Mayan ruins tower over the sea in Tulum. The formerly walled city was one of the last to be built by the Mayans, and its archaeological sites are incredibly well preserved. Take a break from the beach to visit El Castillo, the Temple of the Frescoes, and the Temple of the Descending God. Explore an underground river under a canopy of stalactites in the sacred caverns of LabnaHa Eco Park, or dive into Cenote Dos Ojos to snorkel inside of caves in the middle of a forest.

The most populated of the Turks and Caicos islands, Providenciales is one of the world’s top beach destinations. The diving and snorkeling is as convenient as it is stunning, thanks to miles of coral reef that’s easily accessible from the shore. The upscale resorts and captivating beachscapes of Grace Bay make it a popular choice for waterfront escapes. The cliffs and crags of Chalk Sound make a lovely backdrop for kayaking the bright turquoise waters.

Puerto Rico offers the perfect balance of rum-soaked nightlife and tranquil retreat. The Spanish colonial buildings of San Juan set a perfect backdrop for a day of shopping and sightseeing. Hike the massive El Yunque rainforest to see waterfalls, stone towers, and colorful Puerto Rican wildlife. As far as beaches go, it doesn’t get better than the private sands of Isla de Vieques – particularly Mosquito Bay, where by moonlight the water glows blue-green thanks to magical microorganisms.

Aruba is the quintessential Caribbean island, all sun and sea and stretches of powdery white sand. Time will slow to a pleasant crawl as you linger over a tropical cocktail or flutter serenely underwater, where only the parrotfish are in a hurry. The pastel façades of Oranjestad landmarks and shops lend an inviting and playful vibe to the capital city. Enjoy the shade of an Eagle Beach divi tree while the crashing waves of turquoise water create a soothing soundtrack just for you.

Made up of St. Croix, St. John and St. Thomas, the laidback USVI offer sophisticated dining, turquoise waters and quaint towns. On St. Croix, Christiansted's colorful Danish Colonial buildings provide a lovely backdrop for dining or sailing. Underwater coral gardens are heaven for divers. On St. Thomas, shopping mecca Charlotte Amalie has hopping nightlife. Tranquil St. John offers quiet trails, secluded coves and lively Cruz Bay's shops and bars. Ferries and local air services link the islands.

Get the experience of visiting two island colonies in the same 37 square miles. Saint Maarten/Saint Martin's spicy marriage of Caribbean, French and Dutch cultures matches its physical diversity: the island is both urban and untamed, with rain forest-like landscapes, white beaches, and amazing caves and wildlife.