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.

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.

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.

Jost Van Dyke, the smallest of the four main British Virgin Islands, has fewer than 300 residents on just 3 square miles. They warmly welcome sailors and yachtsmen who anchor in Great Harbour and White Bay year-round. Life centers on the sea-swimming, snorkeling, fishing, and diving-and on tropical drinks and fresh seafood at its famous beach bars and restaurants. Rugged trails cross the island; the toughest, for seasoned hikers and 4x4s, climbs Majohnny Hill for panoramic views from 1,000 feet.

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.