Aug 092011
You’re overworked, fatigued and you need a break.  Dreams of palm trees and pina coladas are invading your thoughts.  You know that you want to visit the Caribbean, but you don’t know where or how to begin researching your trip.  After 20+ visits to the Caribbean, I’ve refined and perfected my trip planning strategy, and now it’s a (mostly) stress-free process.  Here are my 10 tips for planning your perfect Caribbean trip.
1)  Decide when you want to go
This is the critical first step, so plan wisely and do your research!  Are you traveling with young kids?  If so, you may be looking at summer or the school breaks. Considering a trip in September or October?  These are prime months for hurricane activity in the Caribbean, so you may want to focus on your ABC’s (the ABC’s are the islands of Aruba, Bonaire and Curacao which lie beneath and outside of the Caribbean hurricane belt).   The Caribbean hurricane season begins in June and runs through November.  I enjoy traveling to the Caribbean during hurricane season for three main reasons – lower costs, lack of crowds and super warm water.  Despite the benefits, I realize that many travelers simply don’t want to take the risk (especially those on their honeymoon!).
2) Decide where you want to go
Narrow your choices to three islands or countries (no, Mexico isn’t an island).  Peruse magazines like Caribbean Travel and Life or Islands for ideas.
Trunk Bay, St. John

Trunk Bay, St. John

3)  Research your top three choices carefully

Look for the island that best fits your travel style and personality.  Are you a diver or snorkeler?  Make sure to choose an island known for its underwater wonders or vibrant reefs.  Maybe you live to windsurf and need a windy island.  Do you prefer a mountainous island or a flat island?  Is fine dining important to you, or are laid-back beach bars more your style?  Each island has its own distinct vibe!  Sites like and are great for researching your destination.  Don’t forget the little known forums on these sites, where you can find loads of valuable information specific to your destination.

4)  Research air travel to your destination

How easy is it to reach your top three destinations?  Are non-stop flights available?
Search prices from all airports within a 2 hour radius.  Compare fares on travel sites such as, and  Then compare the fares on the airline sites directly.  Make sure to subscribe to the airlines’ fare sale alerts via email.

5)  Research hotels 

Pore over the user-submitted hotel reviews on  Cross reference with ratings on and  Don’t hesitate to ask specific questions on the forums.  Forum members are often very helpful and happy to help other travelers.  Check hotel rate on sites like, and, and then ask for a rate quote from the hotel directly.  Remember that you can book hotels through the airlines as well, so compare the rates on their sites.

6)  Research airfare + hotel packages

Determine if it is most cost effective to book airfare and hotel separately or as a package.  Compare the individual rates against the package rates that you find on sites like, or

7)  Create a Matrix

This step is critical (especially if you lean towards the Type A personality, but I don’t know anyone like that).  I like to create a spreadsheet to help compare costs and analyze the pros and cons of my final three locations.  I call this my Matrix, and Mr. Reeftraveler knows that I’m really serious about something when I’ve created a Matrix.

8)  Book your trip!

By now, you’ve created your Matrix and you’ve reviewed it thoroughly.  Thanks to your tiresome research (and your nifty Matrix), you know how to get the best price at the hotel that best fits your style on the island of your dreams.  Now book that trip before the flight fills up or the prices rise!

9)  Scour the forums for your chosen destination

This is the fun part!  Research activities and restaurants.  Maybe you want to know which dive shop has the best reputation.  Or perhaps you want to know where to find the best seafood on the island?  Determine if you need a rental car.  The message boards are the best source for local intel on the web.  Read and search the forums first, then post a question if the previous posts haven’t answered it for you.

10) Book any activities or make any reservations that have a long lead time

Vacation is my time to unwind.  My internal clock quickly switches to “island time”, and advanced planning becomes a foreign concept.  However, there are certain activities in certain locations that should be pre-planned.  It might be a reservation at a highly sought after restaurant in Anguilla, or perhaps you want a spot on a high-demand, once a year whale shark seeking cruise.  Consider making advanced reservations for certain niche restaurants or activities.

So now that you know how to plan your next Caribbean vacation, where are you going to go?

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