Pleasant sandy shorelines and inviting azure seas are constant delights throughout this 2-week exploration of the Caribbean’s Windward islands. Reinvigorate your summer beach wardrobe with custom matching accessories amid Charlotte Amalie’s fashionable and eclectic St. Thomas boutiques. Ride light breezes aboard a sleek catamaran off Gustavia to uncrowded snorkeling sanctuaries inhabited by vibrant reef fish in St. Barthelemy’s Colombier Bay. Kayak along Montserrat’s lush, tropical coastline to cool caves inhabited by docile fruit bats. Cook up traditional and savory Caribbean dishes in delicious Dominican flavors at an inviting, open-air family kitchen near Roseau. Lace up your shoes and hike through the gently rolling Cas En Bas hills above Pigeon Island’s northeast beaches, amid roaming wild horses, colorful St. Lucia parrots and countless migratory seabirds. Embark on a delectable tasting tour of a Grenada rum distillery and sample sweet local jams and nutmeg syrup outside St. George’s.