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According to Reid, direct flights to St. Martin — the half Dutch, half Caribbean island — from the East Coast go for $350 or less. "Go slightly off-season when it's cheaper on the island. Beaches and parking is free at most places." Reid recommends staying to eat on the French side, boating to one of the many beach bars that are open all day, and taking a daytrip to Anguilla, which is just a 25-minute ferry ride away. "On St. Martin, you can also find suite-style bungalows with jacuzzis at Les Balcons d'Oyster Pond," he says.
"Prices drop by a third after April 15 — starting at 100 euro in high season," says Reid. It's away from the beach, but with gorgeous views of a mountain-backed bay filled with boats you can take out."