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If you’re in Oahu’s North Shore area, stop for lunch at Fumi’s Kahuku Shrimp truck — it’s the one with a mural of a gigantic, rearing shrimp. They’re not rock-bottom cheap, but you get a lot for your money; $13 gets you a plate piled high with fat, juicy shrimp dripping with garlic butter, two big scoops of rice, and a (skippable) salad. Seating is outdoor-only on plastic tables and chairs, but it’s probably the best option for these messy, delicious peel-and-eat shrimp. The pond where they farm their shrimp is right next to where the truck is parked, so you can’t get any fresher than that!

The famous Hotel St-Barth Isle de France officially became a Cheval Blanc property in 2014, reopening as the Cheval Blanc St-Barth Isle de France. In 2018, after a renovation made necessary by Hurricane Irma, the property also debuted a design concept by architect Jacques Grange, complete with 19 new rooms, freshly landscaped gardens, and one-of-a-kind artwork by Jean-Michel Othoniel. In addition to two gourmet restaurants overlooking the ocean, the resort features the only Guerlain spa in the Caribbean, staffed by Cheval Blanc’s trademarked “alchemists”—employees whose sole purpose is to tailor-make memorable experiences for guests. While Cheval Blanc is always popular with couples, its clientele shifts depending on the time of year. Around the holidays and spring break, families come for offerings like the “Pour les Bébés” menu of homemade baby food. In the late spring and summer, honeymooners are drawn by poolside champagne tastings.

A laid-back beachy vibe with a compelling overlay of French style is the hotel’s hallmark. Comfy rattan furniture is offset by a palette of blues and light shades, and rooms are stocked with custom Leanor Greyl products to protect from salt and sun.

Music producer turned hotelier Chris Blackwell has made a name for himself converting Caribbean properties (Pink Sands on Harbour Island, GoldenEye in Jamaica) into jetset destinations with studios where his rock-and-roll friends can kick back while recording their next album, but it all began at Compass Point. Bob Marley, the Rolling Stones, and Eric Clapton have all stayed in some of the resort’s 18 rainbow-hued stand-alone huts, which are inspired by the colors of Bahama’s Junkanoo carnival and are simply furnished to encourage engagement with the outdoors; though the interiors are air-conditioned, most have sea-view balconies that are sighted to catch ocean breezes. In keeping with the theme, each comes with a surround-sound system and a library of CDs by artists who have recorded at Compass Point, but you’re just as likely to keep them off, preferring instead to listen to the waves that crash on the hotel’s small beach.

A visit to John Watling’s Distillery offers both a tour of a historic estate in downtown Nassau and the opportunity to sample locally made John Watling’s rum. The distillery, the only locally owned one on the island, is housed in the Buena Vista Estate, which began construction in 1789. The estate grounds encompass tropical gardens and a 200-year-old water well. Visitors can also take a free tour of the museum and distillery, where you can see the aged white oak barrels filled with rum. Finish the tour with a cocktail from the on-site Red Turtle Tavern, or pick a bottle of John Watling’s rum from the store.

The 1905 Cadillac sparkling under the bright lights really commands the attention of the room. This hot ride, in the center of the Cayman Motor Museum, is the exact model of the first car ever driven on the island. Browse through more than 55 classic and exotic vehicles as well as 18 various vintage motorcycles. This museum displays rare and one of a kind automobiles and isn’t just for motor enthusiasts. Cars like the original Batmobile used in the 1960’s television series of Batman as well as Elton John’s Rolls Royce make this museum a must-see.

A Hawaiian fantasyland on Oahu’s more remote leeward coast, about 40 minutes from Waikiki, Aulani is so seductive—for all ages—that many guests are loath to leave the property at all. And who can blame them? The beach is an idyllic cove (albeit a man-made one) stocked with kayaks, boogie boards, and everything else little beach bums could want. Then there are the three pools, including one for adults only and one filled with tropical fish for snorkelers-in-training, two impressive waterslides, and the biggest crowd-pleaser of them all, a 900-foot-long lazy river where guests, big and small, splash around on inner tubes as they meander around a faux-rock grotto. Goofy, Minnie, Mickey, and the rest—all in their vacation outfits—make occasional cameos at the breakfast buffet or by (sometimes, in) the pool. But while Aulani is most assuredly every kid’s dream, it is not every parent’s nightmare. The resort decor is more traditionally Hawaiian than obnoxiously Magic Kingdom; the lobby is built to recall an old canoe house, on a grand scale, and is covered in murals, painted by local artists, depicting island life. Hawaiian storytellers gather around a fire pit at night, and rooms have warm woods, with a single subtle reference to the Mouse King—a wooden carving of Mickey with a surfboard and ukulele that doubles as a desk lamp. Perhaps best of all, the Aulani has an outstanding, supervised kids’ club that’s free to guests ages 3 to 12. Babysitters are available for kids as young as six weeks old.

Graceful palms and lush gardens greet guests at Grotto Bay Beach Resort. Situated on 21 acres, this peaceful colony of cottage-style rooms overlooks the beautiful blue water of Bailey’s Bay in the Parish of Hamilton. Tangerine salt body scrubs, sweet milk and lavender facials, and hot stone massage will melt away all of the exertion of snorkeling excursions, golfing, exploring the resort’s on-site cave, or bicycling around the island. On the other hand, why not take it easy and lounge by the pool, which features a swim-up bar, or on one of the resorts private beaches. Dine among the island ambience of palms, rattan furnishings, and ceiling fans in the Hibiscus Room or Palm Court Dining Room. Afterwards, you can enjoy drinks and tropical breezes on the terrace before retreating to guest rooms outfitted in bright prints and tropical tones.

One of the best strolls through Venice begins in the neighborhood of Arsenale and finishes on the Island of Sant’Elena. Walk along the main drag of Via Giuseppe Garibaldi, a street full of shops and colourful local life until it dead ends. Make a right on to Viale Giuseppe Garibaldi where a monument to the streets namesake stands. From here the streets become very quiet. Follow Viale Giuseppe Garibaldi to the end and turn left onto the Fondamenta San Giuseppe. This is a mostly residential area where you see laundry hanging from pastel painted houses and hear small fishing boats tapping against the sides of the canal. Make the first right off the Fondamenta and get lost in the twist of back streets here until you come upon the Via XXIV Maggio. From here, look for signs pointing to the Church of Sant’Elena, a beautiful 12th-century monastery on the island.

Much more than just a restaurant or smoothie stop, Choice Health Bar is a culinary fusion of food, lifestyle, and positivity. This small restaurant in the Lahaina industrial park serves fresh kale salads and heaping acai bowls. The place is a favorite hangout for island locals from surfers and paddlers to vegans. Just because it’s healthy, don’t think the food will taste like cardboard. Creative concoctions pepper a menu that is constantly being reinvented, and you’d never expect that a quinoa quiche could possibly taste so good. Locals also love Choice for the laid-back atmosphere and powerful, positive vibes. A sign on the door informs all patrons that this is officially a “bummer free zone,” and instead of simply “super-sizing” your meal, you can “make it epic” with ‘superfoods’ like kale and cacao. Consistently voted as the island’s top pick for healthy, vegan cuisine, Choice is the absolute best spot on the West Side for infusing your body with nutrients.

You are lucky the sun only rises and sets once a day on Hawaii—otherwise, you’d spend all of your time transfixed by the horizon. Hike to the leeward (eastern) side of any island on a clear evening and train your eye over the ocean in search of the “green flash,” an optic phenomenon in which a green sliver of light hovers in the wake of the setting sun. (On Oahu, the remote Kaena Point is a good spot to see the flash.) Sunsets on Kauai, “The Garden Island,” make the beauty of the coastal surroundings even more poignant. If you rise early and tackle the Lanikai Pillboxes trail on Oahu or summit the volcano at Haleakala National Park on Maui, you’ll experience an unforgettable morning as the sun rises over the ocean for a new day.

La Isla de Guilligan (Gilligan’s Island, though not the one from the television show) is a popular hangout for Puerto Rican locals. I myself am only home for several weeks a year and I still go once or twice every year. The island is sometimes isolated and sometimes crowded. It boasts snorkeling (I’ve spotted many anemones, fish, crabs, starfish, and barracudas), calm water perfect for floating and swimming, and several trees from which you can jump into the water. It’s off the coast of Guanica, and there are two ways to get there. Either take a ferry (call 787-821-5706 for more information) or rent a kayak from Mary Lee’s by the Sea. If you choose to do the latter, you might want to take your kayak to Isla Ballena (see my highlight “Kayaking and Snorkeling and Hoping for Whales”). This tends to be a day trip, so I suggest you have some food. You can either pack up your own or, if you take the ferry, place an order before embarking and tell them when you’d like to have it delivered. There are picnic pavilions that you can claim if it’s a calm day or you get there early.

Inspired by the food and feel of New York City, Broadway by Amar Santana offers a taste of the big city just a block from the ocean. Here, the eponymous chef Santana, who competed on Bravo’s Top Chef, serves American cuisine made with seasonal ingredients, like squid ink cavatelli with blue prawns, and grilled skirt steak with chimichurri. Elevate your meal with creative cocktails or a bottle from the well-regarded wine list, or better yet, book the six-seat chef’s table, where Santana will serve a multi-course menu designed just for you and your guests.

Grabbing a table at Huken can get competitive, but it’s worth it. This miniature Tromsø pub strikes the perfect balance between cluttered and cozy. Take in the eclectic furnishings and decor while you wait for your choice of hamburger or pancakes. Huken’s burgers are massive and served dripping with sauces, while the American-style pancakes with blueberries and bacon are a favorite with locals and tourists alike. The beer selection is solid for such a small place, and it draws a crowd of drinkers in the evening—so head here early if you want to savor a big meal.

For a reasonably priced Island eatery, Kona Canoe Club has pupus (appetizers), salads, sandwiches, burgers, fish & chips, and several local entrees. The location is phenomenal for sunset and every dish is served with aloha!

All I could say to myself at the Hotel Christopher was: “I don’t ever want to leave this place.” It was just before the Christmas invasion of celebs and sycophants to the tiny island of Saint Barthélemy or St. Barths. For a confirmed curmudgeon, even I was surprised by my response: I loved every moment at the Zen-like Christopher. Between the infinity pool overlooking the Atlantic and our oceanfront room, where we listened endlessly to the breaking waves and enjoyed daily views of the setting sun, nirvana was never far. Pool boys and girls, servers and greeters, all accessorized in Hermés orange, created an atmosphere of sophisticated yet relaxed luxury. One afternoon, with a glass of the hotel’s signature ice tea in hand, I overheard a fellow guest whisper into her phone, no doubt in response to, “What’s the hotel like?” “Dynamic and tranquil,” she responded. Indeed, since the hotel is located just 15 minutes by car from the island’s capital, Gustavia, we had no problem to-ing and fro-ing “downtown” -- whether to catch a bite, do some shopping, or just people (and yacht) watch. The picture-perfect beaches of Saline and Gouverneur are an even shorter drive from the hotel. But back to the Christopher -- which is what my husband and I said to each other every few hours. Frankly, if we hadn’t gotten married two years ago, we would have done it there. As it was, we were celebrating our anniversary; curmudgeon or not, I can’t imagine a more perfect spot.

Thanks to renovations following Hurricane Irma, the Christopher now features several large villas as well as a newly designed restaurant.