Despite already being an on-the-map destination in Italy thanks to the movie Under the Tuscan Sun, there’s surprisingly still a small world to discover in the tiny town of Cortona.

One of the most charming medieval villages in Italy with Etruscan roots and that old-world charm still intact, Cortona’s centro storico (historic centre) is compact, filled with the cutest and quaintest enotecas, restaurants and boutique shops.

Though you won’t find the famous fountain featured in the film as it was completely fabricated, the picturesque piazza – main square – is just as enchanting if not more so in person.

One of the most beautiful villages in Italy, Cortona is seriously postcard-esque. Once an important ancient settlement dating back to the fifth century BC, Cortona’s Etruscan roots (and Roman) still run deep within this hilltop town, as can be see in its medieval architecture, old palazzos, and narrow cobblestone streets. Cortona is also one of the main art and cultural centres in the Val di Chiana in Tuscany after Arezzo, with stunning views of the valley just below it.

Despite this tiny frozen in time gem not being so hidden anymore, there are wonderful secrets that remain to be discovered here – one in particular being Il Monastero di Cortona Hotel and Spa.

Located just beyond the main entrance gate of the ancient walls, tucked away in a tiny alleyway, is the most unique and luxurious accommodation in the heart of Cortona.

The hotel

Il Monastero di Cortona Hotel and Spa first opened its doors in 2019

Il Monastero di Cortona Hotel and Spa first opened its doors in 2019 and was immediately well received by the locals who lived there – a few of them even donating their own personal art collections to adorn the walls as if to give their blessing.

The only five-star hotel within the walls of Cortona Old Town, this former monastery dating back to 1400 was completely converted into the elegant boutique hotel that you see today.

Classic modern style harmoniously merges with the existing architecture and the old monastery with little tributes throughout the premises from the beamed ceilings, antique wooden doorways, enticing corridors and a labyrinth of loggias.

Renovations were meticulously done in compliance with the Arezzo Monuments and Fine Arts Office as well as the environment, keeping the original layout of the structure and recovering – as well as restoring – some ancient frescoes during the process.

The hotel lobby is beautiful and bright with a gorgeous chandelier made of Murano glass front and centre. Here, you are met with the warmest hospitality and staff with a refreshing welcome drink and a hot or cold towel depending on the season – a simple gesture that sets the tone and makes you feel like you are going to be especially taken care of here.

An authentic accommodation that has all the modern amenities with antique touches that pay homage to its former roots, the grounds of Il Monastero are equally enchanting – from the former abbey courtyard and cloister to their lovely garden where the friar’s orto (vegetable patch) once stood.

Another addition is the new terrace featuring a plunge pool and solarium area with lounge chairs/sun beds – the perfect spot for relaxation at any point of the day, not to mention the most picturesque setting for an aperitivo with a view under the Tuscan sun (sorry for the pun).

Strategically, this splendid property is also the perfect homebase for you to explore the surrounding towns and wineries in Italy’s Tuscan region, but more on that later.

There is a beautiful stillness and tranquillity that can be felt at Il Monastero di Cortona Hotel and Spa, which serves as the ideal escape into the serene Tuscan countryside and the most peaceful refuge and retreat.

Rooms and suites

Il Monastero di Cortona Hotel and Spa is home to 36 exquisite rooms and suites

What were once the monk’s quarters are now home to 36 exquisite rooms and suites – each one unique. Il Monastero di Cortona Hotel has nine room categories – from classic, superior and deluxe to their junior suites, suites and six attic rooms each with a spacious spa style bathroom with a chromotherapy shower and Bulgari products.

The décor is minimal but chic with neutral tones, golden hues, a touch of subtle pastels, the most comfortable bed (larger than your average norm in Italy) and the plushest of pillows.

A few other touches that make your stay at Il Monastero even cosier are marble and parquet floors, white beams and high vaulted ceilings with decorated cornices, and accent pieces handmade by local artisans.

The rooms at Hotel Il Monastero di Cortona define tasteful, timeless elegance and Tuscan countryside living made luxurious.

Food and drink

Osteria del Santo

Osteria del Santo is the hotel’s casual dining restaurant

With the new season, Il Monastero di Cortona has added something new to the mix – the hotel’s second restaurant Osteria del Santo – a more casual dining option to complement the original fine dining Ristorante Gli Affreschi.

Named after Saint Benedetto of Norcia, Umbria whose old statue still stands in the courtyard outside, Il Monastero’s Osteria offers an informal proposal compared to the more upscale eatery in terms of ambience and cuisine.

The warm interiors are designed to look and feel like a rustic-chic/shabby-chic country house with 10 indoor tables and seven outdoor tables.

The restaurant opening was inspired by their hotel guests’ requests and, wanting to meet their needs, they created another dining option so relaxing for them there was no need to even leave the estate. The food is equally warm and cosy and, like most osteria’s offerings, are tied to traditional Italian dishes and regional specialities.

Think light lunch Italian-style with a menu made up of salads, toasts, tagliere and Toscani panini (sandwiches) with the ‘heaviest’ dishes being pasta but of the lightest kind possible, i.e. a simple spaghetti with fresh tomato and basil or some other ingredient in season.

The food menu also features other light fare such as local cured meats and cheeses, pappa al pomodoro, gnudi and other typical Tuscan classics and, last but not least, their ‘brace’ (barbeque/grill in Italian) where you can have all the meats (steak, sausage, chicken) plus fish and grilled cheese.

Everything is seasonal and regional, of course, with chef Michele Ricci of Gli Affreschi still in charge of things in the kitchen.

During my visit, I ordered their signature dish for lunch – stracci di pasta all’uovo ragu – a homemade pasta similar to pappardelle in a ragu sauce made of chianina (a beef typical of Arezzo and Siena) and a 24-month aged Parmigiano Reggiano fondue cheese artfully dolloped on top with a glass of their delicious house red (Cortona DOC Syrah), café, and homemade cantucci (Tuscan biscuits with nuts) one of my favourite Italian cookies and desserts.

Open every day for lunch 12pm to 5pm, Osteria del Santo is also where the most abundant of breakfasts can be found each morning at Il Monastero Hotel and Spa.

Ristorante Gli Affreschi

Ristorante Gli Affreschi is a sanctuary of taste where chef Michele Ricci celebrates Tuscan cuisine with flair and sophistication

The original restaurant of Hotel Il Monastero of Cortona inspired by Tuscany’s culinary traditions but creatively revisited, Ristorante Gli Affreschi’s dining room is almost regal with those same neutral tones found throughout the former monastery coupled with gorgeous dark woods, delicately detailed vaulted ceilings, and an overall golden glow.

The interiors are sophisticated and extremely inviting with oversized one-seater settees with puffy pillows and draped banquet chairs set at rounded tables, which are minimally but elegantly dressed.

Each element is meant to make you feel comfortable and incredibly special before your meal even begins.

Named after the frescoes in the dining hall that were discovered during the hotel’s renovations, Gli Affreschi’s intimate space is also adorned with an elaborate chandelier and tapestries – some dating back to the 17^th century.

And speaking of collections, Ristorante Gli Affreschi also has quite the library of impressive vino with wines spanning Italy and across the globe.

With its excellent selection of wines representing of course Cortona and Tuscany, also travelling up north to Piedmont and Veneto all the way down the boot of Italy to Puglia and Sicily, Gli Affreschi’s wine list was awarded One Glass by Wine Spectator in 2024 and one star from the World of Fine Wine for their cantina collection.

Refined cuisine and innovative dishes that play with your palate yet still strongly linked to Tuscany, plates are created using modern techniques (some with a spin) that are impressive in both flavour as well as aesthetics.

The tasting menus, an ode to the region’s rich terroir, are complemented by the innovative “ingredient of the month,” a 2025 novelty that unveils surprising and daring creations

The ‘Menu Degustazione’ of Gli Affreschi is themed around the ‘Sapori Toscani’ (Tuscan Taste), a five-course tasting menu featuring some of chef Ricci’s signature dishes.

On the menu at the time I dined was: a 65-degree slow cooked egg, spinach pancotto (bready soup) with 24-month aged parmeasan fondue, hand rolled cacio e pepe with Cortona saffron soft gelee, grilled venison fillet, the most sensational cheese selection I have ever tasted outside France, and ‘tiramisu in three consistencie’.

Each course paired perfectly with the right type of wine of course. My wines in order (by plate ate) were: Bubbles for a pre-aperitivo welcome drink (paired with a starter of beetroot chips and potato foam), a Le Mortelle DOC Bianco Vivia 2022 from Maremma Toscana (paired with my egg dish), a really perplexing in a good way rose – Toscana IGT Syrah Rosato Le Petit 2023 from Cantina Canaio (paired with my cacio e pepe) which was a refreshing first.

Mementum 2018 Cortona DOC Syrah from Paolo Magi of 14 per cent part of their private collection – I drank out of bottle number 602 out of the 650 bottles that exist (paired with my grilled venison fillet).

With my second-to-last-course of decadent cheeses came a 2019 Sauternes from Chateau Landion and my dessert wine Baldetti Leopoldo vin santo paired perfectly with my dolce of that deconstructed tiramisu, and a mini truffle and macaroon to end my indulgent evening of eating.

My meal was outstanding from start to finish, of course due to the fabulous food and wines I consumed, but also on account of the fantastic service from maître and sommelier Taziana and her right-hand Ilario, guiding me and keeping me company throughout my culinary journey. Topped by chef Ricci coming around to the tables after dinner was completed to personally greet each one of his guests, my dinner at Gli Affreschi was truly an experience to remember.

Ristorante Gli Affreschi is open every day for dinner from 7pm to 9.30pm.

Spa and wellness

Immerse yourself in the warmth of the large indoor heated pool with its 16 whirlpool stations

Hidden beneath Hotel Monastero is Bagni di Bacco – an exclusive spa concept originating from an ancient Roman cistern, where you can bathe like the Ancient Romans did. Immersing yourself in this surreal underground spa setting, surrounded by the gentle rhythm of flowing water is guaranteed to soothe your mind, body and soul.

Named after Bacchus, the Roman god of wine, agriculture and the arts, this cavernous haven is pure zen with a large indoor heated Jacuzzi pool of various water therapy jets, each with a different hydromassage function whatever your ailment is (or not), a wooden sauna and Turkish bath steam room, a cosy relaxation area and two treatment rooms.

Beauty treatments and spa massage therapies cover it all from facials and purifying peels, to body wraps and scrubs, holistic, aromatherapy and deep tissue massages – there is even one dedicated to new mums. They are all ensured to rebalance and regenerate your physical and emotional state and feature sustainable, innovative, and natural products thanks to a partnership with luxury brand Comfort Zone.

Daily rates are €35/£30 for hotel guests, €40/£34 for non-residential guests which includes a wellness kit (towel, slippers, and bathrobe) and the use of the spa for a maximum of two hours, up to ten people. Open every day from 10.30am to 8pm (guests must be at least 13 years of age). Reservations mandatory.

To do

Cortona’s historic city centre is small and condensed but chockfull of restaurants, enotecas and charming little shops. Image credit: Crisfotolux/Bigstock.com

Cortona’s historic city centre is small and condensed but chockfull of charming little shops and enotecas.

Restaurants

The best restaurant for me besides the two hotel restaurants at Il Monastero di Cortona? While Osteria Teatro gets all the hype, I absolutely fell in love with Ristorante La Loggia the first time I visited.

‘The Lodge’ (in Italian) is a family-run restaurant and a favourite among locals and tourists, who has miraculously kept the integrity of their establishment almost 50 years later.

The restaurant, perched slightly above the main square in Cortona with a clear view of the church, serves some of the most authentic, delicious Tuscan dishes and wine.

There are a few different dining rooms to choose from but all charming, cosy, and colourful and in the warmer months you can dine alfresco in between the lovely loggias which surround the restaurant.

The space, service, and environment are extremely warm and inviting with superb service and wines and the most amazing food, of course, with your typical Tuscan fare along with some unexpected plates such as their risotto with pepper sauce, mint and goat cheese; gnocchi with pumpkin sauce and balsamic vinegar; and scallops with chickpea cream and pepper.

Open for lunch 12pm to 3pm and dinner 7pm to 11pm every day except Wednesday.

Private events or tastings can also be organised at Ristorante La Loggia – visit laloggetta.com for more information.

Also worth noting is the Michelin star restaurant of Relais Chateaux Il Falconiere and Spa, but it is a bit far and not at all in the historic city centre of Cortona – therefore only reachable by car.

Enotecas

Enoteca Molesini Wine Store and Wine Club is a local institution in Cortona. Dating back to 1937 and still family-owned and operated, brothers Marco and Paolo Molesini have a seriously impressive selection of wine bottles and labels from all around Italy, including international wines as well as spirits.

Molesini’s wine shop also sells food and typical Tuscan products – and delivers worldwide.

They also organise wine tastings, lectures, wine tours and winery visits, olive oil tastings and every winter hosts an annual event they’ve created called Molesini’s Big Tasting Week – seven days full of wine excursions, seminars, and tasting dinners showcasing some of the best wines in the region of Tuscany, Italy.

This highly anticipated wine event that grows slightly bigger each year attracts wine connoisseurs, enthusiasts wanting to expand their palate, and people already working in the wine industry. Find out more at molesini-market.com.

Shops

Laura Laureto ‘Timeless Italian Style’ – Laura Laureto makes artisanal designer clothing with cashmere silk, wool, and leather.

And everything in this high-end boutique shop is of the highest quality and made in Italy – lauralaureto.com.

MAEC Museo dell’ Accademia Etrusca is a unique museum in the heart of the old city of Cortona where you can find Etruscan, Roman and even Egyptian treasures. Image credit: Roberto Nencini/Bigstock.com

Sights/attractions

Within the walls you’ll find MAEC Museo dell’ Accademia Etrusca. A unique museum in the heart of the old city of Cortona where you can find Etruscan, Roman and even Egyptian treasures – cortonamaec.org.

Designed in 1854, Teatro Signorelli is an active performing arts venue, theatre and cinema located smack in the centre of Cortona.

Just outside, but walkable, you’ll find Belvedere di Via Santa Margherita (panoramic view and vantage point) and the nearby church of Basilica di Santa Margherita – both about a 15-minute walk down from Cortona’s city walls.

Also worth a visit is Villa Bramasole – the setting of the 2003 movie ‘Under the Tuscan Sun’ – a 27-minute walk from Il Monastero di Cortona.

In the vicinity (by car), you can reach The Hermitage ‘Le Celle’ Monastery. This 13^th century convent located just outside of Cortona proper was one of the first Franciscan settlements chosen by Saint Francis of Assisi.

The Archeological MAEC Park of Cortona is a complex of archaeological monuments and remains from the Ancient Roman and Etruscan period in Tuscany’s Cortona.

Getting there

Il Monastero di Cortona Hotel and Spa is located up in the hills within Cortona’s Etruscan walls on via del Salvatore to be exact. But for more precise navigation instructions that keep the LTZ (Limited Traffic Zone) regulations in mind, they recommend you entering this address in your GPS instead: Piazza Giuseppe Mazzini 52044 Cortona.

Cortona has two train stations (Camucia-Cortona and Terontola-Cortona) but from either you would still need to catch a bus to reach the top of the town where the ancient medieval city lies. Walking from the train stations are NOT an option even for avid hikers. Or you can take the bus for your entire ride which drops you off at Piazza Mercato square, just outside of the city walls and main entrance gate.

Highly recommended, however, is renting a small car when in Tuscany, that way you have the freedom to explore the surrounding Tuscan towns and make day trips on your own and at your leisure.

Il Monastero di Cortona has internal private parking available – and without ever having to leave your hotel (the fifteen spaces are all located underground so reachable by elevator and stairs) for €25 /£21 a day. If you prefer not to arrive by car, the hotel can arrange for a shuttle service from the train station to the hotel, as well as a private car hire for the duration of your stay.

In a nutshell

Il Monastero di Cortona has all the ancient charm with an aura of peace and calm

Il Monastero di Cortona Hotel and Spa has all the ancient charm with an aura of calm. Immersed in quiet nature is a splendid oasis that can be found between worlds old and new, between the Old Town of Cortona and the breath-taking landscape of the Val di Chiana in Tuscany.

This off-the-beaten-path five-star hotel in Italy’s Toscana region blends history, art, luxury, wellness, wine, high-level cuisine, incredible service, the most gracious staff, and a warmth that feels like home.

An extraordinary sanctuary when traveling Italy indeed, Il Monastero in Cortona is a true heritage hotel that combines the rich history of the past with the Italian hospitality of the future.

Factbox

Open from March to November. With room prices starting from €450 /£382.

Address: Via del Salvatore snc – 52044 Cortona (Arezzo)
Email: info@monasterodicortona.com
Website: monasterodicortona.com

Il Monastero di Cortona is part of the Cronos Retreats Group, along with five-star La Villa del Re in Costa Rei, Sardinia and four-star Hotel Barocco in Rome.

All imagery unless stated otherwise credit: Il Monastero di Cortona/Cronos Retreats Group