Caribbean Grand Tour – St. Thomas & San Juan

About this cruise

11 nights starts to feel like a proper adventure. You leave Philadelphia on December 23, 2026 and the route takes you through Philipsburg, St. Thomas, Tortola, San Juan and Puerto Plata (Amber Cove) at a pace where there's never any need to rush. You ease into this one, with a few sea days up front to find your rhythm before the 5 port calls start. Crossing 5 borders through the Caribbean: Sint Maarten, U.S. Virgin Islands, British Virgin Islands, Puerto Rico and Dominican Republic. You'll notice the culture shift at every stop. Tortola stands out. It's BVI's mountainous sailing paradise. Around 10 hours per port on average, which is generous enough to go beyond the obvious. Norwegian Pearl takes the food seriously, with 14 restaurants to choose from. 6 are included, and the rest are worth the splurge. 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. This one's for people who really want to switch off. No half measures. Block out the calendar. All in all, it's a solid trip.