The Ultimate Guide To Taking Cheap Caribbean Vacations

Looking for a cheap Caribbean vacation? Consistently recognized as having some of the world’s finest beaches, the Caribbean is considered a bucket list destination for many travelers around the globe.

Whether you prefer to be wholly tethered to white-sand beaches or experience an entirely different culture rich in history and tradition, the Caribbean islands have something glorious in store for you.

If you relish water sports in crystal clear seas, there are many options available almost year-round – from spectacular snorkeling to world-class diving, the Caribbean is always prepared to deliver.

Even though the beaches are the island’s main draw, there is an abundance of lush rainforests and picturesque peaks replete with various bird species and countless hiking trails. Plus, the islands’ colorful heritage and unique cuisine are both enigmatic and unforgettable.

But for frugal tourists like myself, the expense associated with planning a trip to a widely-popular destination like the Caribbean can be quite prohibitive. Above all, I do not advocate going into debt just to make a dream vacation into a reality. At the end of the day, you want your holiday to be filled with phenomenal memories instead of a sour “broke feeling” aftertaste.

In this post, I’ll explore several strategies to assist you in mapping out your future Caribbean odyssey so you will not inflict a significant dent in your savings accounts.

The Caribbean Islands and Their Highlights

Caribbean political map

Before we jump into cheap Caribbean vacations and how to have one, we first need to know what constitutes a Caribbean vacation. Below is a list of the Caribbean islands you might want to visit and their main attraction(s). While all of these islands would likely make for a fantastic vacation, you can use this simplified list to narrow down what islands you may want to visit most based on what you primarily want to enjoy while there.

  • Anguilla – Beaches
  • Antigua – Beaches, Cuisine
  • Aruba – Beaches, Nightlife
  • Bahamas – Beaches, Nightlife
  • Barbados – Cuisine, Golf
  • Bonaire – Diving, Hiking
  • British Virgin Islands – Beaches, Diving
  • Cayman Islands – Beaches, Shopping
  • Cuba – Beaches, Historic Cities, Cuisine, Hiking, Diving
  • Curacao – Beaches, Hiking, Diving
  • Dominica – Diving, Outdoor
  • Dominican Republic – Beaches, Golf
  • Grenada – Beaches, Outdoor
  • Guadeloupe – Beaches, Diving, Outdoor
  • Jamaica – Golf, Outdoor, Cuisine
  • Martinique – Beaches
  • Montserrat – Diving, Outdoor
  • Puerto Rico – Nightlife, Outdoor, Culture
  • Saba – Diving
  • St. Barthelemy – Beaches
  • St. Eustatius – Diving
  • St. Kitts & Nevis – History, Golf, Outdoor
  • St. Lucia – Outdoor, Beaches
  • St. Maarten – Beaches, Plane-Spotting
  • St. Vincent and the Grenadines – Beaches, Diving, Golf
  • Trinidad & Tobago – Beaches, Diving, Golf, Outdoors
  • Turks & Caicos – Beaches, Diving
  • US Virgin Islands – Beaches, Diving

(Source: Fodor’s Travel)

Where To Go?

Comprising over 20 island nations and territories, figuring out where to go in the Caribbean can be incredibly daunting. Unless you have the luxury of time and money to island-hop every few days, I do not suggest visiting them all in one trip.

Selecting which paradise island to explore will primarily depend on the purpose of your holiday.

Would you like to intersperse lounging at the beach with hiking?

Do you plan to either do professional diving or recreational snorkeling?

Are you a foodie and love chronicling various international cuisines?

If you are a history buff, would you like to visit Alexander Hamilton’s birthplace in Nevis or historic Old Havana?

Are you scouting the perfect romantic getaway for your honeymoon?

Other considerations that can influence your choices revolve around budget and time. Some islands, such as Anguilla, Barbados, St. Barthelemy, and the British Virgin Islands, strictly cater to the well-to-do crowd, making bargain hunting practically impossible. If you are on a shoestring budget, I would cross those off your list.

Once you have narrowed down your potential options based on the factors above, start searching for cheap airfare and wallet-friendly accommodations. You might also consider embarking on a discounted cruise once it is safe to do so. The sections that follow will walk you through this process.

When To Go?

A few years back, I would have strongly recommended avoiding hurricane season. But with climate change in full effect, it has become much more challenging to accurately predict when hurricanes will likely form.

By and large, the Atlantic hurricane season starts at the beginning of June and lasts until November. Historically, powerful hurricanes have occurred between August and October. I would avoid traveling during these months to minimize the risk of inclement weather impacting your vacation.

If a hurricane has disrupted your travel plans, hotels and airlines typically offer refunds or rebooking without a fee. For added protection, I advise purchasing travel insurance.

If you would like to leverage flight deals during hurricane season, the southern islands of Trinidad & Tobago, Aruba, Bonaire, and Curacao have traditionally escaped the wrath of powerful hurricanes in the past.

Finding Cheap Caribbean Vacations

How To Find Cheap Flights

Online Travel Agencies (Otas) vs. Airlines

There are so many airlines that fly to the Caribbean that running individual searches to arrive at the cheapest airfare will surely take an enormous amount of time. Hence, I suggest utilizing OTAs as a starting point as they generally scan all airlines, including budget carriers, for the cheapest airfare.

First, run your searches through these three OTAs as they consistently yield the cheapest airfare possible: Momondo, Skyscanner, and Google Flights.

Next, take note of the exact details of the flights you found and initiate a similar search directly on the airline’s website. Compare both fares and pick the cheaper flight.

If it is a few dollars difference, I’d rather book with the airlines as their terms mainly offer more flexibility. In fact, almost all major U.S. carriers have temporarily started waiving their change fees for flights to the Caribbean. At any rate, it is good practice to verify the terms and conditions of the ticket you are planning to purchase before hitting the buy button.

Explore Option

Another fantastic feature of OTAs is their ability to perform an extensive search for the cheapest flight available in any region. This feature is called the “Explore” option and is available on Momondo and Google Flights.

When searching, write down “Caribbean” in the destination search box. Enter your preferred dates, then jumpstart the search. Select the particular flight that aligns with your preferred travel time (i.e., number of stops, length of layovers) and budget.

This strategy works best if you do not have a specific island in mind and are willing to fly anywhere as long as the price is right.

Mistake Fares

Subscribing to travel websites that comb through the web for cheap flights and mistake fares is another avenue to find airfare deals to the Caribbean.

These websites have devoted employees who meticulously monitor various travel search engines for insanely cheap plane tickets. Subscribers immediately receive a newsletter once these deals get unearthed, so they don’t miss out on these valuable promotions.

If you are curious about error fares, they are usually the outcome of computer glitches that happen quite often. Since these flights are dirt cheap, you need to pounce the moment the deal enters your inbox as they tend to vanish quickly within a few hours.

Some of these platforms require paid subscriptions, but most offer free basic memberships, so I would recommend the latter. The most popular mistake fare websites are Airfare Watchdog, Secret Flying, The Flight Deal, Travel Pirates, Going, and The Thrifty Traveller.

Travel Hacking

Anyone remotely interested in travel should be familiar with how travel hacking works as it has the potential of saving anyone a considerable amount of money.

Every major airline has a loyalty program, and loyalists naturally get rewarded with free flights. Free travel is attained after reaching a certain number of points, usually dependent on the cost of the redemption.

One of the best deals in airfare is the Southwest Companion Pass, which allows you to fly a companion for free for up to two years. It can be earned by reaching 125,000 qualifying points within a calendar year. Check out how to earn the Southwest Companion Pass and use it to fly for cheap to many Caribbean destinations.

Previously, the only way to accumulate these “loyalty” or “frequent flier” points was by repeatedly flying with the same airline. But that is now a thing of the past. Currently, anyone can earn these frequent flier points by travel hacking.

Simply put, travel hacking is the art of saving money on travel. One way to do this is by applying for specific travel credit cards to earn generous sign-up bonuses that can be ultimately redeemed for free flights. It is by far the best strategy to save money on airfare.

However, this approach is sadly not for everyone. If you currently hold a lot of consumer debt or have difficulties paying off your monthly credit card balance in full, this strategy may not be suitable for you. Nevertheless, once debt-free, you can undoubtedly take travel hacking for a test drive to find out if it can work for you, too.

Whether a novice or an expert traveler, I highly recommend dabbling in travel hacking. It has brought me to countless places I would never have imagined visiting for a fraction of the price.

Other Strategies

Aside from the above tactics, there are also additional methods that you can utilize to ensure that you are getting the best bang for your buck.

In short, flexibility is the name of the game. The more fluid your plans are, the higher your likelihood of grabbing deeply discounted tickets. Besides flexibility, other recommended strategies when hunting for cheap airfare include using incognito mode while searching, booking one-way, multi-city, or round-trip and comparing costs, booking one person at a time, and paying with local currency, among others.

How To Find Cheap Accommodations

Online Hotel Search Engines

The strategies for finding reasonably-priced lodging will mirror the techniques for airfare. Performing a search using various online hotel search engines is recommended.

Although frugal tourists naturally gravitate towards inexpensive accommodations, I firmly advise reading customer reviews before finalizing your reservations.

You want to ensure that the property is compatible with what you are looking for, considering the lodging’s safety and security and how comfortable and clean the accommodations are. Also, you would want to know whether the hotel offers refundable rates in case your plans get derailed. Below are some excellent lodging search engines to get you started:

  • – One of my favorites as it gives a free stay after every 10 nights.
  • – Consistently features deeply discounted properties.
  • – Terrific promotions year-round.
  • – If you want to save and do not mind roughing it out, staying in a hostel might be an option.
  • – If you want a property with additional amenities such as a kitchen, parking, etc, then consider staying in an Airbnb.
  • – Another excellent option for long-term stays.

Mix and Match

Some search engines such as Kayak, Expedia, Orbitz, etc. allow travelers to lump airfare and hotels together in the same reservation resulting in hefty savings. Before booking, though, make sure you compare these rates with the fares you get when booking them separately.

Hotel Hacking

Identical to airfare hacking, it is possible to rack up many hotel points when you sign up for hotel credit cards. These points can be exchanged for free nights in virtually every major hotel chain.

Some of these rewards credit cards also give out a free night certificate when you pay the annual fee. Whenever you book a night that is more expensive than the cost of the annual fee then you have come out ahead.

It bears repeating that to maximize these travel hacking offers, you need to have a stellar credit score and be inherently averse to debt. Despite how lucrative these credit card deals are if you tend to encounter difficulties paying off your credit card balances when they are due, then the pursuit of travel hacking may land you in serious debt. Remember, anytime you begin paying credit card interest you are wiping out any rewards you might be earning.

Once you are debt-free and have a substantial travel fund, you can consider the current offers from these popular hotel chains: Hyatt, Marriott, Hilton, and Intercontinental Hotels.

Even though all these hotel brands have a vast footprint in the Caribbean, they are not present in all territories. Verify that the hotel credit card you’re applying for has a property on the island you plan to visit before signing up.

Aside from hotel brand cards, don’t forget about programs that offer reward redemptions at various chains, such as Chase Ultimate Rewards.

Package Tours for Island Hopping

Our final strategy for cheap Caribbean vacations is taking advantage of package tours. The predominant strategy for island hopping on a budget is taking cruises that visit multiple ports. Despite their unsavory reputation as virus Petri dishes, I would be remiss if I do not mention Caribbean cruises as a viable option to save a decent amount of cash.

Here are some excellent options to find deals on cruises.

  • – routinely offers a wide range of low-cost Caribbean cruises.
  • Cheap Caribbean Cruises – scours the web for the most affordable available cruises.
  • Cruise Cheap – year-round discounts for cruises around the globe.
  • Travel Zoo – periodically releases deeply discounted tours.

Saving for Travel

No matter your mastery of travel hacking, there is no such thing as a free trip. Even if you can get significantly discounted flights and accommodations, you’ll still need to pay for food and activities. Thus, saving for travel ahead of time is another strategy to add to your travel hacking arsenal.

I save for my travels by mindfully setting aside a specific amount of money per month so I could have almost all the funds available to withdraw while overseas or to pay my credit card bills upon my return. Since I love travel immensely, I typically save on virtually everything to guarantee that my travel fund is always robust.

With rigorous discipline, it is not only possible to fund cheap Caribbean vacations, but any remaining savings you have can be funneled towards other future bucket-list vacations on your drawing board. Make sure you keep your saved money in a high-interest savings account so your travel fund continues to grow even in your sleep.

Final Thoughts

As you can see, navigating the countless options in booking your future Caribbean voyage can be extremely overwhelming. I hope the frugal strategies I’ve outlined in this post can help you plan your trip confidently while staying within your budget.

The more money we save, the more money we can direct to our travel funds so travel doesn’t become a source of stress due to debt incurred. After all, traveling should never create a financial burden on anyone.

This article originally appeared on Wealth of Geeks and has been republished with permission.




Kristian is an experienced marketing leader who has helped multiple fintech startups scale their marketing over the past few years. He is currently the Director of Marketing at Future Vault ( an online digital vault where advisors and their clients can securely share documents and communicate.

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