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Tucked away on the less-trafficked slopes of Mount Portofino, above the picturesque waterfront town of Camogli and scenic Riviera di Levante, Villa Rosmarino is that Italian friend’s vacation house you’ve been dreaming of. Owners Mario Pietraccetta and Fulvio Zendrini left Milanese corporate life to transform this dilapidated turn-of-the-century palazzo into a midcentury-style oasis with touches of Italian modernism, then moved in permanently, inviting others to experience their personal brand of la dolce vita. The library is outfitted with stylish armchairs, warm wood ceiling beams, and a collection of art and travel books that spans the walls, and the living room’s well-stocked honesty bar is the backdrop for friendly nightcaps. Rooms aren’t numbered, and the sprawling gardens are easy to get lost in. Mario and Fulvio are likely to chat guests up while lounging by the pool or sipping espresso on the balcony, offering their insider knowledge about the area and arranging one-of-a-kind excursions, from visits to secluded beach clubs to rides in their wooden motorboat.

To stay at this three-story courtyard hotel in the historical heart of the Latin Quarter is to be surrounded by intellectual giants: the ghosts of figures such as René Descartes or James Joyce, who each lived nearby, and by present-day students and teachers at the most elite universities and high schools of Paris. The youngsters’ extracurriculars—café lounging, bar hopping, and vintage record, book, and clothes shopping—give the quarter a unique mix of history and life.

Hotel des Grandes Ecoles occupies three 19th-century houses along a private cobbled passageway leading to a courtyard garden. Old-fashioned in the best sense, one of the charms of the place is that the compound feels like an escape to a French granny’s country cottage. Small by American standards, rooms done in toile or floral fabrics exude classic Gallic charm; French cotton lace and matelasse drapes the sitting tables and beds. Bathrooms are immaculate but simple, with either shower or bathtub and toilet.

Towering 42 stories over the Mong Kok district on the Kowloon Peninsula, the Cordis is one of the best options for adventurous travelers looking to experience the “real Hong Kong.” The hotel is surrounded by mazes of markets. as well as shops and restaurants that are popular with locals. But getting off the beaten path doesn’t mean foregoing luxury. The Cordis has rooms with plush bedding and oversized windows, as well as homey touches like soft carpeting.

The biggest draw of the Cordis, Hong Kong, is its collection of 1,500 works of contemporary Chinese art, one of the largest hotel collections in the world. Guests can browse the collection on their own with the help of free iPod art tour cards. The hotel attracts an edgy crowd of young artists and professionals who mingle in the Garage Bar—a food truck and craft beer destination with Western-Asian fusion food and a selection of over 40 brews—late into the Kowloon night.

It appears small from the outside, but Gale South Beach manages to pack a lot into a modest space, including Italian restaurant Dolce, a cocktail lounge, and a nightclub. These attractions, and its prime location on Collins Avenue, just a block from the beach, make the Gale a social hot spot. The landmarked art deco building is, like many of its neighbors, protected from structural changes; as such, the hotel harks back to the golden age of American architecture. Inside, the decor evokes 1940s–1960s style, with throwback typography, black-and-white family photos, newspaper clippings, and mid-20^th-century memorabilia providing atmospheric design touches. The rooms are on the smaller side but tend to let in lots of natural light. The color scheme is nautical, with blue carpeting and white walls, and crisp, bright white linens embroidered with the hotel name in blue. Guests can take advantage of an outdoor bar on the fourth floor, and a rooftop pool. An annex of the hotel is set to open just a few feet away in December 2014. The Gale Suites at Kaskades is a 25-suite complex with a focus on luxury and privacy. It features rooms with Jacuzzi tubs and rain showers and has its own rooftop deck with cabanas.

You will want reservations to get into this place. The Mission Restaurant and Lounge serves modern Latin cuisine in a fantastic bar restaurant with a wonderful outdoor back patio (seen here). The chef is Matthew Carter, also known for the House and Zinc Bistro. For desserts, order the pumpkin bread pudding with scotch, pepitas, and pomegranate.

Avenue Arístides Villanueva, simply known as Aristides by the locals, is Mendoza‘s main nightlife drag. Lined with bars, Irish pubs, restaurants, dance clubs and hostels, Aristides is where all the action happens. In warm weather months, crowds flock to the outdoor tables lining the sidewalk. It’s a great option for bar hopping and getting a dose of the late-night Mendocenan culture.

Playa Veracruz is dotted with about a dozen small ranchitos (concessions) and bars. During weekends, it’s especially popular with young locals, who come here to let loose and dine on super cheap grub. The offerings are good: ceviche, fried fish, and plantains. One of the bars is Karimar Aventura. Veracruz Beach is about seven kilometers (roughly 4.5 miles) from Playa Bonita.

A pleasant way to spend an evening in Milan is to stroll along the Naviglio Grande, a 12th century canal in the south of town. The warehouses along the towpath are now home to lively restaurants and bars. I recommend El Brellin. The second floor restaurant offers refined modern Italian fare with ambiance to match and the bar below gets busy on the weekends.

The Bellini was born in Venice at Harry’s Bar, which has been hopping since 1931. Declared a National Historic Monument by the Italian government in 2001, this San Marco bar and restaurant is a cultural institution. Even though it doesn’t do the best food in Venice, and prices are ridiculously expensive, it’s worth dining here once just for the experience. Over the decades it has served a global collection of writers and artists, including Ernest Hemingway, Charlie Chaplin, and Orson Welles, and today it’s still popular with Venetian movers and shakers.

The interior decor has not changed since Giuseppe Cipriani opened Harry’s on the eve of World War II (and during the war, Harry’s was one of only a handful of restaurants in Venice that would serve Jewish patrons). The food is classic Venetian. Try the baked sea bass with artichokes for a main, and make sure to save room for dessert. Harry’s is famed for crêpes flambées and also its Cipriani chocolate cake. Reservations are imperative; when booking ask for the ground floor because dining here is all about seeing and being seen, and the second floor is considered much less cool by Venice society (although it has much better views and more dining space).

Dining at one of Negril’s excellent cliffside restaurants is highly recommended, and the gorgeous setting of Ivan’s Bar & Restaurant at Catcha Falling Star makes it a very nice option. The longtime favorite has one of the best views along the coast and serves lobster dinners and classic Jamaican cuisine with a bit of a modern twist. Guests are seated under an open-sided thatched roof or out under the stars at private tables on a patio near the cliff’s edge. Another favorite choice for romantic cliffside dining is the restaurant at Rockhouse Hotel. (If you want more cocktails post-dinner, walk down to LTU Pub and mingle with the locals. Casual eateries and cliff bars along West End Road include 3 Dives and Sips & Bites.)

When owner Dave Neupert discovered the history of the Gold-Diggers Entertainment building in East Hollywood, he knew he had to turn it into a music-themed bar and boutique hotel. Originally built as an “inn above a tavern” in 1924, directly on Santa Monica Boulevard back when it was the famous Route 66, the building later became a dive bar with a rehearsal studio in the back that welcomed punk bands and was even used as a sound stage for Ed Wood. Now, the sleek Gold-Diggers bar includes dark-wood chevron paneling, textured wall coverings, a gold-velvet stage curtain, and Art Deco pendant lighting. Justin Gage of Aquarium Drunkard oversees the music and has welcomed such musicians as Iceage, Mary Lattimore, Julianna Barwick, and Luna to perform. There’s also an on-site recording studio, featuring nine professionally designed and acoustically engineered writing, tracking, and mixing studios managed by industry veteran Simon Horrocks and Grammy-award-winning engineer Eric Gorman.

Straddling Cancun’s sandy beach in the heart of the Hotel Zone, the CasaMagna Marriott Cancun Resort features 450 re-modeled rooms and suites with balconies with ocean views. The AAA Four Diamond-award winner houses a wide selection of restaurants and bars, offering Argentine, Japanese, Southwestern, Italian or Thai cuisine. La Isla-Pool Bar serves poolside snacks and drinks in a family setting, while Bahia dishes up fresh seafood on the beach. Las Ventanas Lobby Bar is the place to meet for drinks and appetizers and enjoy nightly entertainment, while Las Ventanas Gift and Coffee shop offers “grab and go” and late night snacks. A full-service fitness center, pool and onsite tennis and water sports complete the recreational package. The Marriott Kid’s Club offers entertainment for the younger guests. High speed Wi-Fi is available in rooms and public areas throughout the resort.

This hotel is on our list of The 11 Best Hotels in Chicago.

Designers Lisa Simeone and Gina Deary of KTGY Simeone Deary Design Group oversaw the original design of the Parisian-inspired Waldorf-Astoria Chicago in 2009, and the pair was once again brought in to breathe new life into this 215-room Gold Coast gem. Rooms are now bright white, well-lit, and include pops of uplifting magenta. Before you hit any of them, however, there’s much to entice at street level. Enter from the circular driveway and marvel at the Swarovski chandelier, modeled after a vintage brooch, along with the herringbone wood floors and black-and-white pinstriped stone. Don’t miss the Peacock Lounge and its secret sister, Bernard’s Bar, an intimate craft cocktail and champagne boîte, which is virtually unknown even by city denizens (which means you can always find a seat). Its Scottish and equestrian themes are almost as anachronistic as the Mansard roof and circular driveway, which just adds charm to this newly beloved Chicago hotel.

The guest rooms feature oversize headboards and abstract floral bedspreads, while bathrooms are a marvel of marble. For something more, splurge on either the new 1,800-square-foot Astoria Suite or the redesigned 2,400-square-foot Presidential Suite, both of which will have you feeling you’ve been transported to a Parisian pied-à-terre (the latter’s primary bedroom features a fireplace).

Peggy Dulany, a New York philanthropist and daughter of David Rockefeller, bought J Bar L to protect the 620-square-mile Centennial Valley, a former Native American hunting ground settled by a few cattle-ranching families in the late 19th century—and which still has no towns, let alone paved roads, gas stations, shops, or subdivisions. To conserve the rangeland way of life, she hired locals to run a holistic grass-fed cattle business on the principles of rotational grazing and natural stockmanship. To share the landscape with nature-loving travelers and to keep the valley looking as it was, Dulany restored several abandoned 19th- and early 20th-century homesteads. These self-contained vacation rental homes range from a Sears Roebuck family house, now solar-powered, to isolated cabins on a bend of the Red Rock River. All come with fully-equipped kitchens and are tastefully filled with Western-themed furnishings and antiques; some have outdoor hot tubs.

J Bar L no longer offers working weeks for would-be cowboys but will match guests with geologists as well as with hiking, bird-watching, and fly-fishing guides. Horse lovers can hire ranch mounts for guided daily rides on rangeland that is home to pronghorn, elk, and Black Angus cattle, or up the slopes of the 10,000-foot Gravelly Mountains where wolves, grizzly bears, and bald eagles roam.

Housed on a 1,100-foot stretch of beachfront, Grace Bay Club is as stylishly current as it was in 1993, when it became the first luxury hotel to open on the then nearly empty sands of Grace Bay. From its original 21 rooms, the upscale property has grown to 82 suites, each of which features ocean views, a private veranda or patio, and chic interiors by renowned designer Thom Felicia. Guests can also look forward to superior service, including a personal concierge available day or night via a provided cell phone.

When hunger strikes, there’s the oceanfront Infiniti Restaurant & Raw Bar, which boasts sea-to-table fare and the longest bar in the Caribbean, as well as several other family-friendly venues, including The Grill. If it’s pampering you seek, make time to visit the spacious Anani Spa, where you’ll find six treatment rooms, including one just for couples. A spa tent is also available for beachfront massages.