Roundtrip Miami

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.

St. Thomas is the gateway isle of the U.S. Virgin Islands in the Caribbean. It's known for its beaches and snorkeling spots. Territorial capital Charlotte Amalie, founded by the Danish in the 1600s, is a busy cruise-ship port. Historic buildings include a 1679 watchtower called Blackbeard’s Castle, in reference to the area’s pirate history. On the harbor, 17th-century Fort Christian is now a local-history museum.

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.

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.

One of the Caribbean’s true gems, St. Barts is where Riviera chic meets Caribbean cool. Day-trippers come from nearby islands for the duty-free shopping, excellent dining and to lounge on the soft, white sands in a secluded palm-fringed cove. Tour Fort Gustav and Fort Carl, historic reminders of Sweden’s short-lived Caribbean possession. Excursions abound, inviting guests to snorkel, sail over the clear blue waters on a catamaran, or horseback ride through shaded jungle trails.