5 Best and 5 Worst Things About Caribbean Cruises

If you’re interested in cruising the Caribbean, I’m going to share with you the five best and the five worst things about a Caribbean cruise.

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Itinerary Choice

One of the best things about cruising the Caribbean is there are three different main itineraries, so even if you’ve been on a Caribbean cruise before, there is another one and another alternative that you can go on. Broadly speaking there is the Eastern Caribbean, the Western Caribbean and Southern Caribbean cruises.

The Eastern Caribbean normally visits places like the Bahamas, Cayman Islands, Haiti, Dominican Republic, the US and British Virgin Islands, Puerto Rico and Dutch Saint Maarten.

If you go on a Western Caribbean, some of the places you could go to include Jamaica, the Cayman Islands are usually included, Mexico’s Cozumel and Costa Maya, sometimes Belize, the Honduran island of Roatan. Increasingly you’ll find that Cuba, so Havana and Santiago de Cuba, are often included in this area. Another development is increasingly there are cruises which only go to Cuba, and you can often do seven-night cruises out of Miami which only go to Cuba.

The Southern Caribbean goes to places like St. Kitts, Antigua, Guadeloupe, Martinique, Dominica, St Lucia, Barbados, Grenada, Saint Vincent and the Grenadines.

Most of the cruises to the Caribbean tend to be seven-night cruises.

Cruise Line Options

Another great thing about a Caribbean cruise is choice. You have the choice of itineraries, but you also have an enormous choice of cruise lines and style of ship to go on. There’s up to 24 different cruise lines of that actually visit the Caribbean in some form or fashion during the course of the year. Big ships, small ships, sailing ships or whatever type of cruise experience you want and whatever price bracket you’re looking for, you’re probably going to find that going to the Caribbean.

So, if you want a party atmosphere ship you’ve got that. If you want a more enrichment type ship you’ve got that. Any type of experience you can find, so it’s very important to think about the type of experience you want to see the Caribbean.

Don’t see all Caribbean cruises as the same. Think about the type of experience you want because there is plenty of choice and options.


Another great thing is that it’s very easy to get to. Most of the Caribbean cruises head out of Florida, many go out of Miami which is the biggest cruise port in the world. The two next biggest cruise ports in the world are in Fort Lauderdale (Port Everglades) and then you have Port Canaveral. Of course, you can go from many other ports both within Florida and more widespread.

It’s very easy to get to. For example, from Florida on a seven-day cruise you’ll normally have one sea day getting to the islands, you’ll visit four or five islands and have one sea day coming back. You’ll normally
have a good long day in the port, getting there about seven or eight o’clock in the morning and normally be there until early evening.

Weather and Beaches

Of course, the best thing about the Caribbean is the weather, the beaches and the outdoors. For a very
large part of the year it’s a great region to cruise to.

The best time of all is really between December and April. December can be very busy, because of the holiday period. April again can also be very busy as it is Spring Break time.

Very importantly, the rainy season runs from May to December. Of course, most important of all is the hurricane season. Hurricane season officially runs from June to the beginning of November, although historically most hurricanes happen between August and October.

The absolute best time to go, in my personal opinion, is early December because the weather’s fantastic and it’s before the big crowds. I also like the February into March period because again the weather’s pretty good, it’s not massively hot, the prices tend to be really good and it’s not a crazy busy time.

If you go to the Caribbean in the run-up to Christmas or in April when it’s spring break and, of course, during the summer it tends to be very busy. It’s much rowdier and it’s much more raucous because that’s a big holiday time.


One of the great things about cruising the Caribbean is all of the islands use the US dollar, so wherever
you go you only have to take one currency and it’s accepted wherever you go. It also means, if you’re familiar with the US dollar, you know whether things are good value or good prices.

Another great thing about a Caribbean cruise is you’re visiting loads of different countries, but you don’t have to keep passing through immigration. You don’t worry about visas and once you’ve boarded the ship and they’ve checked your passport, when you arrive in a port you can get off as soon as the ships clears and head off into town and you head back, and you do not have to worry about any of that hassle.

Those are, in my view, the best things about cruising the Caribbean. What do I think are the worst things about going on a Caribbean cruise?


Probably the worst thing of all of a Caribbean cruise is the crowds and how busy it is. As I mentioned, there’s lots of choice and lots of options and there are so many people and so many cruise ships going to the Caribbean. You’ll find when you arrive in a port there can often be four or five, or even more, ships which means they could be 12,000, 15,000 or over 17,000 people heading off into the port, on the excursions, heading to the beaches.

It gets really busy and a little bit manic. This is probably the worst thing of all of a Caribbean cruise. As the ships get bigger and bigger, there are fewer places that they can call on and you’ll find that many of the itineraries call on the same ports, which is why they get so busy.

If you’re looking to have a quiet. experience on some of the islands, look at more cruise lines like Azamara Club Cruises, Silversea, Regent Seven Seas and those kind of cruise lines which run smaller ships and often go to more unusual places and therefore avoid the crowds.


One of the worst things about cruising the Caribbean is the reports, the news and the concern that crime is
growing across the islands of the Caribbean.

Of course, there’s lots more people going to the Caribbean, there’s many more people heading there and the islands and the people there are relatively poor, and you’ve got all these people arriving that are perceived as being much wealthier. So, like in all major places where there’s lots of tourists, there is a risk of crime. The same is true whether you’re in Venice or you’re in Rome or wherever on a cruise.

It is interesting to note is that many of the governments in big countries like the United States, Canada the UK have started to put out more information specifically for people going cruising, often about the Caribbean.

In terms of the islands where crime has been reported as more of an issue in recent times include the Bahamas, St Lucia, Jamaica, Honduras and Barbados.

Most of the crime is fairly petty like pickpocketing, thefts and the kind of stuff you see whenever there’s lots of tourists in a place. Always bear in mind when you go to these islands, even though it feels carefree and you’re on vacation, act the same as any vacation spot around the world and you need to be sensible and careful.


For me one of the worst parts of a Caribbean cruise, although it’s not probably a massive issue because you can avoid it, is the obsession with shopping, particularly by the cruise lines.

I’ve been on many cruise lines and they have these shopping advisors that give talks and run shopping expeditions and have all sorts of incentives and things to get you shopping. When you come off the
Ship you have to walk through a mall area which is just packed with all the same retail stores like Diamonds International and Tanzanite International.

There’s a real obsession with shopping and one of the most troubling mindsets I’ve heard on a number of cruise lines from these shopping advisors is they talk about the number one activity is
shopping in the Caribbean.

Of course, you can ignore it and you can avoid the shopping, but I dislike that shopping has become a fundamental part of the Caribbean experience and actually when you get to the Caribbean you have to wade through all the shopping malls before you get out into the islands.

Beach Hawkers

Another thing for me that I put in the worst bucket is the amount of hassling you get when you’re on the beach. This differs a little bit by island, but you’ll find normally when you’re on a beach you are constantly harassed by hawkers.

In their defence, these people are trying to make a living and you’ve got all these people coming with money and they’re trying to make a living, but it can become quite troublesome. It depends a lot which island you’re on too. If you’re in Jamaica you’re going to have people offering you everything from drugs through to Knick knacks.

On most islands it’s much more handcrafted goods, drinks and food, but you will generally find that when you’re on the beach you’ll have lots of people try to sell you things and, depending on the island, they can be quite pushy.

Island Blur

One of worst things for me about the Caribbean is how the islands are blurring into one.

On your cruise you’ll go to four or five islands and it is quite hard to remember which island was which often afterwards and what you did where, especially when you’re explaining them to people or discussing amongst yourselves.

Unlike say if you’re travelling to Europe where each of the countries is very different, the islands tend to be very similar and they have created a world where the ports are very similar with the same shops, the excursions are all very similar, so all do the beach breaks, the ATV tours, the zip lining, catamarans and snorkelling.

It can all be very similar, and all starts to blur into one. The islands haven’t tried to make themselves very distinctive and really push the different cultures and they do tend to blur into one. I think that’s a pity in many ways that the islands have become so homogeneous and so similar, and they haven’t really tried to make themselves very different.

All of them are beautiful and you will have a great time, but I don’t think it’s such a pity that they haven’t
created different identities and made you feel very different. Some of them when you go are very memorable but they, tend to be the more southern ones so St Maarten for example is very different to Barbados but they tend to be the islands that are more developed and more commercial.

Final Thoughts

Cruising the Caribbean is fantastic but there are great parts to it and there are more downsides to it. The downsides will not stop me cruising to the Caribbean and should not stop you cruising Caribbean. But I think understanding the best parts of the cruise experience and probably the worst parts will help you make some judgments and decisions as you look to cruise the Caribbean.

Hopefully you found this interesting. If you enjoyed this, I would love it if you watch my Tips for Travellers videos as they are designed to help you make more of your very precious travel time and money on land, on sea and on the rivers.

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Gary Bembridge

I grew up in Zimbabwe, but I have been based in London since 1987. My travel life spans more than three decades and that includes more than 95 cruises. In 2005, I launched Tips for Travellers to make it easy and fun for people to discover, plan and enjoy incredible cruise vacations. And the rest, as they say, is history. I have the largest cruise vlogger channel currently on YouTube, with more than 3 million video views per month.

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1 Response

  1. Anna Koss says:

    Great video. I have been on a few Caribbean cruises and I absolutely agree with you that the islands tend to be very similar. To avoid this island blur as you call it, I always try to organise my own sightseeing tour and try to see sights beyond the cruise port, but still close to it as you mentioned some islands are more dangerous as others. Also, I find that itineraries that include stops at private islands can be a nice and provide this break away from the crowds. For instance Carnival has a private island called Half Moon Cay, which is beautiful.

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