When is the Best Time to Cruise the Caribbean?

Best time to Cruise the Caribbean

It depends!

Don’t you just hate it when someone gives you this vague answer 🙂 Keep on reading and I’ll narrow it down for you.

The best time to cruise the Caribbean is really when it’s convenient for you and based on a few factors, such as budget, availability, kids in school, etc.

For us it’s in late Fall, because golf season is over, and January, because we want to escape winter for a short period! My husband is retired and I work at home on this blog, so we can go any time we want.

Let’s look at different elements that can influence your decision to choose the best time for you to cruise the Caribbean.

Budget Wise

Time of the Year

August to November is hurricane season, so you can expect to pay less but you might encounter cancelled ports.

November to the beginning of December and right after New Year’s will be cheaper.

Around February 15 as a rule could be more expensive because of school break.

Christmas and New Year’s weeks are the most expensive.

CRUISE TIP: Shorter cruises are less expensive. But I strongly suggest you go for at least 7 days, if you really want to fully experience your cruise. Since your first day will be spent getting organized, finding your way around the ship, attending the Drill, and unpacking, it doesn’t really count as a cruise day! 🙂

Cruise Lines

When I was a travel agent, I used to tell my clients that cruise lines can be compared to hotel chains. For instance, they range from 1 or 2 star to 4 or 5 star hotels.

Take a look at the list here where I give an overview of each and decide which ones best fit your budget.

Princess Cruise Line
Princess Cruises


Cruise lines will advertise seasonal sales, destination deals and special offers so don’t forget to check those.

Cruise Tip: go to the websites of all the cruise lines you are interested in and sign up for their newsletter to be notified of any promotion.

As of writing this post, Princess Cruises has a “Sip & Sail” free beverage package, which might be worth checking.

Weather Wise

December to April is a period usually considered the best to cruise the Caribbean, because it is drier and less humid.

During other months, you might encounter some rain, which sometimes doesn’t last long and other times, well you never know!

One year, in November, when we docked in St-Thomas, it was already raining and it didn’t look like it was going to stop soon. We didn’t have any excursion booked, so we decided to stay onboard.

In Jamaica, Ocho Rios is often surrounded by low clouds as they seem to get stuck in the mountains. I must say, it’s not my favorite port.

Aruba, Curaçao and Bonaire probably have the best weather all year round. Whenever we cruised in the Southern Caribbean, it has always been hot and sunny, with lots of breezes, making them in my book the ideal Caribbean islands to visit.

Which Caribbean itinerary is best for you – East, West or South?

Eastern and Western cruises are usually the shortest ones, so 7 – 8 days. However, you can take longer cruises as well if you combine an Eastern and a Western itinerary, usually on the same ship. These are called Back to Back cruises.

Eastern Caribbean itineraries will usually visit more ports. These include St-Thomas, St-Martin, Grand Turk, just to name a few. You’ll find beautiful beaches, shopping and history.

Western Caribbean itineraries will usually visit the ports of Cozumel, Belize, and Roatan. Activities would include snorkeling/diving, visiting Tulum (ancient Mayan site) or enjoying the sun in Grand Cayman or Jamaica.

The Southern cruises (our favorite ones) are normally 10 days or more as the ships have to sail all the way down South and require some sea days. Some of the ports in this itinerary could include Martinique, St.Lucia, Dominica, Grenada, and the ABC island.

Hopefully, I’ve helped you a bit in deciding when it’s the best time for you to cruise the Caribbean. If you have more questions, I would love to have some answers for you.

Happy Cruising!

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