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.

Norman Island is a classic Caribbean paradise: small, privately owned, uninhabited except for wild goats, and reachable only by boat or helicopter. Its north shore holds the sheltered Bight, one of the British Virgin Islands' best anchorages, with sea caves for snorkeling and the offshore "Indians" rock formations nearby. Pirates Bight is the island's only building. Trails offer views of the Bight, Money Bay, Sir Francis Drake Channel, Tortola, and Peter Island.

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.

Saint Barthélemy, or Saint Barth, offers refined Caribbean luxury with a relaxed, barefoot-elegant French style. Its harbor capital, Gustavia, is lined with yachts, boutiques, galleries, and fine French-Caribbean restaurants. The island's white-sand beaches range from secluded Colombier to chic Baie de St. Jean, and its laid-back days give way to lively nightlife after dark.

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.