Tips and Advice for Planning a Cheap Caribbean Tour in 2020

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Family and friends of mine who have been to the Caribbean call it “an entirely different world.” You won’t need to look very far to realize that’s the case. White sandy beaches. Crystal blue waters. Luscious green plant life and palm trees. Everyone’s image of the most beautiful Caribbean islands. Cheap Caribbean travel is impossible, surely?

Actually, no – not necessarily. Obviously, you can’t expect the best Caribbean cruises to be particularly cheap, regardless of what time of year or season you go. But island vacations can be affordable enough if you know where to look and where specifically in the Caribbean to go.

Welcome to your travel guide for all the best Caribbean resorts – whether you are looking for cheap Caribbean vacations or luxury on the best Caribbean cruises. We’ll go over it all – the Caribbean Islands list and what’s good where. The most beautiful Caribbean islands, the best Caribbean island for adventure and more!


Exotic island vacations cannot possibly be cheap, right? Wrong. There is a whole Caribbean Islands list that can be enjoyed on a shoestring budget. Let’s have a little closer look:


Not just the land of cigars. Cuba is also one of the cheapest Caribbean islands and ideal for anyone wanting to make the most of a tropical island vacation without injuring their bank accounts too much.

Snorkeling, boat rides, swimming in those crystal–clear waters that you picture in Caribbean daydreams. A place where the wildlife is not restricted behind bars or bushes. Crabs amble their way quite nonchalantly in and out of rooms (and can show a defensive dislike to being photographed…)

The Caribbean resorts of Cayo Coco and Varadero get my personal recommendation for a visit to Cuba. And remember to bring Cuban pesos – you won’t see even a mention of a dollar, let alone anything else American, during your stay there.

Dominican Republic

The Dominican Republic had a bit of a reputation for petty crime towards tourists a few years ago. Fortunately, we can say it has been virtually stripped of that now and is now regarded as one of the best places in the Caribbean to travel on a shoestring budget, as well as the best Caribbean island for adventure. It has a number of ports worth recommending, as follows:


This one is at the top because it is probably the place in the Dominican Republic to visit if you’re on a budget. Punta Cana has some very decent hotels for only a fraction of the price you would ordinarily expect.

Aside from that, there is also nearby facilities to swim with dolphins if you are so inclined. Who says a cheap Caribbean experience all has to be palm trees and scorching white beaches? Swimming with dolphins is an opportunity that shouldn’t be turned down.


While by every means a resort to consider if you’re doing a cheap Caribbean experience, Samaná is also a popular Caribbean destination for those seeking a more luxurious and slightly more expensive island vacation. You can get a decent three–star stay along the $60 lines – it’s often best to travel during the offseason when you’re looking for cheap Caribbean travel anyway.

For things to do, did someone mention whales? Because of all the places to go humpback whale watching in the Dominican Republic, Samaná is the place to do it!

Riviera de Maya

While it technically belongs to Mexico, the Riviera de Maya is no less in the Caribbean. Several parts of it are celebrated as among the cheapest Caribbean destinations, with hotel stays averaging at around $30 per night (that’s for three–stars, by the way). As such, it is a popular destination for travelers from both North America and across the pond. So much so that they open up an entire sub–list for this travel guide.


The Riviera de Maya is a strip, with two top Caribbean destinations – one to the north end, the other to the south. Playa del Carmen is the destination to the north and makes up the heart of tourism in the Riviera de Maya. A good place for both fishing and scuba diving (see later in the article for what sort of wildlife to expect in the Caribbean islands), the Playa del Carmen also offers a number of casual eating places.

If you’re a traveler that can make do with a hostel rather than a hotel, you’re in luck. Your cheap Caribbean experience just became cheaper, since the hostel rates are as low as 11 US dollars per night.

Our key piece of advice – maybe have some Mexican pesos handy in addition to US dollars. It can vary between establishments in which currency is accepted. Generally, the more expensive the place, the more likely you are to pay in dollars.


To the south of the Riviera de Maya is Tulum. This is one of the Caribbean destinations you go to for soaking up rays on the beaches and views of the strip and the architecture. That includes the clifftop castle El Castillo, which gives the town added historical value and character, as does the ruins of an ancient port town from the Mayan era.


Of all the Caribbean destinations on this Caribbean island list, Barbados is probably the most expensive, with three-star accommodation being in and around the $100 per night range. But, as we have said already, it pays to know at what point in the season you’re planning on traveling.

While the traditional Caribbean exoticness may be lost with the commercialized and urbanized ambiance (for which you can thank the wealth of hotels and tourist resorts), you will get what you pay for by indulging in some fantastic scuba diving.


The country everyone thinks of when it comes to the Caribbean. Home of Bob Marley, good rum, and tasty ginger, among other things. Jamaica also has a number of cheap Caribbean destinations that should definitely be points on your tour if you’re island hopping or even cruising.

Of those destinations, we recommend Montego Bay, Ocho Rios, and Negril for your island vacation.


Going to one of the cheapest Caribbean islands is only a small part of the overall battle, mind you. There are a number of other tactics and means by which you can enjoy cheap Caribbean travel and make the most of a small budget.

Pay Attention to the Season

The time of year in which you travel will make all the difference in the price as well as how you enjoy the weather. The trick to enjoying a Caribbean island vacation is to fly out during the offseason and save bundles on both your flights and accommodation.

A general consensus indicates that the best time of year for a cheap Caribbean travel experience in April, possibly into May as well. You avoid the high prices of the peak season, which covers December through to March, plus you have the heat but not the humidity of the summer months.

Eat and Drink Like Locals

Apply the “When in Rome…” maxim to your cheap Caribbean travels and make them even less expensive. Instead of going for the major brands that you know and love – for both food and drink – you will keep a lot more money in your wallet if you live off the local produce.

Swap your cravings for Budweiser and Corona with the Caribbean Favorite Red Stripe – which all the best places in the Caribbean will serve. When it comes to eating, it may not be in your budget to eat out every night – or any night in some cases. That’s where street food comes in, dealing in some of the finest delicacies to be found in all the best Caribbean destinations. That includes jerk chicken, fried pork rinds, and sumptuous Bajan fishcakes.


For when a cheap Caribbean experience is not on the cards. Obviously, this section is not going to relay all the facilities of the numerous cruise liners out there. That depends entirely on which company you choose to sail with, though our recommendations for the best Caribbean cruises are P&O Cruises and, of course, Royal Caribbean.

What we can give you an idea of is the best places in the Caribbean generally visited on the cruise circuits and what to do in each destination. We will not mention those on the Caribbean island’s list earlier in the article.

St. Lucia the best Caribbean cruises will usually visit St. Lucia at some point during a tour of the Caribbean islands, usually docking at the ports of Pointe Seraphine or Place Carenage. It has a tropical rainforest, guided tours of which are available. But the main must-see is the volcano – La Soufriere. Since it is a dormant volcano, which is actually viewable via drive–through! It is the only volcano in the world to hold this distinction.

St. Kitts and Nevis – this island proves popular with all tourists traveling the Caribbean islands, whether on one of the best Caribbean cruises or otherwise. This is primarily due to the port of Basseterre, which has bloomed into one of the hugest Caribbean destinations for shopping. In particular, the 27–acre Port Zante mall.

Puerto Rico – regardless of whether this one appears on the schedule of the best Caribbean cruises, it is among the cheapest Caribbean islands to visit. The port (and capital) of San Juan, in particular, is great for tourists and cruisers. There are a couple of castles that make for excellent photography and viewing. The same goes for the old town, which also hosts plenty of nightlife if you have time in the evenings.

All I will say is – remember to brush up on your Spanish!


If you hate the cold, the Caribbean weather is totally ideal for you. The climate rarely deviates from an average of 26°C, give or take a couple of degrees. As such, the Caribbean weather has justifiably earned the region the honor of having the most desirable climate in the world.

As such, you will be able to pack light and probably save money in the process (never a bad thing if it’s a cheap Caribbean experience you’re after). Light, loose clothing and plenty of beachwear and swimwear for lounging, swimming, snorkeling and scuba diving.


The Caribbean is home to some incredibly diverse and exotic wildlife, on land, sea, and sky. From the rainforests in St. Lucia, which you can tour to see hummingbirds. We mentioned the swimming with dolphins in the Dominican Republic, as well as humpback whale watching in Cuba.

On boat rides, beware the barracuda – a native to the waters of Caribbean islands. Fine behind glass, but with teeth like needles, they’re not something I fancy sharing the water with. Speaking of aquatic life, the Caribbean Sea is home to over a thousand different species. Some of these are renowned for their beauty, others for their terror. On the one hand, manta rays and angelfish; on the other tiger sharks, bull sharks and moray eels, which divers and snorkelers should try to be careful of.


You can mostly rest easy when it comes to traveling the Caribbean islands. All the best places to visit in the Caribbean will have English as a first or second language, with French and Spanish also being prevalent in others.

For your assistance, a few basics have been outlined for you below. Just to help you get by in the event, you meet any non–English speakers on your travels.

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If my little Caribbean travel guide wasn’t quite enough for you, I can heartily recommend this book from the incomparable Fodor’s. This full–color travel guide has every shred of information you can possibly need as you travel the Caribbean islands.


Even if you’re undertaking one of the best Caribbean cruises, it is likely you are going to have to do some flying (the cruises themselves start out from one of the Caribbean islands). For many – especially if you’re traveling from Europe – this is going to be not such a short journey. To get some comfortable rest on the plane journey will be helped along with this versatile cushion from Travelrest.

ALSO READ: Top Tips and Advice for Planning An Affordable Asia Tour 2019

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