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  • Francisco I Madero, Centro, San Lucas, 23450 Cabo San Lucas, B.C.S., Mexico
    Cuban cigars, considered the best of the best by tobacco connoisseurs, are technically out of reach for most Americans, thanks to the U.S. embargo of Cuban goods. If you’re in Cabo, though, there’s nothing preventing you from taking a puff on an authentic Cuban, and if you enjoy a good cigar, the best place to find one here is at this shop.
  • Waianapanapa State Park, Hana, HI 96713, USA
    This lovely state park stretches along the rugged volcanic shoreline of western Maui, three miles from Hana. It’s best explored on the 2.2-mile hike that starts at the black-sand beach and follows the dramatic coast, passing lava tubes, rock arches, blowholes, and Polynesia’s largest heiau (an ancient Hawaiian temple) along the way. Avoid standing too close to the geysers as well as the lava benches near the ocean, which can crumble easily, and watch out for high surf. If you’re looking to cool down after your trek, take the loop trail to the park’s freshwater caves, where you can explore two separate chambers (the first tends to be clearer and more inviting).
  • Negril, Jamaica
    No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

    As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.
  • Grace Bay Road, Providenciales, Turks and Caicos Islands
    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.
  • 35 Rue du Chevalier de la Barre, 75018 Paris, France
    At the summit of Montmartre, the highest point in the city, you’ll find the Basilica de Sacré-Cœur. Contrasting with the Gothic churches like Notre-Dame, the Romano-Byzantine architecture is both beautiful inside and out. While outside, take in the panorama of Paris and while inside, marvel at the Apse Mosaic—one of the largest mosaics in the world. The Sacré-Cœur website has instructions on how to download the free audio guide on your phone before your visit which is recommended. Also, research the well-known (and apparently tried-and-true) scams before traveling to Paris. Overall, the city seems pretty free of tourist scams, but around Sacré-Cœur especially, visitors should be on alert.
  • Piazza del Duomo, 7, 95024 Acireale CT, Italy
    This stretch of beaches and rocky islets north of Catania were named for their role in Homer’s legend of the Odyssey. In the story, it was here that Odysseus encountered the cyclops Polyphemus, and the lava rocks jutting from the sea are said to have been thrown by Polyphemus as the hero sailed away. Today, the beaches around fishing villages like Acireale and Aci Trezza are beautiful—and popular—summer hangouts.
  • There aren’t too many opportunities in the Caribbean to ride on horseback to a cave. In Los Haitises National Park, located three hours west of the resorts of Punta Cana, Fun Fun (pronounced “Foon Foon”) Cave is officially known as the largest cave in the Caribbean. Though the cave itself is in the National Park, access to the land goes across a private ranch and requires a guided tour. While the nearly three-hour drive from the resorts of Punta Cana is a lengthy, bumpy, journey into the interior, the scenes from the window provide an authentic glimpse into rural Dominican life. Sugar cane sways, schoolchildren wave, and mangoes drip from the trees. Upon reaching the ranch where you begin the tour you are shimmied into a jumpsuit and saddled onto your horse. A 45-minute ride through the shaded forest brings you to the edge of the National Park. From here it’s another 30 minute walk through sun-swallowing trees until you reach the entrance of Fun Fun Cave. Sliding into a harness and climbing gear, entering the cave requires a 50 ft. repel into a tiny hole which can barely fit your shoulders. Once at the bottom, it’s a one hour slog through the depths of the darkness before reaching the other exit. Inside the cave, stalactites and stalagmites pepper the areas which fall in the beam of your flashlight, and at some areas you are forced to swim through the soothing, subterranean waters. Here, a lone rope helps guide visitors through the hidden recesses of the cave.
  • Entrega is Huatulco’s most popular beach, what with clear and calm water, clean sand and nearly a dozen food kiosks. Visitors who want to see marine life beneath the water’s surface can rent snorkeling gear and kick off right from the beach; expect to see plenty of colorful fish. The beach gets particularly crowded on weekends, when locals come to relax, so try to arrive early and stake your spot in the sand.
  • Calle del Scaleter, 2202, 30125 Venezia VE, Italy
    One of the most famous restaurants in Venice, the Michelin-starred Da Fiore occupies an understated-yet-elegant space in what was once an old Venetian tavern. The food is a modern take on traditional Venetian, with lots of fish and seafood, but the menu changes constantly based on what is fresh and locally available. Everything is wonderfully prepared with a lovely fusion of flavors and textures and comes out perfectly plated. There’s also an excellent wine list. You can order à la carte or choose a six- or seven-course tasting menu at dinner.
  • Via di Monte d'Oro, 30, 00186 Roma RM, Italy
    Opened in 2013 in a building that previously housed the University of Rome’s architecture department, JK Place is one of the newer additions to Rome’s growing number of high-end luxury boutique hotels. It is located near the intersection of Via Del Corso and Via dei Condotti, Rome’s most chaotic shopping nexus, but it is just far enough away from the action to maintain an air of seclusion, a rarity for the zone.

    Behind the hotel’s unassuming doorway, classrooms and offices have been transformed into an effortlessly cool retreat. Like its siblings in Florence and Capri, the JK Place Rome is eclectically decorated and packed with artwork. Rooms feature canopied beds, sculptures, and sleek bathrooms decked out in Italian marble. The JK Café Bistro and bar attract well-heeled locals, giving the hotel a more down-to-earth vibe than its boutique neighbors, without sacrificing its unquestionable elegance.
  • Via del Brigantino, 1, 84017 Positano SA, Italy
    Check your email and share your pictures of your fabulous Amalfi Coast vacation on Facebook and Instagram, all while you enjoy a cold drink with a view of the Spiaggia Grande. La Brezza Net Art Café has strong Wi-Fi and is open all day for breakfast, lunch, snacks, aperitivi, and dinner. The menu includes big salads and simple sandwiches. The lemon granita is particularly good. Below the outside terrace, the BioBrezza counter serves fresh fruit smoothies and juices.
  • A visit to the incredible 365-island archipelago (also called the San Blas Islands) within the communal lands of the Guna Yala indigenous nation provides some extraordinary seaside experiences. The islands making up the outer archipelago are unspoiled and feature gorgeous white-sand beaches, turquoise seas, and a one-of-a-kind encounter with Guna culture. Visitors lodge in natural-material huts (cane walls and interwoven palm-frond roofs) or—if you’re in the mood—sleep under the stars in palm-strung hammocks. Local women sport colorful dress made in the style known as mola, a traditional Gula artisanal weaving technique. A highway was built several years back that lets you travel from Panama City to Puerto de Cartí in as few as two hours.
  • 543 Park Ave, Park City, UT 84060, USA
    Located just off Main Street, the Washington School House Hotel eschews Park City’s typical rustic style for a pared-down, flea-market–chic aesthetic. Before being reimagined as a design-oriented inn in 2011, the 1889 building served as a schoolhouse for miners’ children and a dancehall for the local outpost of Veterans of Foreign Wars. Today, the interior is anything but traditional, from the whitewashed living room with 16-foot ceilings to the antique mirror and the white, lacquered antler chandelier. Outside, a heated pool sits on the hillside surrounded by aspens and boulders. There’s also a fire pit, fashioned from a steel Olympic torch from the 2002 Winter Games.

    Each of the guestrooms and suites is unique, though all feature reclaimed wood floors, crystal chandeliers, and tall windows. An artful collection of European antiques and vintage paintings adds a bohemian vibe, while white marble bathrooms offer heated floors, walk-in showers, clawfoot tubs, and period fixtures. Guests can also look forward to plush hooded robes and top-notch toiletries from Molton Brown.
  • Mt Bromo, Area Gn. Bromo, Podokoyo, Tosari, Pasuruan, East Java, Indonesia
    Bright and early, just before the sun comes up over Mount Bromo, Mount Semeru and Mount Batok, with ample rolling fog and an epic eruption for good measure. We climbed Mount Penanjakan in our Toyota 4x4 pre-dawn in the headlights of some 1,200 other vehicles. Once at the viewpoint my travel partner and I decided against the same shooting vantage as everyone else - all 3,000 tourists, gah - and climbed down the hill for a better look (and a few square feet to dig in our tripods). As soon as the sun started to shine and illuminate the volcanoes in the distance, all the nuisance and discomfort of the day, all the pain and suffering associated with actually making the trip to Bromo, it vanished. We spent the next hour shooting one of the most incredible sunrises I have ever witnessed. Getting here is a bit of a package-tour nightmare, but so very much worth it in the end.
  • One of the most popular beaches in Los Cabos, Playa el Médano is considered the safest for swimming. It’s also quite long, offering lots of space for sunbathers to lay out a towel for the day. Those are two reasons why it attracts the crowds; another is Medano’s reputation for a party atmosphere. The beach’s proximity to downtown Cabo San Lucas makes it easy to hop onto the sand, order a margarita or a michelada (a beer-based Mexican concoction) and take part in the local scene.