Despite its humble tin roofs, this otherwise plush hotel ranked at No. 1 in the U.S. for its location: a private island that’s 500 yards from Key West, which is close enough to enjoy the festive vibe, but far enough away to feel tranquil. It also impressed readers with its design, by way of 40 white-washed cottages that come with kitchens, but without any pressure to cook, since a breakfast basket shows up on your veranda in the morning.  The hotel also gives you the best of both worlds in terms of recreation: there’s a private beach on your side, but full access to the big-resort perks (like a 37-slip marina) across the water at the Westin Key West
The chic, intimate modernist interiors of this hotel in Beacon Hill contrast with the exterior—a turn-of-the-century, ten-story Beaux Arts building of iron, limestone, and brick, capped with a copper cornice. The lobby has an original cage elevator, while individually designed rooms in taupes, creams, and espressos come with fireplaces, mahogany built-in cupboards, and contemporary canopied beds. The steak house Mooo... has a vaulted-ceilinged private dining room in the wine cellar. Take advantage of the fleet of chauffeured Lexuses for complimentary trips around downtown Boston.

The chic accommodations at the Four Seasons Hotel Toronto reflect the charm of its Yorkville backdrop. The property's rooms and suites – designed with elegant decor and modern amenities like an in-room iPad to access Four Seasons services and bathrooms equipped with deep soaking tubs and TVs – hold views of the downtown neighborhood's surrounding shops and cafes. Despite the abundance of nearby restaurants, guests suggest enjoying a meal on premises; both Café Boulud and d|bar lounge offer French-inspired menus from Michelin-starred chef Daniel Boulud. Serenity-seekers rave about the spacious, sleek setting in the spa, which comes outfitted with an indoor pool, a steam room, a salon and a long list of treatment options.


Art enthusiasts will want to put a date in the diary to visit the Art Gallery of Ontario, which as well as holding the largest Canadian art collection, has Renaissance art, African and Oceanic art and a Henry Moore sculpture centre. The Museum of Fine Arts in Montreal is a must-see with work by Rembrandt, Picasso and Monet, as well as work by Canadian artists such as Jean-Baptiste Roy-Audy.

DH Lawrence penned a love letter about it, Mussolini held court during the war, Churchill was moved to get out his watercolours and his memory lives on in the ancient resident cat of the same name that slinks around picking up titbits of the Michelin-starred food. This peachy-pink palazzo on the still waters of Lake Garda has been stealing hearts since the 1890s, and at the turn of the millennium, it was opened as a hotel, the loveliest in all of Italy. But what makes it so special are all the non-hotel bits: the exquisite antiques everywhere, the silver photo frames filled with black-and-white family shots, the engraved tumblers of fresh roses, the deep bath tubs, and the circus-striped umbrellas by the charcoal-grey slick of swimming pool. Helicopters land on the pristinely manicured croquet lawn and return guests arrive to a fanfare of hugs and kisses, pats on backs. They come here to feast like kings at night on plates of tortellini carbonara, spend the day lolling fatly by the pool watching the ducks and the windsurfers pootle past, and sleep outrageously well under frescoed ceilings in beds made up with crisp, scallop-edged Frette linen. Steep mountains provide a dramatic backdrop for the garden, and early mornings are particularly magic, the silvery pale ethereal light drifting across the lake. The feel of the place is old-school, spick and span, timeless, a bit matronly – and for anyone who likes a bit of Great Gatsby-style cosseting, it’s a dreamy retreat. By Issy von Simson
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