Traveling to the Caribbean during peak hurricane season is tricky. You do so knowing there’s a risk you may have to change or cancel your trip. Of course, when booking your trip, you hope that never happens. But why would anyone book a trip to the Caribbean during hurricane season?

One word – Sale! At least that’s my reason. Especially if the hurricane season is inactive.  Hurricane season lasts from June 1 to November 30, but peak hurricane season is from late August to October. However, just because it’s hurricane season doesn’t necessarily mean you’ll have a hurricane. I’m from Jamaica, so I know this first-hand.

I had been eyeing Turks & Caicos for a while and lo and behold! Southwest had a sale! Between my husband and I, we had just enough Southwest Rapid Rewards points to snag three plane tickets from Atlanta to Providenciales. Our flight dates were scheduled for the last week in August. Peak hurricane season. But I figured, what the hell? I don’t know when I’ll be able to get this deal again.

It’s a bit of a gamble, but that’s okay, as long as you take certain precautions. Make sure you do the following BEFORE you book a trip to the Caribbean during hurricane season:

1. If you can, avoid booking travel dates between late August and October, during peak hurricane season. Oh, well. Look at that – I broke my first rule
2. Research your airline’s cancellation policy. Southwest Airlines provides you with a full refund if you cancel up to 10 minutes before departure. LOVE THEM! 
3. Research your hotel’s cancellation policy. Our hotel has a 24 hour cancellation policy during that time of the year, so we would get a full refund if we cancelled within 24 hours of our arrival. The cancellation policy is different during the winter (21 days).  
4. If the cancellation policies for your hotel or airline are not flexible, definitely get travel insurance. We didn’t have to in this case, but if we were using another airline or hotel with more restrictive cancellation policies, we definitely would need travel insurance, especially when traveling during the hurricane season. 
5. Pay attention to the weather report. That goes without saying. Make sure you check the weather and pay attention to what’s going on in the Atlantic. A tropical depression can develop into a tropical storm within hours. A tropical storm can quickly develop into a hurricane. 

I had all of these covered, except the first item, but I figured if a hurricane developed we would just cancel our flight and get our points back. No big deal. Same for our hotel, which had a 24 hour cancellation policy during the low season. It was a very quiet hurricane season this year. Not one hurricane, or even a hint of a hurricane, so I was pretty optimistic.

Fast forward to the Saturday before our trip. I had already packed for myself and our son (my husband likes to pack himself … the night before. Drives me nuts!) I got a phone call from my mom telling me about the tropical depression that developed into a tropical storm in the Atlantic.

They called it Dorian. The projected path showed it heading towards Puerto Rico and Hispaniola (Dominican Republic and Haiti), and then … Turks & Caicos. Mind you, I had checked the weather earlier that morning. There was no tropical storm at that time, just a tropical depression. I went online to google Dorian and sure enough, that depression had morphed into a storm and was expected to turn into a hurricane.

I broke the news to my husband and he was in disbelief. “Let’s just wait and see,” I said. “We have until Monday to make a decision (our flight was scheduled for Tuesday).” Growing up in Jamaica, I had already experienced my fair share of tropical storms, and of course, Hurricane Gilbert. The thing with these hurricanes and storms is you never know. It could be heading one way one day and then decide to change paths the next.

The next day my husband and I got into a huge argument. “We should cancel” he said. “What do you mean? I thought we agreed to wait until Monday?” I was a bit confused because I thought we were on the same page.

I tried everything. From using the fact that I took advanced-level geography in the Caribbean so he should trust me when it comes to hurricanes (never mind that was over two decades ago); to trying to convince him that Turks & Caicos, like Jamaica, rarely experience a direct hit.

I had no luck whatsoever. “You really want to leave it up to chance and luck? We have a two-year old son. What if it ends up going right through Turks? I was clearly losing this argument. “What about Hurricane Irma and Hurricane Maria?” He asked. Sigh. I didn’t say they never hit … just not as frequently.

The truth is, my husband had a valid point. He was concerned about Dorian turning into a hurricane, and that we would get stuck in Providenciales when it hit. Dorian was on track to reach the Turks & Caicos islands on Friday and we were scheduled to leave on Saturday. If Dorian did indeed develop into a hurricane and hit Turks & Caicos, it was highly likely they would shut down the airport. “We could just leave earlier” I said. “Everyone will be trying to leave, how do you know if we would get seats?” “Can we just wait until Monday and see what happens?” I asked. “Fine, we’ll wait until Monday, but seriously though, I don’t mess with Mother Nature.”

The next 24 hours were quite stressful. Cancelling wasn’t the issue, I had set it up so we would get a full refund for everything. It was deciding if we really should cancel. I had planned this trip over a month ago and honestly, canceling back then would have been a lot easier.  It’s a different story when it’s two days before. I was already geared up and ready to go. You know, that rush of excitement you get when you’re about to jump on a plane and go somewhere? Yep, I had that rush. I had been looking forward to this trip so much, that I was already packed.

It wasn’t just me, my husband was excited to go too (until he heard about Dorian). It’s been a hectic year for both of us and we were looking forward to this family vacation. Work had been crazy for me and I really wanted to just relax and recharge  with my family. Plus, I was in dire need of a beach and we were so close to spending the next few days in paradise. I was determined to go.

Yet, deep down inside, it didn’t seem right anymore. Mostly because my husband thought Dorian would definitely hit Turks & Caicos and didn’t feel comfortable going. I called him from work that day to tell him the hotel said we had until 8:00 p.m. to cancel. What he said next really got me. “I really don’t feel comfortable going I just have a bad feeling about this hurricane. We have to think of our son. I just want us to be safe.”

He was right. I don’t know if it’s because I had time to sleep on it and think about it. If we went and nothing happened, great. If we went and the hurricane hit, what then? Plus, even if there wasn’t a direct hit, there would likely be a lot of rain. Not exactly what we were looking for in Turks & Caicos. My husband’s pretty cool, calm, and easy-going, so the fact that he didn’t feel comfortable going anymore meant something. And I had to respect that. If the tables were turned, he would never force me to go somewhere if I didn’t feel comfortable. “Okay, hun,” I said. We’re not going.”

I was heartbroken and disappointed … but not defeated. I still had time to make the most of this.

Since I had taken those preliminary steps before booking our trip, we didn’t lose any money and were already in good shape to salvage our vacation.

Find out how in Part 2 of “How to Salvage Your Vacation when a Hurricane Strikes” (what to do if a Hurricane develops right before your trip) – stay tuned