San Juan to Bridgetown

Sitting on the north coast of this lush tropical island, San Juan stands as the second European-founded settlement in the Caribbean and the oldest city under U.S. jurisdiction. The sturdy walls and watchtowers here withstand centuries of history, once fending off invaders like Sir Francis Drake and the pirates who roamed these waters.

Explore massive fortresses, open plazas, and the pure Caribbean charm that make San Juan a jewel of turquoise seas. With over 500 years of European heritage, Old San Juan glows under Puerto Rico’s sunshine, its pastel facades and cobblestone streets exuding timeless allure. Admire decorative balconies and polished wooden doors that bring everyday artistry to streets rich with history.

Experience the island’s rhythm at rum-fueled celebrations and lively salsa dances, or unwind on stretches of gleaming sand. Lounge on the beach, or set out for adventure through sprawling mangrove forests. Paddle into the night on a sea kayaking excursion where the waters glow with neon hues—bioluminescence transforming the bay into a serene, otherworldly spectacle.

Discover rugged limestone cliffs, sea-carved caves, and panoramic viewpoints revealing the Caribbean’s vast beauty. Savor local cuisine with a plate of Mofongo, a hearty mix of green plantains and chicken, and complement it with a refreshing iced mojito crafted from crushed mint and local rum.

Painted in hues of turquoise seas, pearly white sands, and emerald rainforests, St. John captures the Caribbean at its most pristine. The smallest and wildest of the three main U.S. Virgin Islands, the island is edged by powder-soft beaches and crystal-clear waters that gently lap the shore. Swimmers and snorkelers find vibrant reefs alive with darting tropical fish and graceful sea turtles gliding through waving seagrasses.

Few places compare to Trunk Bay, a perfect crescent of gleaming sand framed by lush greenery and shallow, azure waters. At the island’s center, Bordeaux Mountain rises to offer sweeping views across the Virgin Islands, with rainforest-covered slopes descending toward secluded coves and quiet beaches. Narrow, winding roads invite exploration by jeep, while jungle trails lead to hidden stretches of velvety sand shaded by swaying coconut palms.

Inspired by the island’s natural beauty, Laurence Rockefeller donated nearly two-thirds of St. John to create Virgin Islands National Park, preserving its wild character for future generations. Sugar mill ruins recall an 18th-century plantation past, while archaeological sites reveal traces of Taino heritage. Along the shore, beach bars catch the soft tradewinds and serve the island’s signature Painkiller cocktail—a smooth mix of dark rum, pineapple, and spice. With its protected landscapes and rich history, St. John stands as an unforgettable Caribbean treasure.

Glorious golden beaches, fiery sunsets, and verdant tropical backdrops await at Nevis, a picturesque sliver of Caribbean heaven and the smaller twin of Saint Kitts. The sight of the island's golden sands, lying before the verdant backdrop of Nevis Peak's clouded taper, is sure to mesmerize you, just as it moves Christopher Columbus, the first European to encounter these majestic islands in 1493. Charlestown serves as the laid-back capital of Nevis and is peppered with a charming assortment of baby blue colonial architecture. The perfume of incense hangs heavy in the air at the Botanical Gardens of Nevis, where orchids open up in the bright sunshine and fountains trickle among the green haven of tropical plants. The simple pleasure of a vivid sunset is one of a myriad of reasons why Nevis is such a sought-after destination, and the nightly explosions of salmon-pinks and blood-reds that spill across the sky never fade in impact. Head to the magnificent Pinney's Beach, which stretches for more than three miles, to stroll through turquoise water and caramel-colored sand. Lovers Beach offers an alternative flavor in a quieter, breathlessly romantic setting, laying out views across the Atlantic rollers to St. Kitts before you. Shipwrecks wait, strewn just offshore and enthusiastically embraced by abundant marine life. Scuba dive to explore the skeletal wrecks firsthand as clownfish zip between the broken boughs of doomed vessels. Booby High Shoals is a popular diving spot where you meet curious sea turtles gliding through the water.

Days at sea offer the perfect opportunity to relax, unwind, and focus on what you’ve been meaning to do. Whether you head to the gym, visit the spa, watch for whales, catch up on reading, or simply soak up the sun, these blue-sea days provide the ideal balance to time spent exploring ashore.

Bonaire's small, tidy capital city (population 3,000) sits five minutes from the airport. The main drag, J.A. Abraham Boulevard, turns into Kaya Grandi in the center of town. Along it stand most of the island's major stores, boutiques, and restaurants. Across Kaya Grandi, opposite the Littman's jewelry store, lies Kaya L.D. Gerharts with several small supermarkets, a handful of snack shops, and some of the better restaurants. Walk down the narrow waterfront avenue called Kaya C.E.B. Hellmund, which leads straight to the North and South piers. In the center of town, the Harborside Mall offers chic boutiques. Along this route stands Ft Oranje, with its cannons. From December through April, cruise ships dock in the harbor once or twice a week. The diminutive ocher-and-white structure that resembles a tiny Greek temple serves as the produce market, where you find plenty of fresh produce brought over from Venezuela. Pick up the brochure Walking and Shopping in Kralendijk from the tourist office to get a map and a complete list of all the monuments and sights in town.

Bright and brilliant colors coat the waterfront buildings of Willemstad, gleaming attractively beneath the generous Caribbean sun. The capital of the Caribbean island of Curaçao, Willemstad, is famous for its technicolor UNESCO World Heritage Site city center, and a narrow channel connects the sea with the Schottegat Harbor, which expands inland like a blooming flower. Settled by the Dutch in the 1630s, they brought colorful architecture, lavish red-roofed mansions, and elegant European-style waterfront buildings to this beautiful Caribbean island.

Watching over the entrance to this luxurious port stands Rif Fort, a 19th-century fortress that looms above the Sint Anna Bay channel. From here, wind your way to the Queen Emma Bridge, a pontoon bridge known as the Swinging Old Lady, which was built in 1888 to connect Otrobanda and Punda. Enjoy the stunning views of Willemstad’s lavish, pastel-colored Punda waterfront stretching before you. Visit the small boats that pull up side by side to sell juicy fruits and vegetables in a floating market on the waters below.

At sunset, the gingerbread stretches bathed in light, glowing evocatively as the last of the evening light fades away. Wander Willemstad to discover the lemon-shaded Mikve Israel-Emanuel Synagogue, said to be the oldest synagogue in the Americas, see the historic liqueur distillery, or head for Queen Wilhelmina Park, where the letters “DUSHI” stand boldly in a welcoming sign. You hear this word often, the island’s favorite way of describing the little things that make life worth living. The beaches of Curaçao certainly are “dushi,” with tempting sandy curves on nearly every corner. Snorkel in the turquoise waves among colorful fish and graceful sea turtles.

Days at sea offer the perfect opportunity to relax, unwind, and catch up on what you plan to do. Whether that means going to the gym, visiting the spa, watching for whales, catching up on reading, or simply soaking up the sun, these blue-sea days provide the perfect balance to busy days spent exploring ashore.

Bridgetown, the captivating capital of Barbados, combines faded colonial history, rich tradition, and vivid white beaches plucked directly from your wildest imagination of Caribbean perfection. Recently listed as a UNESCO World Heritage Site, thanks to its beautifully preserved colonial architecture, Bridgetown's mask of modernity covers a core of complex history and fascinating culture. Sherbet-colored buildings line up to overlook the waterfront of the Constitution River at “The Careenage,” where gleaming ships bob on the blue water and peaceful strolls along a wooden boardwalk await. Stop for a sobering moment at the commemorative sign honoring the people traded at this spot when Bridgetown served as the British Empire's most important harbor and the first stop on the Transatlantic Slave Trade route. Just a five-minute stroll from here lies Carlisle Bay, a postcard-perfect place where you find crystal-clear turquoise seawater glowing in the Caribbean sun and a mile of soft white powder sand.

A treasure trove for divers, the shipwrecks scattered below the shallow water's waves are now inhabited by turtles and swirling, rainbow-colored tropical fish. Head to the backstreets, where street food vendors serve up spicy chicken soup, barbecued pigtails, and thirst-quenching coconut water. There are bargains aplenty to be found on Broad Street, where duty-free malls and souvenir stalls cram together, vying for your attention. Roebuck Street is the spot where one of the Caribbean's favorite drinks, rum, was discovered, created here from the by-products of the island's booming sugarcane trade. Nowadays, the street is lined with bars pouring every variety of the deliciously spicy dark libation imaginable into glasses. For a touch more culture, visit one of the oldest synagogues in the Americas, Nidhe Israel Synagogue, which was built in 1654. The adjoining museum tells the story of Barbados’ Jewish immigrants, who are instrumental in the island's development.