Travel Advisors Reveal Best Times to Set Sail on a Caribbean Cruise

A Caribbean cruise vacation can be a dream come true for many travelers, but when is the best time to set sail is question travel advisors often receive from clients.

According to CLIA’s 2022 State of the Cruise Industry report, the Caribbean is overwhelmingly the most popular region for cruisers, with 44 percent of travelers identifying it as their favorite region to cruise in the world.

With so much traffic in a region served by a variety of cruise lines, there are benefits and advantages to timing a vacation to meet each traveler’s needs. For many, heading to the Caribbean during the school year can help avoid a higher number of children onboard.

“I feel the best time to go on a Caribbean cruise is when kids are in school,” Scott Lara of TheCruiseGenius.com said. “My wife and I enjoy 14-day Southern Caribbean cruises during the months when fewer kids will be onboard.”

“If you are traveling without children and don’t need to mind any school schedules, autumn and early winter are great times to cruise the Caribbean,” Jeremy Hall of Cruise Vacations International said. “During the summer months, many ships are sailing Europe and Alaska and many of those ships return to the Caribbean for the cooler months.”

“You can find excellent pricing from Halloween through mid-December,” Hall continued. “As the winter weather approaches, it’s always nice to sneak in a cruise to the Caribbean for one last hoorah of heat.”

While there are still concerns about the impact of coronavirus, the industry has bounced back from the COVID-related restrictions that shut down business, and cruise lines are now seeing record numbers of bookings and sold-out itineraries.

In addition to escaping the crowds during the fall and winter periods, avoiding the cold weather in the United States is an attractive benefit of hitting the open seas of the Caribbean.

“Caribbean cruising is year-round,” The Cruise Guy’s Stewart Chiron said. “Winter/spring are among the most enjoyable months to cruise with better weather and fewer people. Take advantage of cruising anytime, anywhere.”

“For me, the best time to take a Caribbean cruise would be in early December pre-holiday,” Ken Heit of Frosch Travel said. “The rates are super low. Hurricane season is over. Ships are usually not full and not crowded. And the weather is great. I love cruising to the Caribbean at that time.”

Cost is also a factor when planning a vacation, and sailing to the Caribbean via cruise ship is no exception. Travel agents are experts at finding the best possible deals for their clients, and years of experience have helped teach them the right times to book and sail.

“The best time to go on a Caribbean cruise is anytime,” CharmedVacations.com’s Valerie Dorsey said. “Right now, the value for your dollar is really good with a lot of the lines offering discounts or perks, post-pandemic.”

“For families planning a year out is best because the times they are available, i.e. Spring Break, Summer and Holidays is our busiest season and get booked early,” Dorsey continued. “Some are afraid of the Hurricane Season which runs from June to the end of November, but the ships Captains know how to avoid the storms, should there be any. So anytime is a great time to go to the Caribbean.”

“It just depends on what the traveler is looking for,” Tom Hollembaek of AcesCruising.com said. “Are they trying to get a deal? September and the first couple weeks of December have great value. If they are looking for the best weather (not as much rain) Jan-March. However, I feel like it’s always a good time to go to the Caribbean.”

Most travel agents agree that a Caribbean cruise vacation is always in style and demand, whether with family, friends or even on your own. While opinions on the best times to sail vary, almost all advisors recommend the experience to their clients.

“There really is no bad time to cruise the Caribbean. Each time of the year has its advantages,” CruiseOne’s Chris Caulfield said. “In the summer the weather will be hotter and more humid and hurricanes are a risk, but you may see a pricing advantage.”

“In the winter the weather is more favorable and there are many more ships to choose from, but demand will be higher,” Caulfield continued. “More ships lead to bigger crowds on the islands. Escaping the cold weather that most of the U.S. experiences in the winter is definitely a plus.”

No matter when travelers decide to book their voyages and set sail, it’s nearly unanimous among advisors that clients should experience a Caribbean cruise at least once in their life.

With a plethora of destination options, a rich cultural experience throughout the region and some of the best food on the planet, a voyage through the Eastern or Western Caribbean is a bucket-list vacation travelers can’t afford to miss.

Whatever the season, it’s always the right time for a Caribbean cruise.