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.

At Sea - Cruising - Cruising

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.

Port of Spain, Trinidad - Nestled along the calm, blue-green waters of the Gulf of Paria, Port of Spain is a popular starting point for those looking to explore the best of Trinidad. The city has its fair share of marvels, too — it’s home to a centuries-old fortress, gorgeous botanical gardens, and a good number of picturesque churches. And nearby you’ll find plenty of outdoor adventures, from the shaded mangroves and winding silver rivers of the Caroni Wetlands, to the postcard-pretty sweep of shore known as Maracas Beach.

Scarborough, Tobago - Travelers often overlook Tobago for its better-known neighbor, Trinidad — but this tiny island is a true Caribbean gem. Its north coast is full of secluded coves waiting to be explored, and its south coast unlocks incredible snorkel and dive sites, including Buccoo Reef, Flying Reef, and Bon Accord Lagoon. Laid-back Scarborough is the perfect jumping off point to explore the island, but it also offers plenty of ways to wile away the day — like a stroll through its botanical gardens, a visit to Fort King George, or a great meal of curry crab and dumplings at one of its charming open-air cafes.

Castries, St. Lucia - Watch natives fashion boats from gum trees, write postcards in a Creole cafe. Shop for black coral carvings and exquisite silk-screened fabrics.

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.