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We have been to 14 different countries in the Caribbean islands over the years. While for the most part, they are quite similar each does have certain things that allow them to stand alone as a destination. Many we have been able to visit via cruises over the years as well. The vibe in the Caribbean is of extreme relaxation and taking things nice and slow. As in the Jamaican saying Aire man!

Here we will highlight the different things that many different islands have to offer, in addition to some of the experiences we have had while enjoying them!


Which island among the many to choose? Big or little, near or far, rural or urban are among the many considerations. We will try to help you narrow this down with this "primer" if you will. Time to prioritize beach time over airport time!


The Bahamas have a myriad of choices, as they have over 700 islands in the Bahamas! From little secret hideaways to extra glossy mega-resorts. The Bahamas are best for island hopping exploring, divers and of course party folks! Harbor Island is one area that stands out with its long stretches of pink sand beaches.

Cayman Islands

Grand Cayman is very similar to South Florida without the traffic! Resorts here of many different types make it very popular with divers, snorkelers and swimmers. Even with giant schools of stingrays! Enjoy a hassle-free holiday here in what will seem like another of the United States, states. 

Dominican Republic

The Dominican Republic is a large country sharing a landmass with Haiti. Best known for its world-class resorts and amazing beaches, with mostly a colonial-era history, with an unhampered inland area with foreboding peaks. Resort seekers and adventure buffs will be very happy here!


Jamaica is most definitely one of our favorites in the Caribbean. Bob Marley aficionados will feel the rhythm here! Vast Jamaica has many resorts ranging from posh to isolated, with a distinct urban culture. Spicy food and music here, incredible resort holidays and many different nature adventures. River tubing here was a lot of fun for Lorie and me!


Puerto Rico

Old San Juan is one of the best places in this region. Kind of a widespread colonial throwback that has an amazing electric atmosphere and vibe. Massive beach resorts, casinos and rich history with Hispanic culture are the highlights here. Lorie and I have a favorite coffee house here, where we have had the greatest cup of coffee! Café Cuatro Sombras. Just a tad to the Northwest of the cruise terminal.

St. Maarten/St. Martin

Two very distinct cultures here one Dutch and the other French share a relatively small space on this very hip and lively island! One side offers french holidays, while the other is a Dutch party town! One thing that is shared here is a very wild airport where the plane landings are within several feet of a beach! Late 2017 this area was decimated by Hurricane Irma and is still this day recovering from the effects.

U.S Virgin Islands

This is usually the first Caribbean stop for many Americans which has many of the same comforts as back home. St. Thomas is quite commercialized, but St. John and St. Croix offer a much different vacation. Mega resorts and nature experiences here are the big draws, along with the Virgin Islands National Park.


In a sea of beaches that set the standard, the beaches on this tiny island come in smaller sizes. Local culture abounds here with luxurious villas scattered about the island. Best for luxurious but laid back vacations. Quite isolated here.


A lot of little beaches surround this medium-sized island which has an abundance of resorts of all sizes. From smaller modest resorts to incredibly large and lavish. English Harbor is a yachties dream! Mostly a colonial heritage.



You will hear a lot of British accents here on this island on the edge of the Atlantic ocean. Many beaches here for surfers and windsurfers alike. Sunbathers galore lining the beaches. London has many nonstop flights here during the busy season. Good budget island for many different activities. 

British Virgin Islands

The British Virgin Islands are a richer much less developed version of the U.S. Virgin Islands. Over 40 islands here with some being quite glamorous. Divers and snorkelers enjoy their time here.


Cuba is like a vanished time capsule of the Caribbean and is a huge island unlike any other. They offer very famous music, many political challenges, and diverse urban beauty. Havana alone is worth several days of exploration with all kinds of thrills. With easing travel restrictions now to Cuba, travel has become much more widespread. Not too expensive, this place needs to be put on your next visit list!


Lacking the beaches found elsewhere, Dominica is an unspoiled gem with a large variety of peaks and valley's surrounded by a large rain forest with many waterfalls. Best for climbers and nature lovers.


Haiti has many unique challenges and is a very impoverished island that has had multiple natural disasters in recent years. However, if you want to explore a rich culture that is the Caribbean most African nation, then you will really enjoy Haiti as Lorie and I have. Best for people that enjoy learning while exploring.

St. Kitts

This island is paired with Nevis and features large hotels and massive condo development. A long day trip can cover the island along with a visit to the pirate era Brimstone Hill Fortress. Best for a short comfortable vacation.

Saint Lucia

This island is loaded with miles of beaches, beautiful resorts and dramatic forested hills which is long popular with the French and honeymooners all over. There is so much to do here in and out of the water. Best for divers, snorkelers, climbers, kite surfers and so much more.

Trinidad & Tobago

Overshadowing it's much smaller neighbor Tobago, Trinidad is a large Caribbean island with a great party scene with one of the worlds largest great Carnival celebrations. Best for a party so large it can rival Rio's! Tobago is a tiny island with pristine nature and a much more laid back environment.

Turks & Caicos

These two consist of a series of little islands with perfect beaches and turquoise water begging for discovery. It is a very quiet place with world-class diving sites.

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