Roundtrip Miami

St. Maarten is the smallest piece of land shared by two sovereign states. Legend has it that the Dutch and French boundaries of the island were determined by two men who challenged one another in a race around the island, with the Frenchman walking faster and claiming more land. Legend or not, both the Dutch and French settled here in the 1630s and despite occupancy by the British twice, the Dutch and French have lived peacefully together ever since they arrived.

Touting 365 beaches, most protected by coral reefs; a ring of forts; and quaint Colonial architecture, Antigua, and particularly St. John’s, is a classic example of the British Caribbean. Sites to see include St. John’s Cathedral, destroyed by earthquakes and rebuilt on the same spot at least three times, the last time in 1845; and the Museum of Antigua & Barbuda, which, in addition to island history, also offers a fascinating exhibition of semiprecious stones. For a stroll in nature, make your way to Nelson’s Dockyard National Park, or the nature trail to Shirley Heights. St. John’s offers several hot spots for nightlife and live music. And be sure to stop at a local restaurant to taste the buttery “flying fish,” unique to this part of the Caribbean.

Basseterre is the capital of the Caribbean island federation of Saint Kitts and Nevis. It’s the gateway to popular Saint Kitts beaches like South Friars Bay. At the city’s heart, Independence Square has an Italian-inspired fountain. Just off the Circus traffic circle, with its Victorian Berkeley Memorial Clock Tower, is the National Museum. In the stately Old Treasury Building, it explores the islands’ colonial past.

Puerto Rico's first inhabitants were the Taino Indians, who encountered Columbus in 1493. The Spanish quickly settled, defending their territory against the Dutch and British. This is evident by the imposing fortresses of Old San Juan, namely the El Morro Castle, dominating the old section of this capital city. In 1897, Spain declared Puerto Rico an autonomous state. Spain later ceded Puerto Rico to the U.S. and residents were granted American citizenship in 1917.