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.

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.

Les Saintes is a volcanic archipelago of two islands and seven uninhabited islets, ringed by coral reefs and clear seas. Terre-de-Haut, just over two square miles, is the most developed, with scenic bays, natural harbors, quiet beaches, and picturesque villages. Its laid-back days center on beachgoing, hiking, snorkeling, and diving. Bourg des Saintes has cafés, the church of Notre-Dame de l'Assomption, and Fort Napoleon, now a museum and botanical garden with sweeping views.

Dominica, the "Nature Island," is all about eco-adventure, with natural highlights like Boiling Lake and Champagne Reef. On Prince Rupert Bay, Portsmouth is the island's second-largest town and a good base for Cabrits National Park and the Indian River. Visit 18th-century Fort Shirley for colonial history, take a quiet boat ride through mangroves, or head to the Lagoon area for a wide yellow-sand beach and laid-back restaurants and bars.

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.

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.