When Is The Best Time To Cruise The Caribbean?

Let’s be real here, when DOESN’T a cruise around the Carribean sound like a good idea?

If your dream vacation this year doesn’t look like this, you’re not alone!

If a tropical escape is on your Bingo card for this year, then you’re in luck because a Caribbean cruise is just what you need! We’re here to provide you all the information you need to decide on the best time of year for your cruise.

So, when is the BEST time to cruise Caribbean? Well, there isn’t exactly a short answer. It truly depends on what you’re hoping to experience, as well as the cruise line you’d like. For example, you’ll need to assess available dates for each cruise line, to determine which works best for your schedule and travel party. Further, the activities and excursions you’ll choose from will depend on the season, the crowds, and even the weather in the Caribbean.

So… who’s ready to plan a Caribbean cruise? Here are the best times to do it!

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Because most kids are back in school after the Winter Break, and pretty much everyone has settled back into their post-Holiday work rhythm, these can be some of the most affordable months to cruise.

The Disney Wish

Because this is the Caribbean and is situated near the equator, you’ll still find mild temperatures during these months with the coolest islands being Bermuda, with temperatures around 69 degrees Fahrenheit and the Cayman Islands topping out at 87 degrees Fahrenheit. So you can pack away those bulky holiday sweaters and slip on your bathing suit!

Disney Wish pool

This is also the beginning of the dry season, so you won’t have to worry about rain showers interfering with your pool lounging or your shore excursions.  This is also when you may experience some island festivals. Carnival, like Mardi Gras, is celebrated across many islands during the days leading up to Ash Wednesday, which, depending on the year, could fall in either February or March.


The weather is consistently warm across all of the islands, usually staying solidly in the mid-80s. The water temperature is around 75 degrees, so perfect for snorkeling and just enjoying those pristine waters.

Mickey and Goofy are ready for a swim!

But this is where we’ll warn you about those Spring Break crowds (and the price tags that go along with those extra cruisers). You’ll see the Disney Cruise ships fill up with families while kids are on Spring Break. And during shore excursions, you may experience some extra rowdy crowds as College Spring Breakers head south for tropical vibes and to blow off some academic steam.


This may just be the Caribbean cruisin’ sweet spot.  It’s less crowded than many other months as different school systems around the world are may still be in session, or are wrapping up and those final examinations receive most of the focus of families and academics. These two months are the calm before the “summer crowd storm,” so to speak.

Relax on a beach!

June is the official start of hurricane season, but it is rare that a major hurricane forms this early into the season. Colleges and other schools start to let out beginning in May, so you might find yourself on a graduation sailing.


You’re in the heat of summer cruising, both literally and figuratively! You’ll find temperatures at their highest, crowds at their peak, and the cruise prices rise to the occasion.

Castaway Cay

You’re also smack in the middle of hurricane season, so you’ll likely experience some rainfall during your cruise, and you’ll want to make sure to purchase that travel insurance in case hurricanes or tropical storms impact your cruise itinerary.


School is back in session, and most families are hunkering down and settling into their Fall rhythm and routine, so vacation cruises aren’t necessarily on the top of their “to do” list.

Daisy, Minnie, and Clarabelle Cow as the Sanderson Sisters!

This is the heart of hurricane season, so cruise lines tend to provide a bit of a discount on some cruises to entice guests to book a trip. September and October also provide some fun Halloween-themed cruises, which might provide even further incentive for a Fall cruise. But again, be sure to grab that travel insurance!


Holidays are a fun time to cruise! The ships and characters get festive, and what a fun way to celebrate a winter holiday than in shorts and bathing suits!


If you’re looking to save some money, you’ll want to cruise in the first two weeks of December. The closer your cruise dates get to Christmas or New Year, the more your wallet will feel it! If you do happen to be on a Caribbean cruise during these holidays, check out some of the local island celebrations. The Bahamian and Jamaican street parade, known as Junkanoo, is held on Boxing Day (December 26) and New Year’s Day each year.


Now, you see why there isn’t exactly an easy answer as to when is the best time to cruise the Caribbean. It all depends on what you want to see and experience! With these tips and details, we hope you can find a cruise that allows you to have the Caribbean vacation of your dreams!

 Click here for more cruise advice!

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Have you ever cruised to the Caribbean? Tell us about it in the comments below! 

The post When Is The Best Time To Cruise The Caribbean? first appeared on the disney food blog.

source https://www.disneyfoodblog.com/2023/05/11/when-is-the-best-time-to-cruise-the-caribbean/

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