An island uniquely divided into two parts: the Dutch side, Sint Maarten, and the French, Saint Martin. The north is known for its French culture, culinary scene and laid back atmosphere. It’s also home to secluded beaches, mountainous views and hilltop forts like Fort Louis in Marigot, the capital city.

With a gorgeous beach for every day of the year, tortoise sanctuaries and loads of succulent seafood, Antigua & Barbuda is truly a hidden gem. The island offers endless amounts of sunbathing, swimming and water sports but still feels quaint and untouched. It also has rich British history, including its role as a British naval headquarters and sugar colony.

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.

Located on Bahía de Cienfuegos, a bay on Cuba’s southern coast, Cienfuegos is a peaceful town oozing charm. Known for colorful colonial-era buildings, the town is a chief seaport for sugarcane, coffee and tobacco.

A UNESCO World Heritage site since 1988 because of its historical importance as a center of the sugar trade in the 18th and 19th centuries, Trinidad is also one of the most well-preserved cities in the Caribbean.

Founded by the Spanish in the 16th century, Havana has had many lives. The city is celebrated for its vibrant culture, rich history and mix of architecture, including Colonial, Baroque and Neoclassical. The tropical climate helps give way to beautiful parks and al fresco dining.