San Juan, Puerto Rico - In days of yore, the waters near Puerto Rico teemed with pirate ships commanded by the likes of Sir Francis Drake. Aye, they are long gone, but in their wake they have left an island of national treasures: La Casa Blanca, built in 1501 for the island's first governor, Ponce de Leon; the cobblestone streets of Old San Juan; the tropical rain forests of El Yunque.

Basseterre, St. Kitts - The island England zealously defended from Brimstone Hill, the "Gibraltar of the West Indies." In Basseterre, a mini-London, there's Piccadilly Circus to shop and a gingerbread version of Big Ben by which to check the hour.

St. John's, Antigua - Saint John's is the capital of the island nation of Antigua and Barbuda. Located in northwestern Antigua, this is a cove of the Caribbean Sea, a major exporter of sugar, rum, cotton, handicrafts, fiber-made items, ceramics and fabrics. The city is also a tourist destination. St. John's skyline, capital and major city in Antigua and Barbuda, is mastered by the baroque magnificence of the St. John's Cathedral's dome and steeple.

Castries, St. Lucia - Watch natives make boats from gum trees, write postcards in a Creole cafe, and shop for black coral carvings and exquisite silk-screened fabrics in St. Lucia's capital.

Bridgetown, Barbados - An island some say is more British than Britain. Here, cricket is the national sport and afternoon tea goes without saying. But Barbados is true blue Caribbean as well, with classic sand beaches, and wild monkeys in the jungle.

At Sea - Cruising - Cruising

Philipsburg, St. Maarten - The capital of the Dutch side of St. Maarten is the town of Philipsburg, though St. Maarten is an island with two distinct sides. To the north is the French side, whose capital is Marigot, while Philipsburg sits on the southern part of the island. When exploring on cruises that go to St. Maarten, it’s important to visit both sides to understand their customs and heritage.

You’ll quickly be charmed by all sides of the island. Of course, this Caribbean island is best known for its beaches, like Maho Beach or Great Bay Beach, one of the area’s best snorkeling spots. Sample local seafood or rum during your time in port, which have become symbols of St. Maarten life. There’s just enough to fill the day here, especially if you hop between the French and Dutch beaches.