Caribbean Grand Tour – Jamaica, Cayman & Puerto Rico

About this cruise

Block out 14 nights from November 28, 2027 and let this sailing from Fort Lauderdale do its thing. The route covers Princess Cays, Falmouth Jamaica and Grand Cayman Island, with additional stops along the Caribbean and there's plenty of room to breathe between each stop. Expect a run of consecutive ports, 7 stops total, with the busiest days packed close together. The sea days around them feel earned. The route threads through 7 countries along the Caribbean coast: Bahamas, Jamaica, Cayman Islands, Mexico, St. Kitts & Nevis, Puerto Rico and Dominican Republic. Don't rush through San Juan, which is known as Where Old World charm meets Caribbean vibes. Roughly 8 hours ashore per stop. No need to rush. Sky Princess has 8 restaurants on board, which means you could eat somewhere different nearly every night. With more nights comes more time for the ship's rhythm to kick in: morning coffee in the same spot, evening shows, late-night conversations on deck. Fort Lauderdale itself is worth spending some time in. Don't just treat it as a departure point. And November is a good call. Still warm, less crowded, and usually cheaper too. All told, 7 ports across 14 nights covers a lot.