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A landmark property perched between the city and the ocean, the El San Juan blends Old World elegance with tropical vibes. The famed hotel reopened on December 14, 2018 after a full restoration following Hurricane Maria and now features updated guestrooms, public spaces, and landscaping. Thankfully, the original feel was left intact, and details like the iconic chandelier and hand-carved mahogany ceiling in the lobby remain. Guests can still sip Champagne under sparkling crystals at the Chandelier Bar or party the night away at BRAVA, but now they can also sample Puerto Rico’s national spirit at rum bar 1958, grab a glass of vino at Wine Bar, or refuel with locally roasted Alto Grande coffee at El Cafecito. Also new to the property is Caña, a locally minded restaurant from Puerto Rican chef Juliana Gonzales, and Chico Cabaret, a hotspot off the lobby featuring live entertainment.

Ranging from guestrooms in the grand tower to villas surrounding the pool and beach, the 388 rooms all feature floor-to-ceiling windows with city, ocean, or pool views, as well as modern conveniences like sensor-activated air-conditioning, large HDTVs, and complimentary Wi-Fi. When not lounging on their Lovell Plush mattresses made exclusively for the hotel, guests can take a dip in one of four pools, sunbathe on the two-mile-long Isla Verde Beach, or visit the brand-new, tri-level Well & Being center for balancing spa treatments and fitness classes on the open-air rooftop.

Some find this narrow, neon-lit French Quarter street appealing, others appalling. But it’s worth a stroll either way. It’s as if all the sins of mankind and then some were rounded up and corralled here—tawdry strip shows, cheap and potent drinks, the coveting of neighbors’ wives, petty larceny, big-ass beers, bad cover bands, and so on. (Bad cover bands were not technically mentioned in the Old Testament, but to many they’re the street’s most shameful sin.) The heart of the party zone stretches eight blocks from Iberville Street to St. Philip Street, with the thickest concentration of bars on the Iberville end. New Orleans allows alcoholic drinks outside, as long as they’re in plastic cups, or “go-cups"—meaning you can roam the length of Bourbon Street with your beer or hurricane in hand.

A whole lot of history converges at the Fairmont San Francisco—as do all of the city’s cable car lines, which offer easy transportation to the Financial District, Union Square, and Fisherman’s Wharf. The hotel was built in 1906 but damaged in the Great Earthquake and subsequent fires before it even opened, so celebrated architect Julia Morgan was brought in to repair the building. Once it debuted, the hotel quickly became a city favorite, hosting more than its share of historic events, including the series of meetings in 1945 that resulted in the formation of the United Nations. The hotel’s storied bar, The Venetian Room, also featured big names, from Ella Fitzgerald and Nat ‘King’ Cole to Tony Bennett, who first performed I Left My Heart in San Francisco here in 1961 (Bennett still frequents the hotel).

Today, the Tonga Room & Hurricane Bar is a draw for tourists and locals seeking a kitschy, iconic San Francisco experience, with live music, Polynesian food, and Mai Tais severed against a backdrop of occasional staged thunderstorms. Other dining options include Laurel Court for all-day coastal California fare and the famous Afternoon Tea, a local tradition since 1907. The opulent design of the hotel extends from its lobby—with marble floors and sumptuous fabrics—to the 606 luxurious rooms, each outfitted with comfortable furnishings and modern technologies. Of the 62 suites, 10 also include balconies with city and bay views.

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.

You don’t have to go far to find fun at Hawks Cay, nor do you have to go far to relax by the water there. The resort, which takes up much of tiny Duck Key, is known for its lagoon, five pools (including one reserved for adults and another featuring a pirate ship slide), and a Dolphin Connection program that offers complimentary viewings and hands-on experiences. Water sports are plentiful as well, with kayaks, paddleboards, and boats to rent, and guests can book fishing trips, scuba and SNUBA diving, and kiteboarding instruction. There’s also a Cliff Drysdale tennis program, a spa and fitness center, and a kids club. The resort closed for one year after Hurricane Irma, reopening in September 2018 after a $50 million renovation to the main hotel, a project that included the redesign of all 177 rooms and suites, as well as the creation of a new upscale steakhouse, a seafood-focused café, and a marketplace with to-go options—these supplement the three poolside grills and cocktail bars. Privately owned two-and three-bedroom homes are also available to rent through the resort.

Hidden Pond blends Maine cottage living with its own quirky, Instagram-worthy take on luxury. The enclave of 14 colorful one- and two-bedroom clapboard bungalows is spread over 60 acres of birch groves and balsam fir, just a 10-minute drive from downtown Kennebunkport. Each private house comes with a full kitchen that practically begs to be used, with first-rate cooking equipment and serving pieces and, for guests staying in the two-bedroom cottages, the option to send along a grocery list prior to arrival. However, dining at Hidden Pond’s farm-to-table Earth restaurant, with its awe-inspiring chandelier made from a preserved apple tree, shouldn’t be missed. For an even more memorable experience, guests can supper in one of two private garden sheds, which are outfitted with a sole table surrounded by hurricane lanterns, pitchforks, and potted plants, and situated steps from a chef’s garden that supplies ingredients for every meal. The Tree Spa is aptly named: Treatment rooms are nestled in the treetops eight feet above ground and are reached via wooden footbridges.

Bypass the roadside watering holes and take a boat ride to Floyd’s Pelican Bar, instead. This thatched hut stands on stilts out in the water, making it a dreamy spot for an afternoon of swimming and shooting the breeze, solo or with friends. It’s 30 minutes from Treasure Beach (arrange a boat ride through your guesthouse or resort), and you can arrive for lunch and stay until after sundown for the just-caught fish, rum, and chilled Red Stripe on the menu. Inside the tiny shack, the flags of various countries hang and previous customers have left messages scrawled on planks and benches. Sit outside and watch the pelicans flying in formation across the horizon.

Roseau’s only oceanside dining option, the elegant Palisades pairs sweeping water views with one of Dominica’s best culinary experiences. Here, creative dishes showcase the island’s natural bounty, including produce sourced from local farms and fish straight from the Caribbean Sea. Start with dishes like BBQ jerk octopus and sesame-crusted tuna with a soy-chili dip. Then, move on to the lion fish, served with green-banana croquettes and mushroom sauce. Fancy something lighter? Try a lentil-black-bean cake or callaloo soup, made with baby taro leaves, coconut milk, yam, and green bananas.

To say St. George’s has a rough past is an understatement. It was christened as Notre Dame Catholic Church in 1670 by French Jesuits, then burned down by the English, who rebuilt it as St. George’s Anglican Church in the early 18th century. Over the next two centuries, the church sustained two more fires, plus multiple earthquakes and hurricanes. Like Lazarus, however, it couldn’t be kept down—it was rebuilt time and time again, most recently after being damaged by Hurricane Hugo in 1989. Today, guests can visit to learn more about the church’s fascinating history, climb the bell tower, or even attend services.

This property is closed due to damage caused by Hurricane Irma.

Tucked behind towering palms and white sandy beaches, this hotel is White Bay’s best-kept secret. The cottages here are either beachfront or garden view, and come with both an indoor and outdoor (enclosed) shower. Shoes optional!

Some may scoff at the absence of beachfront acreage, but what all-inclusive Capella Marigot Bay lacks in sand it makes up for in amenities, including a cabana-lined pool area with swim-up bar and a ferry to nearby LaBas Beach. Backed by a see-and-be-seen marina that offers some of the island’s best people-watching, the hotel features 124 luxurious rooms and suites that are studies in restraint, with dark-wood accents and four-poster beds trimmed in mosquito netting. Guests are surprised with complimentary snacks each day, from house-made plantain chips to local Piton beer, but nourishment is also in abundance at the resort’s four restaurants—think fresh-caught snapper, jerk-spiced ribs, and lionfish ceviche—and during three happy hours. Meanwhile, the celestial-inspired Auriga spa offers locally focused treatments to those less interested in the fitness center and weekly activities such as body-scrub-making workshops and zip-line tours.

Carleton Point is the historic site of the first settlement on Treasure Cay Beach, where 600 Americans loyal to the British migrated in 1783, at the end of the American Revolutionary War, preferring to live in the British-controlled Bahamas rather than the newly independent United States of America. The settlement they built was named Carleton Point after Sir Guy Carleton, a British military commander in New York who oversaw the evacuation of the Loyalists. The settlement was short-lived, however, as the Loyalists abandoned it in 1785 after a hurricane hit, but artifacts have been uncovered at the site, and a plaque now marks its location.

Barbados is considered the most British of the West Indies, and its historic churches, which wouldn’t be out of place in an English village, help it claim that title. On the site of older churches that were destroyed by fire and hurricanes, some dating as far back as the 17th century, St. John’s Parish Church is an early-1800s dark stone Gothic gem. Though the earliest St. John’s church was constructed in 1645, the one that stands today is largely from 1836, replacing a building destroyed by a hurricane in 1831. Its remarkable pulpit is made of ebony, mahogany, locust and other local woods. Many prominent figures are buried in the graveyard, which has views of the coast.

Opened in 2010 by a Dutch couple, Baoase Luxury Resort is an intimate spot with fewer than two-dozen rooms. Despite its size, however, it has all the amenities of a larger property, including a spa, health center, boutique, and more. A 10-minute drive from the center of Willemstad, the Balinese-style spot feels secluded and tranquil, especially when swimming off the lagoon-like beach or sitting next to the banyan tree in the lantern-lit garden.

Privacy and a high level of service are very important here. Only during low season are non-guests welcome at the resort, and even then, they must have a reservation for a beach-day pass. All rooms come with outdoor space overlooking the gardens or pools, and half feature private plunge pools. For something even more discreet, book the exclusive island in the Spanish Water Bay, which features its own four-bedroom retreat. When not relaxing in your room, you can ask the hotel to arrange a motorboat and permit to use during your stay, or visit the on-site restaurant, which is known for beachfront fine dining and a weekly Asian cuisine night. If all the privacy leaves you feeling extra romantic, you can even have the restaurant set up a picnic dinner to enjoy on the beach or under a gazebo.

This late-19th-century city-owned seafood market, which was by and large abandoned after Hurricane Katrina, was reborn as an upscale food hall several years ago. The dilapidated structure was spruced up and the navelike interior painted an austere, modern white. Then a dozen or so food vendors moved in, serving as a sort of incubator for those with an idea but no desire to go the food-truck route. It’s a great place to swing by for lunch or a casual dinner—you can get craft cocktails and spend some time at the oyster bar, then browse the other offerings, which include crab mac and cheese at Fritai and alligator-sausage hash at Elysian Seafood.