Insider Tips on Planning Your Family Trip to the Caribbean

From Jamaica to Aruba, San Martin to the Virgin Islands, the Caribbean has so much to offer.  One of the few places in the world that can offer relaxation, excitement, nature, beauty, and style in an island sort of way, the Caribbean is a family vacation paradise.


Do Your Research First


One thing to remember before you go is that you should always do your research before your family trip!  I know, a family trip is supposed to take you away from obligations and work.  However, unless you do your research, you may find yourself in a jungle instead of at the beach.  The Caribbean is a diverse set of islands, and just a few miles difference could mean the difference between your worst nightmare and family heaven. 


Once again, it is all down to your preferences.  Some people want to relax on a majestic shore with the warm sun and comforting sand, while others want to go on an exciting jungle adventure.  Depending on your style and your family’s personality, you want to make sure you chose the right place to go in the Caribbean.


When To Take a Family Trip


Deciding when to take a family trip to the Caribbean will have a major impact on the things you can do.  The Caribbean is the opposite of U.S. – their dry season is our Winter, and their wet season is our Summer.  So, the most crowded time to go is during our holiday season.  This will also be the most expensive time to take a family trip. 


One benefit of going during the busy season is that everything is open.  All the hotels and attractions will be available.  But taking a family trip to the Caribbean during the off season has a lot of benefits.


First, the price is cut almost in half.  Second, there are far fewer crowds.  You can definitely get a true ‘locals’ experience during the rainy season.  However, the drawbacks during the Caribbean off season is, well the rain.  Some parts rain a lot!  With rain comes Mosquitoes.  Also, you won’t be able to do as much because many of the tourist attractions are closed or close early.

I find that as long as you check the weather before hand, taking a family trip during the off season is the best.  Some places, like Aruba, hardly rain all year, so you can get good deals and still have a great time.


Booking Your Family Trip

Booking your family trip to the Caribbean can take some insider knowledge to make sure you get the best deals.  When booking, the best bet is to get a flight as early as possible.  You probably know by now that the best way to book your family trip is on an online travel website.  Some great sites are Kayak, Expedia, Travelocity, and Orbitz.  I’ve used them all to plan my family trips, often having to check each one for the best deals. 

Rather than flying, a great way to take a family trip to the Caribbean is by going on a cruise.  Carnival usually offers competitive rates, but those liners are more for younger single crowds.  Royal Caribbean is a great cruise line specifically for family trips.


Budgeting Your Family Trip

Finally, you need to budget your family trip.  When coming up with a price range, take into consideration travel, lodging, food, and leisure.  There may be some unexpected medical bills, so make sure your travel insurance covers the family trip.  After you’ve come up with a budget, add on an additional 50%. 


The best travel advice I’ve ever received is from my brother.  He said you will spend more than you bring on any family trip, and wear only half of what you bring.  This always seems to be true, no matter how prepared I was.  You may be more disciplined than I during your family trip, however, it is always a good idea to plan on spending more than you think and taking a smaller suitcase with less clothes.


Taking a family trip anywhere in the world can be a hassle. But, with research and timing, you can make the most of your family trip to the Caribbean





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