Best Itineraries, Tips More

Dreaming of the ultimate tropical escape? Look no further than the Caribbean. With its pristine white sand beaches, turquoise waters, and endless sunshine, the Caribbean is truly paradise on Earth. It’s no wonder, then, that the Caribbean is a top cruising destination. This Caribbean cruise guide lays out all the different itineraries and tips for choosing a Caribbean cruise in 2022.

Tucked between North and South America, the Caribbean is the most popular cruising destination on the planet. Here, you’re spoiled for choice with over 700 islands and 26 countries and territories to choose from. With nonstop flights from many cities in the US, Europe, and the Middle East, it’s a convenient place to vacation. However, there are many key items to consider when planning a Caribbean cruise itinerary, which we’ll cover in detail below.

When choosing a Caribbean cruise, the possibilities are endless. From 5-star luxury cruise lines to small yachts and sailboats, there are so many types of ships to choose from. Some Caribbean cruises are suitable for families with kids while others are geared more towards adults. Take your pick between entertainment at every turn or a three-piece band after dinner; exploration and adventure or glitzy and glamor; mega ship vs. yacht. There are truly countless options to consider when booking a Caribbean cruise.

From the top Caribbean cruise itineraries to the best cruise ships for every type of traveler, this Caribbean cruise guide has got you covered. Here’s everything you need to know before booking a Caribbean cruise in 2022.

Read next: Coolest Islands in the World to Visit

Guest Post by Joanne Miksis from Holiday Travel

Top Caribbean cruise destinations

The Caribbean is made up of hundreds of islands, ranging from large ones like Cuba, Puerto Rico, and Jamaica all the way down to Jost Van Dyke and Bequia (two of my favorites!).

While most cruises start and end in Florida and the Caribbean, some ships leave from the Northeast and Mid-Atlantic. This includes New York City, New Jersey, Norfolk, and Charleston. Keep in mind: it takes 1-1.5 days to arrive in the Caribbean from these cities, which is why most cruisers prefer to leave from places like Florida or Puerto Rico instead.

When choosing a Caribbean cruise, there are three regions to consider: Western, Eastern, and Southern Caribbean. Let’s take a closer look at each:

Western Caribbean

Located south and west of Florida, the Western Caribbean is a popular Caribbean cruise itinerary. Most ships depart from ports in Florida, including Miami, Fort Lauderdale, Port Canaveral, and Tampa, with a stop in Key West. Other cruises depart from Galveston and New Orleans.

From there, Western Caribbean departing from FL cruises hug the coast of Florida, including the Florida Keys, and head west around Cuba towards Mexico and Central America. Popular Western Caribbean destinations include Cozumel, Grand Cayman, Jamaica, Belize, and Roatán (Honduras).

On a Western Caribbean itinerary, consider taking shore excursions at the Mayan ruins in Tulum and Chichen Itza. Are you interested in snorkeling? Grand Cayman is considered one of the best places for snorkeling in the world, offering beautiful reefs, fish, and shipwrecks. It’s also a great destination for diving. If you’re looking for fun in the sun, this is one of the best Caribbean cruise destinations, hands down.

Eastern Caribbean

Looking for a Caribbean cruise route like no other? Extending from Haiti and the Dominican Republic to Barbados, the Eastern Caribbean is another popular region to explore on a cruise.

The Eastern Caribbean consists of well-known islands such as the US Virgin Islands (St. Thomas, St. John, and St. Croix), the British Virgin Islands (Tortola, Virgin Gorda, Anegada, and Jost Van Dyke) and Puerto Rico. Some smaller and lesser-visited islands include St. Barts, Antigua and Barbuda, Anguilla, and Dominica, which are also considered a part of the Southern Caribbean (depends on who you talk to).

Eastern Caribbean itineraries mainly depart from Fort Lauderdale, Miami, Port Canaveral, and San Juan. Departing from San Juan, you can travel as far as Aruba on a 7-night cruise. What more could you want in Eastern Caribbean cruises?

Southern Caribbean

Another region that’s worthy of a spot on your bucket list is the Southern Caribbean. Many travelers choose the Southern Caribbean because it’s pretty much out of the hurricane belt. This is also where you’ll find the islands of the Dutch Caribbean.

Begin your Southern Caribbean cruise in Puerto Rico, Barbados, or St. Maarten. Popular ports of call include the ABC islands (Aruba, Bonaire, and Curaçao), Barbados, St. Maarten, St. Lucia, Grenada, and St. Vincent and the Grenadines.

The Southern Caribbean region is quite spread out, so many cruises tend to be longer than 7 nights. If you’re willing to brave a 14-night cruise from Bridgetown, Barbados, you can even make it as far southwest as Cartagena, Colombia and on to Costa Rica and the Panama Canal. These are becoming increasingly trendy destinations on Caribbean cruise itineraries.

Another top Caribbean cruise destination: The Bahamas

A Caribbean cruise guide wouldn’t be complete without mentioning the Bahamas.

Though it’s not considered the Eastern, Western, or Southern Caribbean, the Bahamas is certainly top of mind for travelers. This Caribbean nation in the West Indies consists of 16 major islands, including Paradise Island which is home to the capital, Nassau, and the world famous Atlantic Paradise Island resort. Another must-see in the West Indies is Turks and Caicos.

Bermuda is not in the Caribbean Sea (but it’s often lumped together!)

And then there’s Bermuda!

Even though Bermuda is out in the middle of the Atlantic Ocean— 650 miles off the coast of North Carolina – it’s important to mention. No, it’s not in the Caribbean Sea, but it’s often categorized with the Caribbean as far as cruising is concerned.

There are some great seasonal itineraries that depart from the Northeast (Boston, New York, and New Jersey), spending 1-3 days at this quaint, British territory. Typically, these roundtrip Bermuda cruises operate from May thru October.

Best Caribbean cruises for every traveler

What kind of cruiser are you? In the Caribbean, there’s truly a cruise for everyone. Ship sizes are all over the map (literally!) from luxurious SeaDream ships (112 passengers) and Windstar cruises (150-350 passengers) all the way up to 6,700 on Royal Caribbean’s Symphony of the Seas. Needless to say, the opportunities are endless.

With so many amazing options, you need to decide what you’re looking for in a Caribbean cruise vacation. Here are some ideas to help you with that:

Best Caribbean cruises for families

From kid’s club programs to onboard amenities like waterslides and go-karts, these family-friendly cruises in the Caribbean will blow your mind.

Top Choice: Disney Cruise Line

If you’re traveling with kids and have a big budget to work with, Disney Cruise Line is an excellent option. Disney will take you anywhere in the Caribbean aboard their world-class ships: the Disney Wonder, Magic, Fantasy, and Dream. In addition, the Disney Wish – a brand new ship powered by liquified natural gas—is making its maiden voyage this year.

Disney’s short cruise itineraries go to the Bahamas while the longer ones cover a variety of destinations around the Caribbean. The highlight of every Disney cruise is the “beach party” at Castaway Cay. Located in the Bahamas, Disney’s private island is nothing short of spectacular.

Disney Cruise Line is wonderful for grandparents, their kids, and grandkids: there’s truly something for everyone. Great entertainment and food, including adults-only restaurants (and pool areas) offer a nice break for every member of the family. In true Disney fashion, nothing has been spared. If Walt Disney were still around, he would surely be proud of where his company is today!

Other family-friendly cruises in the Caribbean: NCL or Royal Caribbean

As far as Caribbean cruises for families go, you can’t go wrong with Norwegian Cruise Line or Royal Caribbean. Each of these major cruise lines are frequently offering promotional rates. So, be sure to shop around and find a cruise that appeals to the whole family!

Coolest Caribbean cruises for couples

Honeymooners, anniversary couples, and couples (in general) would really enjoy any of the following cruise lines: Celebrity, Princess, Viking, Royal Caribbean, and Virgin Voyages. All offer outstanding service, entertainment and amenities, making for the perfect romantic getaway in the Caribbean. Here are some of the unique aspects to each.

Celebrity Cruises

If you’re looking for luxury packaged in a romantic Caribbean cruise, this is a great bet. Celebrity is also known for its Michelin-caliber food. So, take in the panoramic ocean views as you enjoy a romantic dinner date with your significant other.

Princess Cruises

Named the “Best Cruise Line for Romance” by Cruise Critic, Princess is a top romantic getaway at sea. Consider sailing aboard “The Love Boat,” a themed vessel that makes a 7-day voyage from Los Angeles to the Mexican Riviera.

Viking Ocean Cruises

These ships are small and intimate, typically accommodating less than 1,000 guests. Because of their size, Viking Cruises can dock in small ports at quieter and lesser-known destinations.

Royal Caribbean

For adventure travel couples and families, it doesn’t get any better than Royal Caribbean. Enjoy the FlowRider and waterslides onboard and take advantage of the adventure activities onshore. This is one of the best cruise lines for couples (and just about everyone else).

Virgin Cruises

As an adults-only cruise, Virgin Voyages is a popular option for couples sailing in the Caribbean. It’s also great for friend group getaways.

To figure out which cruise line/ship suits you best, check out the different itineraries, offers, dates, and airfare prices on the cruise line websites above

Read next: Tips for Traveling as a Couple

Top Caribbean cruises for solo travelers

In the cruise ship industry, solo travelers often get shafted having to cover the cost of a “missing passenger” in a standard stateroom. However, there are a few Caribbean cruise lines that offer studio cabins.

Norwegian Cruise Line’s Epic was the trailblazer with this idea and still leads with the number of cabins offered: 128. Celebrity, Costa, Holland America, and Royal Caribbean offer this on some ships, although not nearly as many (12-20 studio cabins on average).

Studio cabins are very small – some are only 100 square feet. The Norwegian Epic’s cabins offer a porthole that looks out to the hallway – a unique feature, though definitely not for everyone. The Epic also has a nice gathering area for solo travelers looking to meet for a light breakfast or cocktails.

Typically, cruise lines charge 200% of the cruise fare for single travelers. So these studio cabins are very appealing!

Best small Caribbean cruises

Looking to sail aboard the top small luxury cruises in the Caribbean? Sea Dream has got you covered. They offer two ships: SeaDream I and SeaDream II. Each yacht accommodates just 112 passengers.

Another small yet luxurious Caribbean cruise line is Windstar. There are six ships in all ranging from 150 to 350 passengers.

As you can probably imagine, these cruise lines are not for the kiddos. No children’s programs are offered, and there are no surf simulators, rock climbing walls, or go karts aboard these vessels.

Cruising on these yachts will allow you to visit very small islands such as Jost Van Dyke in the British Virgin Islands. Population 320! I recently spent the day here on Windstar’s Star Legend. Very quaint with not a whole lot going on. We went to a beach on an island close by (population zero) by catamaran and stopped at another spot to snorkel. Have you ever heard of “Sandy Spit”? It’s the teeny island they filmed the Corona Beer commercial on. Very cool seeing that! Sailing by that was like a mirage. If you’re looking to sail with one of the best small cruise ships in Caribbean, this is it!

Coolest large Caribbean cruises

Looking to explore the Caribbean in style. Add one of these large Caribbean cruise ships to your itinerary.

The best mid-size luxury lines in the Caribbean are Crystal (2 ships with 900 passengers each), Oceania (6 ships – 680 each), and Seabourn (5 ships – 500 each). All have top-notch services and food.

Crystal Cruises appeals to retirees for the most part and those who love dressing up (jackets in the evening for the guys). Most cruises with Seabourn appeal to the 60+ category, but it’s not uncommon to see forty-somethings as well. You won’t find any children’s programs on these vessels. Though you may find sparsely attended programs during school vacations (and in the summer). Owned by Norwegian Cruise Line, Oceania is a culinary and destination-focused cruise line in the Caribbean.

If you’re seeking a mid and large-sized cruise in the Caribbean, these cruise lines will not disappoint!

Best Caribbean cruises for budget travelers

Looking to go cruise the Caribbean on a budget? Carnival is for you. Costa and MSC are great low cost options, too. These budget-friendly cruise lines advertise ridiculously low prices, sometimes as low as $89-$99 for a 4-night cruise (per person based on a double inside cabin). Of course, you also must factor in government fees, port taxes, and gratuities to get the real cost. But regardless, these lines usually come in the best for pricing.

Know before you go: Carnival is known to operate “party” ships. So, don’t be surprised to hear loud voices and laughter in the hallway at 3am. It’s certainly not a Caribbean cruise line for everyone!

Unique Caribbean cruises for adventure seekers

Craving adventure on your next cruise in the Caribbean? Check out one of the Star Clippers ships or Windstar’s Wind Surf.

The Star Flyer, a 4 masted vessel, can be seen in many Caribbean ports in the winter. In addition, the Wind Surf (5 masts!) is anchored or docked at various ports as well. Both offer the comforts and amenities you will find on a luxury Caribbean cruise line. Though unlike many of the other luxury lines, there aren’t any water parks or Broadway shows.

In addition to luxury amenities, both Star Clippers and Windstar have an open bridge policy. As such, the captain and crew are happy to answer your questions while they are underway. It’s such a unique experience.

For an ultra-luxury experience in the Caribbean like no other, consider sailing with Silver Spirit. This all-inclusive Caribbean cruise offers eight superlative dining options onboard, as well as a spa, panorama lounge, and more. The advertised prices also include airport transfers and food and beverage butler service. What more could you want in a top luxury cruise in the Caribbean?

Cool and unique cruises in the Caribbean

Now that we’ve covered the traditional Caribbean cruises, let’s talk about some unique ones. Here are the shortest and the longest itineraries that you should consider for your next Caribbean cruise vacation.

New for 2022: The Margaritaville at Sea Paradise by Jimmy Buffett. Decked out in Margaritaville’s signature style, the Paradise will be based out of Palm Beach, Florida with 2-night cruises sailing to Grand Bahama Island. The unique Caribbean cruise will be starting at just $169 per person.

New for 2023: Looking to cruise around the whole world? Make sure to put in for 274 vacation days in 2023! Royal Caribbean is taking cruising to a whole new level with the inaugural voyage of Ultimate World Cruise. This incredible cruise aboard Serenade of the Seas will visit all 7 continents, including over 150 destinations in 65 countries and 11 wonders of the world. It’s slated to be the longest cruise in the world, sailing roundtrip from Miami on Dec. 10, 2023 and returning Sept. 10, 2024. Given the popularity that comes with this superlative cruise, expect that it will sell out over a year in advance, so plan accordingly!

Another popular Caribbean itinerary could involve the Panama Canal, one of the 7 Wonders of the Modern World! These sailings might include other Western Caribbean destinations, including Costa Rica, Colombia, Grand Cayman, Mexico, and of course Panama.

Due to the distance involved, these Panama Canal cruises typically run 9+ nights. Some sailings will go as far as the manmade Gatun Lake—a major part of the Panama Canal— before turning around. A complete sailing through the canal can be 14+ nights and leave from Florida, make 2-3 Caribbean stops and on the Pacific side before disembarking in California. It takes about 10 hours to navigate the 12 locks in the 50-mile canal. Good trivia questions for your friends. A marvel, for sure! 

Tips for planning a Caribbean cruise

Planning a Caribbean cruise in the near future? Here are some Caribbean cruise tips that will come in handy.

How to save money on Caribbean cruises

Want to save on a cruise vacation in the Caribbean? Think about booking a repositioning cruise. This is a one-way cruise itinerary that typically occurs in between seasons.

For example, when the weather gets cold in Boston or NYC, many cruise ships will move to places like the Caribbean where it’s much warmer. Rather than having an empty ship sail down south for the season, cruise lines will market repositioning cruises for travelers wishing to board a one-way itinerary and flying home from the last port.

Typically, repositioning cruises to the Caribbean are longer due to the distance involved. A classic repositioning cruise would be from Barcelona or Lisbon to Miami, Ft. Lauderdale, or Barbados. Usually, the only stop is in Tenerife and the remaining days are at sea. Cruise lines operate ships in the Mediterranean from May to October then brings them back to the Caribbean for the busy winter season. If you enjoy relaxing days at sea, this could be a great idea for you!

Other reliable ways to save money on Caribbean cruises include being flexible with your dates, booking your next cruise onboard for steep discounts, and sailing from a cruise port close to home. You can never go wrong with doing research ahead of time and looking for special offers on cruise websites. It also pays to read blogs like this Caribbean cruise guide!

How do gratuities work for cruises in Caribbean?

If you’re sailing in the Caribbean, all cruise lines require that guests pay gratuities for the cabin steward and wait staff. Typically, these prices are about $15 per guest per day. You may choose to pre-pay for gratuities before setting sail or you can pay onboard. I usually pay before I travel, as it’s one less thing to think about! Cruise lines operate cashless, so guests charge all onboard expenses (shore excursions, gift shop purchases, etc.) and settle your account at the end of the week.

Besides paying for gratuities, it’s also a good idea to bring some cash to hand out to your favorite barista, server, or cabin steward. Servers aboard ships will always go above and beyond to make your experience the best it can be. All cabins have a safe, so you can be sure that your valuables are safe and sound.

Some Caribbean cruise lines (usually the luxury lines) include gratuities as part of the cruise fare. Often you will see promotions offered that will include gratuities as well as drink packages, specialty dining, and shore excursions. In a highly competitive market, the offers are plenty! Always look at the fine print to see what’s included in the price.

Caribbean cruise tip: double check your passport to make sure it’s not expiring soon

Do you need a passport to go on a Caribbean cruise departing from a U.S. port? Yes and no. When sailing on a closed loop cruise (depart and return from the US) the cruise line will HIGHLY RECOMMEND you bring a passport rather than a birth certificate and government-issued photo ID (license).

Without a passport, you are assuming unnecessary risk while onboard cruises in Caribbean. What happens if you fall ill or for whatever reason need to fly home from one of the international ports you are visiting? You would not be able to get home, as passengers are required to show a valid passport to fly internationally. So, apply for a US passport – better safe than sorry!

Know before you go: Many Caribbean islands and countries require passports to be valid 6 months after your travel dates.

Tip for flying back home after a Caribbean cruise itinerary

If you’re taking a connecting flight back home from an international trip, be careful if you plan on purchasing items at the airport.

Say, you are flying home to Boston from Barbados and connecting in NYC. You check your bag in Barbados, then decide to do some shopping at the airport and find hot sauce made on island – a nice gift for someone back home. Upon arrival in NYC, TSA will go through your bag and see an 8-oz bottle and confiscate it (as it’s over 3 oz). Duty-free items shouldn’t be a problem, as the store seals them. Just don’t imbibe onboard your flight and you’ll be all set! Also, remember to eat that piece of fruit in your carry-on, as they will take that, too.

Before planning a Caribbean cruise, consider all amenities on board!

These days, you can find just about everything on cruises in the Caribbean: from waterparks and racetracks to rock-climbing walls and skydiving simulations. Mega ships also offer other forms of entertainment, including Broadway shows. If you closed your eyes, you would think you were at a NYC theater!

In addition, celebrity chef restaurants abound on these floating cities. Take advantage of themed restaurants like American steakhouses, French bistros, or Japanese sushi restaurants. You’ll also find more casual dining options such as BBQ grills, pizzerias, and bakeries.

Many Caribbean travelers are simply happy with beach, pool, and sunshine. Grab a book and a cappuccino and find a quiet spot by the pool. Others want to attend a talk given by an enrichment speaker on the next port of call. Or all the above!

From relaxing massage treatments to facials, the spa is another must for so many cruise-goers. Most ships also offer fitness centers, some with classes. And of course – Bingo is a big favorite, as are casinos. Whether you’re looking for fun or relaxation, you’ll find that the best Caribbean cruises have so much to offer.

Popular shore excursions on Caribbean cruise itineraries

All Caribbean cruise ships offer shore excursions, ranging from guided walking and bus tours to ziplining and snorkeling. Here are four of my favorite Caribbean shore excursions:

San Juan, Puerto Rico: Toro Verde Adventure Park (1.5 hours from the pier) – “The Monster” zip line is one of the longest in the world at over 1.5 miles long. Yes – on ONE line! In some areas, you’ll fly 1000+ feet over the ground. Very comfortable “superman” style harness.

Cozumel, Mexico: Rio Secreto (1.25 hours from the pier including a ferry) – Hiking and swimming excursions along a turquoise underground river with stalactites & stalagmites.

Aruba: Aruba Natural Pool (30 minutes from the cruise terminal) – Rent a jeep (or take a jeep tour) and drive to the windswept eastern shores of Aruba. Here, there’s a crystal clear emerald pool just begging to be jumped into. Most locals call it the Aruba Natural Pool, or the Conchi Natural Pool. You’ll find this unique swimming hole in Arikok National Park.

Jamaica: Dunn’s River Falls (1 hour from Falmouth Cruise Terminal) Have you ever climbed up a waterfall? Enjoy climbing up 960 feet and hanging out in one of the several lagoons or pools along the way! Dunn’s River Falls is completely natural. All the structures, crevices, and natural pools of water were created by the flow of the water’s current. Pretty cool!

When is the best time for cruises in the Caribbean?

With a tropical climate, you can expect warm and hot weather temperatures in the Caribbean year-round. However, be aware that hurricane season runs from June 1 through the end of November. The most active months for hurricanes are July, August, September, and October. So, plan your Caribbean cruise vacation accordingly!

During hurricane season, Aruba is a popular destination as it’s located south of the “hurricane belt.” The Dutch Caribbean island prides itself on having just one hurricane every hundred years. You will see cactus everywhere – proof of the fact that this “One Happy Island” averages 12 inches of rain annually.

In the Caribbean, high season runs from December through March – the winter months in the northern hemisphere. Off season is in the summer when the region is most hot and humid. For the best cruise deals, consider visiting the Caribbean after the kids go back to school in the fall. But keep in mind that this coincides with peak hurricane season, so hope for good weather.

COVID-19 tips for cruising in the Caribbean

In light of COVID-19, the cruise line industry has imposed strict measures to keep passengers safe. The onboard experiences and rules will vary based on the different cruise lines and ports visited. This includes everything from mask and vaccination requirements to sanitization and reduced occupancy.

Before booking a Caribbean cruise, make sure you familiarize yourself with the safety, testing, and cancellation policies of the cruise line. Each cruise has its own testing requirements, which tend to change often.

In addition to rules specific to the cruises, you’ll want to pay attention to the traveling requirements at each of the destinations you’ll be visiting. Cruise lines have this information available on their websites. Another reliable resource is JetBlue’s COVID-19 Info Hub, which contains everything you need to know about travel restrictions, testing requirements, and more.

Cruises to Caribbean islands in 2022

Hope you enjoyed reading about these destinations, itineraries, and tips for booking a cruise in the Caribbean! Have any questions about Caribbean cruises in 2022? Drop a comment below 🙂

Looking for help planning a dream Caribbean vacation? Reach out to Joanne Miksis at Holiday Travel of Wakefield.

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