Day 1 San Juan (Puerto Rico), Puerto Rico
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.
Day 2 Philipsburg, Sint Maarten (Dutch part)
The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.
Day 3 Charlotte Amalie, U.S. Virgin Islands
Day 4 Basseterre, Saint Kitts, Saint Kitts and Nevis
Mountainous St. Kitts, the first English settlement in the Leeward Islands, crams some stunning scenery into its 65 square miles (168 square km). Vast, brilliant green fields of sugarcane (the former cash crop, now slowly being replanted) run to the shore. The fertile, lush island has some fascinating natural and historical attractions: a rain forest replete with waterfalls, thick vines, and secret trails; a central mountain range dominated by the 3,792-foot Mt. Liamuiga, whose crater has long been dormant; and Brimstone Hill, known in the 18th century as the Gibraltar of the West Indies. St. Kitts and Nevis, along with Anguilla, achieved self-government as an associated state of Great Britain in 1967. In 1983 St. Kitts and Nevis became an independent nation. English with a strong West Indian lilt is spoken here. People are friendly but shy; always ask before you take photographs. Also, be sure to wear wraps or shorts over beach attire when you're in public places.
Day 7 Nassau, Bahamas
Nassau's sheltered harbor bustles with cruise-ship activity, while a block away Bay Street's sidewalks are crowded with shoppers who duck into air-conditioned boutiques and relax on benches in the shade of mahogany and lignum vitae trees. Shops angle for tourist dollars with fine imported goods at duty-free prices, yet you'll find a handful of stores overflowing with authentic Bahamian crafts, food supplies, and other delights. With a revitalization of downtown ongoing—the revamped British Colonial Hilton leading the way—Nassau is recapturing some of its past glamour. Nevertheless, modern influences are completely apparent: fancy restaurants, suave clubs, and trendy coffeehouses have popped up everywhere. These changes have come partly in response to the growing number of upper-crust crowds that now supplement the spring breakers and cruise passengers who have traditionally flocked to Nassau. Of course, you can still find a wild club or a rowdy bar, but you can also sip cappuccino while viewing contemporary Bahamian art or dine by candlelight beneath prints of old Nassau, serenaded by soft, island-inspired calypso music. A trip to Nassau wouldn't be complete without a stop at some of the island's well-preserved historic buildings. The large, pink colonial-style edifices house Parliament and some of the courts, while others, like Fort Charlotte, date back to the days when pirates ruled the town. Take a tour via horse-drawn carriage for the full effect.
Day 8 Fort Lauderdale, Florida, United States
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.
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