One of Europe's favorite playgrounds, Ibiza boasts more than 100 miles of coastline frosted with exquisite beaches. It's a hub of sun worship, white sand, beach bars and clubs that buzz all night. And there's history too. The fortified Old Town, known as Dalt Vila, is a UNESCO World Heritage site and a spectacular example of Renaissance military architecture. Carrer del Calvari leads to Portal Nou, the entrance through the old city walls, and a walk up the hill reveals panoramic views of the city.

Just south of La Romana is an island paradise that gives an idea of what these environs were like back in 1698 when pirate William Kidd anchored his ship offshore and fled his English pursuers. While less than six square miles in size, Isla Catalina supports diverse ecosystems including sand dunes, mangrove forests and impressive coral reefs. The entire island is a national park and rich in wildlife with numerous species of birds and tropical fish. Catalina is a haven for diving and snorkeling, and equipment can easily be rented.

The site of a Puritan colony established in 1629, Providencia is a remote gem of striking topography, golden beaches and turquoise blue waters. Pirate Henry Morgan made this his base to raid the Spanish empire, and treasure is rumored to be buried here. Far from the Colombian mainland, the island feels more Caribbean than Colombian and more English than Spanish, as Creole is spoken and road signs have English town names.

Of the four main British Virgin Islands, Jost Van Dyke is the smallest. Fewer than 300 residents call its three square miles home, but they extend a warm welcome to the sailors and yachtsmen who drop anchor in Great Harbour and White Bay throughout the year. Life here revolves around the surrounding seas – swimming, snorkeling, fishing and diving – and communing over a tropical cocktail and a freshly caught meal at one of Jost Van Dyke’s legendary beach bars and restaurants. The island’s rugged terrain is crossed with trails.

Surrounded by rugged terrain and lush vegetation, La Romana is home to crystalline waters, white sand beaches and impressive coral reef life. It's a gateway to charming villages such as Bayahibe, ecological trails and numerous golf resorts. In the town center is El Obelisco, painted with images of local Dominican life. Nearby Altos de Chavon is a replica 16th-century village and cultural center featuring artist studios, galleries, an archaeological museum and sweeping views of the Chavon River.