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.

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.

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.

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.