Cruising is a popular option for many vacationers nowadays, and for good reason. Cruising is an easy and affordable way to see the world, from the comfort and safety of a large (or sometimes small) luxury liner. Cruising allows you to visit multiple destinations on a single vacation, and to customize your experience to maximize your personal preferences. It’s all-inclusive, so food, beverages, and entertainment on board are all generally part of the package. From the Mediterranean to the Mexican Riviera, your options for cruising are endless.

If you love a tropical vacation, filled with never-ending sunshine, balmy temps, lazy waves, and powdery sand, a Caribbean cruise is a perfect choice for you. The islands of the Caribbean are a bevy of tropical hot-spots, generally offering laid-back vibes, a friendly atmosphere, and cool cultural experiences. A Caribbean cruise allows you the ease and flexibility of departing from a domestic port, so you can skip the hassle and cost of international airfare. You’re just a hop, skip, and a jump away from a warm-weather paradise on a floating piece of heaven.

The Caribbean is full of intrigue, history, and definitely mystery. Originally populated by various indigenous tribes, most of the islands were colonized by various European powers beginning in the late-15th century. England, Spain, France, and the Netherlands all vied for power in the region, and many of the islands are dotted with remnants of historic colonialism, from crumbling forts to rotting sugarcane plantations. If you love history (and a good mystery or two), there are tons to be found on the Caribbean isles. From slave rebellions and voodoo to mafia hideaways and unexplained disappearances, there is no shortage of curiosities to be discovered.

Why cruise the Caribbean?

Obviously cruising isn’t the only way to vacation in the Caribbean. You could just pick an island, book airfare, and settle into a comfortable beachfront resort for a week or two. There is nothing wrong with that, if that’s your cup of tea. Staying put in one destination allows you the freedom to explore that island from top to bottom, without a ship’s horn calling you back onboard to sail away after a single day’s exploration. However, visiting a single island at a time (presuming you take one big vacation a year) could make it take a lifetime to explore the entirety of the Caribbean, and unless you’re a gazillionaire, you likely don’t have the time or dollars to make that possible.

On the flip side, taking a Caribbean cruise can help you check multiple islands and ports off your bucket list each time you cruise, and if you pick a different itinerary each time, before you know it you’ll have visited all the major Caribbean ports of call. There are cruise options to fit every vacation budget, cruise lines that cater to different preferences, and a port of call to tickle every vacationer’s fancy. And don’t forget, most large cruise ships have 24-hour dining options, over-the-top entertainment, and enough swimming pools to hold an entire army. When compared to a week spent at a single resort, a cruise is sounding better and better.

When do Caribbean cruises run?

Unlike certain regions of the world, where cruises are seasonal only, in the Caribbean you’ll find year-round options for cruising. Some parts of the world are too cold to be enjoyable during the winter months, but not the Caribbean — you can still expect sunshine and daytime temps in the 80s in January, and possibly warmer the closer you get to the equator. You’ll often find more sailings in the colder months than in the warmer, because the cold months get extra cruise ships that are rerouted from places like Alaska, New England, and the Baltic, where it’s too cold for winter sailings. The bottom line when it comes to Caribbean cruises is that you can sail anytime you want.

One thing to keep in mind, though, is that August and September are at the peak of hurricane season for the Caribbean, so you may find cheaper sailings during those months, but there is risk involved. Not to worry, though — cruise lines are well aware of how tropical storms and hurricanes work and are generally quick to reroute your vessel to be out of harm’s way. If this occurs, your ports of call will shift to destinations not in the hurricane’s path. While this may be disappointing, it’s not a common occurrence.

Caribbean cruise route options.

With minor variations, there are three common Caribbean cruise routes to choose from: Eastern Caribbean, Western Caribbean, and Southern Caribbean. Each has a unique set of islands that it hits, and which route you choose will depend greatly on what you’re looking to see. Cruise itineraries generally are concentrated on a single region, but if you select a longer itinerary, you may see additional ports added from multiple regions, as well as places like the Bahamas or Florida, which fall outside any of the regions. Here is what you can expect with each of the three main routes:

Eastern Caribbean.

Eastern Caribbean cruises are popular with first-time cruisers, because they tend to depart from easy-to-reach destinations like Miami, Fort Lauderdale, and Cape Canaveral (near Orlando). Eastern Caribbean cruises run anywhere from four to 12 nights, with seven being the most common itinerary length. Common islands visited are St. Thomas, St. Martin, Grand Turk, the Dominican Republic, and Puerto Rico, and a visit to the cruise line’s private island or a stop in the Bahamas may also be on the itinerary. Eastern Caribbean cruises tend to center around ports of call where world-class beaches and duty-free shopping are the focal point.

Western Caribbean.

Western Caribbean cruises are also popular with first-time cruisers, for the same reason as Eastern Caribbean cruises — they tend to depart from easy-to-reach domestic ports. Western Caribbean cruises also run four to 12 nights, with seven being the most common itinerary length. Common islands visited are Jamaica and Grand Cayman, with at least one port in Mexico, although you will find variations that drop down to Central American ports in Belize or Honduras. Longer itineraries may include stops at a cruise line’s private island and/or the Bahamas as well. Western Caribbean cruises are great for travelers who are interested in Mayan or Mexican culture and history, as well as offering access to world-class beaches and other cultural attractions.

Southern Caribbean.

Southern Caribbean cruises tend to be preferred by seasoned cruisers who’ve already explored the other regions, primarily because the islands visited on this itinerary are farther away from domestic ports and often depart directly from an island port. This can mean the purchase of international airfare and require a passport. Southern Caribbean cruises generally run a minimum of seven nights, although eight nights or longer are very common for this route. Common islands visited are Aruba, Bonaire, Curacao, Barbados, Trinidad, St. Lucia, Dominica, Martinique, and Grenada. Because these islands are farther from the U.S. they tend to have less cruise traffic, meaning less crowding and more exclusivity. Southern Caribbean cruises offer everything the other routes do, from amazing beaches to unique historical sites and more.

Caribbean cruise line options.

There are literally dozens of cruise lines that offer Caribbean sailings, and it can be tough to know which one to pick. Most major cruise lines operate in the Caribbean, and which one to choose will be based primarily on two things: your budget and your preferred onboard experience. Royal Caribbean, Carnival, and Norwegian cruise lines are the region’s big three, and they’re a good jumping off point for cruise newbies. Each offers large luxury liners full of onboard experiences like water slides, casinos, movie theaters, roller coasters, and more, and each will have a myriad of itinerary and date options to fit most travelers’ needs. Celebrity, Princess, and Disney cruise lines all offer a higher-end experience, and smaller cruise lines like Seabourn, Silversea, and Regent offer a more intimate luxury experience, with fewer onboard activities but a whole host of ways to spoil you rotten while you sail.

Top Caribbean cruise tips.

These top travel-industry tips will help make planning your Caribbean cruise a fun and stress-free experience.

  1. If you can be flexible with your sail dates, you can almost always find a great deal on a Caribbean cruise.
  2. If you have specific date requirements, it is best to book as far in advance as possible — a nine-month minimum if you can. The farther out you book, the more options you’ll find.
  3. If you live near or can drive to a departure port, you can often find a screamin’ deal on last minute cabins within a few weeks of departure. These Caribbean cruises will often be bookable for discounts of 50% off or more.
  4. January and February are known as “wave season” in the cruise industry and these are the times that the best promotions are offered on Caribbean cruises, so if you can book in January or February, your wallet will thank you.
  5. Although not always required (depending on your ports of call), it is always a good idea to bring a passport along on a Caribbean cruise. It may come in handy if you have an emergency and have to disembark in a foreign port of call.
  6. Bring plenty of sunscreen. If you think you have enough, pack an extra bottle because you will run out and it’s expensive to purchase onboard. The sun is very strong in the Caribbean, and you’ll find yourself needing to reapply more often than you may be used to. You get a bonus point if you remember to opt for reef-safe sunscreen!
  7. A sunhat and/or moisture-wicking clothing are also smart things to pack. Anything you can do to prevent personal discomfort on vacation is always a good idea.
  8. Plan to arrive a day earlier than your cruise’s departure date. It’s always risky to fly or drive in the same day your ship departs. Depending on your departure port, your club may have a resort you can take advantage of for a night or two ahead of sailing.

WorldMark by Wyndham Travel, your Caribbean cruise connoisseurs.

WorldMark by Wyndham Travel, your exclusive full-service owner travel agency, can turn any dream vacation into a reality, and their friendly Travel Guides are truly Caribbean cruise connoisseurs. If you need advice or assistance on booking your Caribbean cruise, visit their online booking page or give them a call. They can save you time and money (and they’re really nice, too). There’s no better way to plan your Caribbean cruise than with WorldMark by Wyndham Travel.

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