Caribbean Cruise

The Caribbean splits into three regions that produce three different trips: the Eastern Caribbean for beaches and shopping, the Western for Mayan ruins and diving, the Southern for less crowded islands. The season runs October to April, with softer fares during hurricane season, June through November.

Eastern, Western or Southern: what is the difference?

This is the first question to settle, and the one most sites skip.

The Eastern Caribbean runs from Florida to St. Thomas, St. Maarten and San Juan. Crossings are short, the beaches are excellent, and it is the best-selling itinerary. For a first cruise, it is the default choice.

The Western Caribbean targets Cozumel, Grand Cayman, Ocho Rios and Honduras. You go for Chichén Itzá and Tulum, for diving the reef, and for port calls that lean cultural rather than beach.

The Southern Caribbean often leaves San Juan or Barbados for Aruba, Curaçao and Barbados. These islands sit outside the hurricane belt, draw fewer ships, and the calls run longer. It is the better choice for a second or third cruise.

Where do the ships leave from?

Miami and Fort Lauderdale carry most departures, with daily non-stop flights from Montreal. San Juan opens the Southern itineraries and saves two sea days. Nassau appears on nearly every short run.

When should you go?

December to April for the most reliable weather: clear skies, calm seas, low humidity. It is also the priciest and busiest window, particularly over spring break and the holidays.

Hurricane season officially runs 1 June to 30 November, peaking in September. Ships avoid storms by rerouting, so the risk is not danger, it is a changed itinerary. A flexible traveller finds notably softer fares; a traveller set on seeing St. Maarten should pick February.

Which lines sail the Caribbean?

Almost all of them, which makes choosing hard without advice.

How long is a Caribbean cruise?

Seven days is the dominant format, from Miami or Fort Lauderdale. Three- to five-day runs to the Bahamas often serve as a first try. Ten- to fourteen-day itineraries combine two regions and cut the ratio of sea days to distance covered.

What you are not always told

Sea days are not wasted days, but you have to want them

A seven-day Eastern Caribbean run includes two to three full days without a port. Some travellers love it, others are restless by the second. Itineraries from San Juan have far fewer.

The private island is not a Caribbean island

Nearly every line now owns a private beach in the Bahamas. It is clean, organised and pleasant, but it is a branded stop, not an encounter with a country. An itinerary with two of them in seven days tells you something.

Book excursions before you leave

The best ones sell out weeks ahead, and onboard prices run higher. This is where an advisor saves the most, by comparing the ship's excursion with the local operator doing the same thing.

How do you get there from Montreal?

Daily non-stop flights to Miami and Fort Lauderdale, about three and a half hours. San Juan usually needs a connection. The rule holds here as elsewhere: arrive the day before. A February snowstorm in Montreal has cost plenty of people their embarkation.

To compare itineraries and lines against your profile, reach an advisor at 1 866 628-6241. See also our cruise lines and ships and our other destinations.

Frequently Asked Questions

Eastern targets St. Thomas, St. Maarten and San Juan: beaches, shopping, short crossings. Western targets Cozumel, Grand Cayman and Jamaica: Mayan ruins, diving, more cultural calls. For a first cruise, Eastern is the default.
Yes, and fares are notably softer. The real risk is not danger, since ships route around storms, but a changed itinerary. The Southern Caribbean, outside the hurricane belt, is the best compromise from June to November.
Seven days is the dominant format from Miami or Fort Lauderdale. Three- to five-day runs to the Bahamas often serve as a first try. Ten- to fourteen-day itineraries combine two regions.
Carnival for atmosphere and price, Royal Caribbean for big ships and teenagers, MSC for value, Celebrity and Princess for quiet and food, Disney for young children, Virgin Voyages for a child-free trip. The right choice depends on who is travelling with you.
Yes for a departure from the United States. The Canadian passport must be valid, and several lines require six months of validity beyond the return. Plan for the electronic travel authorisation as well if you transit by air through the United States.
Two to three full days without a port on an Eastern Caribbean run from Florida. Itineraries leaving San Juan have far fewer, because the islands sit closer together.
Yes. The best ones fill weeks before departure, and onboard prices run higher. An advisor compares the ship's excursion with the local operator running the same route, often for half the price.