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How to Hurricane-Proof your Caribbean Trip Plans

Updated: Mar 24, 2021

At risk of sounding callous, my wife and I rather enjoyed our first hurricane experience.

In September of 2017 we had the distinct pleasure of hunkering down with dear friends in Florida, and escaping reality for a few days while Irma blasted her way up from earlier havoc in the Keys and several Caribbean countries.

Hurricane battering palm trees on a tropical coastline

Like most people, we simply made the best of the situation. In this instance, the best was pretty good. We played countless board games and ate basically every avocado in the garden, lest they end up as debris and cast deliciously at the building by an angry Mother Nature. Did I mention there were margaritas in the pool? We'll be forever grateful to have had this positive experience and can't thank our friends and hosts enough!

A positive outcome for us, not so for everyone

Regardless the positive outcome for us, our trip plans were indeed affected. As a travel professional I’ve seen countless examples of where things have gone right and where they have gone wrong when it comes to Caribbean travel at this time of year.

Perhaps among the biggest pain points is the unpredictable nature of such events. They've been occurring for longer than people have been recording the weather, but the random pattern and path perhaps leads to more stress than is necessary.

Some welcome news

The majority of destinations throughout the Caribbean remained unaffected throughout a rather tumultuous September in the 2017 hurricane season. Despite this, news and concern among travelers and would-be travelers painted a picture of stress and of worry. Two things that are exactly the opposite of what you want in a vacation!

You may not know that throughout this contentious time (2017), the Caribbean remained a top destination for travelers; Owing to the fantastic local people, incredible experiences, beaches & weather, and of course, the great value to be found for all budgets and tastes.

But what happens to my booking? Can I cancel? Is it safe? What about the beaches?

Countless questions surround such events but credible answers remain rare. I fear a story becomes misquoted through repetition or that repetition ad nauseum allows the evolution of a concept to change in a way that doesn’t quite reflect reality by the time many people receive it. We live in a new time when it comes to the news cycle.

You might not believe it, but 2018 has already featured a number of named storms, including two hurricanes, Chris and Beryl. Both of which came to pass without much media attention as they proved uneventful. I’ll add that is unclear if Chris and Beryl still hang out at this time or the general health of their friendship.

As we approach the traditional peak of hurricane season, I thought I’d showcase a few top items for consideration when it comes to making plans or to navigate plans already set for fun in the sun at your favorite Caribbean destination!

Be prepared to prepare

That means signing up to your favorite trusted news source to ensure that you will receive relevant news – I suggest favorite because you have to actually read this news in order to gain an understanding of its relevance. It’s fine to sign up for an RSS feed or download Twitter for your holiday, but if you don’t have the habit of reading these things already it might be a waste of keystrokes or space in your inbox.

If you do have Twitter and have allowed push notifications, you can follow the National Hurricane Center (Natl Hurricane Ctr) on @NWSNHC or even the National Oceanic and Atmospheric Administration (NOAA) on @NOAA.

Not only will you be able to check in or receive notifications, but you might also enjoy some of the cool maps and content they produce to help you better understand the world when you’re not worrying about your trip plans!

Beyond the tweets

Beyond notifications and news, I would argue that for those of you who’ve already booked or are on the cusp of committing to a holiday, you should visit the relevant travel authority for your home government and both review and register your travel plans.

At Odyssean Travel, we regularly review destinations and check conditions for all new destinations to ensure client safety alongside practical matters, such as terms of entry or exit.

Where we are able, we like to register client trip plans and encourage our Odyssean Travelers to participate, especially solo travelers, families, and those with specific medical needs. But such registration services are generally available and everyone would be served well by taking advantage!

***Update 2019*** We are no longer able to register on behalf of Canadian travelers.

For Canadian passport holders: For news and advisories or to register your trip plans

Anyone with an email address can sign up for the US STEP advisories page, it is a useful tool in staying abreast of news and seeing what major world governments are suggesting for their citizens.

Just remember that anything to do with insurance coverage (more on that below) will likely be limited to those updates released by the government relevant to your geographic area of residence at the time of booking.

Why should you register?

I’ve touched on this numerous times in past articles and talk about it with all of my clients, but registering your trip plans with your home government has a two-fold effect should there be need for additional services:

It allows you to stay on top of relevant advisories before you depart or during your decision making process, but it also makes your presence and trip plans known while you’re abroad. This will speed along any process of a consular nature as your home government will be aware of your presence and may be better able to contact you or provide you aid and assistance should the worst occur during your trip.

It works like this, if you let the consulate know that you are going to visit a destination and then there is a disaster, they know not only to look out for you but will have a better idea of where to start that search.

Conversely, if your consulate isn't aware of your presence, they won't necessarily assume it. If they don’t know you’ve arrived locally, they won’t know to search in the first place, let alone where to start – leaving family and friends (or your travel advisor!) back home to initiate any process and navigate through difficulties in communication typically seen during hurricanes and other disasters.

Whatever the weather, I'm going on holiday!

Now, if you’re like me you’ve just carried on with life and continue to make travel plans, whatever the weather! You'll prefer to be excited to spend time in a world-class setting and getting on with your daily life. Enjoying the anticipation and not stressing about the weather.

I find that nothing reduces stress like gaining an understanding. An all-around superior pre-trip experience often centers on the comfort that comes from knowing your plans are safe and that you’ve got alternate options to execute if necessary.

During the booking process you would have been prompted to review the terms and conditions of your booking, the “T&Cs”. The honest truth is that most will categorize hurricanes under the exemptions of Force Majeure, but it is a good starting point nonetheless.

Don't panic

Next, it would help to know which entity or entities might be involved in any decision process. This should be outlined on any invoicing, but you can always refer to your travel professional as there will be a record available.

For example, if you’re bound for all-inclusive, there’s a good chance that your entire booking was concluded in one reservation number. This is a good thing from some perspectives as it can mean fewer points of contact for making any change – especially if the supplier owns or has chartered your flight and transfer..

For those of us headed on a separate flight and activity or accommodations booking, such as a cruise or yacht charter, or even to join a tour group, there may be more than one entity involved in the transaction and the path to success will appear in a slightly different manner.

No problem, don’t panic, it’s just something to keep in mind as you look to secure any outstanding financial aspects.

Changing flight schedules during landfall of Hurricane Irma

As alluded to earlier, I was in South Florida during the September weekend that Irma made landfall. I had been on a business trip to Las Vegas earlier in the week and was due to meet my then fiancée, now wife Holly in Florida on its conclusion. More or less as I arrived in Las Vegas, it became clear that Florida would be severely affected and I actually made a change in my plans to fly back into the path of the storm (a good husband, I know haha).

Unsurprisingly, there were plenty of available seats for my change...

I imagine the change was not ideal for my hosts in Vegas and probably contributed to the failure of that endeavor (a story for another day), but the process of making changes to my flights was a winner and was accomplished without stress or further delay.

You may be offered a waiver for any change fees

Change and cancellation fees are fairly ubiquitous in the industry, changes can lead to further additional costs as the difference in fare will likely be added to the final tally. However, it is not uncommon for airlines and other travel suppliers to offer a complimentary change during large disturbances, such as a category 3+ hurricane!

Likely owing to an abhorrence for bad PR, no one wants to be seen as the bad-guy business who strong-armed passengers into maintaining their trip plans to a potential disaster zone.

I was able to change my flight twice, actually – once without a penalty in change fees, although there was a difference in fare to be paid. The second change was down to a rather comical circumstance in which the plane for my originally scheduled flight never arrived from LA. It was delayed because of another storm local to me in Las Vegas!

I would have actually missed my connection and been stuck in a connecting city for who knows how long...

JetBlue to the rescue

JetBlue to the rescue this time, given the circumstance they were very happy to have me transfer my booking from a code-share airline (Virgin, at that time not yet consumed by Alaska Airlines) and onto a non-stop with far better comfort and convenience.

Thank you, JetBlue!

The cruise industry was another overall win for travel and tourism, not only were many vessels re-purposed for evacuation and the distribution of aid, but the industry proved dynamic in its ability to reschedule ports of call and to alter itineraries whilst at sea.

I feel as though many ports of call that were on the short list for development during the next couple of years suddenly became a priority for the larger cruise lines. The result of which included an improved economic distribution for passengers and showcased the ability for cruise lines to keep guest safety and experiences high. I’m sure there were still a few frowns following cancelled shore excursions, but that the overall outcome can be called a success.

I temper this last point against the fact that unless it is clearly outlined in the terms and conditions, travel suppliers are not obligated to provide fee-free changes and that there are no standardized industry regulations across the globe.

Which is a brilliant segue to my final recommendation to protect your travel investment, from a financial perspective. Fee-free changes are only good if there's an alternate flight or travel arrangement available.

What is your current insurance policy situation?

This is something I can’t stress enough, but which is unfortunately overlooked with great frequency. Everyone should travel with adequate coverage, that doesn’t just extend to your medical needs – although I’m sure many would argue this has the greatest potential for both necessity and cost.

Aim to better understand any existing policy you might hold, whether that be provided by your workplace, through the credit card you used to make payment, or even those policies you purchased as a bundle with the original booking. If it is not sufficient, seek out additional coverage.

Policies are not created equally and the levels of coverage and triggers therein can be vastly different.

Cancel for any reason

For example, a popular option is to purchase a policy which includes a “cancel for any reason” attribute. These are often only available at the time of purchase or immediately afterward, but can provide a near-instant reprieve should your plans suddenly become unwanted.

As the name says on the tin, you can just cancel. Just be aware that the timeline and amount can differ and that 100% compensation might not be part of the your policy.

Pay particular attention to the collapsing timeline of coverage amounts. Look for key conditions such as the number of hours or days in advance your cancellation might allow and the associated percentages of coverage or even coverage maximums.

Many insurance providers will be happy to add cancellation or interruption policies to existing purchases, even far closer to the date of proposed travel. Just remember that if there is any indication a storm has become active by the time you’ve made your purchase, you will likely have already forfeited coverage for that incident.

You are supposed to be unaware of any reason you might need to cancel when you first purchase any policy or risk delays or even denials based on the fact that you held doubt when you made the purchase – an active travel advisory would certainly fit that profile. As I suggested earlier, the advisory will likely be relevant to sovereign policies and is another point to be confirmed while planning for success.

We travel to relieve stress, not add it

In the end, we travel to relieve ourselves of our stresses, not to add to them. Your travel dream to the Caribbean should be celebrated, you deserve to make incredible memories and there are so many wonderful places to achieve this.

Know that there are options and fail-safes, that the industry is working with you in achieving your goals and not simply trying to squeeze the bottom dollar from your fun.

Travel safely, folks!


Our Mission

Here at Odyssean Travel, our mission is pretty simple. We want you to make better vacation memories with the people who matter most in your life.

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