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Have you ever sat at work, bored, and wishing you could be somewhere that looks a little more like paradise? Has your mind drifted back to memories of vacations past to some of your favorite trips to the beach? What if you could plan a vacation to a new place when your next vacation rolls around?

You may have heard about and even considered visiting the Caribbean islands. They are beautiful, each one with its own character, unique locales, and so much more. “Wait just a minute”, you might be thinking, “Isn’t a trip to the Caribbean islands expensive?”

You would be correct in thinking that trips to the Caribbean islands can get pricey, but did you know that you could save a good bit of money during certain times of the year, depending on how you plan your vacation? If you’re ready to save some money in your bank account for your next vacation while also enjoying a great time in a tropical Caribbean destination, then these next bits of advice are just for you.

Planning Your Caribbean Vacation

If you like the thought of saving as much money as possible on your vacation to the islands, then you’re going to want to know about the times of the year where you might save some money. Luckily, there are several months in the year where you can find good deals on travel to the Caribbean islands.

Generally, winter and spring in the northern hemisphere, December through May, is going to be the most expensive time of year to head to the Caribbean. This is the “high season” and usually you’ll be paying top dollar. It is the other months of the year, the summer months and fall when cheap flights and great deals are available.

The Cheapest Time of Year to Go to the Caribbean Islands

Planning a vacation can take a good amount of smart scheduling and staying on top of travel prices. To help you save as much cash as possible during your vacation this year, try to plan your trip around the cheapest time of year to travel to the Caribbean islands – June through November.

Let’s break it down by month to make it super simple.

Planning a Trip in June-August

The months of June to August are great times to plan a trip to the Caribbean islands, as it is the start of hurricane season or the “low season”, and fewer tourists are likely to be in the area.

At the start of the season, hurricanes are more likely to be experienced in the Gulf of Mexico than in the Caribbean region, so June-July is an ideal time to score good low season deals for islands in the eastern Caribbean like Turks and Caicos, Puerto Rico and the US Virgin Islands – St. John, St. Croix and St. Thomas.

During these months, you will also find that the beaches may not be as full as other times of the year, since many schools are still going to be in session. Less busy islands equal more savings for the vacationer on a budget, so keep this time of year in mind if you want to save some money on your tropical vacation.

Temperatures, as usual in the Caribbean, are consistently warm across most of the islands. The average temperatures on the islands can be anywhere from the high 70s to the mid or high 80s. Perfect weather for hitting the beach!

If planning a trip to the Caribbean this time of year, you might want to consider bringing a light jacket if it rains. Thunderstorms become more frequent on the islands as the hurricane season progresses.

Planning a Trip in September-November

The months of September to November can be a great time to plan a trip for folks looking for the cheapest time to go to the Caribbean. The month of September is the very peak of hurricane season, making it one of the best times to find low prices at some of the most desirable inclusive resorts.

On average, the southern Caribbean is less likely to be broadsided by a hurricane than other parts of the Caribbean Sea. Places such as the ABC islands (Aruba, Bonaire, Curacao) as well as Trinidad and Tobago are situated somewhat south of the usual hurricane tracks and can be good destinations for low season vacations.

With this being the peak of the low season, there are going to be a lot fewer tourists around than normal, meaning prices for travel and lodging should be much lower. As a bonus, you won’t have to worry about sharing the beaches or your hotel with too many other guests.

Around October, the weather is quite warm and full of humidity. You can still expect the occasional thunderstorm around this time of year, but you will find that October on the Caribbean islands is going to be another of the cheapest months for traveling if you want to save as much money as you can.

Sailrock Resort - Beach Hammock


November is going to be one of the last months you can really save some money on travel and lodging in the Caribbean islands until peak season is over. Once it’s December and the high season rolls around, vacationers are going to be showing up for a Caribbean Christmas or New Year, and other winter months are no less busy than December is when it comes to tourists flocking to the islands.

You may also find much cheaper or heavily discounted hotel rates in the time leading up to December, so keep an eye out for prices in your budget for travel accommodations.

November does have several fun events on some of the islands that you might wish to consider checking out, including:

  • The famous Food and Rum Festival on the island of
  • Jamaica’s always fun Restaurant Week
  • The island of Trinidad hosting Divali.

For saving as much money as possible on your vacation to the Caribbean islands, these are going to be your best options when you’re thinking about the cheapest time to go to the Caribbean islands.

Find your island and have some fun

Now that you know how you can save some extra money on your trip, all that is left for you to do is to find the Caribbean island of your dreams, find the best rates for your travel and accommodations, and begin planning the best tropical vacation possible!