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Greek theatre, Taormina, Sicily

Luxury holidays in Italy

Greek theatre, Taormina, Sicily

By Italy specialist Shannon

Italy does luxury very well. Of course, I’d expect nothing less from a country where the national hobby seems to be the pursuit of la dolce vita. Here, I’ve listed some of the most decadent hotels and experiences I’ve encountered in my decades of visiting Italy, from palatial villas to private cruises. If you’re looking for a taste of that sweet life, I can easily add just one or two to your trip. Or you can include everything for a sybaritic grand tour through the country’s many pleasures.

Luxury hotels and experiences in Venice

Belmond Hotel Cipriani, Venice
Belmond Hotel Cipriani, Venice
Street scene, Venice
Street scene, Venice

The perfect embodiment of Old World sophistication, The Orient Express is perhaps the most indulgent way to enter Italy. With its gleaming brass, plush upholstery, polished wood, and a personal steward for each sleeper car, I’m already in an opulent frame of mind even before I step off the train in Venice and take a water taxi to my hotel. There are two I particularly love in Venice and which you choose depends entirely on your personal style.

If you prefer privacy, I suggest the Belmond Hotel Cipriani. Tucked away in a quiet corner of Giudecca Island, it’s an oasis of old-fashioned glamour. Think plush velvet chairs, floor-skimming damask curtains, delicately gilded antiques, and original oil paintings on the walls. I suggest a suite with a balcony — the views of the lagoon are entirely postcard worthy. When you’re ready to explore, the hotel has a sleek shuttle boat to ferry you to and from the central part of the city.

For those who prefer to be right in the heart of the action, however, I recommend Gritti Palace. Right on the Grand Canal, the hotel has arguably the best views in the city. The decor is classic Venetian with a bold sensibility — you’ll find bright palettes, textured wallpaper, and floral settees. Here, again, I suggest a room with a balcony to take advantage of the canal-side location.

While you’re in Venice, I’ll arrange for private guides to help you explore. Venice is popular, with good reason, but your guide can help steer you away from the crowds and see the less-visited corners and canals of the city. You might explore the secret passages of the Doge’s Palace, sip wine in small waterside bars where only the locals go, or browse the art at the Ca' Pesaro International Gallery.

Luxury hotels and experiences on Lake Como

Bellagio, Lake Como
Bellagio, Lake Como
Grand Hotel Tremezzo, Tremezzo
Grand Hotel Tremezzo, Lake Como

Lake Como’s deep blue waters and wooded hillsides have attracted European aristocrats and Hollywood royalty alike for decades. The shoreline is sprinkled with palatial private villas and you’re likely to glimpse familiar faces as you stroll through lakeside towns such as Bellagio or Tremezzo. Because the area is so popular with the jet set, you’ll find a wealth of luxe hotels. I’ve chosen three that suit different styles, but you have plenty of other options, too.

Just a brief drive from the lively town of Como, Mandarin Oriental is a great choice for those who want classic luxury in a 19th-century setting. For maximum privacy, I suggest one of the free-standing villas, which all have dreamy views of the lake below. Highlights include the salt-water pool suspended in the lake and breakfast on the waterside terrace.

For a more contemporary stay, Il Sereno is an airy boutique hotel with a sleek, minimalist aesthetic and floor-to-ceiling windows to make the most of the water views. Lounge in the infinity pool, relax in the spa, or sun yourself on the private beach. It’s just a short walk to the nearby village of Torno and a brief drive to Como.

The grande dame of the lake, Grand Hotel Tremezzo, was built in 1910 for the glitterati — today, this lakeside showstopper combines modern comforts with classic Golden Age style. Just across from Bellagio, the location showcases the lake’s most beautiful scenery, so I suggest opting for a suite on the northern corner, which lets you enjoy both the water and the mountains. Or you can go for for the top-deck suites with their 360-degree views.

There’s plenty to do here, including a motorcycle tour of nearby Switzerland and an e-bike food tour through Como’s many villages and towns. But the big attraction here is Lake Como itself and I’ll arrange for a private captain to take you wherever you want to go on their gleaming hardwood electric boat. You might relax over a long lunch, wander through small villages, or simply zip around the lake admiring the views.

One unmissable sight is Villa del Balbianello, a lusciously romantic 18th-century villa with formal gardens that you may have seen in Casino Royale or A Month by the Lake. Most visitors land at the public dock and have to walk 20 minutes up to the villa but if you arrive via private boat, you’ll have the quiet entrance near the house all to yourself.

Luxury hotels and experiences in Florence

Villa San Michele, Florence
Villa San Michele, Florence
Uffizi Gallery, Florence
Uffizi Gallery, Florence

Florence holds a special place in my heart — I lived here when I was studying art history in university. There’s only one hotel for me when I splurge on a visit: the Villa San Michele. Perched up in the residential Fiesole, the hotel has sweeping views of the city that are entirely worth the short ride into the heart of Florence.

The rooms here are deeply informed by the city’s Renaissance history — for example, the linens in the Limonaia draw upon the design of period embroidery and breakfast on the terrace lets you revel in the soft morning light that fills the valley.

A private tour of the Uffizi and the Accademia with an art historian can help you understand exactly why the hotel — and Florence as a whole — is so steeped in Renaissance art. That creative ethos has also attracted master artisans for centuries, from leather workers to perfumers, and I can arrange a private tour of some of the city’s historic workshops for you. Florence is also the birthplace of luxe brands like Gucci and Ferragamo, and if you’re in the mood for some retail therapy, I’ll introduce you to a personal shopper.

Luxury hotels and experiences in Tuscany

Borgo Santo Pietro
Borgo Santo Pietro, Tuscany
Rosewood Castiglion del Bosco, Montalcino
Rosewood Castiglion del Bosco, Tuscany

Once you venture outside Florence into the Tuscan country, many of my fellow Italophiles love the frank luxury of Rosewood Castiglion del Bosco, but I prefer the more laid-back luxury of Borgo Santo Pietro. Borgo means ‘village’ — a hint at the nature of this remarkable hotel, where each room is a converted building in what was once a small farming village.

The hotel is surrounded by gardens, fields, orchards, and vineyards, and a stay here helps you understand Tuscany’s intimate relationship between the food, the land, and the people. The chefs use only the food produced on the estate — the only exception is the very well-stocked wine cellar — and I love the private dining experiences that the hotel can arrange, from a candlelit meal in the wine grotto to a lazy afternoon picnic under the golden Tuscan sun.

I also love the roster of experiences that the hotel offers. Painting classes, wine tastings, cheesemaking workshops, beekeeping demonstrations… the list goes on and on, each illuminating a different facet of Tuscany’s twin agricultural and artistic heritages.

Luxury hotels and experiences on the Amalfi Coast & Capri

Il San Pietro Positano, Amalfi Coast
Il San Pietro Positano, Amalfi Coast
Coastal view, Capri
Capri, Amalfi Coast

Sun-drenched and glamorous, the Amalfi Coast is the playground for the glitterati and it’s easy to find luxury here. If forced to choose, however, I’d focus on either Capri or Positano.

With Michelin-starred dining and steps to the sea, Capri’s most exclusive beach club is the Il Riccio at the Capri Palace, and I know people who stay here for that reason alone. I’m not a beach person, but I love the hotel for the classic Amalfi style. Rooms are airy and gleaming white with wide windows looking out onto the glittering sea.

On the mainland, Le Sirenuse is the place to visit if you want to indulge in some people watching. Located about halfway up the cliff, it’s the place to see and be seen. Myself, I prefer Il San Pietro Positano (not to be confused with the stay I suggested in Tuscany). Carved directly into the rockface, this is my idea of classic Amalfi luxury. Rooms are all decorated with traditional tiles from nearby Vietri and have private terraces with sweeping sea views. The service here is also the best I’ve ever encountered in Italy — or possibly anywhere in the world.

There are plenty of things to do in Amalfi, but my top suggestion is to spend a day or three exploring via private boat. Your captain will take you to the hidden coves and grottoes around Capri as you sip Champagne and soak up the Mediterranean sun.

Luxury hotels and experiences in Sicily

Stratovolcano, Mount Etna
Mount Etna, Sicily
Belmond Villa Sant'Andrea, Taormina
Belmond Villa Sant'Andrea, Sicily

The second season of The White Lotus has made Sicily an increasingly popular luxury destination. The show is set in Taormina’s San Domenico Palace, an indulgent hotel converted from a one-time Dominican monastery. You enter through the original 14th-century cloisters and dine in what was once the refractory. The grounds are sprawling and beautifully manicured, and many of the rooms have private plunge pools.

What the hotel does not have is a private beach — the show takes some liberties there. If you want one, I suggest heading instead to Belmond Villa Sant'Andrea, which is built right into a rocky promontory and has a private pebbled beach for guests. Almost every room here has great views of the Bay of Mazzarò, and breakfast is served on the beachside terrace.

Sicily is a big island and you can easily spend a week (or more) there — driving through little villages, visiting the ancient Greek and Roman ruins, and sampling the local wines. For something a little more in-depth, I suggest a visit to Mount Etna with a volcanologist, followed by a wine tasting. If you’re visiting in the warmer months, the local Greek Theatre hosts performances of operas in the same place where the ancients once enjoyed plays by the likes of Sophocles.

Luxury hotels and experiences in Rome

Palazzo Manfredi, Rome
Palazzo Manfredi, Rome
Rome, Rome
Rome's skyline

A visit to Rome feels like coming home to me. Every visit, I make time to go say hello to old friends like Caravaggio’s The Inspiration of Saint Matthew and stop at the same small pasticceria for a chocolate treat. Just being in the Eternal City feels luxurious to me, so I love to stay right in the heart of the city.

That makes my top pick the Hotel Hassler, a grande dame that’s perched practically at the top of the Spanish Steps. Rooms at the Hassler have an understated elegance that I appreciate and the Michelin-starred restaurant, Imàgo, offers both astounding food and panoramic views of the city.

The views at the Hassler are excellent but if you’re looking for something truly spectacular, allow me to suggest Palazzo Manfredi, which overlooks the Colosseum and has perhaps the best view in the city. This chic boutique hotel has a playful sense of style, with pops of bright scarlet or shocking teal throughout the rooms.

Just a short walk away, Villa Spalletti Trivelli is a converted private mansion with the quiet air of a tucked-away retreat, as if you’re the personal guests of the Trivelli family themselves, who still own and run the hotel. I love to wander into the drawing room and pour myself a nightcap from the drinks cabinet and sit admiring the original Rubens that hangs there.

Of course, the city is much more popular than when I was a university student in the 1990s and the major sights are often crowded. If you want to visit headline sights like the Vatican or the Colosseum, I’ll arrange private guides and suggest times that help you avoid the throngs and experience these familiar landmarks in your very own way.

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Start thinking about your experience. These itineraries are simply suggestions for how you could enjoy some of the same experiences as our specialists. They're just for inspiration, because your trip will be created around your particular tastes.

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