San Juan, Puerto Rico - The vibrant capital of Puerto Rico, San Juan offers something for every traveler — world-famous beaches with crystal clear waters, incredible cuisine, rugged natural beauty and a rich history that goes back 500 years. With its ancient fortresses and colorful colonial-era buildings, San Juan makes it easy to feel as though you’ve slipped into the past. Life moves at a slower pace along the sunny cobblestone streets of Old San Juan, and salsa beats seem to waft perpetually from open windows. If you’re craving a hike, head to El Yunque National Forest. And if you’re more in the mood to unwind, set your sights on the beautiful shores of Isla Verde or El Condado. Mealtime is also an adventure, with so many delicious options to try — from mofongo and pastelon to chillo frito and alcapurrias. Pair every bite with a piña colada — Puerto Rico’s national drink.

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.