Bermuda & Caribbean Cruise: Hamilton, Philipsburg & San Juan

From Wall Street's skyscrapers to the neon of Times Square to Central Park's leafy paths, New York City pulses with an irrepressible energy. History meets hipness in this global center of entertainment, fashion, media, and finance. World-class museums like MoMA and unforgettable icons like the Statue of Liberty beckon, but discovering the subtler strains of New York's vast ambition is equally rewarding: ethnic enclaves and shops, historic streets of dignified brownstones, and trendy bars and eateries all add to the urban buzz.

New York City needs little by way of introduction, as its reputation for outstanding theatre, music, museums, restaurants, sports, eclectic neighborhoods, and vibrant nightlife is famous throughout the world.

With a permanent resident population of 1,500 households, Hamilton doesn't qualify as a major metropolis. Yet it has enough stores, restaurants, and offices to amp up the island’s energy level. Moreover, it has a thriving international business community (centered on financial and investment services, insurance, telecommunications, global management of intellectual property, shipping, and aircraft and ship registration), which lends it a degree of sophistication seldom found in so small a center. The central parishes cover the large area of Paget, Warwick, and Devonshire. These parishes are much sleepier than Hamilton and provide great nature and beach respites when you tire of city life. Convenient bus and ferry connections connect the parishes, so trips outside of Hamilton are easy and a fun way to get off the tourist track.

The stories about Bermuda are true: The sand is pink, the water an irresistible turquoise, golf courses are everywhere, and traffic in Hamilton is directed by constables wearing (you guessed it) Bermuda shorts.

With a permanent resident population of 1,500 households, Hamilton doesn't qualify as a major metropolis. Yet it has enough stores, restaurants, and offices to amp up the island’s energy level. Moreover, it has a thriving international business community (centered on financial and investment services, insurance, telecommunications, global management of intellectual property, shipping, and aircraft and ship registration), which lends it a degree of sophistication seldom found in so small a center. The central parishes cover the large area of Paget, Warwick, and Devonshire. These parishes are much sleepier than Hamilton and provide great nature and beach respites when you tire of city life. Convenient bus and ferry connections connect the parishes, so trips outside of Hamilton are easy and a fun way to get off the tourist track.

The stories about Bermuda are true: The sand is pink, the water an irresistible turquoise, golf courses are everywhere, and traffic in Hamilton is directed by constables wearing (you guessed it) Bermuda shorts.

With a permanent resident population of 1,500 households, Hamilton doesn't qualify as a major metropolis. Yet it has enough stores, restaurants, and offices to amp up the island’s energy level. Moreover, it has a thriving international business community (centered on financial and investment services, insurance, telecommunications, global management of intellectual property, shipping, and aircraft and ship registration), which lends it a degree of sophistication seldom found in so small a center. The central parishes cover the large area of Paget, Warwick, and Devonshire. These parishes are much sleepier than Hamilton and provide great nature and beach respites when you tire of city life. Convenient bus and ferry connections connect the parishes, so trips outside of Hamilton are easy and a fun way to get off the tourist track.

The stories about Bermuda are true: The sand is pink, the water an irresistible turquoise, golf courses are everywhere, and traffic in Hamilton is directed by constables wearing (you guessed it) Bermuda shorts.

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.

It’s hard to get lost in Philipsburg—one mile of colorful Creole houses long and four streets deep—but it’s also a place where you may find yourself on the brink of an adventure you have long imagined.

The largest of the British Virgin Islands and home of the capital, Road Town, Tortola is a big draw for outdoor enthusiasts thanks to fantastic hiking trails in the lush interior hills. For a more laid back island experience, Tortola is home to some of the best beaches in the Caribbean. Imbibe on Brewer’s Bay beach, or dig your toes into the sand on Cane Beach, by far the most famous and popular beach on the island.

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.

Ponce de Leon never did find the Fountain of Youth, but he did stumble upon San Juan, which had to be a close second, featuring an appealing array of golf courses, rainforests and beaches galore.