Windward Islands Surf & Sunsets

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.

Nutmeg, cinnamon, cloves, cocoa those heady aromas fill the air in Grenada (pronounced gruh-nay-da). Only 21 miles (33½ km) long and 12 miles (19½ km) wide, the Isle of Spice is a tropical gem of lush rain forests, white-sand beaches, secluded coves, exotic flowers, and enough locally grown spices to fill anyone's kitchen cabinet. St. George's is one of the most picturesque capital cities in the Caribbean, St. George's Harbour is one of the most picturesque harbors, and Grenada's Grand Anse Beach is one of the region's finest beaches. The island has friendly, hospitable people and enough good shopping, restaurants, historic sites, and natural wonders to make it a popular port of call. About one-third of Grenada's visitors arrive by cruise ship, and that number continues to grow each year. Grenada's capital is a bustling West Indian city, much of which remains unchanged from colonial days. Narrow streets lined with shops wind up, down, and across steep hills. Brick warehouses cling to the waterfront, and pastel-painted homes rise from the waterfront and disappear into steep green hills. The horseshoe-shaped St. George's Harbour, a submerged volcanic crater, is arguably the prettiest harbor in the Caribbean. Schooners, ferries, and tour boats tie up along the seawall or at the small dinghy dock. The Carenage (pronounced car-a-nahzh), which surrounds the harbor, is the capital's center. Warehouses, shops, and restaurants line the waterfront. The Christ of the Deep statue that sits on the pedestrian plaza at the center of The Carenage was presented to Grenada by Costa Cruise Line in remembrance of its ship, Bianca C, which burned and sank in the harbor in 1961 and is now a favorite dive site. An engineering feat for its time, the 340-foot-long Sendall Tunnel was built in 1895 and named for Walter Sendall, an early governor. The narrow tunnel, used by both pedestrians and vehicles, separates the harbor side of St. George's from the Esplanade on the bay side of town, where you can find the markets (produce, meat, and fish), the Cruise Ship Terminal, the Esplanade Mall, and the public bus station.

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southwestern shore; with a population of 5,000, it's the largest of the Grenadines. Although boatbuilding, whaling, and fishing have been the predominant industries here for generations, sailing has now become almost synonymous with Bequia. Admiralty Bay is a favored anchorage for both privately owned and chartered yachts. Lodgings range from comfortable resorts and villas to cozy West Indian—style inns. Bequia's airport and the frequent ferry service from St. Vincent make this a favorite destination for day-trippers, as well. The ferry docks in Port Elizabeth, a tiny town with waterfront bars, restaurants, and shops where you can buy handmade souvenirs—including the exquisitely detailed model sailboats that are a famous Bequia export. The Easter Regatta is held during the four-day Easter weekend, when revelers gather to watch boat races and celebrate the island's seafaring traditions with food, music, dancing, and competitive games.To see the views, villages, beaches, and boatbuilding sites around Bequia, hire a taxi at the jetty in Port Elizabeth. Several usually line up under the almond trees to meet each ferry from St. Vincent.

This small group of islands lies opposite the western part of Guadeloupe. They were discovered in November 1493 by Columbus, who named them Los Santos. French settlers established themselves in 1648 and changed the name to Iles des Saintes, commonly known as Les Saintes. Since then the islands have been closely connected with Guadeloupe. Until a recent influx of tourism, Les Saintes were among the Caribbean’s most unspoiled destinations. Only two of the eight islands are inhabited: Terre-de-Bas and Terre-de-Haut. The latter is known for its impressive Fort Napoleon built in the early 19th century to replace an earlier 17th-century fort. From its vantage point there are fine views of the many tiny islets scattered in the bay and across to Guadeloupe. Terre-de-Haut is the main island of Les Saintes, with steeply scarped hills, scenic valleys, hidden coves and beautiful beaches. Its main settlement consists of a charming village of red-roofed houses situated along a curving bay. A number of small boutiques and gift shops invite browsing. Quaint cafés and restaurants offer food and drink. To the east of the village lies Grande Anse, a fine sand beach. Most of the attractions on this small island can be seen on foot. With just a few vehicles on the island, there are no organized tours possible. Time ashore here is at your leisure.

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.

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.