To Sail or Not to Sail? That is the question… or is it?

So you have decided to sail and of course – sail Disney! But the trouble is where do you want to go? One of the most popular itineraries with the Disney Cruise Line® is the Caribbean getaway! Sailing to the Caribbean means that not only will you travel to multiple tropical ports, you will get to experience Disney’s private island, Disney’s Castaway Cay and the ever popular on-board celebration of Pirate Night! When setting sail to the Caribbean often people are concerned with the “when”. We are certainly here to help you answer that question, but first we will need to find out what you and your family are in search of.  Is your family looking for particular weather or activities or perhaps you just want to get away with the best deal? Either way, we are here to help!


When setting sail to a Caribbean destination, two major factors are important to consider: the temperature and the amount of rainfall.

If it is sunshine and heat you are in search of, the best time of year to sail to the Caribbean is during the months of April – early June. Snorkeling, jet-skiing, and water sports will be at your finger tips and with the comfort of blazing sunshine. In the tropics – there is always a chance of rain with that gorgeous sunshine.

If it is dry weather that you are looking for then sailing December – April is recommended. Typically the average rainfall in the Caribbean is typically lower during these months. While temperatures will certainly be warm, that water and evenings can be cool, so pack a jacket. 

The dreaded word Hurricane will always cross the minds of travelers. Hurricane Season runs from June – November. It tends to peak during the months of September and October, so just be wary. Either way, we recommend having a travel protection plan in place with us in case of the unexpected.


The Caribbean is warm all the time – sometimes it is warmer than others, but still warm. If the Caribbean calls to you anytime, it might be price comparison that you are after. Typically sailing to the Caribbean during the months of January – April are the most economical. During summer travel, the holiday season and Spring Break, prices are at their highest. When children are off of school and adults have “break” or vacation, prices will rise. 

With this in mind, it is highly important that in order to save on your Disney Cruise vacation, you need to book immediately after the itineraries are announced. The more the ship fills, the higher the prices go. The closer to travel, the prices rise. This is why it is always so important to have a plan in place well in advance. This will give you the most savings for your vacation. Sometimes and we mean sometimes, we might be able to find you a last minute deal, but it is not always the case. So it’s time to start planning now!

Special Events

Setting sail during the holidays will be a trip unlike any other. Disney Cruise Line® offers special cruises for Halloween and Christmas. Between the months of September – December guests can sail Halloween on the High Seas as well as the Very Merrytime Cruises. The ships will be adorned with decorations, activities and treats themed to each event. These cruises fill up fast, so if it’s on your radar it’s time to start looking into them.

Marvel and Star Wars Day at Sea are specially themed cruises that include unique activities, events, treats and parties themed to  Marvel and Star Wars. Do not worry! If you are not the biggest of fans during these sailings. The celebrations only last a day!

Disney Cruise Line also offers two specially-themed cruises: Marvel and Star Wars. Select Caribbean cruises include a day at sea focused on one of these two franchises, including characters, deck parties, film screenings, games, and more.


Sailing Disney will be beyond magical. So let us find the perfect destination for you. If you are ready to set sail then we are here to help you. As vacation planners specializing in all Disney Destinations, it is our pleasure to help you plan your dream vacation. We will take the stress out of planning so you can focus on fun and family. We are here for you 100% from the planning stages through your trip. And let’s not forget – our services are free!

Your referrals are our most MAGICAL compliments!

Contact us today!

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