San Juan to Miami, FL

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.

Spend a glorious day swimming at famed Cane Bay Garden Beach, hiking the island’s rainforest and enjoying a scenic drive around this lush island. Swim with dolphins, go sea kayaking or head over to Virgin Gorda and climb down to the famous Baths for a day of swimming and exploring this natural phenomenon. Take home charming local crafts, straw items, artwork and resort wear. Enjoy local fish dishes or perhaps a pub lunch or burger!

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.

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.

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.

Discover the luxurious resort town of La Romana with its sugar-white sand beaches, and pristine turquoise water. Explore Altos de Chavon, the beautiful and authentically recreated Mediterranean Village clinging to the cliff above La Romana. Stroll through the cobblestone streets and visit the stunning Church of St. Stanislausis and the pre-Columbian Indian artifacts in the Regional Museum of Archaeology. Browse through the boutiques and galleries of La Marina. Look for exquisite Larimar stone jewelry and amber, designer clothing, fine hand-rolled cigars, embroidered linens, pottery, fine arts and woven crafts.

The 700 islands of the Bahamas Islands begin 50 miles off the coast of Florida, stretching 760 miles to the southeast. The heritage of Old Nassau blends the Southern charm of British loyalists from the Carolinas, the African tribal traditions of freed slaves, and a bawdy history of blockade-running during the Civil War and rum-running in the Roaring 1920s. Over it all is a subtle layer of civility and sophistication, derived from three centuries of British rule.

Sunny Florida skies, year-round warmth and sunshine, a buzzing nightlife and a mix of cultures define this cosmopolitan city. Celebrity-drenched South Beach attracts people-watchers and the Art Deco District is the largest collection of Art Deco architecture in the world. Tropical style shopping experience's are readily available from Bal Harbor to Lincoln Road and Coconut Grove. Enjoy authentic Cuban cuisine and culture along Calle Ocho or travel back in time with a visit to the historic Venetian Pool. There is something for everyone in this city dubbed the "Gateway to the America's."