The Caribbean is cheapest in late summer, and weather is better than you might think
Many of us start dreaming of Caribbean vacations only when it starts to approach freezing where we live, but winter is also very crowded and expensive in the Caribbean, and some people can't take time off. The good news is that the savvy traveler knows that you can take a fabulous tropical holiday in the second half of summer for literally half the price of winter, and the weather there is almost as nice as well.
Below we'll discuss some strategies for getting the best deals and also strategies for dealing with the weather. The Caribbean is very popular with Europeans during July and August, when so many of them take an entire month, and there's no reason the rest of us shouldn't be more willing to join them.
The best off-season bargains are package deals and all-inclusives
First off, for context, check our list of the cheapest Caribbean destinations and islands, which is based on high-season prices, but the order stays basically the same in the off season.
It's actually true all year, but the difference is much more dramatic during the off season. For some reason, individual hotels don't lower their rates by more than 10 or 20% during even the slowest months, even though they offer up to 50% off as part of airfare packages.
In other words, it's probably barely worth even checking individual prices of hotels and airfare to form your own package, although doing so should make you feel even better about the package price you are comparing it to. Summer airfares tend to be a bit higher than in winter or spring, so you'd really need to find a rare hotel bargain to make up for it. You can check for cheap flights and hotels as well here.
Look for “deals of the week” for the biggest savings
It really pays to be flexible during the low season because it allows you to jump on deals that you might not have considered on your own. Some people have a favorite island or beach or even resort and they have their heart set on it, but taking advantage of weekly deals will usually get you a nicer place for even less than you were planning.
Since so many resorts hover closer to 50% booked than 100% booked during the slow months, the ones with the most empty rooms will cut their prices the most aggressively to fill them up. Often it's even highly-rated resorts that do this because booking patterns can be somewhat random during this season, even for resorts that are always fully booked in winter.
You should also think about a cruise, which should be amazingly cheap during these months. Our list of Caribbean cruise lines by price should help narrow down your search.
Check the Cheap Caribbean Hot Deals for weekly sales and the best package prices. They are a partner of ours, but they are also the cheapest of the online agencies.
The late-summer Caribbean weather is still fantastic
It's a common myth that the entire Caribbean is blazing hot all summer and into autumn, which is sort of understandable because many assume that if it's warm in winter it must be ridiculous in summer. It isn't.
Look at the temperature and rain charts (in the left column) for cities like San Juan, Puerto Rico or St. Lucia and you'll notice that there is only a slight difference between any two months there. Even the rainfall totals are close through most of the Caribbean (though not in Central America).
The “rainy season” means a couple of short storms per week in most places
Okay, so it's true that June through November is the “rainy season” in the Caribbean, but it's not as bad as you might suspect. While in Costa Rica or Thailand they can get buckets of rain in a storm, in the Caribbean it's usually a 30-minute storm in the late afternoon, only 2 or 3 days a week, followed by a lovely sunset where it's clearing up.
So you might want to avoid a late-afternoon fishing or scuba trip if clouds are rolling in, but otherwise it's very easy to dodge storms, and they make a great excuse to have an extra cocktail or two as you watch it from the poolside bar.
The hurricane season is a tiny gamble, but it's not dangerous
If you are an incredibly pessimistic person you might think that hurricanes are just waiting to form once you've gone to the airport for your holiday flight, but if you really look at the numbers you'll realize that hurricanes are extrmely rare in any given place at any given time. You could spend a week on a new beach each month of this period and chances are it would be many years before you even encountered a Hurricane Watch, much less one that clobbers your hotel.
It's also important to keep in mind that hurricanes are tracked for about a week after they form and before they hit the resort islands. So as long as you listen to the resort manager, the worst that will happen is that you might have to leave a few days early, or postpone your trip if it's coming before you arrive.
Honestly, the chances of something like this happening are extremely small, but this is also why travel insurance is a great investment for trips like this. For around 10% of the price of your trip (which will be very cheap to begin with) you can be sure that you'll either get a full trip or a full refund.
The amazing deals make it worth the gamble
The fact that so many people are irrationally put off by weather problems is why you can save 50% on wonderful resorts this time of year. You can pay full price and be more certain that the weather will be perfect, or half price knowing that it's almost perfect and there is under a 1% chance that your trip will be interrupted somehow. The choice is yours.
Again, check the Cheap Caribbean Hot Deals for weekly sales and the best package prices. They are a partner of ours, but they are also the cheapest of the online agencies.