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  • East End Village 2640, Anguilla
    Located in East End Village and painted in Anguillan flag colors, the Heritage Collection is Anguilla’s only museum. It showcases the island’s history and geology from the time of the Arawaks to the 1969 Anguillan revolution, with additional displays on the British invasion (derisively called the “Bay of Piglets” by the press) as well as on Queen Elizabeth II’s royal visit. Established in 1996, its collection includes photographs and artifacts from the island’s major eras, including the days of slavery and the phosphate trade. If you’re lucky you’ll meet Colville Petty, the museum curator and founder, and garner some of his unique insight on Anguillan history.
  • Dawn Beach, Sint Maarten
    For those wanting an active adventure on the water, Captain Alan’s Boat Charters offers snorkeling as well as clothing-optional boat trips. Their Snorkel and Beach excursion allows you to experience four hours of snorkeling and swimming around St. Maarten, Pinel Island, and the uninhabited Tintamarren while riding in one of their 30- to 38-foot off-shore power boats. Enjoy a swim with tropical fish and sea turtles, and then head back onto the boat for snacks, an open bar, and music. Captain Alan’s Boat Charters also offers a 6-hour adventure, trips to nearby Anguilla and St. Barth’s, and a clothing-optional nude cruise.
  • 2640, Anguilla
    Anguilla is blessed with numerous talented artists, but Cheddie Richardson has long been a standout on the island for his carvings. A craftsman since his childhood days and with no formal training, he grew famous over the years—both locally and internationally—for his unique pieces depicting various types of Anguillan flora and fauna, including birds, fish, and turtles. His studio is filled with them, fashioned from driftwood, mahogany, walnut, coral, or stone; there are a few bronze pieces as well. In 1994, one of Cheddie’s carvings was given to Queen Elizabeth II during her official visit to Anguilla, and it now sits in the Royal Collection.
  • Consistently ranked among the world’s top beaches, and easily among the most popular and visited ones in Anguilla, the white and light pink sands of Shoal Bay host a casual and social atmosphere, with a plethora of bars and eats. The bright turquoise water is what Anguillan dreams are made of; water-sports options abound, from snorkeling right off the beach to parasailing and diving. Weekends get busy, with families flocking here and music echoing along the strand, especially from Gwen’s Reggae Grill. But if you just want to rent a chair and relax for the day, you can normally find a spot of Shoal Bay to call your own.
  • John Hodge Rd, Meads Bay 2640, Anguilla
    Straw Hat, on quiet Meads Bay, is an established favorite with over 20 years to its name. Its creative menu of Caribbean cuisine with a twist will have you returning to this beautiful indoor-outdoor beachfront restaurant. It’s the perfect spot for a meal and an afternoon on the sand, or for watching sports. Try the ceviche of red snapper, the bigeye tuna flatbread, or the grilled crayfish with Anguillan rice and peas, among many other picks.
  • Route 1
    Anguilla’s most social beach is full of local flavor. From visiting boats to residents who flock here for the best island-style bar-and-nightlife atmosphere—home to Johnno’s, Elvis’ Beach Bar, and the Pumphouse—there’s never a dull moment on Sandy Ground’s long, soft strand. The water here is calm, making it an ideal stretch of sand for families as well. Sandy Ground is also the site of Anguilla’s August Monday, the most important day of the summer carnival season, when the entire country seems to be in the same location to celebrate J’ouvert: some folks on the beach, some on boats blasting music. By 1 p.m., the August Monday sailboat race kicks off—the first round of qualifying for the final carnival boat race at week’s end.
  • North Hill Village 2640, Anguilla
    If you’re a major foodie, or if you just want a romantic dinner night, Veya is one of the best picks on Anguilla. Set above Sandy Ground, this home-turned-restaurant serves up Caribbean fusion food in a Moroccan-style lounge, and outdoors on a veranda. The breeze, the candlelit atmosphere, the live music—not to mention the menu (which the restaurant describes as “cuisine of the sun”)—more than make up for not being directly next to the sea. Expect unusual dishes like Moroccan-spiced shrimp “cigars,” grilled jerk-spiced tuna with a rum-coffee glaze, and risotto with basil goat cheese, or try the five-course chef’s tasting menu. Veya is also known for whipping up the best desserts on Anguilla, and the list of options is long.
  • 5218 Sandy Ground, Sandy Ground 2640, Anguilla
    Sailing is Anguilla’s national sport, but it’s also the best way to explore the island’s dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here.
  • Punta Cana 23000, Dominican Republic
    This three-mile stretch of white sand is the only public beach at the gated Puntacana Resort & Club. Even so, non-guests can only reach the beach after dining at the resort’s oceanfront Playa Blanca Restaurant. It’s worth it, though, as the calm turquoise water is ideal for swimming, kayaking, and catamaran sailing. A mesh barrier keeps seaweed out of the swimming and beach areas, ensuring pristine water and sand as far as the eye can see.
  • Coronation Avenue
    Said to be the oldest structure on the island, Wallblake House is also the only surviving 18th-century plantation home that has been restored and that can be toured. Located in the Valley, capital of Anguilla, the 1787 property was once part of a 97-acre sugar and cotton plantation. Bestowed to the Catholic Church in 1976, it was abandoned until it was finally refurbished in 2004. The main home, which suffered a fire at the hands of the invading French forces, and the outbuildings are intact in design. Though the house is currently used as a rectory, tours can be arranged by emailing in advance.
  • Southwest of Anguilla is one of the island’s top three beach areas: the two-mile-long brilliantly white stretch at Rendezvous Bay. Its long shore, steady breeze, and calm Caribbean waters provide a break from the crowds at Shoal Bay and Sandy Ground. The western end does offer some fun daytime beach-bar action, which grows rowdier at night and on the weekends, when the famous Bankie Banx’s Dune Preserve venue attracts residents and visitors for live music. You can view St. Martin, across the channel, from shore.