Just off Piazza del Popolo, this historic five-star hotel once hosted Picasso, who has a suite named after him. Its 121 rooms and suites marry a modern sensibility with whimsical touches like Fornasetti wallpaper and statuettes that nod to ancient Rome, but it’s the exceptional service that truly sets this property apart. Another highlight: the secret garden, a romantic hideaway for an al fresco lunch, dinner, or aperitivo.

Discreetly tucked away near the Spanish Steps, J.K. Place Roma feels like the private home of some very chic Romans. Light floods in through the skylight of its bright, airy lobby lounge, which is lined with classical marble statues, while its 30 moody and masculine (and very comfortable) rooms and suites were inspired by Tom Ford’s film A Single Man. Don't miss a meal at the chic restaurant downstairs, which serves a mix of Roman and international classics including burgers and Cobb salads.

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At this tiny hotel smack in the centro storico, patina walls and original floors are the perfect foil to vintage and midcentury modern furniture, whose rough-luxe look is punctuated by statement pieces: your suite (there are only 10) might have a Sputnik light fixture suspended over a dining table, a Murano glass chandelier, or lamp by Giò Ponti. The swanky lobby bar, with its mirrored subway tiles, draws in many passersby from the street, but guests can enjoy more privacy in the small dining room in the back.

Palazzo Dama may be in Italy’s capital, just off Piazza del Popolo, but a French influence seems to pervade. Formerly the villa of a noble Roman family, the property boasts 30 rooms and suites decked out in jewel-toned velvets, glossy coffee table books, and Diptyque bath products, in addition to original Art Nouveau doors and mosaics as well as a neo-Rococo bar covered in 19th-century paintings. Bonus: it’s one of the few hotels in the city center with a pool.

If you want to bask in the glory of Rome’s Dolce Vita past, the Hassler is the place to go. From movie stars like Audrey Hepburn to royalty like Prince Charles and Princess Diana, everyone who’s anyone has stayed at this iconic hotel on the Trinità dei Monti, or Spanish Steps. Classic elegance reigns in its public spaces, though the rooms vary in style from old-fashioned (wooden furniture, antiquities) to contemporary (recessed lighting, whimsical black-and-white accents). The Michelin-starred Imàgo is one of Rome’s top restaurants.

Housed in a 15th-century architectural masterpiece by Renaissance architect Filippo Brunelleschi, the St. Regis Florence is the ultimate palace hotel. You can't go wrong with any of the property’s opulent rooms and suites, which are done up according to a Medici, Florentine, or Renaissance style (many of which feature wall frescoes and chandeliers). Guests especially love the hotel’s location on the banks of the Arno, not to mention St. Regis’s signature white-glove service.

This 10-room bed & breakfast, formerly a 16th-century palazzo, brings a welcome dose of contemporary style to typically old-world Florence. Located in up-and-coming Oltrarno, across the river from major city sights, the intimate property juxtaposes frescoed ceilings with vintage flea market finds and handcrafted pieces from Tuscany and beyond. Fresh pastries, a cozy library, and friendly staff make travelers feel at home.

It doesn’t get much more central than the Hotel Savoy, a Rocco Forte Hotel, whose doors open right onto Piazza della Repubblica and sits just steps from the Duomo. Inside, the design combines a clean-lined contemporary style with hits of color in the form of pattered armchairs and vivid pop-art prints. Fulvio Pierangelini—considered to be one of the best chefs in all of Italy—helms the signature restaurant, Irene, a retro bistro where he dishes out soulful Tuscan cuisine.

Built in the early 18th century for the pope’s treasurer, this 24-room ornate palazzo near Piazza Santa Croce updates its colorful ceiling frescoes, terra cotta floors, old music room, and marble fireplace with clean-lined contemporary furnishings like black leather chairs and tulle-shrouded chandeliers. It's also home to the three-Michelin-starred restaurant Enoteca Pinchiorri, where you'll find one of Italy’s best wine cellars.

If you dream of sojourning at a Renaissance villa in Tuscany’s rolling hills, book a room at the Villa Mangiacane. Just seven miles outside the center of Florence, the property, a member of Small Luxury Hotels, has two outdoor pools, its own olive grove, and a luxurious spa. Spend your days visiting nearby vineyards in the Chianti region, indulging in hearty Tuscan fare at the restaurant, and browsing the Shona artwork from the Zimbabwean owners’ collection scattered around the manicured grounds.

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For a city hotel with views stretching all the way to Capri, this five-star property overlooking the Bay of Naples is a good bet. Inside you’ll find sleek rooms and suites with high-tech lights, showers, iPod docking stations, and Bang & Olufson telephones. Above all, Naples is known for its top-notch cuisine, and you'll find some of the best at this property's Michelin-starred Il Comandante restaurant, located on the rooftop alongside a swoon-worthy pool.

A haven of tranquility in the heart of an otherwise chaotic city, this 14th-century fortress has been softened up and modernized with streamlined furnishings, marble bathrooms, and one of the best breakfast buffets in Naples—though it's the leafy central cloister and original floor plan that truly sets it apart. Accessible rates also make this one of the city’s best values.

Just a few minutes away from the city’s main train station, this restored 1800s hotel is a great base if you plan to visit Pompeii and beyond. The design speaks to the area’s history, with parts of the building’s original wall playing off colors like Pompeii red and olive green. Head up to the rooftop restaurant for traditional Neapolitan dishes with views of Mt. Vesuvius.

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English marine biologist George Bidder Parker (a one-time owner of the hotel) gave his name to this stately 19th-century villa, presiding over a quieter corner of the city center. Its gilded décor—crystal chandeliers, statues, a library stocked with antique editions—harkens back to that era, ensuring guests connect with the property’s past, while rooms and suites feature parquet floors, Italian marble bathrooms, and antiques of their own. Out-of-towners come here for the restaurant and rooftop terrace, which offer panoramic views of the sea and the distant Mt. Vesuvius, though it's the spa most return for.

Wes Anderson could set a movie inside this Belle Époque grande dame perched above the port of Sorrento, just a quick ferry ride from Naples. White-paneled walls, colorful tiled floors, and antiques aplenty form the backdrop for a stay at this picturesque property, which has hosted names like the Queen of Sweden, tenor Enrico Caruso, and Pierce Brosnan. When booking, be sure to request a room with a balcony overlooking the sea.

You’ll feel like Venetian royalty at this five-star property, once the private home of Duke Andrea Gritti. An opulent jewel box perfectly positioned on the Grand Canal, it imparts a palpable sense of history from you moment you cross the threshold, thanks to gold-trimmed ceilings, period antiques, and a covetable hand-painted grand piano. Stays here were meant for living it up: take your morning cappuccino on the canal-side terrace before going for a spin aboard the hotel’s private Riva yacht.

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George and Amal Clooney got married at this sumptuous 16th-century palazzo on the Grand Canal, which is filled with original Tiepolo frescoes, ornate wood carvings, gilded ceilings, contemporary furnishings, and museum-quality art and antiques and was depicted in artwork by both Italian Renaissance painter Paolo Veronese and English Romanticist JMW Turner. Need we say more?

Escape the crowds of St. Mark’s Square by retreating to the JW Marriott, which occupies its own private island in the lagoon just a short boat ride away. The resort’s complimentary shuttle ferries guests to the historic city center, but when it’s time to unwind, you can return to settle into your contemporary suite designed by Italian architect and designer Matteo Thun. Better yet, take a spin around the 40-acre grounds, which house no less than three pools, four restaurants, a kids' club, a cooking academy, and a slick spa—the largest in Venice.

Philippe Starck is the creative genius behind PalazzinaG, and it shows in the hotel’s exuberant design. Surreal reimaginings of Murano’s glass chandeliers, oversize mirrors, and playful animal sculptures mingle in the hotel’s public spaces, which also include a Krug champagne bar. During the Venice Film Festival and the Biennale, PalazzinaG is a hotspot for artists and celebs.

Most Venice hotels are tight on space—not so at this five-star property on San Clemente Island, a 10-minute boat ride from St. Mark’s Square. Here, you’ll find plenty of room to unwind among its fragrant gardens, heated swimming pool, golf course, tennis courts, and three restaurants, not to mention a network of trails that crisscross the island and sumptuous Venetian-style rooms (terrazzo floors, Murano chandeliers, tasselled drapes) with views towards Giudecca. When you’re ready to venture out, take advantage of the complimentary boat service.

One of Milan’s most iconic hotels, the glamorous Principe di Savoia has long been a favorite of fashionistas, royalty, and other A-listers since its heyday in the 1920s. The historic grande dame still exudes old-fashioned elegance with its chandeliers, luxurious brocade fabrics, and plush velvet armchairs, while its spaces remain one of the city's most fashionable hangouts, including a lobby bar that draws a well-dressed crowd and a rooftop spa which pampers weary travelers.

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The Grand in this hotel’s name is certainly no exaggeration. With its massive skylight, swanky Gerry’s Bar, winter garden, and rooms filled with antiques, the property—just steps from La Scala—has long been a fittingly dramatic home away from home for some of the world’s most important opera singers and composers (including Giuseppe Verdi, who spent some 27 years here).

Despite being a newcomer to Milan’s hotel scene, this midcentury-inspired property has quickly become a favorite of design aficionados thanks to a quirky, playful style courtesy of Patricia Urquoia, the creative director of Italian furniture brand Cassina. Expect colorful furniture and retro geometric patterns combined with modern amenities (metal wardrobes, social spaces) in a very of-the-moment way.

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When in Italy’s fashion capital, why not step into the impeccably sleek world of Giorgio Armani, if only for a night or two? The legendary designer put his stamp on each and every detail of this chic hotel, from the color scheme (neutral, with lots of beige and black marble) to the furniture (backlit headboards, sliding panels). A favorite guest pastime: gazing out at the city from the sybaritic top-floor spa.

Known for its English club-style restaurant Il Baretto al Baglioni, this chic sleep has a killer location with a discreet entrance on Via della Spiga (Milan’s main fashion street) and contemporary art that livens up the interiors in the lobby and casual Caffè Baglioni. Choose from classic, Art Deco, or modern rooms—a mix of styles keeps things interesting.