Italy has long attracted travelers, from the starlets drawn to it in the 1950s to modern-day influencers sharing Positano selfies with their followers. Indeed, Italy feels like multiple countries within its 800-mile length. That’s because prior to its 1861 unification, the Italian peninsula was fragmented into several kingdoms, duchies, and city-states, each with its landscape, culture, food, and grapes. As a result, only a cynic would grow weary of visiting repeatedly. For everyone else, most start planning their next holiday before the current one ends.
One day you’re tucking into prawns by the sea; the next, you’re researching boat trips around Capri. And while there’s no one way to do Italy right, staying at the right hotel makes a good trip unforgettable.
From cliffside monasteries to Milanese fashion hideouts to Venetian palaces that feel like a movie set, these properties bring a little magic to your trip.
Here are nine places in Italy to check in, which you’ll never want to check out.
Portrait Milano, Milan
Why Book: Historic architecture meets fashion-world polish
Where: Corso Venezia, at the edge of Milan’s Quadrilatero della Moda
Hidden behind heavy gates on one of Milan’s most elegant streets, Portrait Milano occupies a 16th-century former seminary—one of the oldest of its kind in Europe, and until a few years ago, practically abandoned and closed to the public. Now, it’s home to a Ferragamo family masterpiece that blends reverence for the past with modern design savvy. The central cloistered courtyard is the hotel’s signature—a grand, open-air space lined with boutiques and colonnades that’s rare in this part of town.
Rooms are warm and tailored, with wood, leather, and linen finishes that reflect Milanese craftsmanship at its best. For food, there are two standout options: 10_11, an all-day spot ideal for aperitivo under the arches, and Beefbar, which brings a retro-modern steakhouse energy to the mix. Think Art Deco meets Italian gloss, paired with a deep, smartly curated wine list.
There’s also a Longevity Suite spa, and just beyond the hotel’s private gates are Milan’s top shopping streets, buzzing cafes, and low-key power lunches. This is a stay that feels both hidden and central, polished and relaxed.
Best For: Fashion insiders, design obsessives, and travelers who want to stay where the city actually moves.
Tivoli Palazzo Gaddi, Florence
Why Book: Old-world beauty, modern comfort, and the kind of rooftop bar you’ll remember long after checkout
Where: In Florence’s Centro Storico, a few quiet turns off the main tourist track
Some hotels play the Renaissance card too hard. Palazzo Gaddi doesn’t have to. Built in the 16th century for one of Florence’s noble families, it still feels grand—frescoed ceilings, wide stone staircases, and salons lined with centuries-old art—but it’s not trying to impress you with its history, just fold you into it.
The rooms are elegant, but the townhouse-style duplex suites stand out due to their airy, high ceilings, views across the rooftops, and ample space for relaxing. Downstairs, the Milton Bar achieves something rare—it feels classic without being dated. The bar features mahogany wood, a working fireplace, and cocktails named after famous Florentine gardens. It feels like the kind of place where a well-dressed traveler would have stopped 100 years ago, and yet it feels relevant today.
Aria, located on the roof, offers an unparalleled experience. Come for the golden-hour views of the Duomo, and stay for the hors d’oeuvres and aperitivo, a session that can easily turn into dinner. When you are ready for something more formal, Terrae Restaurant offers a refined menu led by Chef Iside De Cesare of Michelin-starred La Paroli. The cuisine combines a unique blend of technique and restraint, highlighting the power of local ingredients.
Events—think destination weddings—are set in a series of frescoed salons and a historic ballroom lined with artworks from one of the Gaddi family’s most famous patrons, Niccolò di Sinibaldo. But even if you’re not here for a private event, the whole hotel feels like an occasion worth dressing up for.
Best For: Travelers with taste, returning visitors, and anyone looking to experience Florence without getting swept up in the crowd
The Rome EDITION, Rome
Why Book: A modern sanctuary with cinematic scale in the heart of the city
Where: Just off Piazza Barberini, within walking distance of Villa Medici and the Colosseum
Rome, a city rich in history and beauty, is equally beset by traffic and crowds. The Rome EDITION alleviates the visual and audible noise by providing space, clarity, and scale. Inside a stately 1940s building designed by Cesare Pascoletti and Marcello Piacentini, the hotel features a lush courtyard that feels like a secret garden.
Step inside, and everything shifts again: you will find a soaring lobby draped in floor-to-ceiling green velvet, original marble staircases, statues, and vintage lighting that remain from the building’s former life as a bank. The color palette is muted yet textured, featuring wood, stone, and the interplay of shadow and light. It’s dramatic without being cold.
Ian Schrager’s signature style, clean and contemporary, underpins the rooms with an ever-so-naughty playfulness. After a day of elbowing through crowds at the Forum or the Vatican, entering your room or suite feels like a chance to exhale in solitude.
Additionally, there is a rooftop pool (yes, you can actually swim in it), a courtyard garden bar, an iteration of the brand’s signature cocktail bar Punch Room, and the excellent restaurant Anima, which is a culinary standout in a tourist-heavy neighborhood. Helmed by chef Antonio Gentile, the food is seasonal, creative, and absolutely worth seeking—even if you’re not staying the night.
Best For: Travelers who want Rome’s energy but also a place to retreat and eat well while doing it
CPH | Pevero Hotel, Costa Smeralda, Sardinia
Why Book: Understated luxury that mirrors the Sardinian landscape
Where: Overlooking Piccolo and Grande Pevero bays, just outside Porto Cervo
CPH | Pevero Hotel blends into its surroundings in all the right ways. Warm, natural tones color the buildings, echoing the granite hills of the coastline. The low-key lobby creates a welcoming atmosphere at check-in, reflecting the laid-back yet upscale attitude of both the property and its staff.
Recently refreshed rooms strike a clean, modern tone while maintaining a connection to the island through local materials and organic textures as well as a soft pink color palette evocative of the pink granite beaches. Balconies open to expansive views of Sardinia’s trademark turquoise waters.
The hotel sits on a gentle slope. Instead of succumbing to space constraints, the architects designed a dramatic series of pools that are set into the hillside and cascade like the terraces of a waterfall. If you ever tire of the pools—which is unlikely—you can take a five-minute walk to the bathtub-like waters of Grande Pevero Beach. In summer, the beach is packed with tourists, but if you get there early, you’ll have it to yourself.
Lunch at Le Piscine is a highlight: it’s a place to relax with expertly cooked pasta along with grilled seafood and vegetables. The bottarga and clam linguine is the dish to order, with its briny, unctuous, and yet balanced flavors in the form of a swirl of pasta topped with thin slices of the local delicacy from Cabras. For dinner, Zafferano offers a refined experience with views of the ocean. Enjoy a cocktail, and then explore the extensive selection of Sardinian wines to pair with a salt-baked whole sea bream for two.
Don’t miss the excellent spa, where you can select a facial or deep tissue massage; the therapists, blessed with strong, steady hands, will alleviate the kinks from overnight flights.
Best For: Couples, design-conscious travelers, and anyone looking for a relaxed Sardinian base close to the sea
Anantara Convento di Amalfi, Amalfi Coast
Why Book: Historic soul, panoramic drama, and just the right amount of indulgence
Where: Tucked into the cliffs above Amalfi town
Anantara Convento di Amalfi, originally a 13th-century Capuchin monastery, honors its history without succumbing to it. The setting is dramatic: arched corridors, vaulted ceilings, and preserved stonework contribute to a dramatic ambiance, while modern comforts provide a comfortable, upscale experience. From nearly every corner, the views turn cinematic, especially from the sea-facing guest rooms that frame both the coast and the shifting shades of blue in the water. On the roof, an infinity pool stretches toward Capri, while a spa welcomes guests who have had a long day of travel.
Mornings start with espresso on the terrace; evenings are made for cocktails on the lawn before a bowl of fresh pasta at Dei Cappuccini, the hotel’s signature Italian restaurant run by Chef Claudio Lanuto. Service is thoughtful, never overbearing, and gracious given the otherwise glamorous location. Of course, it helps that the setting does most of the work.
Best For: Romantic escapes, slow mornings, and travelers who want the Amalfi Coast without the frenzy
ROMEO Napoli, Naples
Why Book: A bold blend of cutting-edge design, good food, and holistic wellness
Where: Naples waterfront, near the ferry terminal
Naples thrives on contrasts, and ROMEO Hotel perfectly embodies that spirit. Designed by Japanese architecture firm Kenzo Tange & Associates, this sleek, modern, maximalist hotel stands out with its sharp lines and contemporary art, all set against the historic backdrop of the city. Its prime location offers quick access to both the bustling city center and ferry departures to Capri and Ischia.
Despite the lure of pizza across the city, don’t miss dining at the property. Culinary experiences here are exceptional. Il Ristorante Alain Ducasse Napoli, for example, offers Michelin-starred dining with panoramic views of the city. For a more relaxed affair, La Terrazza on the 10th floor offers a rooftop bar and restaurant experience adjacent to the infinity pool, with views of the Gulf of Naples.
Wellness is a cornerstone of Romeo’s experience. LA SPA Sisley Paris offers various treatments, such as aromatherapy, body wraps, and facials, all set in a tranquil environment that features a gym, Kneipp path, hot tubs, saunas, and sensory showers.
Best For: Travelers seeking a luxurious stay that combines modern design, gourmet dining, and comprehensive wellness facilities
The Gritti Palace, Venice
Why Book: Iconic Venetian opulence right on the Grand Canal
Where: San Marco district, Venice
The Gritti Palace has long been associated with the opulence of Venice. Now, the hotel has added a new chapter to its storied history. The Luxury Collection, of which Gritti Palace is a member, has partnered with MAD Academy, the food sustainability organization founded by world-renowned chef René Redzepi, to redefine sustainability in hospitality. As a result, the hotel’s culinary team has reimagined how it sources ingredients, creates and composes dishes, and handles food waste.
For example, the hotel’s cooking classes at the Gritti Epicurean School offer guests the chance to select fresh, locally sourced seafood and produce at the nearby Rialto Fish Market before preparing Venetian-inspired dishes back at the hotel with executive chef Alberto Fol.
The hotel’s commitment to local seasonal produce extends to its gardens on Giudecca and Mazzorbetto islands, which supply fresh ingredients for its flagship restaurant, Club del Doge, as well as its other drinking and dining venues, including the fabulous waterfront Riva Lounge, the seasonal Gritti Terrace, and the elegant jewel-box Bar Longhi.
Best For: Travelers seeking classic Venetian luxury with a contemporary, eco-conscious twist.
Dimora delle Balze, Siracusa, Sicily
Why Book: An escape to Sicily that feels personal, not packaged
Where: Between Noto and Siracusa, in the hills of Val di Noto
Skip the crowds in Taormina and head south, where Sicily opens up into expansive sea and countryside views. Dimora delle Balze sits on 60 acres of countryside, with stone courtyards, citrus trees, and rolling hills unfurling in every direction.
The building occupies a restored 19th-century masseria accented with original frescoes, arched ceilings, and thick plaster walls. Each of the 11 rooms feels handmade, not designed by a corporate committee. There’s a saltwater pool, a small spa, and a restaurant serving ingredients grown right on the land. It feels like staying at the restored home of an interior designer.
The hotel is close to the coast and the gorgeous golden town of Noto. Go for a drink to see sunset light up the city, then head back in the evening for dinner.
Best For: Travelers who want space to slow down and a stay that actually reflects the place
Hotel Capo d’Orso, Palau, Sardinia
Why Book: For easy access to the Maddalena Islands, minus the crowds
Where: Cala Capra Bay, just outside Palau, northern Sardinia
Tucked into a quiet cove and surrounded by pines, wildflowers, and stone paths, Hotel Capo d’Orso feels hidden in the best way. It’s part of the family-run Delphina group, known for putting Sardinian hospitality and wellness at the center of their properties. The hotel isn’t the flashiest resort on the island—and that’s the point. It blends into the landscape, wrapped in a protected park that feels a world away from the busy coastal scene.
What is the true magic of this place? Thanks to company partner Poseidon, the hotel boasts a private marina and a fleet of small boats. For example, the company’s experienced skipper Allesandro might take you out to see the otherworldly beauty of the Maddalena Islands, drop you in Maddalena town for a sunset aperitivo, and then return you in time for dinner. Guests can even book a day trip to Corsica, only a mere 30 minutes by boat from the property.
The hotel’s flagship Italian restaurant, Il Paguro, is a destination-worthy experience; the waterfront restaurant offers fresh-caught fish and local lobster, handmade Sardinian pastas, and a strong wine list with a memorable staff, including the manager Angelo, who’s been working there for decades. It’s the only restaurant on-site that accepts outside guests. You might find yourself sitting next to the owner of a mega-yacht parked just off the coast who arrived via tender tied up out front.
During the day, the property has a plethora of nooks in which to escape, from quiet decks tucked under trees or on the water, plus a wild beach, a yoga deck, and an outdoor gym. For spa enthusiasts, book a massage and then spend the afternoon hopping between the saltwater Thalasso pools.
Best For: Nature lovers, island hoppers, and anyone who wants Sardinia without the scene