Hey there.

Welcome to the world through my eyes. I'm an internationally published travel writer and photographer who has travelled to 80+ countries, and has tried to capture some of that along the way. Travel means the world to me, and my goal is to offer tips and advice to help you feel the same! 

The Top 10 Most Beautiful Places in the Caribbean

The Top 10 Most Beautiful Places in the Caribbean

It’s a rather precarious task to decide upon the “most beautiful places in the Caribbean” when the region itself is renowned for its breathtaking beauty, but here goes.

I’ve had the pleasure of visiting the Caribbean many times over the years, and I’ve rarely been disappointed, but there are some Caribbean islands that I feel are especially worth visiting right now. In looking at the most beautiful places in the Caribbean I wanted to cast my net pretty wide here, and that meant looking at eastern Caribbean Islands, western Caribbean Islands, southern Caribbean Islands and, you guessed it, northern Caribbean Islands.

What makes the Caribbean special is that, in general, it’s one of the best tropical places to vacation and one of the top tropical vacation spots on the planet. In fact, it’s probably the are people think of first when they’re mulling over the best tropical vacation destinations.

Frankly, there are sights that you can find in the Caribbean that will make you forget what worrying even is. It is, quite simply, another level of beauty, especially for a young man like myself who was born and raised in Canada, also known as the Great White North.

With winter on its way in North America, I thought this would be a nice time to post something on some of the top Caribbean islands to visit, as, in the depths of winter, you might need a little escape.

What’s the Best Way to Visit Popular Caribbean Islands?

One of the most beautiful places in the Caribbean

How you choose to visit the Caribbean is really going to depend on your travel style. Some travellers like to visit one island, like Jamaica, and just spend a week there soaking in the sights, sounds and flavours. Other travellers like to get a little taste of everything, which is where a Caribbean cruise comes into play.

If you were following along on Instagram and the like, you’ll know that this summer Bri and I went on our first cruise, and actually really loved the experience. It gave Bri her chance to just relax in the sun and so forth while we were on the ship, and once we got off, I had the chance to dive into the culture of the island and go on excursions. It was the best of both worlds considering our respective travel styles.

We spent some time on St.Thomas, a part of the US Virgin Islands, as well as in the Bahamas, and St. Maarten/St.Martin. It was a week where we separated a bit from our phones and technology, and we just soaked in the rays. I really don’t think you can go wrong on your hunt for the most beautiful Caribbean islands, but a Caribbean cruise certainly is worth looking into, even if it’s just a quick escape.

Of course, there’s always an option to stay in Caribbean villas as well.

Did you know that Ontario has a famous island of its own? Check out this article on Pelee Island if you’re interested in learning more!

What to Pack for the Caribbean

Of course, what everyone decides to pack for the Caribbean is going to depend on what they personally appreciate, but here are a few things that I wish I had thought to pack for the Caribbean when I was down there.

  1. Lonely Planet Caribbean Islands - Whatever islands you’re on in the Caribbean, you’re covered with this book, and that’s pretty comforting in my perspective.

  2. Lonely Planet Cruise Ports Caribbean - If you’re on a cruise and you want to explore Caribbean cruise ports on your own terms, then this is the book for you.

  3. A mesh bag that’s made for the beach - I like these ones in particular because they’re very easy to drain water and sand out of, which ends up being pretty helpful when you’re on the move.

  4. A badass snorkel set - Everything you need in one bag for all your snorkelling needs, and surprisingly easy to pack.

  5. Waterproof pouches - Seriously, these things are a godsend.

  6. Nintendo Switch - This is the ultimate travel gaming system regardless of age. It’s redefining gaming on the road. I’m not a massive gamer per se, but, typically, you’re going to the Caribbean to get some downtime and have some fun - well why not make things more fun? Needless to say, I’m a fan.

The Top Ten Most Beautiful Caribbean Islands

Let’s be honest, this list is subjective, but if you’re a travel blogger and you’re not subjective, you likely shouldn’t have a platform. That being said, I’d love to here in the comments below if you feel there have been any glaring omissions. As always, you can be assured that I’ll reply back.

NOTE: This post may contain some affiliate links. That means, simply, that I may get a commission at no cost to you. That being said, my opinions are fully my own.

10. Aruba


Not far from the coast of Venezuela (in fact less than 30 kilometres) lies the islands of Aruba, which is the “A” in the Caribbean’s famous ABC Islands - the other two being Bonaire and Curaçao (which might just make the list a little higher up, wink wink).

Aruba, to this day, is still part of the Kingdom of the Netherlands, which means that the citizens of Aruba are considered to be Dutch nationals. I actually visited St. Martin a couple of months ago, another Dutch island, and I was happy to see how much money they’d poured into the hurricane relief efforts, as the island has been desperately battered in recent memory by hurricanes.

What’s unique about Aruba is the diversity of landscape. There just aren’t that many Caribbean islands that have a dry climate that allows for a different blend of flora and fauna to thrive. Furthermore, if you’re someone who chases good weather, then Aruba is a good bet to find sunny skies, and that might be its best asset when it comes to tourism.

Aruba lies outside of Hurricane Alley and, for better or worse, this alone makes it one of the most popular Caribbean islands. Not to mention, there are so many things to do in Aruba that aren’t just beaches.

9. Holbox (in Mexico)

Holbox is a well kept secret when it comes to Caribbean Islands

Within the past year, Bri and I had the pleasure to spend some time on the island of Holbox, and we were far from disappointed. Our stay on Holbox offered the Caribbean getaway that we were hoping for, but without the over-tourism. The article I’ve linked to in the previous sentence provides more information as to how to logistically get to Holbox, but, for now, it’s just worth knowing that Holbox is an island on the north coast of the Yucatán Peninsula, and I’m a big fan.

Holbox is stunning in a humble sort of way. At this point, tourism isn’t even necessarily the main driver of the island life and I appreciate that. If you have heard of Holbox, it’s likely because they’re famous for their whale shark viewing, but it’s quite clear that island of Holbox is slowly becoming “found.”

I’ve mentioned this before on several occasions, but I do find it a bit of an ethical challenge to write about places like Holbox. On the one hand, I loved my time there and relished what Holbox offered and I very much want others to experience it. On the other hand, I don’t want to aid in a tourism boom that may not be carried out responsibly, which could lead to the downfall of an island as serene and delicate as Holbox.

In the case of Holbox, I do think with the flora and fauna there, the island offers something unique and special and it’s an island that’s worth a second look - just do your best to be a responsible tourist and spend your money in ways that actually give back to the community.

8. Barbados

The Barbados is considered to be one of the most beautiful places in the Caribbean

I’m not sure about you, but simply hearing “Barbados” instantly conjures up images in my head of one of the most beautiful places in the Caribbean. I’ve spoken to innumerable people who have visited and many say that Barbados has to be in the running for “prettiest Caribbean island.”

Barbados is only 34 kilometres wide and 23 kilometres long, but most of that is delightfully picturesque. As with Aruba, Barbados is outside of the principal hurricane strike zone, so it’s often spared the devastating effects of tropical storms.

The island of Barbados can firmly rest its hat on the notion that it’s one of the foremost tropical vacation spots, but it’s also worth noting that it’s host to a variety of nesting turtles, and actually has the second-largest hawksbill turtle breeding population in the Caribbean. One note on that - make sure you aren’t driving on beaches if you do rent a car, as this can negatively effect nesting turtle populations!

If you like this post, you’ll love my article on the best beaches on Spain’s Costa Brava!

7. St. Lucia

St. Lucia can offer one of the best Caribbean holidays

St. Lucia is a fairly sizeable island by Caribbean standards and, as such, it’s got a whole lot to offer. The Tet Paul Nature Trail is as revered a hiking trail as the Caribbean has, and Pigeon Island National Park offers incredible access to old military forts with no shortage of views.

What makes St. Lucia special is that you’ve got a good opportunity to be active while you’re there, as opposed to just vegging on the beach. Some of the best views on the island require that you sweat a little bit to get there, and I think that’s a good thing as long as its not too scorching on that particular day.

St. Lucia offers one of the best Caribbean holidays just because there’s a little something for everyone whether you’re into natural beauty, history, or being a little more outdoorsy. Make no mistake, it’s one of the nicest caribbean islands around.

6. Puerto Rico

Puerto Rico needs to be in the discussion for most beautiful place in the Caribbean

Puerto Rico is undoubtedly one of the Caribbean islands to visit in your lifetime. I was blown away when I there by how colourful and vibrant the culture was, and the people were as warm as the weather. Sure, it’s one of the most beautiful places in the Caribbean, but it was the historical sights that stole my heart.

For starters, it doesn’t get a whole lot better than Old San Juan. I’ve been blessed to do a fair bit of globetrotting so far in this life, and I can only distinctly recall a handful of places more picturesque than Old San Juan. If you’ve got a quality camera and some time, Old San Juan will be a dream come true for you. From a historical perspective, you’d also be remiss not to spend a little time at the famed Castillo San Felipe del Morro, a 16th century coastal citadel.

The beaches are lovely, but if you’re into rare birds and wildlife, then the El Yunque National Forest is going to be your best bet. As far as I last checked, camping is still something you can do there if you’re interested in spending extra time in Puerto Rico’s foremost tropical rainforest and nature reserve.

Honestly, Puerto Rico offers one of the best caribbean holidays because it’s a rich culture with scenic views.

5. Cuba

Cuba offers one of the best Caribbean holidays

I’ve been to Cuba once, and my goodness would I ever like to go back once more. Cuba, without question, is a country that will stay with you once you’ve had the chance to visit. Buckle up, though, as the largest island in the Caribbean, a trip to Cuba is sure to result in a jam-packed itinerary.

With Cuba, you can easily come just for the beach by heading to somewhere like Holguin, but not getting a chance to see Havana would be a mistake. Havana is one of those cities that lives up to its name - the pastel houses and old cars are just as cool as you’d think they’d be. However, Havana is much more than that, as demonstrated by the romantic Malecón, an 8km esplanade spanning several neighbourhoods that are culturally important.

I’m going to be honest when saying that Cuban food didn’t exactly steal my heart, but the culture at large sure did. I would do almost anything to be on an eclectic Havana street right now, sipping on a cold drink, and listening to a little music. Travel in Cuba, yeah it’s the real deal.

So, Cuba is a good option is you’re looking for beaches, as it is one of the best tropical vacation destinations, but just don’t forget that it’s also much, much more than that.

If you’re a Rick Steves fan, don’t forget to check out my podcast, “Rick Steves Over Brunch.”

4. Grenada

Grenada is one of the top tropical vacation spots

I’d like to think I’m someone who follows trends in travel pretty closely, and I’ll say that Grenada is being mentioned more and more as one of the top tropical vacation destinations. It isn’t a large island, seeing as it’s only about 350 square kilometres in size, but that doesn’t mean it can’t be considered one of the most beautiful places in the Caribbean.

The island itself is located northwest of Trinidad and Tobago, northeast of Venezuela, and southwest of Saint Vincent and the Grenadines. It’s one of the top Caribbean islands to visit for a number of reasons, its natural beauty perhaps being foremost, but it is also known as the “Island of Spice.” Grenada is huge player in the nutmeg and mace export business, being one of the world’s largest exporters of the latter.

The history of Grenada is something to behold when we consider how many imperial powers tried to get their hands on this beloved piece of land (a not terribly uncommon narrative for the region, sadly). It has, at different points, been a French colony, a British colony, and even famously invaded by the United States.

Now, Grenada is looking firmly towards the future and seems to be situated rather nicely. History aside, Grenada is a natural wonder in many respects. Grand Etang Lake offers something unique, as it is a crater lake in an extinct volcano, while places like “Pink Gin Beach,” can surely breed nothing but smiles.

3. Curaçao

Curacao is one of the top tropical vacation spots

In the southern Caribbean sea lies a lesser Antilles islands by the name of Curaçao, which is quietly gaining a reputation as one of the world’s best tropical vacation destinations, and nicest Caribbean islands. Of course, Curaçao is a former Dutch island territory, exemplified by its very Dutch sounding capital to this day, Willemstad.

As with other popular Caribbean islands, Curaçao is noted for its exceptional opportunities for scuba-diving and snorkelling, remarkable beaches, and great weather. Of particular note while visiting are places like Kenapa Beach, Kleine Knip, and Cas Abao Beach. However, a friend I have in travel also told me that Shete Boka National Park is not to be missed.

My friend also noted that she wouldn’t leave the island without spending time in the capital, Willemstad. In particular, she loved spending time on the main street in the harbour, which she said was bright and vibrant. If you’re looking for it, it’s known as Handelskade.

Personally, when I’m thinking about tropical places to visit, Curaçao is really near the top of my list.

2. Turks and Caicos

Turks and Caicos is one of the top tropical vacation spots.

Turks and Caicos, shortened to TCI for the “Turks and Caicos Islands,” offers that classic postcard beauty that so many people are looking for when trying to find the nicest Caribbean Islands.

Turks and Caicos are a British Overseas Territory, which, not surprisingly based on the name, consist of the larger Caicos Islands, and the smaller Turks Islands. TCI is known primarily for tourism because of the multitude of beaches, resorts, sunshine, and the colour of the water. That being said, it’s also known as an offshore financial centre.

If you’re in Turks and Caicos and you don’t manage to get to Grace Bay, you’ve been horribly misled. Grace Bay Beach in particular is the most famous beach on the island and is actually public, though very close to many popular resorts in the area. If it is not the prettiest Caribbean island, it sure would be in the running for the prettiest sounding locations. Along with Grace Bay, you’ve also got Parrot Cay, Pine Cay, Long Bay Beach, Turtle Cove, Turtle Tail Drive, and that’s just the tip of the iceberg.

There’s a lot going on with the Turks and Caicos Islands, but I’d venture to say that the water alone ensures its place in the conversation of the most beautiful place in the Caribbean.

If you’re a senior traveller and looking for some meaningful travel experiences, this post on travel for seniors has you covered!

  1. Anguilla

Anguilla is one of the top tropical vacation destinations

It’s a difficult task to crown a champion when you’re talking about the most beautiful Caribbean islands, but someone has to win and today that winner goes by the name of Anguilla.

Anguilla, like Turks and Caicos, is a British Overseas Territory, and it lies east of Puerto Rico, and north of Saint Martin/Saint Maarten. The total land area of Anguilla is less than 100 kilometres squared, with a permanent population of around 15,000.

I’m personally a big fan of the name of their capital city which is known only as “The Valley,” and has a bustling population of, you know, about a thousand people.

Anguilla is actually known as a popular tax haven for those trying to save a little extra change.

If you’re in Anguilla, you need to promise me that you’ll arrange a meeting with someone at Rendezvous Bay, which, joking aside, is probably Anguilla’s most popular bay, though some say that Shoal Bay is in fact prettier. One thing I’ve heard over and over again is that it’s worth taking the time to explore the Cays which have no permanent population, but have undeniably perfect beauty.

So there it is, congratulations Anguilla on your big win today as the most beautiful place in the Caribbean!

<! data-preserve-html-node="true"-- Anything inside will go away once widget is loaded. --> Booking.com

Can You Really Decide on the Prettiest Caribbean Island?

The prettiest caribbean island

Despite the time I took to put forth this article, I would actually say you really cant. My ranking system wasn’t all that rigid to be honest, I more just put forth places that piqued my interest because the truth is that Caribbean at large is beautiful.

If you’re a car nut, then Cuba is going to be your place, and if you love the perfect old town then Puerto Rico’s Old San Juan is going to capture your heart. Conversely, if the beach is where you thrive, then it’s likely that Turks and Caikos’s Grace Bay Beach is where you need to go.

In short, I hope you use this list to help you figure out where to go next, and to recognize that all of these islands have value in their own right, and a culture worth learning about and appreciating.

If you enjoyed this post, don’t forget to leave a comment below. Frankly, even if you didn’t enjoy it, I’d love to hear what you think. Feel free to let me know if you think an island should be on the list that isn’t there or is on the list that shouldn’t be. As always, thanks for stopping by!

Like it? Pin it!

Escape Toronto for a Weekend in Norfolk County, Ontario

Escape Toronto for a Weekend in Norfolk County, Ontario

Meaningful Travel for Seniors: International Opportunities and Courses

Meaningful Travel for Seniors: International Opportunities and Courses