered generous and appropriate when you choose to leave one.

    Services where tipping is commonly given include:
    • Restaurants
    • Taxis
    • Tour guides
    • Chefs leading cooking classes
    • Hotel concierge services and bellhops
    • Cleaning services in private residences (Cortona) and hotels

    Ultimately, tipping is at your discretion and should reflect the level of service you receive.

  • In Italy, including Cortona, heating is regulated by national energy laws designed to conserve energy and protect the environment. These regulations determine when heating systems may be used and the maximum number of hours per day they can operate.

    Cortona is located in Climate Zone E, where heating is legally permitted only between October 15 and April 15, for up to 14 hours per day. Indoor temperatures in residential buildings are also limited to approximately 66–68°F (19–20°C). Property owners who do not comply with these regulations may face significant fines, ranging from €500 to €3,000.

    As a result, even if the weather feels chilly outside the permitted heating period, property owners are legally required to keep heating systems turned off. We appreciate your understanding as we follow these local regulations to ensure a comfortable, lawful, and enjoyable stay.

SHOPS & BOUTIQUES

  • Two sets of scalloped ceramic bowls with black and green splatter pattern, stacked with oranges on top, placed on a matching splatter tray in front of a bed with white and blue pillows, against a plain wall.

    TERRABRUGA CERAMICA

    Via Nazionale 54, Cortona, Italy

    Giulio Lucarini makes traditional Cortona ceramics using motifs and patterns that are typical of Cortona and Tuscany. Giulio and Antonella, whose splatterware has been featured in the New York Times Style Magazine, are the proud owners of this shop, located right in the center of town. When you go, be sure to tell them you are friends of Rob and Stacey.

  • A woman inside a rustic shop, seen through a glass window with patterned stained glass at the top, arranging jewelry or decorative items. The shop has wooden shelves and display cases with various items, with a focus on the woman reaching up.

    ROSSI WOODWORKERS

    Via Guelfa 28, Cortona AR

    Giancarlo Rossi, the young shop owner, is not only a longtime family friend but also an internationally renowned artist with a following in many countries. Giancarlo’s sensational wood pieces are painstakingly handcrafted on a lathe from local materials. Today, his once-common trade is dying, and he is one of the last artisan woodworkers working by hand without the aid of computerized machinery.

  • An art gallery with a stone brick wall and a curved brick ceiling, displaying framed landscape photographs and paintings. There are vases on a staircase and a wooden bench with books and more framed art pieces.

    IL POZZO

    Via Nazionale 12, Cortona AR

    At street level, Il Pozzo appears as an upscale tabaccheria selling gifts, postcards, and tickets. Below, a restored cellar opens into a stunning art gallery built around an ancient well preserved at its center. Owner Ivan Botanici spent over 20 years excavating and transforming the space, now home to beautiful handmade crafts, paintings, and jewelry. A true Cortona original, Ivan himself is reason enough to stop in.

  • Close-up of a necklace with black oval beads, gold leaf-shaped pendants, and gold chain links on a black background.

    ANTONIO MASSARUTTO JEWELRY

    Via Nazionale 67, Cortona AR

    One of our favorite Cortona jewelry boutiques. Antonio’s jewelry and sculpture is one-of-a-kind. His beautifully minimalist shop is the perfect backdrop for his exquisite designs.

  • Display of various perfume bottles with gold caps on a white surface, set against a teal wall with shelves holding candles and other items.

    SANTA MARIA NOVELLA

    Piazza Pescheria 2, Cortona AR

    Step inside this elegant Cortona outpost of Florence’s legendary Santa Maria Novella perfumery for a sensory pause from sightseeing. One of the world’s oldest fragrance houses, the shop offers exquisitely crafted perfumes, candles, soaps, and herbal remedies rooted in centuries-old recipes.

  • Display of decorative ceramic plates on a dark textured wall in a room with green walls, a wooden table with a vase and small cups, and a chair, with shelves of more ceramics and a mirror in the background.

    IVO ANGEL STORE

    Vicolo Fierli, 3, 52044 Cortona AR, Italy

    Inspired by time spent alongside her Italian grandmother, founder Jennifer brings a lifelong love of creativity. Her ceramic designs were born in Italy and reflect the simple, beautiful moments that unfold around the table. Each piece is crafted in Tuscany and Umbria by skilled artisans using traditional Italian techniques. Every item retains its own character—thoughtfully designed, beautifully made, and rooted in a deep respect for quality and tradition

LANDMARKS & SITES

  • View of an elegant, empty theater with red velvet seats and ornate white and gold balconies, seen from the stage.

    TEATRO SIGNORELLI

    Piazza Luca Signorelli, 52044

    Cortona has the rare bonus of having two piazzas, the second being Piazza Signorelli, where there are some lovely restaurants and cafe-bars. There is a bar/restaurant inside the Teatro Signorelli, a historic opera building. When the weather is nice, you can sit on the open air loggia and look over the piazza. Take the opportunity to take a peek at the theater in the back of the building, it is magnificent with the old opera box seats and gilded red curtains. We recommend seeing a movie or performance here during your stay.

  • View of a historic cemetery through an open window, with a large chapel in the background and mountains in the distance.

    IL CIMITERO DI CORTONA

    SC del Sodo, 10, 52044

    Cortona’s walled cemetery just below the town is a stunning and fascinating place to visit.

  • Stone walkway with rusted metal railings leading to an old stone building on a hilltop, overlooking a green landscape and distant cityscape under a blue sky.

    FORTEZZA DEL GIRAFALCO

    Via di Fortezza, 52044 Cortona AR

    Just above and behind Santa Margherita, you will find a large stone structure, the Medici Fortress, or Fortezza del Girafalco, one of the many Medici fortresses that were built during the Renaissance period.

  • Interior view of a church or cathedral with ornate religious paintings, stained glass window depicting a religious figure, decorative ceiling with gold accents, and a wrought iron gate in the foreground.

    BASILICA SANTA MARGHERITA DI CORTONA

    Via S. Margherita, 1, 52044 Cortona AR

    Located at the summit of the hill, the church of Santa Margherita is Cortona’s main church and its most famous. The Church is home to Santa Margherita, Cortona’s patron saint, whom you can read about here. Her remains can be viewed in a glass case at the exquisite head altar

  • A hillside house with orange exterior walls and green shutters, surrounded by lush landscaping, with a large tall pine tree in the foreground and other trees on the hillside.

    VILLA BRAMASOLE

    Località Torreone, 151, 52044 Cortona AR, Italy

    Located just past the park is the Villa Bramasole, a home made famous by the book Under the Tuscan Sun (Francis Mayes, 1996). To see this famous house, proceed through the park until the very end, where you will come to a road that continues on around the mountain (to the left). Walk up this road (it is an uphill walk from this point) for about 15 minutes and you will find Bramasole, a large, pink stucco home, on your left. The home features beautiful terraced grounds going up the hill with the palm tree out front. It is a wonderful walk around the mountain, and a great opportunity to immerse yourself in the splendor of the Tuscan hills.

  • Stone buildings with tiled roofs, overlooking a flower garden with pink and red roses, a small fountain, and a green hillside in the background.

    HERMITAGE LE CELLE

    Case Sparse, 73, 06065 Torreone, Cortona AR, Italy

    The Convent de Le Celle is a 13th-century Franciscan Convent located in Le Celle, just outside Cortona. A small hermitage was erected in circa 1211 or 1221, and it briefly housed St Francis of Assisi himself in his lifetime. The rustic stone buildings nestle in terraces on a mountain-side with a Holly Oak and cypress grove. The main convent is accessed through a stone pedestrian bridge spanning a small spring stream. The church has a few ancient works, but many of the present artwork is modern.

RESTAURANTS

  • Two cafe workers, a woman and a man, behind a counter with sandwiches, wine, and glasses. The woman holds a sandwich, while the man is opening a bottle of wine. Both are wearing black berets, and the background shows a cozy kitchen with shelves and hanging copper pots.

    LA DISPENSA

    Via Guelfa, 5-7, 52044 Cortona

    La Dispensa offers traditional Tuscan cooking with a rustic, welcoming feel in the heart of Cortona.

    Insider tip: If it’s on the menu, order the pici al tartufo; it’s one of our favorite Cortona dishes, featuring a light, creamy sauce that lets the truffle shine.

  • A plate of spaghetti with tomato sauce, topped with shredded cheese and garnished with fresh basil leaves, with additional sauce and black pepper around the dish.

    CORTONA BISTROT

    Via S. Margherita, 13, 52044 Cortona

    Off the main tourist path, Cortona Bistrot is a true hidden gem, offering inventive Tuscan cuisine, a cozy vintage vibe, and a terrace overlooking the valley.

    Insider tip: Gluten-free options are available, and the desserts are not to be missed!

  • Person grating chocolate over a plated dish with stuffed rolls topped with sauce and herbs.

    QUANTO BASTA

    Via Nazionale 78, 52044 Cortona

    Restaurant located in Piazza Garibaldi, offering a blend of tradition and innovation in its menu. The dishes feature Calabrian influences and highlight local products and national excellence. With a panoramic view of the Valdichiana from the Cortona Belvedere, it provides a relaxing atmosphere for visitors.

  • An outdoor dining table set with wine glasses, water glasses, and napkins, with rustic buildings in the background.

    LA LOGGETTA

    Piazza Pescheria, 3, 52044 Cortona

    Enjoy classic Tuscan cuisine on the beautiful terrace overlooking Cortona’s main piazza and clock tower. Don’t miss the pici—a beloved Cortona staple.

    Insider tip: The terrace was recently featured as a filming location in HBO’s Succession.

  • Vintage black-and-white photo of a restaurant interior with tables covered in checkered tablecloths, a bar with shelves filled with bottles, two waitstaff standing behind the bar, and decorative items including a bird sculpture, a plant, a globe, and framed pictures.

    TRATTORIA DARDANO

    Via Dardano, 24, 52044 Cortona

    Built in the 1980’s, Dardano is a typical Tuscan trattoria that preserves the culinary traditions of the region. Warm, casual, and friendly, this restaurant is a fantastic lunch or dinner spot for both locals and visitors alike.

    Insider tip: Don’t miss Cortona’s signature Orecchiette al Fumo—tomato cream sauce with smoked pancetta and rosemary.

  • Interior of a historic restaurant with arched ceilings, decorative frescoes, a large window, and tables set for dining.

    OSTERIA DEL TEATRO

    Via Giuseppe Maffei, 2, 52044 Cortona

    Enjoy refined Tuscan cuisine with a creative touch at Osteria del Teatro, tucked along a charming street near Cortona’s historic center.

    Insider tip: This is a favorite for a more intimate, elevated dining experience, perfect for a relaxed, lingering meal.

  • A white plate with a black geometric pattern around the rim, containing cooked lamb chops, garnished with redcurrants, green herbs, and sauce drizzles.

    PRELUDIO

    Via Guelfa, 11, 52044 Cortona

    Preludio offers modern Tuscan cuisine in a stylish, intimate setting just steps from Cortona’s historic center.

    Insider tip: Try the Cortonese dish, pici al ragù di cinghiale, hand-rolled pici pasta served with rich wild boar sauce. It’s a true local classic and widely loved in Cortona.

  • The storefront of La Saletta bar with a yellow awning and large wooden sign, displaying potted plants and a small shelf outside the entrance.

    BAR CAFFÉ LA SALETTA

    Via Nazionale, 26, 52044 Cortona

    Caffè Saletta is a no-frills local favorite on Via Nazionale, perfect for coffee or a quick snack. With cozy leather benches and dark tables, it feels like stepping into another era—and it’s also a great spot to settle in and work on your laptop outside the house.

    Insider tip: The fresh-squeezed orange juice is not to be missed!

  • A plate of pasta with sauce and a side salad with lettuce, cherry tomatoes, and carrots on a table at a restaurant.

    BIRRIFICIO CORTONESE

    Via Guelfa, 16, 52044 Cortona

    One of our favorite spots for wonderful pizza and home cooking, great for a casual lunch or dinner over handcrafted beers. There are outdoor tables on Via Guelfa, great for people watching and enjoying the fresh air.

    Insider Tip: The Ragout is one of our favorites in town!

MARKETS

  • Display of various fruits at a market stand, including peaches, grapes, oranges, and bananas, with price tags and a storefront window behind.

    FRUTTE E VERDURA

    Piazza della Repubblica 24, Cortona AR

    Located just next to Molesini Market, this produce shop sells excellent fresh fruits and vegetables year-round. Be sure to mention to the owners Robbi and Nunzi that you know Stacey and Rob. Insider tip: Don’t touch the produce yourself, ask one of them to handle it for you!

  • Small Italian pasta shop with a wooden sign reading "Bottega della Pasta Fresca" on top. The storefront has pictures of various pasta dishes and food items displayed on the sides.

    BOTTEGA DELLA PASTA FRESCA

    Via Dardano 29, Cortona AR

    A great local pasta shop serving delicious fresh pastas in many shapes and varieties.

  • Hanging cured sausages and meats in a butcher shop with workers preparing meat.

    MACELLERIA CIPOLLINI

    Via Benedetti 16, Cortona AR

    A trusted local butcher, Cipollini provides high quality meats from the local area.

BEYOND CORTONA

  • A historic castle on a small, forested island surrounded by a large body of water, with mountains and land visible in the background.

    LAKE TRASIMENO

    This spectacular lake is located just 15 minutes by car from Cortona. It has walking and biking trails as well as some wonderful villages to visit. Notable towns close to Cortona are Passignano sul Trasimeno, Tuoro sul Trasimeno, and Castiglione del Lago, where there are many restaurants and cafe options, as well as stunning lakeside promenades.

    At Tuoro sul Trasimeno, you can swim at the beach, rent paddle boats or take the ferry to the only populated island on the lake, Isola Maggiore, where there are several restaurants with outdoor dining and spectacular lake vistas.

    For more information about the famous Lake Trasimeno, visit www.trasimeno.ws/index.html.

  • An outdoor flea market in a European city square with vendors and shoppers browsing antique furniture, lamps, and decorative items against historic buildings.

    AREZZO ANTIQUE MARKET

    To shop like a local, come early on Saturday morning before the crowds arrive so you get first pick of unique pieces — from vintage jewelry and antique prints to furniture and curiosities — and locals often start setting up even before the official opening.

    Insider Tip: Don’t be shy about haggling politely (it’s expected), and bring cash for the best bargains. After a few hours of browsing, duck into a café in Piazza San Francesco for an espresso or lunch to recharge

  • Assorted ceramic dishware, including plates, bowls, and jars with lids, featuring blue, green, and yellow floral patterns.

    GIALLETTI - DERUTA POTTERY

    Via Tiberina Sud, 304 Deruta - Perugia

    Founded in 1959 by Virgilio and Giulio Gialletti, this ceramics studio has always based its production on the classic styles from Deruta, painted by their skilled workers capable of reviving the Deruta tradition of the artistic Renaissance majolica, without ever neglecting the search for new forms and patterns.

  • The ruins of an old stone church or cathedral with tall arched windows and columns, and a clear blue sky above.

    ABBEY OF SAN GALGANO

    Strada Comunale di S. Galgano, 167, 53012 Chiusdino SI, Italy

    A truly atmospheric stop in the Tuscan countryside, the Abbey of San Galgano is a roofless 13th-century Gothic monastery whose dramatic ruins are framed by rolling hills — perfect for photos and a moment of reflection. Plan to arrive early if you want striking light and fewer crowds, and wear comfortable shoes — most of the grounds are gravel and open air.

    Insider Tip: Don’t miss the nearby Montesiepi Chapel to see the legendary Sword in the Stone, tied to the story of Saint Galgano’s renunciation of knighthood. The site is best reached by car, with free parking nearby and a lovely farmhouse cafe close at hand.

  • Hand holding a taco wrapped in white paper in front of a building with wooden doors and two women sitting outside.

    LA TUA PIADINA

    Via Dè Cenci, 18, 52100 Arezzo AR, Italy

    Located in the town of Arezzo, the nearest large city to Cortona, La Tua Piadina is a local and family favorite. Known for their melt-in-your-mouth flatbread sandwiches stuffed with delicious local ingredients, La Tua Piadina is a must-visit quick lunch spot for all those passing through Arezzo.

  • A covered patio area overlooking a swimming pool and scenic landscape at sunset, with lounge chairs and umbrellas surrounding the pool.

    TERME SAN GIOVANNI

    Via Terme S. Giovanni, 52, 53040 Rapolano Terme SI, Italy

    Set in the gentle hills of the Crete Senesi near Siena, this classic Tuscan thermal spa is best enjoyed at a relaxed pace — plan to arrive early or mid-week to soak in the outdoor pools with fewer crowds and better views over the countryside. The natural sulfur-rich waters — ranging from warm to hot — are known for their soothing effect on muscles and skin, so linger longer in the hottest pool for maximum benefit. Pair your dip with a light lunch or aperitivo at the on-site Coffee Relax Bistro terrace overlooking the gardens, and don’t forget your own flip-flops and robe for comfort between pools. If you’re there at sunset, the warm glow over the hills makes for one of the most peaceful bathing experiences in Tuscany.