San Juan & the Virgin Islands

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.

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.

You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.

Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.

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.

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

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.

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean's small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Jost Van Dyke, four miles long, is truly known as the 'barefoot island'. The smallest of the British Virgin Islands, it is known as a popular destination for yachts and is celebrated for its casual lifestyle, protected anchorages, fine beaches and beachfront restaurants and bars. The island has fewer than 200 inhabitants and they are widely known as a welcoming people. The island's name conjures up its rich, colorful past. Jost Van Dyke is said to have been named for an early Dutch settler, a former pirate. At Great Harbour, Little Harbour, and White Bay there are safe, protected bays and pristine beaches shaded with coconut palms and seagrape trees. Discover inviting shops selling local treasures, restaurants, and bars. 'The Painkiller', one of the Caribbean’s most popular drinks, originated at the Soggy Dollar Bar. Foxy’s and Gertrude's in White Bay are renowned for drinks made with the island's famous rum, frosty beers, and tales of pirates and sunken treasure. Explore Jost Van Dyke's history in the vegetation-covered ruins of centuries-old sugar mills, or on the old trails that crisscross the island. Revel in the natural beauty of the pristine, untouched beaches. Hike up to the highest spot on the island, Majohnny Point, and take in a stunning 360 degree view of the Caribbean. Relax in the natural 'bubble pool', a popular tourist attraction. Jost Van Dyke conjures up images of what the British Virgin Islands may have looked like many years ago.

For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.

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.

The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.