Which Caribbean Island's Best for You?

Playa Lagun, Curacao

An ideal Caribbean vacation puts a smile on your face every morning that doesn't fade throughout the day.

While there's certainly history and more serious pursuits as in other parts of the world, that's really not the point of going there.

The Caribbean's all about reaching that state of mind Jimmy Buffett and Kenny Chesney sing about, just kicked back in a lounge chair, barefoot, sipping an ice cold beverage before taking another dip in the warm turquoise water.

Beach At Tulum, Mexico

If you do it right, the only stress is getting there, so I'd recommend  considering air schedules carefully.

From the East Coast, it's much easier, with non-stops to places like Punta Cana and Jamaica, but from the West Coast, you have to plan on having at least one stop, and try to make it a quick connection.

However, there are non-stop flights to Cancun from the West Coast.  You can find beautiful beaches and warm Caribbean waters in the Riviera Maya region.  If you're planning to stay at an all-inclusive resort, you'll want to put this area on your list under convenient and cost-effective.

With great properties by Excellence, Hard Rock and many others, you can enjoy a terrific Caribbean vacation geared to your preferences coupled with easy flights to Cancun.

Wes and Friends at Frenchman's Reef Marriott, St. Thomas

All-inclusive resorts like Sandals and Beaches sometimes render what island you choose as mostly irrelevant, because you may never want to leave the property.

As long as you stay on site, you can enjoy the beaches, entertainment and parties without encountering hassles of transportation.

In that case, you want to focus on a property that's geared to your objectives featuring the amenities you want, whether scuba, golf, kid-friendly activities or rocking nightclubs.

Turtle Seen While Snorkeling in St. Thomas

A resort that suits a family may not be ideal for a couple on a honeymoon.

But you want specifics.

St. Thomas in the Eastern Caribbean has lots of activities.  Julie and I enjoyed a wonderful week there after dropping Amy off for her freshman year at college in Connecticut a few years back.


Because it is one of the U.S. Virgin Islands, there's no problem with language or currency (although this is generally true throughout the Caribbean).

St Lucia Pitons

It's easy to take a boat trip from St. Thomas to neighboring islands like St. John and Tortola for a change of pace, but there's plenty of great snorkeling, beaches and restaurants without leaving the island.

On our recent extended Southern Caribbean cruise, Curacao became my personal favorite Caribbean island.

And sometimes it comes down to making a dream come true.  Perhaps the word Jamaica excites you, or you saw a great spread in Travel+Leisure about St. Lucia and could never get it out of your mind.

By all means, go there next.  Live your dream at least once.

Spoiler alert: Living your dreams can be habit forming.

Wes and Julie at Margaritaville in Ocho Rios, Jamaica

If you truly want my opinion about the best way to visit the Caribbean, I have to say cruising.

Royal Caribbean Solarium Pool

Flying to Miami, Ft. Lauderdale or Orlando non-stop is easy from many major airports, and from there you can board a floating resort that will bring a few of these wonderful islands to your doorstep.

There are also Caribbean cruises embarking even closer to home from ports like New Orleans, New York City and Galveston, Texas.

In a week, you'll usually get three or four ports, and while that sounds like a lot of time at sea, you may find by the end that you're reluctant to get off the ship for the final port.

This is especially true if you're on a truly amazing ship suited to your personality.

Consider the cruise Julie and I took recently to the Southern Caribbean.

I can say that every port would make an excellent place for an extended stay.

Eclipse: Rare and Unexpected

I'm Leaving On a Jet Plane

Aruba

The Dream Isle of Curacao

Playa Lagun in Curacao

Barbados

St. Lucia

Antigua and Dining Aboard Eclipse

St. Kitts

St. Maarten

St. Martin View from Celebrity Eclipse

To get that many ports took two weeks, and other than St. Maarten (St. Martin), which can be found on many Eastern Caribbean sailings, most have been reached in the past primarily by flying to San Juan, Puerto Rico, which is another great place to visit but is a considerably harder flight from most of the country than Miami/Ft. Lauderdale.

However, recently Princess, Carnival and others lines have added 7 or 8 night cruises from Florida that reach pretty deep in to the Southern Caribbean to ports like Aruba and Curacao.  We saw Carnival Sunshine at several ports on our cruise, and she was only on an eight-night voyage.

That's the nature of cruising.  Cruise lines figure out what the market wants and then make it happen, competing to tempt vacationers to sample their newest twist, whether that be adding new islands or unexpected onboard experiences.

But if you still prefer a resort stay on one island, that can certainly be arranged too.

Don't make it harder than it needs to be. Book through a friendly travel agent.