San Juan to Fort Lauderdale

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.

Santo Domingo is the capital of the Dominican Republic and one of the Caribbean's oldest cities. Its walled, cobblestoned historic core, the Zona Colonial, has buildings that date to the 1500s, including the cathedral, which was the first built in the New World. On the cafe-lined Plaza de España is the Alcázar de Colón palace. It’s now one of the city’s many museums, displaying notable medieval and Renaissance art

Santo Domingo is the capital of the Dominican Republic and one of the Caribbean's oldest cities. Its walled, cobblestoned historic core, the Zona Colonial, has buildings that date to the 1500s, including the cathedral, which was the first built in the New World. On the cafe-lined Plaza de España is the Alcázar de Colón palace. It’s now one of the city’s many museums, displaying notable medieval and Renaissance art

Port Antonio, on the Northeast coast of Jamaica, is the islands third largest port, mainly for bananas and coconuts. It is also an important tourist destination. In fact, it has been featured as a model of paradise in several famous Hollywood films such as Club Paradise and Cocktail. Port Antonio was a sleepy coastal town until the 1880s, when Lorenzo Dow Baker, an American businessman, started the banana trade in Jamaica and promoted Port Antonio as a vacation spot for wealthy Americans. "Portie", as it is nicknamed, became a boom town. Even the movie star Errol Flynn was enamoured and ended up buying property here after his yacht washed ashore in 1946. Today it is still a major destination with plenty to do and see, from stunning scenery, creative arts and crafts, and cultural and historical sites.

One of Jamaica's largest resort cities, Montego Bay offers a range of activities bound to interest an array of visitors, from arts enthusiasts to the more adventurous type.

Begin exploring the capital by strolling along the waterfront Harbour Drive to Elmslie Memorial United Church, named after the first Presbyterian missionary to serve in Cayman. Its vaulted ceiling, wooden arches, and sedate nave reflect the religious nature of island residents. In front of the court building, in the center of town, names of influential Caymanians are inscribed on the Wall of History, which commemorates the islands' quincentennial in 2003. Across the street is the Cayman Islands Legislative Assembly Building, next door to the 1919 Peace Memorial Building. In the middle of the financial district is the General Post Office, built in 1939. Let the kids pet the big blue iguana statues.

Like many southeast Florida neighbors, Fort Lauderdale has long been revitalizing. In a state where gaudy tourist zones often stand aloof from workaday downtowns, Fort Lauderdale exhibits consistency at both ends of the 2-mile Las Olas corridor. The sparkling look results from upgrades both downtown and on the beachfront. Matching the downtown's innovative arts district, cafés, and boutiques is an equally inventive beach area, with hotels, cafés, and shops facing an undeveloped shoreline, and new resort-style hotels replacing faded icons of yesteryear. Despite wariness of pretentious overdevelopment, city leaders have allowed a striking number of glittering high-rises. Nostalgic locals and frequent visitors fret over the diminishing vision of sailboats bobbing in waters near downtown; however, Fort Lauderdale remains the yachting capital of the world, and the water toys don’t seem to be going anywhere.