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Coney Island’s history dates back to the 1800’s, when it was envisioned as a working man’s paradise. For pocket change, you could enjoy rides and hot dogs. While you’ll need a little more than pocket change now, this venture outside Manhattan has a true charm, and can connect with most anyone’s inner child. Over the summer you’ll find packed beaches, Friday night fireworks, and the famous Nathan’s hot dog eating contest on July 4. But if you’re coming from Midtown or the Upper East/West Sides, be sure to take an express train or you’ll be in for a ride not quite as amusing as the Cyclone.

The Piazza Della Repubblica was the place to be in Florence in the evenings. Tourists and locals alike dined at the restaurants lining the square, student groups gathered, families enjoyed the Carousel, and gypsies and other migrants tried to sell everything from silk scarves to toys..right up until the police arrived and they all magically disappeared.

From the dusty street, the Hotel El Convento in León, Nicaragua, beckons with its stately façade and red Spanish-tiled roof. Step inside and you instantly feel at home amidst ornate period furnishings that are surely a far cry from the building’s humble beginnings as the 1639 San Francisco Convent. The elegant Restaurante El Victoriano offers an indoor-outdoor retreat centered on the hotel’s manicured, tropical courtyard—an example of the colonial hacienda style found throughout León. The restaurant is a meeting place for people from all walks of life—aged former Sandinistas who now hold positions of leadership, locals splurging on a fine meal, or foreign students from one of the city’s many Spanish language schools seeking tranquility and an excellent cup of coffee.

Of all the accommodations in Maui’s tony Wailea resort community, the 22-acre, waterfront Fairmont Kea Lani may be the most family-friendly of the bunch thanks in large part to its all-suite-and-villa setup. The property’s 450 guest rooms are some of the biggest on the island—the smallest suites start at a generous 860 square feet, while the two- and three-bedroom beachfront villas weigh in at 1,800 square feet and up. All cater to families, with separate sleeping and living areas, entertainment systems, furnished outdoor space (for lounging and dining), sleeper sofas, and some type of kitchen facilities, while villas encourage group gatherings with plunge pools and BBQ grills. Both adults and kids will love the deep-soaking tubs, too. Elsewhere, three indoor and three outdoor pools provide space for fun when kids’ club activities (among them volcano building, hula lessons, and tide pool excursions) aren’t on the agenda. Grown-ups can also amuse themselves with activities like outrigger canoe journeys, cultural programs, tee times at three nearby championship golf courses, and locally inspired treatments at the Willow Stream Spa, which offers dedicated fitness and wellness programs. Fuel your adventures at the five on-site restaurants, including the seafood-focused Nick’s Fishmarket Maui (with its 2,000-bottle-strong wine cellar) and the award-winning Kō, where the flavors are inspired by Hawaii, the Philippines, Korea, and beyond.

Whistler Blackcomb receives lots of press about its big-mountain features, but the resort offers plenty of terrain for every family member and skill level. The Whistler Blackcomb Snow School, among the best in North America, is great for both seasoned skiers and kids as young as toddlers. Even tweens and teens can enjoy small-group lessons, which offer equal parts socializing and instruction in the terrain parks and beyond. Welcome on the Whistler and Peak 2 Peak gondolas, non-skiers will have the village to themselves during the day. When back with their group, they can hang at one of the more than 25 on-mountain restaurants.

Rarely has a public building courted so much controversy as Ilfracombe’s Landmark Theatre. The architecture resembles the cooling towers of a power station, and some locals claim it is at odds with the character of the Victorian houses of the town. Judge for yourself by visiting the theater’s Rendezvous Café for morning coffee, lunch or afternoon tea. Get there early to snag a sea-view vantage point on the sunny terrace.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

A pilgrimage to this enchanting park is a must for any Antoni Gaudí fan. Located atop Carmel Hill to the north of the city, the park was inspired by English landscape gardens, but its fantastical elements make sure you know it was created by Catalonia’s most eccentric architect. Though there are multiple entrances, the most impressive is via a grand staircase guarded by an enormous, mosaic-tiled dragon. It leads to a sprawling plaza with a mosaic-covered cement bench stretching some 328 feet around the perimeter. Park Güell was originally designed as a gated residential development, but it failed; a show home built to lure buyers is now the Gaudí House Museum (not included with park admission). Visitors should reserve an online ticket to avoid lines.

Explore lesser-known gems (plus stay in distinctive and new hotels) when you go off the beaten path on this seven-day trip along coastal Ireland to Belfast and beyond.