Caribbean Grand Tour – St. Thomas & San Juan

About this cruise

A 11-night sailing gives you something shorter trips can't: the feeling that you're not just visiting places but actually living somewhere else for a while. This one leaves Philadelphia on December 23, 2026 and visits Philipsburg, St. Thomas, Tortola, San Juan and Puerto Plata (Amber Cove). You ease into this one, with a few sea days up front to find your rhythm before the 5 port calls start. It's a proper Caribbean tour: 5 countries, from Sint Maarten to Dominican Republic. Of the stops, Tortola tends to be the one people talk about: BVI's mountainous sailing paradise. Around 10 hours per port on average, which is generous enough to go beyond the obvious. From casual buffets to proper sit-down restaurants, Norwegian Pearl has 14 dining spots on board, most of them included. There are enough performances, events, and social mixers on a cruise this length that you couldn't do them all if you tried. And that's a good problem. Sometimes the best trips are the ones you just go ahead and book.