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
This is da place to stay in Old San Juan! There are only a handful of hotels in this part of the city, and this gem, called Da'House is the best of them all. A boutique hotel, it is housed in a colonial building, a former Spanish convent. Occupying the upper floors of a bright blue building, Da' House has renovated this old space into an airy, artistic hotel. It's a unique oasis of art and style that is a breath of fresh air while staying in the historic quarter of San Juan. The walls are covered with modern art from Puerto Rican artists, and the works are for sale if you fancy one. The rooms tend to be a bit small and there is no TV, if that is important to you. There is however, wifi. If you have a lot of luggage be forewarned, there is no elevator, and that means a 2 or 3 floor climb. Note: the entrance doors seem like an afterthought, as they are modestly placed on the alley side of the building, not on the main street like one would expect. Well, did I say this place was eclectic. Oh, the price - that's the best part. Rooms go from $80-$120. 
You've heard of the U.S. and British Virgin Islands, but what about the Spanish? Top among the Spanish V.I. is Vieques, located just eight miles off the eastern tip of Puerto Rico. It's small, verdant and easy to reach, accessible by frequent ferry from Fajardo, or by air from San Juan and Tortola. For 60 years, most of Vieques was off limits, the U.S. military treating it like a punching bag using the western and eastern parts of the island as a weapons testing ground. When the military took leave just a few years ago, these areas opened as protected parkland. Lack of development has been a boon for this island. The pristine coastline is punctuated with wonderful sandy coves and natural beaches -- most still bearing droll military nomenclature like Green, Red and Blue beach.
