How to Plan the Perfect Caribbean Vacation

I am on a flight homeward bound from an amazing family vacation and am already planning our next getaway – a Caribbean vacation!

Although we live in Florida, it is very rare that we get to enjoy the beach.  We’re either working or running around with the kids.  I decided that the only way we are going to soak in the sunrays is going to be to look into a Caribbean vacation destination.

SO MANY DESTINATIONS…

There are so many different destinations to choose from when it comes to the Caribbean, so it’s important to do your research.

The British Virgin Islands

The British Virgin Islands is ranked as the number 1 in Best Places to Visit in the Caribbean by U.S. News and World Report.  If you’re interested in both gorgeous beaches and hiking, you may want to look into Virgin Gorda vacations.  Also be sure to check out The Baths, the island’s most popular attraction, huge granite boulders on the south coast. (R and I went to St. Lucia years and years ago and can attest to the beauty of the British Virgin Islands.)

U.S. Virgin Islands

When I was little my aunt took my sister and me on vacation to St. John.  It was the first time I visited somewhere outside of the United States (and did not need a passport – a plus!).  The island itself is tiny, but filled with beautiful beaches and the nicest people!

St. Thomas is known for Carnival season in April as well as luxurious boating and shopping.  St. John is all about the pristine beaches; whereas St. Croix infuses a bit of history into your trip with visits to sugarcane plantations and rum distilleries.

Turks & Caicos

I have not yet been to the Turks and Caicos, but it is on my short list!  Comprised of 40 islands, this Caribbean destination offers a little bit of history and culture (Grand Turk), breathtaking diving (Salt Cay), and luxury cruising and hotels (Provo).

But Wait, There’s More!

There are so many other Caribbean destinations to check out:

• Cayman Islands
• Curacao
• Antigua
• Barbados
• St. Martin
• Aruba

It is super important to do your homework ahead of time to ensure an amazing experience.

TIMING

It is important to take into consideration what time of year you plan on traveling over to the Caribbean.  A lot of the islands lie within hurricane-prone areas, so although it may be a lot less expensive to book during peak hurricane season (June 1 – November 1), keep in mind that your vacay may be derailed by inclement weather.

Curacao, for example, is outside of that “hurricane band”, so it may be a better option if you choose to visit during those months.  Midwinter is the most popular time of year to visit the islands.

WHO YOU’RE TRAVELING WITH

Where you go may be dependent on whom you are traveling with.  I would choose a more family-friendly option for this next trip because the whole crew is going.  Aruba is known for family fun!  BUT if it was just Rich and I, I would opt for a more romantic, secluded location.  St. Lucia was the perfect choice when it was just the two of us.

ACCOMMODATIONS

You are going to spend the bulk of your time wherever you lay your head at night.  There are so many options these days:

• Hotels
• All-inclusive resorts
• Bed and breakfasts
• Villas/rentals
• Cruise lines
• Air BnB

I personally like the idea of having a small kitchen and ample space to stretch out, especially when it is the four of us.  Sharing a hotel room is OK for a night or two, but any more than that and I start looking into vacation rentals.

TRANSPORTATION

Depending on where you decide to go may determine if you will need to rent a car or not.  A lot of hotels and resorts provide transportation to and from the airport for free (or a nominal fee).  Tours also may offer pick-up and drop off services, so be sure to look into that as well.

ACTIVITIES

If it was just going to be me, I would look for as little activities as possible.  When the family is involved, I try to find super fun things that we can do together to create amazing memories – and avoid hearing the dreaded “I’m bored” or have them glued to their electronics.

Contact the concierge at the hotel or resort that you choose to inquire about popular tours or excursions available.  Research online to see what other travelers recommend via Travelocity reviews or Yelp.  See if Groupon or Living Social is available – you may find some great deals on excursions, restaurants and more!

PACKING

Over the years I have honed my packing skills.  I used to grossly overpack, but now I have a checklist to ensure that I have everything the family will realistically need.  I purchase loofah sponges that I can toss when we are ready to go home, as well as bottles for my favorite shampoo, conditioner, and lotions.

Caribbean vacationing calls for less clothing than, let’s say, an Alaskan cruise. (I can totally vouch for that!)  If you are going on a 4-day vacation, I would recommend packing (per person):

• 2 bottoms
• 4 tops
• A sundress
• Sandals
• Undergarments
• A sweater or jean jacket in case it gets chillier at night
• 2 bathing suits and one coverup
• PJs

Be realistic – are you really going to work out on vacation?  If so, pack those sneakers.

CARIBBEAN VACATION, HERE I COME!

I hope this helps when planning your next Caribbean vacation!  I can’t wait to figure out where we are going – stay tuned!