Orient Bay, St Martin - The Saint Tropez of the Caribbean. Beach bars and a nudist resort keep this mile long stretch from getting boring
Grand Cayman - Seven Mile Beach. Despite the name, the beach is only about 5.5 miles long, all of which is built up with hotels
Negril, Jamaica - Vendors and jerk chicken are the diversions on this 7 mile long Caribbean strand
Varadero, Cuba - 12 miles of sand along a peninsula, not even a mile wide at its widest point. Tips: Possible salsa band sightings
Punta Cana, Dominican Republic - Seemingly endless stretch of beach and coconut palms, at least 30 miles long fronted by enormous resorts
Grand Anse Beach, Grenada - 2 miles of fluffy, golden sand along a sheltered bay
Harbour Island, The Bahamas - Pink Sands Beach. Solitude, tranquility and quiet are the hallmarks of this four mile long beach
Eagle Beach, Aruba - Miles of gorgeous, blazingly white sand. Watch the windsurfers zoom by
Horseshoe Bay, Bermuda - pink sand, framed by rocky coastline punctuated by sandy coves. Not officially Caribbean, but still rates an official tip
Luquillo Beach, Puerto Rico - Palm trees, hammocks, locals, snacks and miles of fine Caribbean sand and surf
Architecture fans take note! The octagonal former prison for 'criminals and public enemies' which dates from 1800, is currently occupied by the Public Library. Due to the unusual shape, the library houses their stacks in former cells that radiate out like the spokes of a wheel from the central reading room.
My favorite Bahamian out island, Harbour Island or Briland as it is known to residents, is approximately 3.5 miles long by 1.5 miles wide. Quaint New England style architecture and miles of pink sand beach puts this out island firmly on the best tropical island list. 
The Coral Sands Hotel is a charming property directly overlooking the exquisite Pink Sand Beach on quaint Harbour Island in The Bahamas. This is a 39 room gem that has what few other small hotels possess - property. There are tennis courts and enough room to roam to enjoy an evening walk and still be on site. Throughout the hotel the decor has been carefully designed to say: colonial meets Caribbean. With the juxtaposition of louvered windows, dark wood floors and cool pastel colored walls, the refined lobby harkens back to the days of the Caribbean Great House. Just outside the lobby, the open air - yet covered restaurant offers a view of the kidney-shaped pool which is flanked by parasol covered daybeds. Further on toward the beach is the 'Beach Bar and Lounge'. Perched on stilts, and jutting slightly over the pink sand beach, lunch and drinks are served here.
