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This is the address for those who want to be in the island’s epicenter, near the party scenes and shopping. In 1951, Rémy de Haenen, who is considered the father of St. Barth’s, bought this hilly point. He was the first person to land a plane on the island in 1945, and legend has it that he was greeted by a herd of goats. He paid only $200 for the prime real estate that pokes into the sea off St. Jean Beach, and the day after he bought it, the seller tried to give him some of his money back, as they worried that he had overpaid. De Haenen built his home on the highest point of the outcropping, and it later became the island’s first hotel, hosting people like Baron Rothschild, David Rockefeller, Brigitte Bardot, Howard Hughes and Greta Garbo. The charismatic treasure hunter, aviator and womanizer became the island’s first mayor, bringing electricity and telephones to the island, among other improvements. De Haenen, now ninety, still lives in Gustavia and only recently gave up his pilot’s license. In 1995, he sold the hotel to David and Jane Matthews. The British couple was traveling on a friends’ boat, stopped on the island and, like de Haenen, they immediately felt that they must live there. (They bought the piece of land from de Haenen and have been embarking on their own island upgrade ever since.) Rather than keep the house to themselves, they decided to transform the neglected property from a quirky guesthouse into a 21st-century resort to rival the best in the world. They shipped over what Matthews calls “bits and bobs” from a country house in England, which lend the public areas an eccentric, personal flair. There may be Italian sheets on the beds and plasma-screen TVs in each room, but Garbo’s favorite suite still bears her name and stuffed animal heads keep watch on guests at the check-in desk. The Matthews added new cottages on the cliffs, bringing the total to fifteen. In 2003, they acquired the Filao Beach hotel next door. A year later, they razed all the rooms and built one- and two-bedroom split-level villas. When the most palatial accommodations, Villa Nina and Villa Rockstar, debut this winter and spring respectively, the hotel will have a total of forty units. Two of the best restaurants, Sandbar (for lunch) and On the Rocks (for dinner), and a treasure-filled boutique are on the property and every kind of activity from Champagne picnics to wreck dives can be organized. Doubles from $669; minimum stays required during certain time periods.

Who it’s best for: People who have arrived and like to see and be seen—rock stars, not wallflowers.

Best rooms: The Garbo Suite, in the main house, is considered the most romantic and is the most requested. The Howard Hughes loft in the main house, with its own kitchen and two bathrooms and terraces with 360-degree views of the bay, provides the most privacy. The De Haenen Suite, just below the main reception area, is perched on the cliff in a way that makes it feel almost like a boat. The James Suite, which opened last year in the onetime offices, sits closest to the road, but step through the front door, and the nautical-inspired living room, which faces a deck area with a private pocket-size pool and a hot tub, seems to drop into the sea. For families, the Heavenly Beach Houses on the Filao Beach side are best, as they have multiple bedrooms with living areas. The ultimate bragging rights, though, will belong to the new Villa Nina and Villa Rockstar.

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Commonly called Isle de France, this thirty-three-room hotel on Flamands Beach epitomizes the island’s laid-back style. The main white building has a plantation-style design with wide verandas and an oft-photographed breezeway that frames a view of the Caribbean. The hotel is set on ten acres, with beautiful Flamands beach on one side and a grove of palm trees on the other. Many fashion photographers shoot on this stretch of beach, thanks to its picturesque backdrop. The island’s English vicar, Charles vere Nicoll, and his attractive wife, Mandie, bought the hotel seven years ago and have been steadily polishing it ever since. World travelers, the couple are attuned to the expectations of their sophisticated clients and have crafted an alluring cocktail of cozy and chic. Mandie has a fantastically stylish eye, like so many St. Barth transplants, which is evident in touches around the hotel as well as in the resort’s boutique. Combine that aesthetic flair with their deep commitment to the community, and you have a rare hotel that manages to be at once glamorous and welcoming. If you feel as though you arrived in the midst of a convivial house party as a long-lost relative, you’re not alone. The guest rooms feel less like hotel accommodations than the bedrooms of an elegant Provençal family. White dominates—on the walls and floors and in the sumptuous bed linens—but is warmed by soft floral fabrics on comfy armchairs or a bench at the foot of the bed. Colorful lamp shades and exquisite quilts from France add indulgent touches. Blue-and-white Chinese ceramics line bookshelves in the hallways that offer a mix of old and new novels just as you’d come across in a summerhouse. There’s an offbeat refinement to the bar area as well, with white painted wicker furniture jazzed up by blue-and-white ikat-print pillows; and the locals who come to lounge on them at the end of the day are clearly a cool crowd but friendly too. A tennis court is on the premises, and a pro can be summoned. The island’s only Molton Brown spa provides heavenly treatments performed by English transplants who are giddy from the warm climate. And every Tuesday night, hotel and restaurant guests are treated to a fashion show, courtesy of Mandie, who stocks her closet-sized shop with fantastic resort wear. In the Boutique Isle de France, you’ll discover everything from straw hats and necklaces to go over caftans and vibrant Pucci bikinis to comfortable wedges for your feet. Tuesdays at 6:30 p.m., Mandie persuades local beauties to parade around the wooden deck area. Disco music plays as models strut their finery, with even young hotel guests participating. A six-year-old British girl (with Posh fantasies no doubt) joined in the last time I was there. She sashayed around the beachfront “catwalk” in a caftan and a tankini and basked in the applause.

Who it’s right for: Those who like a stylish scene but are secure in their status and discreet in their ways.

Best rooms: The six ones in the main building on the top floor, which have balconies over the main deck and views of the sea. You can keep an eye on all of the beautiful people cavorting below without leaving your room. If you want more privacy or are traveling with a family, three of the garden villas have their own pools, Nos. 17, 18, 23 and 27. Rooms from $711, rates include breakfast and airport transfer. Closed annually Aug. 31–Oct. 15.

Insider tip: It’s not just the hotel rates that go down during the low season but the spa treatments too. Massage rates drop from 120 euros ($169) to 85 ($120), and this year they had a special spa package for 95 euros ($133) which included a spa treatment, lunch at Le Case de L’Isle restaurant and a Molton Brown gift.

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