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Located in South Walton—roughly in between Panama City and Destin on Florida’s scenic coastal route, 30A—Rosemary Beach’s perfect white sand and clear turquoise waters are as close to the Caribbean as Florida comes. Unless there’s a storm a brewing, the Gulf of Mexico waters are delightfully calm and very nearly lake-like, making the beach a favorite for families with young children as well as those who love paddleboarding and kayaking (you can rent gear nearby). And classic Gulf of Mexico sunsets, as you might imagine, are another Rosemary Beach specialty.

Once summer has arrived in all her glory, city folk yearn to escape the concrete jungle. The cheap and chic solution for locals is to pack a picnic and head for a beach day on the Toronto Islands, just a short ferry ride away. Of the three primary islands, all of which are connected by paths and bridges, Centre Island boasts the highest number of visitors; people head straight to its main strip to get to the beach and the amusement park. Ward’s Island offers more charm: In addition to the sandy shore, there are small summer cottages and gardens. Those intent on exercise can rent bicycles or paddleboats.

A tiny, man-made island in Clifton Harbour built with discarded conch shells, Happy Island is really just a small bar where you can tie up for a while and have a drink, a meal, and a conversation with Janti Ramage, the island’s joyful builder, owner, and operator. Just be sure to call ahead, as Ramage keeps flexible hours.

Opened in 1962, Curtain Bluff is Antigua’s oldest luxury resort, and one of the island’s finest. It is the kind of place guests return to through the generations, with the same expectation of timelessness they’ve experienced for as long as they can remember. Located at the southern end of the island on a promontory that divides an often roiling Atlantic from a much calmer bay, the resort offers sea views from every room, two beaches, a top-notch tennis center, a pair of restaurants that can boast one of the Caribbean’s most outstanding wine cellars, and a staff whose commitment has often been passed from parent to child. And except for spa treatments, a premium bottle of wine, and the occasional Cuban cigar, there is little that’s not included in the rate, making a stay a better value than the price might at first indicate.

Lime Cay, an uninhabited island about two miles off of Port Royal, is a favorite destination of Kingstonians for white-sand beaches, sunbathing, and swim time. This is an ideal deserted escape on weekdays, and weekends are usually only a bit busier and bring a few vendors. Don’t count on the vendors, though: Bring your own food, water, sunscreen, and snorkeling gear. Wear water shoes, as there can be urchins. To arrange a trip over, ask at your hotel, or inquire at the bar on Morgan’s Harbour called the Y-Knot—they’ll help you find a boat ride or fisherman willing to take you to the island for no more than US$20.

Yes, New Mexico actually has an official “state question"--since 1996, referring to the ubiquitous chile sauce, it’s “red or green?” Fortunately you don’t have to choose just one; the local way to say ‘can I have both’ is just one word: “Christmas.” If you’re driving through New Mexico on the way to Arizona and points beyond, the only town of any size on I-40 between Albuquerque and Flagstaff is Gallup. For road-trip food here, get away from the Interstate and its humdrum chain restaurants. Seek out Jerry’s--a block off old Route 66. You can’t miss the retro neon sign, and there’s often a line out the door for its New Mexico-style fare. Gallup is surrounded by Navajo, Hopi, and Zuni lands--you might well be one of the few non-Native-Americans eating here at breakfast or lunch. The restaurant allows local vendors to come in and show their wares--usually jewelry and bracelets--while you eat. (You can request a ‘do not disturb’ sign for your booth if you want.) “Hole in the wall” gets overused, but Jerry’s definitely fits that description. Nothing pretentious here--but the flavor of the chile sauce is as good as you’ll find in Albuquerque or Santa Fe. A recommendation: the flat cheese-and-onion-enchiladas, topped “Christmas” style with a fried egg on top. And don’t forget to sop up the sauce with the sopaipillas, saving some of the frybread to top with honey as a dessert afterwards...

Snorkel, fish, relax and recover while you’re in Panama on Contador Island, in the Pearl Islands Archipelago. These beautiful boats are ready for hire (in hugely affordable fashion) once you’ve left Panama City and landed on this enchanting island. With Air Panama there appear to be two or three short (45 minutes) flights a day that will get you there from Panama City. Be sure to pack your swimsuit, a good book and some sunscreen. This is a very small island and you can explore land on foot or by a rental scooter to see it all. In Spanish, Contador means ‘the one that counts’, and it’s easy to make your day on the island count with a local rental boat. Your captain (that will inevitably also be fishing while you’re moving) are a reliable way to go and find nearby remote snorkel locations. Be sure to agree on the price before you head out for your big day on the water.

Named after dishwasher-turned-James-Beard-Award-winning-superstar-chef Hugo Ortega, Hugo’s is a Montrose mainstay. Hugo’s is housed in a 1925 art deco building by Houston architect Joseph Finger. Here, the dishes dive deep into Mexico’s rich culinary heritage, like fall-off-the-bone tender garlic-marinated goat and lechón (roast pork) with crackling, crispy skin. But save room for dessert—options include churros stuffed with dulce de leche and flan topped with tangy passion fruit glaze, candied pistachios, strawberries, and whipped cream.

Just a five-minute boat ride from St. Vincent, Young Island is both a private resort and the first in the Grenadine islands chain. Here, you’ll find a small, white-sand beach facing the channel that separates the island from the mainland. It’s technically for hotel guests only, but go for lunch at the very good beachside restaurant and bring your bathing suit—the resort won’t mind if you take a quick dip after your meal.

Tucked away on a quiet San Miguel Chapultepec street, but just next door to lively Colonia Condesa, this odd restaurant’s yellow façade leads to a culinary experience that goes way beyond the food served. Under the direction of Norma Listman and Saqib Keval, Masala y Maíz is a space of culinary encounter between Mexico and India; entrees often mix pickled fruits and vegetables in Latin American styles. The makai pakka combines Mexican esquites with a similar dish from Kenya. The partner-chefs connect food and current events as well; they commit to a socially responsible work environment and the restaurant serves as a progressive events forum. Open for breakfast and lunch, plus Saturday-only brunch.

If you want to vacation like British royalty, visit the mosquito-shaped island of Mustique, which Naomi Campbell, Mick Jagger, and Princess Margaret have all called their home away from home. Once on land, there’s no better place to stay than the Cotton House, a private retreat that feels like the lap of luxury. Set on 13 acres of cerulean beachfront and gardens thick with jasmine and frangipani, the 20 rooms and suites are awash in neutral hues inspired by their surroundings, with wicker pendant lighting, ikat throw pillows, and breezy mosquito nets over the beds. Explore the coral reefs near the shoreline in a glass-bottom kayak, or improve your backhand with help from the resident tennis pro. After a day of sun-soaked adventure, dine on fresh-caught specialties (pan-seared barracuda, Caribbean-style sushi) at Veranda restaurant, then retire to the Great Room, a colonial-inspired lounge offering rare and local rums.

Scrub Island is one place where being shipwrecked might actually be a good thing—pity that dockside boat slips abound. Located on a volcanic speck just 75 miles east of Puerto Rico, Scrub Island Resort is the ultimate tropical idyll, with a spa, marina, and three restaurants. Its 52 suites and villas sit on 230 pristine acres, complete with neutral, colonial–style interiors (think four-poster beds, marble baths with soaking tubs, and floral curtains) that intensify the ocean views. Charter a boat to explore hidden coves or test your nautical skills at the resort’s sailing school. You can always forget what you know once the time comes to lift anchor and head for the mainland.

The Mafia Archipelago (its name is said to come from the Arabic word morfiyeh, which means “archipelago”) consists of several islands and atolls, the largest of which is Mafia Island itself. Mafia Island is a nearly undiscovered alternative to Zanzibar, with similar picture-perfect beaches and diverse marine life, but without the crowds of tourists. Its history can be traced back to the 8th century, when boats would stop to refuel and repair along the lucrative coastal trade route. This legacy is evident in the crumbling ruins of a former town called Kua, which include a mosque and unexcavated Chinese and Persian pottery. South of the island is the submerged town of Kisimani Mafia, which was destroyed and submerged by an 1872 cyclone and has yet to be fully excavated. A protected marine preserve encompasses the islands and reefs, making this region is a diver’s paradise. Mafia Island Lodge offers makuti (similar to thatch-roofed) rooms with sea views, plus fishing, biking, walking, diving, and snorkeling, as well as historical and cultural tours.

A brother-sister expat duo has opened this chic slice of Brooklyn in Colonia Juárez, the neighborhood currently angling to be Mexico City’s hippest. No complaints on that account at Cicatriz, whose open, industrial-styled storefront is a forum for several daily moods. No-compromise coffee and a variety of alternative baked goods form the morning agenda; lunch means a major emphasis on locally sourced greens in great salads and roasted iterations; the meatball and fried-chicken sandwich are both major crowd-pleasers as well. After five, it’s time to get your drink on; the bartenders deliver superior, crafted quaffs, but free from all the fuss you’ll see at other haute mixology spots. The earnest, healthful menu is enhanced by an overall vibe of do-it-yourself chic.

There’s a little slice of New Brunswick, Canada, off the coast of Maine, and it’s well worth a visit. Grand Manan Island is accessed by ferry from Black’s Harbour NB. The island is only 34km long and 18km wide, so it doesn’t take long to explore by car. Another popular option is to walk onto the ferry and rent bikes on the island. The main sights on Grand Manan are the beaches, rocky cliffs, and lighthouses. It’s a haven for artists, bird-watchers, and hikers. It’s also a great spot to enjoy fresh seafood. The journey to the island is one of the best parts as you often see whales, seals and other sea life from the ferry decks.