You are using an older browser version. Please use a supported version for the best MSN experience.

Caribbean cruise guide: Best itineraries, planning tips and things to do

The Points Guy logo The Points Guy 5/18/2022 Erica Silverstein
MSN has partnered with The Points Guy for our coverage of credit card products. MSN and The Points Guy may receive a commission from card issuers.

“All the leaves are brown, and the sky is gray …” When the weather turns cold, you could be California dreamin’ but doesn’t a Caribbean cruise sound so much more relaxing?

Many people would agree with me that a Caribbean cruise is the perfect antidote to the winter doldrums and work stress, plus a wonderful way to reconnect with friends and loved ones. The ship takes care of everything — transportation, accommodation, meals and entertainment – so you can skip much of the daily planning drama and simply enjoy your vacation and travel companions. Every day you wake up to warm weather and sunny skies (well, most of the time) and a new destination promising white sand beaches, fun activities and memories to be made.

The biggest decision you have to make is between a pina colada and a strawberry daiquiri.

For cruise news, reviews and tips, sign up for TPG’s cruise newsletter.

Before you go, however, you have lots of choices to make: Which is the best cruise line? Which are the best Caribbean cruise ports for the activities you most enjoy? What time of year should you travel?

Don’t let planning a rejuvenating vacation add more stress to your life. This Caribbean cruise guide gives you the lowdown on everything you need to know to plan the perfect island getaway.

In This Post

Why cruise to the Caribbean?

(Photo by Stephen Frink/Getty Images) © The Points Guy (Photo by Stephen Frink/Getty Images)

Sun, sand and sea are what most travelers want when they book a cruise to the Caribbean. If you want to trade chilly weather at home for warm, sunny days spent relaxing on a beach or swimming in clear blue waters, a Caribbean cruise is an ideal vacation. Unlike a resort stay, you can sample multiple beaches in various destinations, as well as the pool life on board the ship.

Many people choose Caribbean cruises because they’re affordable getaways to tropical destinations. The sailings depart from several U.S. home ports — from Galveston, Texas, to Boston — so many Americans can drive to their departure ports and avoid paying for airfare.

Plus, cruise ships can change course to avoid bad weather, such as hurricanes, so you can salvage your beach vacation when a storm is headed toward a particular island by cruising to a different one. If you booked a land-based stay, you’d be forced to cancel — or hunker down and wait for the rain and winds to pass.

When do cruises go to the Caribbean?

Caribbean cruises sail year-round, so you can plan your trip for the winter holidays, spring break or summer vacation. However, more ships sail this region of the world in the winter, when other destinations (such as the Mediterranean, Baltic, Canada/New England and Bermuda) are too chilly for vacations at sea.

The luxury and upscale cruise lines especially tend to only base ships in the Caribbean during the winter because their fleets are too small to base a ship there year-round — and their passengers want to explore bucket list destinations around the world.

Best Caribbean itineraries

(Photo by Westend61/Getty Images) © The Points Guy (Photo by Westend61/Getty Images)

Cruise lines divide the Caribbean into three regions: Eastern, Western and Southern. Itineraries tend to concentrate on one area, but longer itineraries may include islands in two or all of the regions, as well as ports in the Bahamas and Florida.

Which itinerary is best for you will depend primarily on which port you want to depart from and how long a vacation you can take. Once you see the options that fit your parameters, you’ll want to look at how many port stops versus sea days an itinerary has and which specific islands you’ll visit.

The best Caribbean itineraries for first-time cruisers are often the seven-night Eastern or seven-night Western Caribbean cruises out of Florida home ports, such as Miami, Fort Lauderdale or Port Canaveral (near Orlando).

Western Caribbean

You’ll find two main types of Western Caribbean cruises, and both are fabulous introductions to Caribbean culture and attractions. The classic Western Caribbean itinerary visits Mexico (typically Cozumel or Costa Maya), Jamaica, Grand Cayman and a cruise line’s private island, which is typically in the Bahamas.

However, some ships sail a Western Caribbean itinerary that’s more focused on Central America, with stops in Mexico, Belize and Honduras. These itineraries are great for travelers who are interested in Mayan or Mexican culture in addition to beaches and water sports.

Western Caribbean itineraries are typically a week, but can be as short as four days (with just one stop in Mexico) or as long as 12 days (though these might include stops in the Bahamas, too). You can find departures from ports all along the U.S. East Coast, Gulf Coast and Florida.

Eastern Caribbean

Another popular itinerary for first-timers is the Eastern Caribbean, with visits to St. Thomas, St. Maarten, Grand Turk, the Dominican Republic and/or San Juan, Puerto Rico. Private island and Bahamas stops are common. Longer cruises or smaller-ship itineraries might stop elsewhere in the U.S. and British Virgin Islands, St. Barts, Antigua or St. Kitts.

These itineraries are slightly more targeted toward beach time and water sports, with fewer options for historical or cultural attractions than their Western Caribbean counterparts.

As with the Western Caribbean, seven-night Eastern Caribbean cruises are the most common itinerary length. The shortest options are four nights, typically visiting only Grand Turk or Puerto Plata, Dominican Republic. The longest, around 10 to 12 nights, will often include Southern Caribbean ports or start from more northerly home ports.

You can find departures from ports as far west as Galveston and as far north as the New York area, but the majority of true Eastern Caribbean cruises set sail from Florida or Puerto Rico.

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

Southern Caribbean

Southern Caribbean cruises tend to attract luxury travelers and repeat cruisers. That’s because these islands are farther from U.S. shores, meaning you’ll need to fly to an island to catch your cruise ship or need more than a week’s vacation to get from Florida all the way south to ports in Aruba or St. Lucia and back. The islands themselves tend to be more exclusive, with fewer ships visiting on any given day.

Common destinations on Southern Caribbean cruise itineraries include Aruba, Bonaire, Curacao, Barbados, Trinidad, St. Lucia, Dominica, Martinique and Grenada. You’ll find everything from gorgeous beaches and diving destinations to lush rainforests and flowing waterfalls.

The shortest Southern Caribbean cruises are five or six days and leave from places such as Barbados, San Juan and St. Thomas. You can find weeklong sailings from Florida, but more commonly, they’re eight nights or longer.

Video: What to know before booking your cruise vacation (TODAY)


The Bahamas and Florida

Yes, I know that the Bahamas is technically located in the Atlantic, but it’s an easy mistake to think the balmy islands are found in the Caribbean. Besides, many cruises add stops in the Bahamas to a Caribbean cruise. The majority of the cruise line private islands are located in the Bahamas, and these appear regularly on all Caribbean itineraries. The Bahamian ports of Nassau and Freeport, even Florida’s Key West, may appear on Caribbean-centric cruises.

Why? They’re close to the U.S. and cruise lines use these ports to break up the multiple days at sea needed to sail farther south into the Caribbean proper.

Related: Caribbean vs. Bahamas cruises: Which itinerary will I like better?

Best Caribbean cruise lines

Norwegian Bliss in the Caribbean. (Photo courtesy of Norwegian Cruise Line) © The Points Guy Norwegian Bliss in the Caribbean. (Photo courtesy of Norwegian Cruise Line)

You’ll be hard-pressed to find a cruise line that does not sail to the Caribbean at least for a few months a year. The big-ship lines will station multiple ships in this region year-round, with additional ships swinging by during the colder months.

If you consider the best Caribbean cruise lines to be the ones with the most ship and itinerary choices, look to the big-ship lines such as Carnival, Royal Caribbean and Norwegian Cruise Line.

These lines offer a range of itinerary lengths, port combinations and departure cities from the Gulf Coast to the East Coast. Their biggest and newest ships are often deployed to the Caribbean, so you can find all the latest celebrity-backed restaurants, crazy top-deck attractions (like waterslides, climbing walls and roller coaster rides) and expanded cabin choices. These lines cater to all ages, including older couples and families with children.

Related: The best Caribbean cruise for every type of traveler

If you’re looking for an adults-only option, Virgin Voyages caters to the young at heart with its edgy new ships. It offers six- and seven-night Caribbean cruises from the late fall until early spring. Viking takes an entirely different approach to no-kids cruises, catering to mature travelers craving culture and educational vacations. It also offers wintertime Caribbean cruises, though many are paired with a Panama Canal crossing.

Luxury lovers should look at the smaller ships of the Seabourn, Silversea and Regent Seven Seas fleets for opulent accommodations and fine dining while sailing the tropics. Oceania, Azamara and Windstar Cruises are less inclusive, but still high end.

For something a little different, try SeaDream Yacht Club for a super-small ship that feels like a private yacht, complete with an emphasis on alfresco recreation and dining. Star Clippers appeals to sailing enthusiasts with its masted ships, simple entertainment and emphasis on water sports.

Things to do in the Caribbean

White sand beaches and crystal-clear turquoise waters are the biggest attractions for most Caribbean cruisers. You’ll be hard-pressed to find a Caribbean cruise port that does not offer beach access. Whether you enjoy a cruise line’s private beach, a public beach lined with bars or get a day pass to a resort or beach club, you can rarely go wrong with a beach day in the islands.

Water sports are another quintessential Caribbean attraction. Cruisers can swim, snorkel and scuba dive, of course, but they can also kayak, snuba, Jet Ski, sail and parasail. Sometimes you can do these things right from whatever beach is your destination for the day. Otherwise, book a tour to the best spots or for a guided activity. Or, book a leisurely sunset sail or high-octane party cruise to get on the water, not necessarily in it.

Shopping is a popular diversion, from high-end French stores in Martinique and St. Barts to crafts markets and souvenir shops. Historical attractions range from forts erected to protect against pirates to Mayan temples. Cultural tours focus on local cuisine, wine and spirits, and dancing. (Yes, even you can learn to salsa.) Active travelers will find plenty of hiking, biking, zip lining and ATV tours.

Best Caribbean cruise ports

(Photo by HaizhanZheng/Getty Images) © The Points Guy (Photo by HaizhanZheng/Getty Images)

A single cruise line might call at 20 to 30 different ports in the Caribbean. Although you might think they all look like stock photos of white sand beaches with palm trees and blue skies, each island has its own look, culture and vibe. I’ve sailed to a large number of those ports and would be hard-pressed to pick a favorite. They all have their charms for different reasons.

The following Caribbean cruise ports are generally standouts, no matter your travel style.

Cozumel, Mexico

Cozumel is an island in the Caribbean just offshore from Playa del Carmen and just south of Cancun. It truly offers something for everyone. You can head to the beach, go scuba diving or snorkeling or head to the mainland to see Mayan cultural sites like Tulum and Chichen Itza. Stick around town to find cheap drinks at Senor Frog’s or shop for souvenirs.


Cruise ships call at a number of ports in Jamaica: Ocho Rios, Montego Bay, Kingston and Falmouth. Many folks spend the day on the beach, often at one of the resorts, but climbing up Dunn’s River Falls is a unique experience not to be missed. Cruisers seeking a thrill can find bobsled, zip line, river tubing and ATV tours. And, yes, reggae fans — there is a Bob Marley tour you can take.

San Juan, Puerto Rico

San Juan is both a popular departure port and port of call on Eastern and Southern Caribbean cruise itineraries. Its Old Town and historic fort overlooking the water are top attractions, but cruisers have the opportunity to visit El Yunque National Forest (the only tropical rainforest on U.S. soil) or head to the beach.

Belize City, Belize

Travelers don’t tend to spend much time in Belize City itself, but it’s a great jumping-off point for all Belize has to offer. Visit the Altun Ha Mayan ruins, go river tubing and spelunking in caves, zip line through the jungle or go snorkeling or diving along Belize’s famous barrier reef (the northern hemisphere’s largest).

St. Thomas, U.S. Virgin Islands

This island is known for its gorgeous Magens Bay beach. However, if you’d rather not share the beach with several ships’ worth of cruisers, take the ferry to nearby St. John for the day and find a U.S. national park and a more chill beach experience. Take the kids to the Coral World Ocean Park, your sweetie on a catamaran sail or snorkel trip and your crazy friends on a helmet dive or BOSS underwater scooter adventure.

St. Lucia

Known for its lush green twin peaks known as the Pitons, St. Lucia entices travelers with postcard-perfect beaches set against jungle scenery. It even has its own volcano with sulphur springs to visit and all the usual land and sea activities.


Beach, beach and more beach — Aruba is definitely a port to be in, on or near the water. It’s one of the southernmost Caribbean islands, found just off the coast of Venezuela, and its location protects it from the summer and fall hurricanes that can hammer the islands to its north and east. Animal lovers might want to check out its ostrich farm — not something you usually find in a Caribbean cruise port.

When to book a Caribbean cruise

(Photo by Roberto Moiola Sysaworld/Getty Images) © The Points Guy (Photo by Roberto Moiola Sysaworld/Getty Images)

The best time to book a Caribbean cruise is clearly right now! Seriously, you can almost always find a deal on a Caribbean cruise if you’re flexible enough with your travel dates and cabin types.

If you want to book a popular sail date (such as a Christmas and New Year’s Eve sailing) or are looking for a cabin type that’s in limited supply (connecting cabins or studio rooms for solo travelers), book as far in advance as you can, at least nine months out if not longer. If you’re retired and can drive to a port, you can likely find an inside cabin to book just a few weeks prior to sailing.

The first few months of the year, known as “wave season” in the cruise industry, is a time when cruise lines all offer some kind of booking promotion, and you can often find discounted fares or free booking perks on Caribbean cruises. Many cruise lines also run sales at the end of the summer or during Black Friday/Cyber Monday, and Caribbean sailings are almost always included.

What to bring on a Caribbean cruise

Swimsuits and warm-weather clothing should top your Caribbean cruise packing list, but don’t forget the sunscreen. The sun is stronger than you might expect in this part of the world, and you can easily burn during a long day at the beach if you don’t apply and reapply plenty of sunscreen. Hats, sunglasses, moisture-wicking athletic clothing and your favorite cover-ups and sundresses are all must-pack items.

I also recommend that all passengers bring a passport on their Caribbean sailing. If you’re cruising round-trip from a U.S. port, a passport is not required by law — but it’s a good idea to pack one in case of an unexpected medical emergency or mechanical problem that forces you to debark the ship in a foreign country.

Bottom line

Whether you’re new to cruising or a hardy sailor, the Caribbean is the perfect place for a cruise vacation. If you’ve never been, any of the islands will delight. If you’ve sailed before, there’s always some destination you’ve never visited or an activity you haven’t tried.

When winter in your hometown drags on, or the stress of the workweek gets you down, a Caribbean cruise is often just what the doctor ordered to lift the weight of the world from your shoulders and let you escape to a tropical paradise for a few days.

Planning a cruise? Start with these stories:

Featured photo by Jeff R Clow/Getty Images.

SPONSORED: With states reopening, enjoying a meal from a restaurant no longer just means curbside pickup.

And when you do spend on dining, you should use a credit card that will maximize your rewards and potentially even score special discounts. Thanks to temporary card bonuses and changes due to coronavirus, you may even be able to score a meal at your favorite restaurant for free. 

These are the best credit cards for dining out, taking out, and ordering in to maximize every meal purchase.


Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.


More From The Points Guy

The Points Guy
The Points Guy
image beaconimage beaconimage beacon