Busting with idyllic beaches, parrot sanctuaries and wild zip lines, Sint Maarten is a Dutch territory and country of the Kingdom of the Netherlands. Part of the Leeward Islands in the Caribbean Sea, this little island is also home to Saint Martin in the north.

An island off the eastern coast of Puerto Rico, Vieques is a land of untouched beaches, roaming wild horses and spark-filled Bioluminescent Bay.

Established in 1521 by the Spanish, Old San Juan is the oldest city in the United States and its territories. There you'll find colonial architecture, impressive fortifications, cobblestone streets, open plazas, and hidden patios. Nearby, el Yunque National Forest is the sole tropical rain forest in the U.S.

Viñales a small town west of Havana with green rolling hills planted with fruit, vegetables, coffee and tobacco. It’s known for steep limestone hills called mogotes which dot the landscape and gardens full of palms and orchids.