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1.Maundays Bay, Anguilla
It's hard to debate this one. Anguilla is blessed with many a stunning beach, but Maundays Bay—on this skinny island's southwesterly tip—wins for crystal-clear water, a gradual slope, pristine sand, and a perfect half moon arc. Technically a public beach, it is rarely crowded and populated predominantly by guests at the Belmond Cap Juluca—recently reborn after a glorious heyday in the '90s. Of note, Maundays is ideal for families with kids, as sight lines are uninterrupted, there are rarely any waves, and the beach is neatly bookended by two small breakwaters.
Where to Stay: Without a doubt, the highly-rated Belmond Cap Juluca. The Morocco-meets-Mykonos property sits on a white-sand beach on a Caribbean island known as much for its welcoming people as its haute resorts. Large enough to keep a couple or a family busy for days, but small enough to feel like
2.Blue Beach (La Chiva), Vieques, Puerto Rico
A long, thin stretch of white sand and clear water makes this one of the Caribbean's top beaches. Getting there is part of the adventure: It can only be accessed by parking in one of 21 tiny turn-offs along a bumpy, unpaved road in the middle of the island's western National Wildlife Refuge (formerly off-limits as a U.S. Navy training base). Snorkel on your own around a small cay, or book a trip with one of the island's operators to check out its secret underwater spots.
Where to stay: The W on Vieques was nearly completely destroyed by Hurricane Maria in 2017. However, other properties on the island survived, and one of our all-time favorites—and Hot List 2014 winner—is El Blok. In a nod to 1950’s tropical modernism, the 22-room inn has a curvaceous exterior with intricately carved louvers that prompt the bright Caribbean sun to cast dramatic shadows. Interiors have a restful vibe, thanks to clean-lined wooden furnishings and strategically placed sculptures.
