Which Caribbean Island is for you?

You know you want to go to the Caribbean but you just don’t know where. You have specific tastes. You’ve watched other videos countdowns about Caribbean Islands but you always come away just as confused as you were when the video started.

You only want to know the Top Caribbean islands to find what you're specifically looking for.

You don’t care about the Gross Domestic Product or Syberian Wildflowers. You just want to know if this Caribbean Expedition will be right for you.

The same thing happens to me when I research places I’m unfamiliar with but want to visit.

That’s why I created this list. By the end, you will know exactly which island to visit to find what you’re personally looking for.

Your Instagram photos of your vacation will be a viral sensation to friends and family but more importantly, each picture will bring back memories that you’ll never want to forget

• What are the most visited Caribbean Islands?
• What is the Safest Caribbean Island to visit?
• The Most Expensive Caribbean Island right now
• The Island with the least strict rules for Covid-19
• Where to find love in the Caribbean
• What is the number 1 Caribbean island to Vacation?

This list covers where most people will be, which island has the nicest scenery, which Caribbean Island is the safest, where to go if you want to splurge a small fortune, where to find love or a quick island fling, Or do you just want to know which islands have the least strict Covid regulations - so you can actually get there? 

I’ve been all over the Caribbean and today I will show you the Top 10 Caribbean Islands to find EXACTLY what you’re looking for. 

Number 2 on this list will shock the bejesus out of you. Engage!

What is the most visited Caribbean Island?

6. The Dominican Republic

Coming in with close to 7 million tourists a year, The Dominican Republic is first on the list. If you want to go where everyone is going for 1 reason or another the DR is it. One of those "other" reasons may make DR show up on this list again later.

I understand why so many people come here. 

The weather is nice and the people are super friendly.

If you ever get to visit the 3 eyes cave in Santo Domingo, Paradise Mano in Los Melones or, any of the all-inclusive resorts in Punta Cana, you’ll see why so many people are making The Dominican Republic their Vacation of Choice.

The most popping time of the year for visits to the DR is between December and March.

Snobby travel gurus may tell you to wait until the peak season is over and to go right before the rainy season around July-September.

Not me. 

I think you should go when the atmosphere is lively. 

Go while festivals are going on and while everyone is outside.

Get the full experience of the Dominican Republic, especially if it’s going to be your first time.

There's a reason why some islands are visited more than others. 

There is more to see and do in hotspots and the rest of the world’s travelers know it already. 

Choosing the most visited Caribbean islands is a great way to catch up with what other tourists already know. 

Which are the Safest Caribbean islands to visit?

5. Montserrat 

20 years ago, thanks to the eruption of Soufriere Hills Volcano that killed 19 people, more than half of Monserrat’s population relocated to other islands. 

Around 2020, as soon as the residents started moving back and as tourism was starting to get back on track, they then had to deal with Covid.

So why in the hell would I rank this island the safest?

Montserrat is probably the safest place in the world to visit. 

It’s been 13 years since anyone on this island has had to pop a cap in someone else’s ass.

Whatever they’re doing to keep their murder rate down to 0, (yes I said 0) they need to teach it to the rest of the world.

This place is gorgeous. The 0 murders probably have a lot to do with them living on the real-world version of Risa! 

(Yes, that’s a Star Trek reference. So what? Google it. I’ll wait!)

You back? 

Ok, maybe it’s not quite like Risa because half of this island is still covered in Volcanic ash.

The government has marked off what’s now called the “Exclusion Zone” on the Southern Side of this island for public safety.

As of October 10th, 2021 fully vaxxed visitors will finally be able to step foot back on the most beautiful, secluded, exotic island your eyes will ever see. 

You’ll only be able to visit ⅓ of the island but it’ll be very safe and well worth it.

Their Slave Revolt celebration happens in Mid-March. It lasts for about a week. 

God willing, I’ll be there in 2022 to celebrate right along with them.

It will be a very expensive trip.

If you have doubts about visiting Montserrat, read some of the reviews about Rendezvous Beach on TripAdvisor. 

I’m sure you’ll want to come right along with me.

The Most Expensive Caribbean Island right now

4. Anguilla

Like Monserrat, the Anguilla residents are 90% black.

This island is expensive but you'll get exactly what you pay for. 

You know how sometimes you get to an island but all of the tourist attractions make it seem like you're in just another coastal American city? 

You will NOT experience that in Anguilla!

That’s why you’ll be willing to pay the big bucks while visiting Anguilla.

You'll most likely have to fly into Puerto Rico or Sint Martin to get to Anguilla. 

The J.Lloyd Airport in Anguilla (which was once called Wallblake) had a runway so small, it used to be the hardest level on the Microsoft flight simulator game. (That’s not a joke)

As of recent, a lot of renovations have been done so it may now be more accommodating to larger planes.

Before you step foot on this island, you're required to pay a $1000 Visitor’s fee. Then you’ll pay a $20 departure fee when leaving. 

You may be able to find some cheap Resorts in Anguilla like Royal Palms and Turtle’s Nest, but more popular resort rooms are $750 a night and up. 

And it’s usually the “and up!”

Even a value Meal in Mcdonalds in Anguilla is over $16

If you're willing to spend the type of money that it takes to get to Anguilla, then I’m sure fast food is not your style anyway.

Anguilla is like the MTV cribs of luxury resorts. 

If you have plans to splurge on a wedding or celebrate a million-dollar business deal, Anguilla is the place to do it.

The Island with the least Covid-19

3. The Cayman Islands

According to the JHU CSSE Covid-19 Data, Cayman islands has had a total of 960 cases and only 2 deaths from covid.

While many other islands soar around level 3-4, Cayman Islands enjoyed being at a steady level 1. 

When you visit the Travel.State.gov site for the Cayman Islands, it will read:

“The Centers for Disease Control and Prevention (CDC) has issued a Level 1 Travel Health Notice for the Cayman Islands due to COVID-19 indicating a low level of COVID-19 in the country. Your risk of contracting COVID-19 and developing severe symptoms may be lower if you are fully vaccinated with an FDA-authorized vaccine. 

Before planning any international travel, please review the CDC's specific recommendations for vaccinated and unvaccinated travelers.

There are restrictions in place affecting U.S. citizen entry into the Caymans.

Visit the Embassy's COVID-19 page for more information on COVID-19 and related restrictions and conditions in the Cayman Islands.”

To visit the Cayman Islands from the USA, you have to be fully Vaccinated.

Side Note: You won't get banned on Youtube for talking about Covid 19 if you use facts backed up by data and evidence… It’s just a side note. Nothing else.

Where to find love in the Caribbean

2. Trinidad

If you've met a Trini girl that lives in America, you probably thought, "yeah she’s cute but there’s no way I’m dealing with a chick with an attitude like that."

In my teens and early 20s, I used to think that all people from the islands hated American black dudes.

The island girls usually wouldn't give me or any of my friends the time of day even though I was a prolific game spitter in my days.

So like me, you may have been under the impression that the men in Trinidad are ready to wrap those feathered Carnival wings around those chick's necks. 

But that's not the case.

Trinidad girls who still live in Trinidad are really freaking cool.

Moving to America made them the assholes that some of them have become. 

This is the same thing that happens to girls from other islands that moved to America, like Dominicans, Barbadians, and Jamaicans 

What I’ve come to realize is that it's not Caribbean hate for African Americans. 

It's a Caribbeans' attempt at being a racist white person that makes them this way.

Some islanders were taught that all they would need to do to assimilate into America and reap the benefits that America has to offer, is love anything white and hate anything black.

What's more American than racism?

The sad thing that can sometimes take them a decade to realize, is that everyone in America categorizes them as black too.

Soon enough, the same hate they're dishing out will come back to them. 

Then they’ll be like, oooooh! (In Caribbean Accent)

Fortunately, in a lot of cases, the girls who have always lived in Trinidad and Tobago have family members that are as white as a toilet, and some family members who are as black as pure vanilla.

Like most women, the only color a lot of them see is green. 

If you meet a Trini girl who’s not a gold digger, they’re going to be beautiful, with a great sense of humor, and will treat you with the utmost respect. 

Multiply all of that times 2 if you’re rich and in shape. 

The same goes for women looking to date a Trini dude.

Make sure this country hasn't confused them yet.

What is the number 1 Caribbean island to Vacation?

1. Jamaica

Jamaica wins another Passport Kings Countdown!

The Parties in Jamaica are Epic and everyone there understands that Jamaica is the land of inhibition. 

The Jamaican women are sweet to us tourist dudes, and Jamaican men are experts at charming tourist chicks' pants off.

The excursions, resorts, and Airbnbs are the main ingredient in the formula for viral Instagram pictures.

Once you visit Jamaica the first time, going back will always be on your to-do list. 

Jamaica has a vibe that you can’t find anywhere else. I have 3 videos on youtube where I'm in Jamaica trying to put into words what the vibe of Jamaica is like.

Click on the end screen playlist to check those videos out.

However, I feel like watching a video won't describe what I’m talking about.

You need to be there... while reggae music is playing, tourists are dancing and Jamaican people are vibing. 

In Jamaica, you’ll feel everything is falling into place for you...  Like a King...

This question comes from Trini-girl on my video called "The best Caribbean Carnivals you need to visit."

She writes;

"You don't know what you're talking about. The Trini carnival started all the Caribbean Carnivals. How could you possibly put Barbados in the number 1 spot?"

Get my answer to this question and all of my video comment questions on my Podcast called: Travel Heads Radio. The link to my podcast is in the description. I hope to see you there. Peace!