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.

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.

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.

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.

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.

Antigua's capital, with some 45,000 inhabitants (approximately half the island's population), lies at sea level at the inland end of a sheltered northwestern bay. Although it has seen better days, a couple of notable historic sights and some good waterfront shopping areas make it worth a visit. At the far south end of town, where Market Street forks into Valley and All Saints roads, haggling goes on every Friday and Saturday, when locals jam the Public Market to buy and sell fruits, vegetables, fish, and spices. Ask before you aim a camera; your subject may expect a tip. This is old-time Caribbean shopping, a jambalaya of sights, sounds, and smells.

With a lush interior featuring towering mountains, dense rain forest, fertile valleys, and acres of banana plantations, St. Lucia is mostly distinguished by the Pitons—twin peaks that soar high above the ocean floor on the southwest coast. Whether you stay in Soufrière, in the north in or around Rodney Bay Village, or even farther north at Cap Estate, exploring the iconic natural sights—and local history—in Soufrière is a day well spent. Except for a small area in the extreme northeast, one main highway circles all of St. Lucia. The road snakes along the coast, cuts across mountains, makes hairpin turns and sheer drops, and reaches dizzying heights. It takes at least four hours to drive the whole loop. Even at a leisurely pace with frequent sightseeing stops, and whether you’re driving or being driven, the curvy roads make it a tiring drive in a single outing. The West Coast Road between Castries and Soufrière (a 1½-hour journey) has steep hills and sharp turns, but it's well marked and incredibly scenic. South of Castries, the road tunnels through Morne Fortune, skirts the island's largest banana plantation (more than 127 varieties of bananas, called "figs" in this part of the Caribbean, grow on the island), and passes through tiny fishing villages. Just north of Soufrière the road negotiates the island's fruit basket, where most of the mangoes, breadfruit, tomatoes, limes, and oranges are grown. In the mountainous region that forms a backdrop for Soufrière, you will notice 3,118-foot Mt. Gimie (pronounced Jimmy), St. Lucia's highest peak. Approaching Soufrière, you'll have spectacular views of the Pitons; the spume of smoke wafting out of the thickly forested mountainside just east of Soufrière emanates from the so-called "drive-in" volcano. The landscape changes dramatically between the Pitons and Vieux Fort on the island's southeastern tip. Along the South Coast Road traveling southeasterly from Soufrière, the terrain starts as steep mountainside with dense vegetation, progresses to undulating hills, and finally becomes rather flat and comparatively arid. Anyone arriving at Hewanorra International Airport, which is in Vieux Fort, and staying at a resort near Soufrière will travel along this route, a journey of about 45 minutes each way. From Vieux Fort north to Castries, a 1½-hour drive, the East Coast Road twists through Micoud, Dennery, and other coastal villages. It then winds up, down, and around mountains, crosses Barre de l'Isle Ridge, and slices through the rain forest. Much of the scenery is breathtaking. The Atlantic Ocean pounds against rocky cliffs, and acres and acres of bananas and coconut palms blanket the hillsides. If you arrive at Hewanorra and stay at a resort near Castries or Rodney Bay, you'll travel along the East Coast Road.

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.

This bustling capital city is a major duty-free port with a compact shopping area. The principal thoroughfare is Broad Street, which leads west from National Heroes Square.

Amongst top attractions here, the Pelican Villagea cluster of workshops located halfway between the cruise-ship terminal and downtown Bridgetown where craftspeople create and sell locally made leather goods, batik, basketry, carvings, jewelry, glass art, paintings, pottery, and other items. It's open weekdays 9 to 5 and Saturday 9 to 2; things here are most active when cruise ships are in port.

Alternatively, sightseers will want to go to the Nidhe Israel Synagogue, which has been providing for the spiritual needs of one of the oldest Jewish congregations in the Western Hemisphere. This synagogue was formed by Jews who left Brazil in the 1620s and introduced sugarcane to Barbados. The adjoining cemetery has tombstones dating from the 1630s. The original house of worship, built in 1654, was destroyed in an 1831 hurricane, rebuilt in 1833, and restored with the assistance of the Barbados National Trust in 1987. Friday-night services are held during the winter months, but the building is open to the public year-round. Shorts are not acceptable during services but may be worn at other times.