Ultimate Guide to Planning the Perfect Caribbean Cruise Vacation
Year in and year out, one of the most popular trip types is the Caribbean cruise. If you've never been on a cruise, you should get started. There are so many ways to cruise the Caribbean that you could go every year for the rest of your life and never exhaust the possibilities.
Whether you’re new to Caribbean cruising or have been there many times, here’s everything you need to know about planning, choosing, and protecting your next Caribbean cruise.
Don't forget: Why Travel Insurance is Crucial for Cruise Trips
What do I need to know before going on a Caribbean cruise?
You need to know what you like to do and see, and you need to know when hurricane season is, so you’re aware of the risks of cruising during that time.
Do you like traveling on a floating recreation facility with all manner of beverages at your fingertips and a buffet with every kind of cheesecake you can imagine?
If so, large-ship Caribbean cruising is for you.
Large-ship cruising has so much mass appeal that it’s spawned a class of cruisers who have adopted a cruise ship as their new assisted-living facility – because who doesn’t want an assisted-living facility with a Guy Fieri burger bar and three different discos?
If this doesn’t appeal to you, don’t worry, there are cruise-ship experiences that align with your family status, hobbies, favorite foods, astrological signs, and many other traits.
Have kids? Disney Cruise Lines. Don’t like kids? Virgin Voyages. Want to bring your dog on a cruise? There are theme cruises galore – you’re likely to find one that fits your style.
Caribbean cruises can be your gateway to a universe of experiences, including:
History: Old San Juan, Puerto Rico, provides a glimpse into the Spanish colonial history of much of the region. Be sure to check out Castillo San Felipe del Morro, part of the San Juan National Historic Site. If you want to experience the history of British colonialism in the region, St. George, Bermuda, is your destination. And if you want to dive into the history of reggae, a cruise can get you there.
Diving: Aruba and the Cayman Islands are some of the world’s best destinations for serious divers. Not quite so serious? In the Caribbean, even first-time snorkelers can get a glimpse into a world of incredible beauty.
Food: Whether it’s jerk chicken in Jamaica or rice and peas elsewhere, the Caribbean offers interesting street food that combines Spanish, English, and native elements, mixing local products like plantains, goat and spices with staples like rice. Also read: Best Restaurants in the Caribbean
Scenery: While some of the islands are flat and somewhat uninteresting, islands like Dominica are volcanic wonders with mountains, rainforests, rocky outcroppings, and more.
Beaches: Caribbean sand varies in color from black to pink to white, but it’s almost always like warm superfine sugar studded with the occasional seashell.
Excursions: Whether you want to swim with dolphins, ride horses through the surf, taste chocolate or rum, or sail on a racing boat, there’s likely an excursion for you.
Nightlife: Island nightlife runs from mild to wild. At the very least, it’s a change from the shipboard experience.
Given these factors, the best way to plan a Caribbean cruise is to mix and match ships, ports of call and experiences. This can be hard to do on your own but not hard at all for a cruise specialist.
Find a travel professional who specializes in cruises and lay out your want list, and before you know it they’ll have the perfect cruise itinerary for you.
You can get our cruise packing list that's easy to print or fill out digitally or watch this video:
What do I need to know about hurricane season?
Caribbean cruise season (most popularly in the summer) and hurricane season traditionally runs from June to November, but the Caribbean’s high water temperatures have lengthened the season a bit. Plan cruises carefully during that season and consider travel protection that can help in case a trip-wrecking storm comes your way.
On the other hand, when they’re not churning up category-5 storms, the Caribbean’s waters are famously calm and clear, making them perfect for first-time cruisers. And outside of those nasty hurricanes the weather is tropical year-round, with warm temperatures and gentle sea breezes.
See our guide: Buying Travel Insurance for Hurricane Season Trips
Popular Caribbean cruise routes
Caribbean cruises tend to focus on one sector of the Caribbean, with the thought being that you can knock off another sector next time, and then another and another.
Caribbean cruises most often sail one of three basic itineraries:
Western Caribbean
Western routes often stop in Mexico, Belize, Honduras, and Jamaica, offering a blend of ancient ruins, tropical forests, and vibrant local cultures.
Southern Caribbean
Southern Caribbean cruises tend to be more hurricane-free than other routes. They include destinations like Aruba, Trinidad, and Barbados and are excellent for divers and people who enjoy exploring “the hidden Caribbean.”
Eastern Caribbean
Eastern Caribbean cruises frequent the Bahamas and the U.S. and British Virgin Islands. These are great for people who enjoy white-sand beaches and water sports.
Best ports of call/islands
While virtually every port-of-call has something to recommend, these stand out.
Anguilla
A low-key island that for many offers the best all-around laid-back Caribbean experience.
Cozumel, Mexico
A snorkeling and diving paradise, Cozumel is also rich in Mayan culture, with the ruins of San Gervasio a must-visit for history buffs.
San Juan, Puerto Rico
This historic city is known for its well-preserved Spanish architecture, forts, and vibrant arts scene. San Juan is a departure port for many cruises.
St. Maarten/St. Martin
A tale of two nations on one idyllic island, Dutch and French cultures split the island into a vibrant Caribbean melting pot. From the Dutch side's lively nightlife and casinos to the French side's chic boutiques and Gallic charm, this dual-personality island offers something for every traveler.
Bridgetown, Barbados
Barbados’ capital is surrounded by beautiful beaches and offers a mix of history, British colonial architecture and relaxation.
Dominica
Many cruise ships don’t stop at this small commonwealth, which means more hikes, rainforests, mountain climbing, volcanic scenery, and parrots for the rest of us.
St. Thomas, U.S. Virgin Islands
With one of the world’s most beautiful harbors, St. Thomas offers fantastic shopping, breathtaking views, and excellent beaches.
Also see: The 6 Best Caribbean Islands for Family Vacations
When to take a cruise
Peak season
Peak cruising season in the Caribbean runs from December to April, and features minimal rainfall and warm, sunny days.
Off-peak
If you prefer fewer crowds and don't mind an increased threat of rain, consider cruising during late April into May, or between September and early November. Rates are often lower, and ports are less crowded. Hurricanes are a threat, however.
Last-minute
It’s possible to score last-minute deals on cruises. You need to be ready to go at a moment’s notice, however, and you’ll have a limited selection of itineraries that are guaranteed to include the actuarial science theme cruise.
Find the Best Caribbean Islands for Every Month of the Year
Getting to your cruise
Some cruises include airfare as part of the total cruise cost; most don’t.
If your cruise doesn’t include airfare, make your plane reservations early. Allow plenty of time to get from the airport to your cruise.
Because things happen with flights many savvy cruisers allow themselves one to two days of cushion in their departure port on either end of their cruise.
Guide: How Cruises are Different Than Other Travel When It Comes to Cancellations
More tips for a great Caribbean cruise
- Know your drop-dead date: There’s a date after which you won’t be eligible for any refunds if you have to cancel your cruise. Know when this drop-dead date is. (Generally it’s a week or two before your sailing date.)
- Research your ports: Learn what each island is famous for so you can maximize your time ashore. This is especially true if you’re hoping to check out markets and/or street food.
- Choose excursions carefully: Cruises can offer an overwhelming assortment of excursions. Read reviews and be careful with excursions not offered by the cruise ship, as there’s no guarantee the ship will wait for you if your non-sanctioned excursion runs late.
- Pack accordingly: Caribbean weather is warm, but evenings on the ship can be cool. Pack light layers (including rainwear), roll don’t fold, use packing cubes, and don’t forget your swimming suits!
Travel insurance and assistance services
Unforeseen events, like medical emergencies or trip cancellation or interruption for a myriad of covered reasons, can disrupt a cruise and jeopardize your cruise investment. For that reason, you may insure your cruise with a travel protection plan.
The travel protection plans offered by Generali Global Assistance may cover the nonrefundable, prepaid expenses associated with a cruise – i.e., just about everything having to do with a cruise, from airfare to excursions.
Generali Global Assistance plans may offer coverage for medical emergencies (important on a cruise, since shipboard medical services are expensive and almost always out-of-network) and coverage for trip cancellation and interruption as well as travel delay.
Quotes are fast, and getting covered is easy.
Caribbean cruising is fun and relatively simple compared to other travel types. With some intelligent choices, prudent advance planning, and travel protection from Generali Global Assistance you’ll be all set for a memorable time in the Caribbean.
6937272410
