7 Things To Consider When Caribbean Cruising

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A Cruise Is One Of Many Options You Have To Head South

If it is still cold in Canada or in the northern U.S., people think often about escaping and heading south. There are a lot of warm weather options. If you are looking at a cruise in the south, here are 7 things to consider when Caribbean cruising.

1) What Caribbean Cruise Itinerary?

Having decided that cruising is a great choice for you, the first of the 7 things to consider when Caribbean cruising is what you want to see on the cruise. At a simplistic level you need to decide if you are cruising the Eastern or Western Caribbean.

Most Eastern Caribbean cruises are all about visiting the wide array of islands that make up the Caribbean. On our last Eastern Caribbean cruise we visited a number of islands that we had never visited before. It was great to add Puerto Rico, St. Maarten, St. Barts, Antigua, Grenada, St. Lucia and Barbados.

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The Western Caribbean cruises generally travel down along the west coast of Mexico and Central America. On our Western Caribbean cruise we even got to visit Cartagena, Columbia for one day. These cruises will typically take you to places like Mexico’s Maya coast, Guatemala, Honduras, Costa Rica and Panama.

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Bahamas, Grand Cayman and Jamaica are more or less in the middle. They may be added to Eastern or Western Caribbean cruises depending on the route of the ship and the cruise duration.

We had originally booked the Eastern Caribbean cruise and were offered a great deal to add on the Western Caribbean cruise. If you can afford the time, it is sometimes a great deal to combine two cruises into a larger cruise. There are even options to add onto the Western Caribbean a trip through the Panama canal and then up or down the west coast.

The individual destinations on both the Eastern and Western Caribbean were very different, although there were similar themes as we travelled from spot to spot. It is great to get a taste test of different possible destinations on a Caribbean cruise! The specific places you want to sample is just one of the things to consider.

2) The Goldilocks Question – Too Big, Too Small or Just Right?

One of the key things to consider when Caribbean cruising is the size of the ship. You don’t want to feel like Goldilocks in the wrong bed!

There are quite a number of cruise companies and they can sometimes be categorized by cruise ship size. There are large cruise ships and some of those cruise ships can even be classed as “mega ships” (more than 5,000 passengers). Large ships hold a lot of people and have a very wide variety of food and entertainment options, often targeted for a very wide age range. We did the larger cruise ship experience when our child was younger. The cruise ship provided good entertainment options for the children, leaving us with a few free hours every day. If you get bored easily and need lots to do, if you will have lots of days at sea or if you are travelling with an inter-generational group, the large ships might meet your needs.

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The mid-size ships tend to be more intimate, a bit more up-scale and offer reasonable variety in food and entertainment. We have found that most of the mid-size ships cater to a bit older group and we rarely have found children on board. The mid-size ships are smaller and may be able to get into some destinations that the larger ships can’t. With a larger ships, you are more likely to be anchored out and you must take a boat to shore. If you don’t like large crowds and lines, don’t need extensive entertainment and aren’t travelling with kids, a mid-size ship may be a better choice for you.

There are also a number of boutique lines that are offering much smaller ships. These are typically going to a bit more exotic locations (e.g. Antarctica, Galapagos, the Hawaiian Islands or a cruise around the Islands of the Bahamas). The small size of the ships means they can get into a lot more places and typically they visit many different spots in any one place. As you might expect, there is much less variety in the food (although we have heard the quality is often very good) and much less formal entertainment. If you are looking for more exotic spots, more stops in a special destination or just want a close intimate group, then the smaller cruises may be for you.

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If ship size is important in your list of things to consider when Caribbean cruising, it will quickly let you shortlist the cruise companies to look at.

3) When Do You Want to Cruise in the Caribbean?

Most people are heading for a Caribbean cruise when it is cold at home – winter and spring. At this time of the year, most of the cruise lines have moved their ships into the Caribbean and offer a wide variety of cruise itineraries. Most of the cruises start in Miami and unless you are doing a back-to-back cruise that keeps going along the route, most of the cruises end up back in Miami.

If you have kids, maybe one of the things to consider is a Caribbean cruise for the Christmas holiday season, March Break or even Easter. If you don’t have kids, you may want to avoid these times as well as Spring Break (when university students are off school).

You might want to target a cruise for a special festival in one of the destination ports (e.g. Junkanoo Carnival in the The Bahamas on New Years or Antigua’s iconic regatta in April).

While there are some cruises available in the summer from Miami to The Bahamas, most of the cruise lines stop Caribbean cruises in April or May when they move their ships to the summer destinations (e.g. Alaska, Europe or the far East). One of the things to consider when Caribbean cruising is booking one of these “re-positioning cruises” to get your last taste of the Caribbean and then head off with the ship to its new port.

4) Do You Want More Vacation Before and After The Cruise?

Most cruise lines offer discounted airfare in their cruise deals. They will get you to the ship on time to board and hustle you off the ship at the crack of dawn to get you to your departure airport – if you book the transfers with them. If you choose to find a cheaper airport transfer – make sure you have left enough time! The boat might wait for the cruise ship transfers but not if you are making your way on your own. You might even decide to book your own airfare or for many people already in Florida for the winter, it is an easy drive to the cruise terminal in Miami.

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But one of the things to consider when Caribbean cruising may be extending your vacation south with a longer stay in the port of departure or arrival. For most Caribbean cruises this means Miami! Miami and the broader state of Florida offers a lot to do if you want to extend your stay in the sunny south. Just consider this before committing to the “free” airfare that might be packaged with your cruise.

If you have booked your airfare through the cruise line, they will typically have a hotel offer if you want to extend your stay at the start or the end. We generally have booked our own hotels. If you decide to add days to your trip, you will generally have to pay a “deviation” fee to change your flight days (a flat fee plus any airfare difference). Generally if we are adding on more than a day to our cruise, we have chosen to not take the airfare with the cruise line and book our own flights and hotels to have much more flexibility and control over our costs. In our experience, the cruise line had limits on how far out you could move dates (e.g. we tried for 2 weeks once and were denied).

5) Packing For A Cruise

I will start this section by admitting that I am the wrong person to give packing advice. I have failed in adopting every packing tip that anyone has suggested. Packing “light” may be one of the things to consider but I always over-pack and very rarely do I find myself missing something.

The first thing to ask about is the dress code for the cruise line you are on – especially for any special events or special dining venues. If you decide to skip these special events, you can generally ignore dress code requirements other than reasonable ones. It is polite to wear shirts and shoes when you are in any restaurant. If you are at an outdoor grill, it may be ok to wear a bathing suit cover-up but please put on clothes if you are heading into the buffet and don’t sit on chairs with a wet swim suit. Save your bathrobe and slippers for breakfast in your cabin. General etiquette does not go away just because the “hotel” is floating.

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If you do want to go to events that require a dress code, it is generally “resort casual”. Most women find this pretty easy – a dress or dress pants works. For men, it usually means no shorts and the need for a collared shirt. But those general guidelines leave room for a breadth of discretion. Even if you can get away with a striped golf shirt, is this really what you want to wear for dinner at the Captain’s table? Bring at least one respectable outfit and wash it if you need to!

If you are cruising for more than a week, you can usually do laundry on the ship. It means fighting for a space in the lineup, an early trip to the laundromat or doing laundry when mostly everyone else is away for port excursions. Most cruise lines will do your laundry for a high cost.

Another one of the things to consider when Caribbean cruising is the type of excursions you want to do. If we are heading south, we often want to scuba dive so we might add some of our own scuba equipment to the packing list. Scuba diving as a cruise excursion is a bit like resort scuba diving – so you need to how much of your scuba gear bag you really want to haul with you. If you are heading for a jungle tour, you may want long sleeved clothing and bug spray.

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Don’t forget to pack any medicines you will need as we found it very hard to find a pharmacy in many of the Caribbean ports. The ship doctor or gift shop may have some very standard medicines but it will cost you. If you are prone to sea sickness (or even just in case), consider some dramamine and maybe a seasickness band. When cruising in the Caribbean you will generally have at least one full day at sea and sometimes the ship will toss quite a bit. A hat and sunscreen goes without saying, especially if you are doing water activities.

Most ships these days have hand sanitizer dispensers everywhere, so there is little need to bring your own supply on board. Just make sure to use them regularly to avoid any spread of germs. You may want to take some hand sanitizer when you are in port or on excursions – you can look into getting a bottle of Hand Sanitizer Canada to take out and about with you. And ladies, don’t forget that extra supply of tissue just in case.

One of the last things to consider when Caribbean cruising are the new services that will ship your bags to the cruise port. The cost depends on the size of bag and the distance to ship. If you are doing a cruise in the middle of a longer trip and you need very different clothes for the cruise, this might make sense. So far, we have not really looked at this option.

6) Keeping Busy On The Ship

There are always lots of things to do on the ship. You may be surprised to find yourself leaving the ship without doing everything you wanted to.

You will generally get a detailed daily agenda for the coming day. It provides information about dining, events on the ship and an excursion summary if you are in port that day. Make sure to look at the times on this agenda. Sometimes changes are made depending on the port schedule (e.g. sometimes meals start early if you arrive in port early). If you are at sea for a day, there will be a larger number of on-ship activities to choose from.

As geeky as it sounds, one of the things to consider is creating a calendar for each day. Start with any excursions you book as the excursions will often drive much of your schedule for those days. Add in any reservations you have for special dining venues. Include any on-ship activities that are on your must-do list. Then you know what free time you may have for other things to do.

Make sure to pay special attention to the activities that are available on at-sea days. These are often a mix of education and entertainment. There will typically be sessions to give you in-depth information about the ports you are visiting. We learned so much about the Panama Canal before we left the ship. One of our favourite sessions was an Italian cooking class. We liked it so much we went back a second time.

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We laughed when we saw a session on needlepoint. And then one day we saw how many people were actually attending that session. The wine class was a good choice but we missed the session on cognacs! There was Bingo and team trivia battles almost every day. You will find something to keep you amused.

One of the most important things to consider when Caribbean cruising is that this is a vacation. Not every minute needs to be booked. Find time to walk the deck and watch the sunset. Laze by the pool with a drink, listen to the bands playing around the ship or read a book in one of the many nooks you will find. Get a group together for cards or just take a nap.

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7) Excursions in the Ports

Most people are taking a cruise so they can taste test as many different places as the ship lands. Sometimes you want fixed excursions and sometimes you may just wander around the port. Sometimes in port you just want to spend the day on a nice quiet ship after everyone else leaves!

Cruise ships offer a wide range of choices for excursions in all cruise ports. The type of activities depend on the port. Sometimes excursions are influenced by the cruise ship demographics (e.g. are kid-friendly activities needed?). It is easy, if expensive, to select off the menu of options and keep yourself busy in each port.

One of the things to consider is how physically active you want to be. Activities range from cultural and historic bus tours, to active adventures (scuba, snorkel, 4x4s) and everything in between. The tours will generally have an activity level rating. The rating will show you how much walking there is or how physically fit you need to be. If you are uncertain about your fitness for a specific excursion, talk to the tour desk before you book it.

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If you do not want to take the time to find and book your own tours, you can book with the cruise line. Most cruise lines will offer you a discount if you pick your excursions in advance and if you do a number of excursions. Most booked tours are not refundable, so be careful what you are committing to.

You can probably find most of the same tours if you go to the dock and ask around. Research in advance may give you other options. The major downside of booking your own tours is that if you get delayed, the boat is not waiting for you. You will then need to find your own way to the next port. With excursions booked by the cruise line, the boat will wait until all their tours are back. If you have a full day in port, you probably have the flexibility to do a tour on your own. But if it is a short stop, going off on your own beyond the port may be too risky.

One of the other things to consider is language when booking your own excursion. If you book a tour over the internet in English, local vendors may not understand what you want as clearly. Or a local may lose all English skills when a problem comes up. Be careful and book your own tours with someone with good ratings.

On our cruises we have done a mix of excursions. We have done a broad set of the cruise-offered excursions, wandered around the port on our own and we have arranged our own tour. When we booked our own tour we did run for the last shuttle boat to our cruise ship!

We learned that we need to pick excursions that will be a mix of learning and some more active adventures. An 8 hour bus tour of Grenada taught us a lot. But we missed out on a great chance to snorkel on the underwater sculptures. We did a combined train and bus trip along the Panama Canal with several stops and the whole trip was great. Kayaking in Antigua, touring St. Barts by ATV and then racing the America’s Cup yachts in St. Maarten were exciting and memorable. Barbados was back on a bus to tour the island.

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Making the vacation special for you is a critical item on the list of things to consider when Caribbean cruising. Pick your excursions to meet your interests. And remember this is just a small taste test of any one destination and you can always go back.

A Few Things To Consider When Caribbean Cruising

Having decided to do a cruise, you should now be all ready to start planning your cruise. We have given you a few things to consider when Caribbean cruising.

You may choose an Eastern Caribbean or the Western Caribbean cruise. Using the list of things to consider may not always get you the same answer. We almost didn’t take our first Mediterranean luxury cruise because we had only experienced a larger family ship in the Caribbean. Our needs had changed and our cruising decisions needed to change too. What are you looking for on this cruising trip?

What things would you consider when Caribbean cruising? Or do you just pack and go if the price is right?

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Travel blogger and photographer! Scuba diving, luxury cruising, chocoholic, sea and sunshine addicts, camera attached and just generally curious! Join us on our adventures!


  1. I have not gone for Caribbean cruising but would love to go for this exotic cruising one day. It is good to know some useful details and tips to consider before going for Caribbean cruising. I too agree and want to book big sized cruises as they have many options of entertainment, food and other things if we feel bored. Small cruises are good for private family outings. I always agree that general etiquette should not be left out as we are in the public place or in the “hotel” which is floating. Thanks for sharing all tips.

    • Yukti, I hope you get to visit the Caribbean and cruise one day. It is a great way to see many different islands at the same time. And the ships always have so much to do on sea days too. Linda

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