STAY: Cotton Tree, a waterfront property whose four luxe stand-alone cottages are decked out with spa-inspired bathrooms and full kitchens (check your fridge for pre-stocked breakfast goodies).
FRIDAY: After your arrival, hop in a cab and head north, past Seven Mile beach, to the West Bay neighborhood where Cotton Tree is located. After you check out your plantation-style cottage and take a dip in the freshwater pool, get a treatment at the tricked-out spa cabana just steps from the waves.
SATURDAY: Check out Stingray City if you haven’t been, then snorkel Cemetery Reef. As evening descends, head to Ristoronte Pappagallo, where an African grey parrot named Humphrey Bogart welcomes you to this Cayman staple.
SUNDAY: Join the locals with a drive to Rum Point and an afternoon at Wreck Bar, frosty mudslide in hand. —Tara Bradley
Cotton Tree
375 Conch Point Road
Grand Cayman, Cayman Islands
345-943-0700; caymancottontree.com
Ristorante Pappagallo
444B Conch Point Road
Grand Cayman, Cayman Islands
345-949-1119; pappagallo.ky
Wreck Bar
Rum Point (can be reached by boat)
Grand Cayman, Cayman Islands
345-947-9412
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