San Juan, Puerto Rico's capital, blends old and new. Founded in 1521, it was a key Spanish colonial port; El Morro still guards the harbor. Old San Juan, behind thick stone walls, keeps blue cobblestone streets, plazas, and colorful heritage buildings, and serves as the island's cultural hub. Nearby Santurce is the trendiest district, with shops, restaurants, and nightlife. Minutes away, Condado and Isla Verde offer iconic palm-lined Atlantic beaches.

Just off Puerto Rico's eastern coast, Culebra feels refreshingly untouched. Flamenco Beach unfurls in a wide crescent of powder-white sand and clear, shallow water, often considered among the Caribbean's most beautiful beaches. Offshore, coral reefs invite easy snorkeling, while inland roads wind past low hills dotted with wild horses. The island's small scale encourages slow exploration, split between beach time and quiet coastal viewpoints.

Once a sleepy fishing village, Marigot became St. Martin's capital under Louis XVI, who built Fort Louis to guard the harbor. Its ruins overlook Marigot Bay and are worth the short hike. The town charms with winding streets, colorful buildings, duty-free boutiques, and Marigot Market for local food, spices, art, and crafts. Try mauby and enjoy French, Creole, and international dining. Nearby Grand Case is famous for top eateries, and Marigot is a great base for exploring St. Martin's 37 beaches.

Anguilla combines celebrated Caribbean beaches with a laid-back, off-the-beaten-path feel. Relax on Sandy Ground's soft sands and calm, clear waters, swim or lounge in the sun, and sip the island's famous rum punch. In about 20 minutes, you can reach other sights, from luxury resorts and golf courses to Wallblake House, the island's only remaining plantation home. Kayak or take a glass-bottom boat to secluded bays, limestone cliffs, sea caves, and coral reefs.

Virgin Gorda is known for dramatic geology, unspoiled scenery, quiet coves, and beautiful beaches. Gorda Peak National Park offers panoramic views, while the Baths-its best-known landmark-features huge granite boulders, tidal pools, grottoes, and arches around Devil's Bay and Spring Bay. Spanish Town and Virgin Gorda Yacht Harbour are the main hubs. Visit the copper mine ruins or Little Fort National Park, and explore the boat-access-only North Sound, home to upscale resorts and watersports.

St. John, the smallest of the three main U.S. Virgin Islands, is a pioneer in Caribbean eco-tourism. Over half its 20 square miles are undeveloped, protected as Virgin Islands National Park, created in 1956 from land donated by Laurance Rockefeller. Its beaches, coast, and seas are also protected. Days center on hiking, swimming, snorkeling, and sailing. Cruz Bay is the commercial hub and ferry landing from St. Thomas. A winding road leads to quiet Coral Bay and its sheltered harbor.

San Juan, Puerto Rico's capital, blends old and new. Founded in 1521, it was a key Spanish colonial port; El Morro still guards the harbor. Old San Juan, behind thick stone walls, keeps blue cobblestone streets, plazas, and colorful heritage buildings, and serves as the island's cultural hub. Nearby Santurce is the trendiest district, with shops, restaurants, and nightlife. Minutes away, Condado and Isla Verde offer iconic palm-lined Atlantic beaches.