Cacao & Indigo Wake – Bridgetown, Castries & Oranjestad

About this cruise

This is the kind of cruise where you actually have time to go back to a port highlight you missed the first time. 14 nights from Fort Lauderdale on November 29, 2027, visiting Philipsburg, Basseterre and Roseau, with additional stops along the Caribbean. It starts gently with sea days, so by the time you reach the first port you'll have explored the ship and actually feel on holiday. It's a proper Caribbean tour: 8 countries, from Sint Maarten to Curaçao. You get around 10 hours in each port, which is enough for an excursion, lunch, and some wandering around on your own. When you're not ashore, From casual buffets to proper sit-down restaurants, Island Princess has 6 dining spots on board, most of them included. One of the underrated parts of a longer cruise: you actually get to know people. The couple from dinner, the group at trivia, the bartender who remembers your drink. A November sailing dodges the peak crowds while the weather is still cooperating. Well timed. 14 nights of not thinking about anything except where to eat next. That's the pitch.