Cruising the Caribbean Islands – all you need to know

After almost a decade, I decided to return to the Americas in April 2024. Cruising the Caribbeans had always been on my bucket list, and I couldn’t wait to find my perfect itinerary and cruise line. Let me start by saying, the options are so many that it’s overwhelming! Starting from which cruise line to choose what islands to visit, duration of the cruise and the requirements to enter the ports you’re visiting, this trip required a lot of research but for someone like me, the research itself is half the fun of the trip! I tend to live the trip while I am reading about it almost as much as I live it while I am experiencing it. So, while it was a Herculean task to find my perfect cruise itinerary, I thoroughly enjoyed the process! However, let me make it slightly easier for you. Tips to plan the perfect cruise itinerary for the Caribbean Islands. Use a planning platform:

I always find Cruisecritic to be the best cruise planning website as it allows you to do an advanced search using your preferred travel dates, the port of embarkation, the ports of visit, the duration of the cruise and displays all the possible choices from different cruise lines, with a visual itinerary and costs of different types of rooms. This helps filter your choices to a great extent Duration of the cruise:

If you’re cruising the Caribbeans from the US ports, you will need a minimum of 7 days to cover some good ground. You need to choose between Eastern Caribbeans (Antigua and Barbuda, Dominica, Grenada, Montserrat, Saint Kitts and Nevis, Saint Lucia and Saint Vincent and the Grenadines) vs Western Caribbeans (islands due south of Florida, such as Grand Cayman and Jamaica; destinations on Mexico's Caribbean coast on or near the Yucatan Peninsula, such as Costa Maya, Cozumel and Progreso; and Central American destinations in the Caribbean, such as Belize and Honduras). Most cruises to Eastern Caribbeans tend to be longer duration (as it takes more time to get to those islands) vs the Western Caribbeans. So, keep at least 8-10 days for the former and 6-9 days for the latter. Choosing between Western & Eastern Caribbean Islands:

This perhaps was the hardest of all. While the Eastern Caribbeans are further away and require longer duration journeys, they’re prettier when it comes to the ocean/ beaches, less commercial, more untouched and thus for the people who’re looking for more adventure, don’t care a lot about convenience of transportation, are into hiking and exploring but lesser commercial activities. These cruises are mostly available from Fort Lauderdale or Miami, Florida. The Western Caribbeans, on the other hand, are a lot more commercialised, have more excursions/ activity choices, better for families and more convenient to explore. The cruises to these islands are shorter in terms of the duration, especially if you choose to board them from Galveston in Texas instead of Miami, Florida, though both are equally good options.

Choosing the cruise line:

If you’re flexible on the dates of travel, you will be spoiled for choice. While no two cruises will offer the exact same itinerary, the choice must be made between the best cruise line with good reviews + the perfect itinerary that you may wish to follow. Some of the well-known cruises serving the Caribbeans are Royal Caribbean, MSC Cruises, Carnival Cruise line, Norwegian Cruise Line, Disney Cruises, Princess Cruises, Celebrity Cruises, Costa Cruises & Holland America Line. Since our dates of travel weren’t flexible at all, we landed up with the choice of Holland America & MSC Cruises.

Holland America vs MSC cruises: While choosing your cruise line, it always helps to check YouTube for a cruise tour. You will find extensive tours of each of the ships on YouTube and this was the biggest factor that helped us decided between the two. MSC Cruises offered a LOT of activities, swanky interiors, several restaurants, bars, swimming pools, performances, parties, pool deck with a movie screen, rides, water slides, etc while Holland America line seemed quieter, smaller and cozier. Given our age, our personalities and the fact that we were going to spend at least 2-3 days just cruising (and not stopping at a port), we felt MSC was an obvious choice for us. We were NOT disappointed. Booking the cruise:

There are several third-party websites that will offer you the option to book your cruise and the offers are likely to vary from one to another. We found a fantastic offer in terms of the price of the cruise on Expedia.com so we booked through them, but other websites could give you better offers on beverage / spa packages whilst they offer a higher price for booking the cruise itself.

Booking your excursions:

This wasn’t my first cruise experience, so I knew that needs to be done in terms of booking excursions. When I had travelled to Malaysia on a cruise (from Singapore), I had not booked any excursions and at all and decided to DIY after landing at the ports. You have several choices of how you can explore the cities you’re going to land at:

• Book an excursion though the cruise ship: The advantage of this is that you have 0 worries about anything. The options available are all following the time limits to ensure that you’re brought back to the cruise well before the departure time and the cruise line will take responsibility of ensuring that there are no circumstances under which you shall miss your excursion or your cruise. The disadvantage is that these are significantly higher priced than any other option.
• Book a shore excursion through a third-party travel company: There is no dearth of third-party travel companies that will offer you several options when it comes to shore excursions. The advantage is the variety of options available as well as the price which is much lower than what the cruise itself will offer you. The disadvantage is that the cruise will not assume any responsibility in case you’re not able to make it back in time for the sailing. You assume the risk on yourself and need to ensure that the excursion you’re booking is well within the time limit of the cruise docking time at that port.
• DIY (do-it-yourself): This is the cheapest but the most inconvenient of all options in the sense that you will assume the entire responsibility of getting yourself from one place to another and back to the ship in time. The advantage is the price as well as the flexibility of being able to choose your own destinations and the time you spend in each. The disadvantage is having the find public transportation at each of the locations while ensuring that you’re not running short on time, with the pressure of returning to the cruise before sailing.

Adding extras:

If you haven’t cruised before and this is your first one, it is essential for you to know what’s included in the usual price of a cruise booking. Most cruises will offer all meals (breakfast, lunch, dinner) at the main restaurant (usually a buffet) at a fixed time (in order to be able to accommodate everyone) and access to all facilities such as swimming pools, jacuzzies, theatre, deck, etc. What is not included and can be purchased in addition to this:

• Beverage package: This is quite an important one, especially if you like to have alcohol which can be quite expensive on-board vs buying a package beforehand. While some cruises allow you to carry a limited number of bottles on board, others don't allow ANY, so if you wish to enjoy easy and unlimited access without any worries of the quantity and price you’ll pay, buying a beverage package beforehand is your best bet. First check with your cruise company the allowance and then try asking the company through which you’ve booked your cruise for any offers available on the beverage packages. MSC Cruises didn't allow us to carry any alcohol on board but we aren't heavy drinkers, so we didn't mind paying the $11 per drink instead of buying the $330 for 7 nights beverage package.
• Wi-Fi: Even if you’ve purchased a local sim or have roaming activated on your sim card, you’re unlikely to receive connectivity while you’re cruising. So, unless you’re someone who wants to use this opportunity to disconnect, it might make sense to purchase Wi-Fi for the whole duration of the cruise. Unfortunately, you do not have the option to purchase wi-fi for a partial duration, it’s either none or the full duration!
• Spa / Bottle Service / Fine Dine packages: Every cruise is likely to have a spa so if you’re looking to get a treatment done, you can buy one on board or even beforehand. Bottle Service will allow you to enjoy some wine or beers from the comfort of your own room (even if you haven’t purchased the beverage package and if you have a room with a balcony, this is a great option!). Every cruise also has some specialty restaurants which won’t be included in your price. If you wish to dine at one of these, you’ll need to pay extra.

Our cruise of choice was MSC Seascape, departing from the port of Miami, cruising the Western Caribbean islands of The Bahamas, Grand Cayman, Jamaica, and Cozumel, Mexico, in the month of April. I shall soon write my experience with the cruise itself and what to be prepared for, should you plan to take this specific cruise line and follow a similar itinerary. Stay tuned!