Barnes Bay, West End
If you're looking to escape your social scene on the Upper East Side, don’t come to this chicest-beach-house-you-have-ever-seen, designed by Kelly Wearstler, where the look is more heels than flip flops. The restaurants and bars are a step above your typical Caribbean resort experience—fresh made pasta at the signature restaurant Cobà, frozen cocktails and hummus wraps at the Half Shell, and cocktails and sushi for a very buzzy happy hour at the Sunset Lounge. The two-story spa and cute boutique that features local jewelry designers makes it a fun place to come with girlfriends.
Maundays Bay, West End
Anguilla isn’t the easiest spot to access by any stretch—after a flight from Miami to St. Maarten, you’ll need to board a boat to transfer you to the island—but that’s actually the point. Cap Juluca has all of the amenities you’d expect from a luxury Carribbean resort (comfortable décor, excellent service, top-notch spa, and a lovely pool), but when it comes down to it, this spot is really all about the beach. The rooms are stretched along on that's both private and a mile long; so each room looks out over the dreamy white sand and classic, brilliantly blue water. The white-washed, Moroccan style buildings each have double doors that open up to the ocean, so you can hear the sound of the waves and feel the Caribbean trade winds wash through the room as you snuggle up under the Frette linens.