Cruises to Caribbean
176 ships from 28 cruise lines across 27 countries
Ships by type: 165 ocean 5 river 11 expedition · a ship that visits several places here is counted once; an expedition ship that also sails as an ocean ship appears under both types.
Caribbean Cruises
Sailings that call at Caribbean, earliest departure first.
Why Book With Waterways Cruise?
Four decades of expertise, one dedicated advisor, and every detail handled, from your front door to the gangway and back.
Cruise Concierge
A dedicated advisor who learns your name, your travel style and your preferences, then stays with you from the first conversation to the day you return home. Not a call center. Never a stranger.
100% Custom‑Built
No cookie-cutter packages. Flights, hotels, transfers and shore days are designed from scratch around how you actually like to travel, then refined until the trip feels like yours.
40+ Years in Travel
Founded by J. Richard, a four-decade veteran of the travel industry, and focused solely on premium river and ocean cruising. Decades of ship and itinerary knowledge go into every recommendation.
Book With Total Confidence
A travel agency that is a proud member of Signature Travel Network, CLIA, ASTA and IATA.
8 Days One-Way from Philipsburg St Maarten to Bridgetown
SeaDream I
Cruise Lines Visiting Caribbean
