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The best time to cruise to the Caribbean


When is the best time to cruise to the Caribbean? The easy answer is, whenever it suits you. There’s never a bad time to sail to this giant blue fishbowl with a bazillion beaches to explore. That’s because the Caribbean is warm and mostly sunny year-round. You can find hundreds of cruise options every single month.

That’s not to say that every season is the same, though. If I had to pick based on weather, cost and crowds, I’d vote for winter as the best time to cruise to the Caribbean.

If I were to narrow it down even further, I’d say the best time to cruise to the Caribbean is early December. It’s a fun way to create a break between Thanksgiving and the December holidays. Picture yourself shopping for unique gifts after your snorkel excursion or before your spa appointment instead of slogging through slushy mall parking lots with the tip of your nose threatening to freeze, and I think you’ll agree.

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Here’s how the entire year stacks up so you can identify the best time for your travel party to cruise the Caribbean.

Winter: Moderate fares and quiet crowds (except during the holidays)

A Carnival cruise ship anchored off Grand Cayman in the Cayman Islands. SERGIO PITAMITZ/GETTY IMAGES

Let’s start with my favorite time to cruise the Caribbean: winter (December, January and February). The temperatures throughout the region are a couple of degrees cooler than the rest of the year, and the average ultraviolet index dips down to 5 or 6 (moderate to high exposure). Rain typically comes in the form of passing afternoon showers, not tropical storms.

Pros

Except for the weeks that include holidays, ships aren’t likely to be at capacity or filled with screaming children.

Fares for winter sailings are a bit below the yearly average (excluding the holiday weeks, which are often the highest of the year). Also, deals that bring prices down even lower are typically available. Look particularly for last-minute sales for those first two weeks in December.

Cons

The weather at home can be unpredictable in winter, possibly affecting your departure travel plans and preventing you from reaching your Caribbean cruise. Also, winter storms in the U.S. can increase wave action in the Atlantic and in the Gulf of Mexico. The farther north your departure port is, the more likely you are to experience a rough ride until your ship sails south into calmer water.

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While most of the winter season offers moderate fares, if your cruise dates are limited to holiday breaks, be prepared for prices close to double what you’d pay during the few weeks before that. To find lower fares, book holiday sailings well in advance.

Bonus

Ships that sail seasonally in Alaska and Europe often call the waters of the Caribbean home for a few months in winter, resulting in more choices during this time of year.

Are there cruise lines or specific ships you’d like to try? Winter in the Caribbean is an ideal time to test them out — especially luxury and premium cruise lines that often feature lower prices on Caribbean sailings than on their cruises elsewhere in the world. If you prefer childless cruising during the holidays, you can choose an adults-only cruise line like Viking or Virgin Voyages.

Related: The best Caribbean cruise for every type of traveler

Spring: Near-perfect weather with spring break crowds

AMANDA MARSAILS/NORWEGIAN CRUISE LINE

If you don’t mind spring break crowds, spring is a wonderful time to cruise. The weather in the Caribbean in March, April and May is idyllic, and the seas are likely to be calm. Plus, escaping the last of winter’s wrath at home can be just what the doctor ordered to save your sanity.

Pros

Prices during the first week of March aren’t too high before they edge up throughout the rest of the month. It’s even possible to find deals in early May.

If your aim is to cruise with your own children while they are on break, there are plenty of ships with age-appropriate facilities. You’ll have options like splash zones for the little ones, monster slides for the adventurers and kids clubs for all ages. Don’t forget indoor activities such as laser tag and ice skating.

Related: The 5 best cruise lines for families

Cons

The spring break rowdies start in March and often continue well into April. Soon after, in mid-May, the graduation parties begin. If your goal is to avoid crowds of kids and partiers, skip the cheapest and shortest cruises and avoid cruise ships with water parks and thrill rides.

Be aware that spring break is a high season for travel disruptions caused by peak demand. Airlines may overbook. I was once bumped from a flight home after a spring cruise when a high school Spanish club from Wisconsin needed the seats to travel home together as a group. I was compensated and flew out the next day, but what if I had been bumped on my cruise embarkation day?

If you plan a springtime Caribbean cruise, make sure you have a backup plan, including travel insurance, in case your travel itinerary gets rearranged at the last minute.

Bonus

Spring in the Caribbean — particularly in March and April — often boasts sunny days and calm seas. Clear skies make for fantastic underwater visibility, so if diving or snorkeling is on your list, spring could be a good option for you. Additionally, temperatures haven’t yet reached scorching summer levels.

Summer: Fewer storms, many families and prices that may beat land-based trips

Stingray City in Grand Cayman. HOLGER LEUE/GETTY IMAGES

Summer cruising in the Caribbean is ideal for lovers of the sun, sea and sand looking for a fun escape with their kids or grandchildren while school is out. June, July and August temperatures average near 90 degrees throughout the region. While there’s a possibility of tropical storms or hurricanes, the Atlantic hurricane season doesn’t peak until late August through October.

Pros

These are the months when you rarely need to worry about the weather shutting down onboard water attractions or canceling your in-port fun.

Summer months are also perfect for multigenerational cruising, as they are often the only months when everyone’s schedules align. And when you have a group to manage, you need as many activities as possible to keep everyone entertained. Summer cruises in the Caribbean make that easy with plenty of options, both on board and in port.

Cons

Cruise fares are higher overall in summer than in the other three seasons. Ships sail at or near capacity. Even the ports themselves will likely be crowded. Shops and attractions will overflow with passengers from other ships and land-based vacationers.

You’ll also need to plan for mosquitos in port and for serious sun protection. Most of the Caribbean averages a UV index of 7 (considered high risk) during the summer months, holding at a high or extremely high level for long stretches of the day.

Related: Eastern Caribbean vs. Western Caribbean cruises: Which itinerary will I like more?

Bonus

Despite high fares, summer cruise pricing and crowd levels stack up favorably against most land-based vacations.

Once you factor in the included meals, entertainment and activities on a cruise, then consider traffic congestion, long lines, and skyrocketing hotel costs associated with other vacation options like theme parks and even popular national parks, a summer Caribbean cruise with the family can seem downright affordable and less anxiety-filled.

Fall: Low prices, low occupancy, risky weather

St. Maarten. RON BUSKIRK/GETTY IMAGES

Fall, especially September and early October, is not a bad time to cruise to the Caribbean — unless you are a worrier or someone who can’t go with the flow when travel plans go awry. That’s because the autumn months are the peak season for hurricanes and tropical storms. When it isn’t stormy, it might still be a bit warm and sticky for some early in the season. Temperatures remain near the 90-degree mark well into October.

Pros

The weather isn’t all bad in fall, and Caribbean cruise prices are low during these months. I’ve been on lovely cruises in the Caribbean in September and October with calm seas and uncrowded, quiet ships, all at a fraction of the price of cruises just a handful of weeks earlier in the year.

If you want to save money, avoid the spring and summer crowds and don’t mind a bit of rain, a fall cruise might be perfect for you.

Related: From Alaska to the Panama Canal: Here are 9 of TPG’s favorite fall cruise itineraries

Cons

Weather happens — and in the Caribbean, it happens a lot in September and October. Even if a hurricane doesn’t cause you grief, rain might.

A few years ago, I cruised the Western Caribbean near the end of October, and it poured the whole time. I had no idea it could rain that hard in Cozumel. And Grand Cayman? That’s where I learned the meaning of the word “torrential.” Even with all that rain, it wasn’t a bad cruise. The rain didn’t interfere with my scuba diving plans.

Bonus

November feels like a bonus cruise month. The temperatures have dropped a few degrees from summer’s heat, and the chance of storms has mostly passed. Extra ships begin arriving for their winter season, and prices remain low for most of the month.

Back home, everyone else is busy buying turkeys and cranberries and catering to the in-laws. You, however, could be lounging on deck sipping a frozen tropical concoction while waiting for your samba class to start.

Related: Caribbean cruise packing list: What to pack for a tropical sailing

Bottom line

Now we’re back where we started — with you booking a Caribbean cruise that works for you and your travel group. Each season has something to offer someone, which is what makes this whole year-round Caribbean cruise thing work. If we all thought early December was truly the best time to cruise to the Caribbean, it would cease to be so.

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