Where You Should Travel Now in the Caribbean

When people think of the Caribbean, there are a few things that typically immediately come to mind: sugar-white beaches, green mountains, pastel houses, rum drinks, teal blue water and colorful, glowing sunsets just to name a few. 

Yes, the Caribbean’s reputation truly precedes it, and it is without a doubt one of the world’s most popular beach regions. So it goes without saying that here at Travel Now we think you should start looking at Caribbean beach villas as soon as humanly possible. 

The only trick is, the Caribbean is a lot bigger than people realize, as it is home to several regions all full of a seemingly countless amount of islands.

To help you choose which island to visit when you come to the Caribbean, we've put together a list of a few of our favorites and a mini-guide to one that is our ultimate favorite island. 

We hope you can find some inspiration in this list and who knows, maybe we will even see you there this winter.


Jamaica is without a doubt one of the most quintessential Caribbean islands, yet it is very unique. What makes Jamaica to special is that besides its natural beauty chock full of rivers, mountains, and beaches, the island nation of over 2 million’s culture has produced musicians like Bob Marley and athletes like Usain Bolt that have inspired and touched the world. 

Jamaica is the kind of country that even if you haven’t been to yet, you feel a connection there. From the waterfalls that you can hike at Dunn's River Falls to the sunset cliff diving at Rick's Cafe in Negril, Jamaica keeps you entertained and tantalizes you with the aroma of its culture and its jerk spices at every corner.


Known as “Little Britain in the Caribbean“, Barbados is a bastion of British culture thousands of miles from the motherland. For starters, Bajans drive on the left side of the road and live and die with their cricket team’s wins and losses. Barbados also features a host of water sports activities like surfing. 

Our favorite thing to do in Barbados though is to just soak up local vibes at The Boatyard, one of the coolest little rum shack/beach bars we've ever been to. 


While the first two islands we have written about will usually roll right off people’s tongue’s when they are asked to think of Caribbean nations, Grenada flies a bit under the radar. That is to your advantage as “The Spice Island” is left for the rest of us to enjoy. 

Why is it called the spice island? Well, Grenada is only known for being one of the world leaders for cloves, ginger, nutmeg, cinnamon, and cocoa. The landscape in Grenada is just as stimulating as those spices as waterfalls are plentiful along with beaches, hiking trails, and some of the friendliest locals in the Caribbean. 

Puerto Rico

With a completely different vibe than the rest of the Caribbean, Puerto Rico is truly unique. Puerto Rico, where Spanish is most widely spoken, seems to have one foot in the Caribbean and one foot in the United States. Yes, it is technically a U.S. territory, but you won’t feel like you are anywhere in the U.S. when you are walking around San Juan’s old town. 

Sure, Puerto Rico has the picture perfect beaches, waterfalls, and nightlife if you are looking for it, but the true gem here is a unique culture, which like the rest of the Caribbean is a true melting pot.


(We've saved our favorite for last and we are going to write a little more about it, as since we are Canadians we have been allowed to visit Cuba for decades, but our American friends are just now being allowed to join the party.) 

For most of us, Cuba conjures up images of stunning beaches, colorful, vintage US cars, Che Guevara and of course ... rum. And it's all true. If you’re after a holiday somewhere a bit different that is rich in history, sun-kissed beach, and lively nightlife, then Cuba may just be the best of all worlds. 

There’s no denying the attraction of Varadero. It has great beaches and is full of hotels, but if you want to go off the beaten track, head to Playa del Este in Havanas Riviera. 
Just 15 minutes’ drive from central Havana, this 10-mile strip of white, sandy beaches is less touristy and enables you to soak up the rays with a more chilled out vibe. 

A day spent soaking up the sun doing little else can surprisingly work up an appetite, so dust of your Cuban heels and set your sights on Havana for a night of indulgence. There are plenty of restaurants to choose from, but pick wisely. We always enjoy the rustic feel at Prado y Neptuno, while the service can be spotty, the food is divine. 

Even if you don't take our recommendation, you will generally find good food at very competitive prices.

No matter where you go though, make sure you leave some room for a few mojitos afterwards. Yes, Cuba is the birthplace of one of the worlds’ most popular cocktails, and there are a handful of bars which claim to have got there first. Many believe the first to be La Bodeguita Del Medio, and who cares if they’re lying or not, lol, it’s a great bar that serves a mean mojito. And so they should.

If a few tipples have loosened you up a touch and you want to party like a true Cuban, head to Tropicana Club, where rum and salsa takes precedence. Drinks are a little more here, but still affordable and worth it for the fantastic cabaret show. 

The next day, after you’ve slept off the inevitable Cuban rum cobwebs, you might want to head down to El Malecon. This ocean front pedestrian walkway stretches across the coast of Havana, and attracts locals who can be seen relaxing and you are more than welcome to join them. 

No comments:

Post a Comment