Caribbean Cruises 2027
Year-round sailing, so the real decisions are route, ship and timing.
Photo: Jayen466, Public domain
The Caribbean is the largest cruise market in the world and the only one that runs at full strength every month of the year. That makes the decision less about whether you can go and more about choosing among three route families, a long list of departure ports, and a hurricane season that sits across the late summer and autumn.
Most travelers pick on three things: how many days they have, which port they can reach cheaply, and whether they want a sea-days-heavy ship or a port-heavy itinerary. The sections below walk through those choices. For anything about a specific island, go to its port guide.
When to sail
- Best months
- December to April, the dry season, with the calmest seas and the most reliable weather. It is also the most popular and most expensive stretch.
- Shoulder season
- May, June and early November. Warm, a little humid, usually good value, and mostly ahead of or after the peak storm months.
- When to think twice
- August to October is the peak of Atlantic hurricane season. Cruises still sail, but itineraries are more often rerouted. If you book then, be flexible and read the line's itinerary-change policy.
When to book for 2027
Holiday weeks, February and spring break sail full early, so book those further ahead. Late summer and autumn sailings are the ones where late deals appear. Whichever you choose, travel insurance that covers weather disruption is worth reading closely.
Check prices and dates with your cruise line or travel agent. We do not quote fares because they change daily.
Where Caribbean cruises sail from
The homeport you choose often matters as much as the ship.
Miami and Fort Lauderdale
Two of the largest homeports in the world, with the widest choice of ships and routes.
Port Canaveral and Tampa
Florida alternatives, close to Orlando, popular for Bahamas and Western Caribbean sailings.
Galveston and New Orleans
Gulf departures for Western Caribbean routes, reachable by car for much of the south.
San Juan
A fly-in port where many Southern Caribbean sailings begin, often with a day or two to explore first.
New York, Baltimore and Charleston
Northeast and Mid-Atlantic homeports for Bahamas and Caribbean sailings without flying.
How Caribbean cruises are shaped
The main route styles, and who each one suits.
Eastern Caribbean
7 nightsSt. Thomas, St. Maarten and often a Bahamas stop. A balanced mix of beach and shopping ports.
Western Caribbean
7 nightsCozumel, Grand Cayman, Roatan, Belize and Costa Maya. Strong for beaches and snorkelling.
Southern Caribbean
7 to 10 nightsAruba, Curaçao, Barbados and St. Lucia, usually from San Juan or Florida. Less often affected by storms.
Bahamas short break
3 to 5 nightsNassau and a private island. The usual first-cruise length.
Cruise lines that sail Caribbean
Each line has its own style. See the fleet pages for their ships.
Royal Caribbean
The largest fleet in the Caribbean, with big-ship entertainment and its own private islands.
Carnival Cruise Line
Casual and value-focused, with the widest range of short sailings.
Norwegian Cruise Line
Freestyle dining and a Bahamas private island, Great Stirrup Cay.
Disney Cruise Line
The family choice, with Castaway Cay and a characters-first onboard program.
MSC Cruises
European-flavoured ships and an increasingly large Caribbean presence.
Celebrity Cruises
Premium and quieter, with a strong Eastern and Western Caribbean schedule.
Departure port guides
Terminals, airports and parking for the ports these cruises sail from.
Ports to look for
What is near the pier, shore excursions vs DIY, and what to skip.
Cozumel
World-class reefs, turquoise water, and the best tacos al pastor in the Caribbean.
Nassau
Pink-sand beaches, colonial history, and Atlantis just a bridge away.
St. Maarten / St. Martin
Two countries, one island — world-famous beach, duty-free shopping, and jet-blast thrills.
St. Thomas
Duty-free shopping capital of the Caribbean — and a gateway to the world's best snorkelling at Buck Island.
Grand Cayman
Stingray City, Seven Mile Beach, and the clearest water in the western Caribbean.
Aruba
Constant trade winds, powder-white beaches, and a sun that almost never stops shining.
Perfect Day at CocoCay
Royal Caribbean's private island playground with beach clubs, a giant waterpark, and clear Bahamian water.
Labadee
A dramatic Haitian peninsula leased for cruise guests, known for beaches, zip lines, and mountain views.
Roatán
The Caribbean's best-value diving — pristine Mesoamerican Barrier Reef, West Bay Beach, and jungle zip-lines.
San Juan
Pastel colonial streets, a 16th-century fortress, and the birthplace of the piña colada.
Ships that sail Caribbean
A sample of ships that usually sail here, newest first. Deployments change each season, so confirm with your line.
Legend of the Seas
Royal Caribbean's fourth Icon-class ship — a Mediterranean debut before settling into Fort Lauderdale.
Norwegian Luna
NCL's newest Prima Plus ship — a sister to Norwegian Aqua, with a wraparound promenade and a slide-coaster.
MSC World America
MSC's bold North American debut — European elegance meets mega-ship scale.
Norwegian Aqua
NCL's most innovative ship — home to the world's first hybrid water-coaster at sea.
Celebrity Xcel
Celebrity's newest and largest Edge-class ship — shaped by guest input, and the first in the fleet built to run on methanol.
Brilliant Lady
Virgin Voyages' newest Lady — a fourth adults-only ship debuting exclusive Spanish tapas and a 1920s dinner show.
Star of the Seas
Icon of the Seas' sister ship — the same record-breaking scale, a fresh lineup of venues.
Disney Destiny
Disney's newest ship — a 'Heroes and Villains' theme with the line's biggest Marvel presence yet.
Sun Princess
Princess' most ambitious ship — incredible destinations, beautiful ship.
Caribbean cruise questions
What is the best month for a Caribbean cruise?+
February to April for the driest, sunniest weather, at peak prices. If you want to save money and are comfortable with a little more risk, May and June give good value before the heart of hurricane season.
Is it safe to cruise the Caribbean during hurricane season?+
Ships track storms closely and routinely change itineraries to avoid them, so it is usually an inconvenience rather than a danger. The risk is a changed port list, so check what your line offers if an itinerary is altered and consider insurance that covers it.
Which Caribbean route is best for a first cruise?+
A 7-night Eastern or Western route is the common starting point. If you are unsure you will like cruising, a 3 to 5-night Bahamas sailing is a lower-commitment way to find out.
Which Caribbean route has the best beaches?+
Western Caribbean routes through Cozumel, Grand Cayman and Roatan are strong for snorkelling and calm water. The Southern Caribbean has the most dramatic scenery and quieter beaches, and the private islands offer easy, guaranteed beach days.