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.

Bequia is the Grenadines' "big" small island, just seven square miles of natural beauty and classic Caribbean charm. Its capital, Port Elizabeth, has a yachting-village feel on Admiralty Bay. Princess Margaret Beach is a standout, while turquoise waters and reefs offer excellent snorkeling and diving. Inland hikes reward views of St. Vincent and nearby islands like Mustique. Its warm hospitality attracts sailors, beachgoers, and expats.

Canouan is a secluded Grenadine retreat with soft white-sand beaches, coves, turquoise seas, and offshore reefs for snorkeling and diving. Its name comes from an Arawak word for turtles; turtles nest on windward sands amid coral reefs, sea fans, and tropical fish. On the southern leeward coast, Charlestown is the main settlement, with a natural anchorage for sailboats and yachts. Mount Royal offers scenic hiking trails and tropical wildlife.

St. Lucia's iconic Pitons rise over Soufrière, the original French capital. Less than two hours from Castries, the town offers tropical colonial charm and easy access to the Sulphur Springs "drive-in" volcano, Tet Paul Nature Trail gardens, and guided rainforest hikes. North of Soufrière, the west coast's bays and coves offer calm swimming, snorkeling, and quiet beaches, with luxury estates and resorts like Jade Mountain.

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.

Falmouth Harbour, on Antigua's scenic south coast, is a celebrated yachting haven where sheltered waters, palm-fringed shores and a relaxed Caribbean rhythm set the tone. Nearby English Harbour and Nelson's Dockyard offer a glimpse of the island's maritime heritage, while the surrounding beaches, viewpoints and clear blue sea invite swimming, sailing and leisurely exploration.

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.