Flying over Puerto Rico

Uncommon Advice: Why You Should Leave the Caribbean Early

Wait, what? Yes, on a site dedicated to Caribbean travel and exploring the cultural, historical, and natural beauty of the region, my latest Caribbean travel hack could be seen as a bit unusual. Seriously, though, if you’re in the Caribbean or planning to visit, leave as early as possible!

Sad endings

We’ve all been there.

You’ve just spent the past few days soaked in the best of the Caribbean. Water clearer and more refreshing than the best pool boy’s handiwork has enveloped you. You’ve dined on Caribbean lobster for lunch… For multiple days in a row. Rum now flows fabulously through your veins. The West Indian sun has warmed you clear through to your soul. You’ve learned all the words to your new favorite soca, calypso, reggae, dancehall, bachata, salsa, reggaeton, or zouk song. And you keep thinking that moving here was the best decision of your life. That is, before remembering your scheduled return flight home.

And then it happens: Your phone vibrates (or beeps, if you’re that kind of person) and a notification pops up.

Time to check in to your flight.

For most of you, this intrusion comes right as you’re having lobster for lunch. (Again?)

This ruined lunch begins a downward spiral. Hurried plans for the night turn into a futile effort to cram in one more island memory fueled by questionable choices governing rum intake.

But the worst part is the morning. You wake up dreading the end. You try as hard as possible to force a relaxing am experience, but your flight casts a dark cloud over your sunny plans. Plus you still have to check out of your hotel. And if wheels-up is around 3 PM, then you need to stash your stuff if you want to squeeze in one last dash to the beach. If you do, though, how will you shower off the sea and get dressed for the plane after stashing all your stuff?!

To make up for the hectic morning, you try for one last taste of the Caribbean at lunch… Only to end up stuck at security instead.

So, it’s PopCorners for lunch.

Finally, with the beauty of the past few days in the rearview mirror, you find yourself stewing on a plane — hungry, with sand in your underwear, and miserable.

Like I said, we’ve all been there.

Anyway, as a guy who travels for a living, I’ve done this dance over and over again, but this last time it was different.


Early morning return flights change everything.

You see, this time, my departure dance started when my phone buzzed at breakfast.

Now, while some will say breakfast is the most important meal of the day, it’s also the most boring. For me, it’s generally coffee, eggs of some sort, breakfast meat, maybe a little fresh tropical juice for regional flavor (mmmm, guava), and, if I’m fortunate, some johnny cake.

(I know, I know, breakfast can be more fun than that, especially with regional dishes like boiled fish in The Bahamas as options, but I think my point stands.)

So, was my breakfast ruined? No, not really. Nonchalantly, I checked in and arranged a taxi for my 8 AM flight.

From there, without having to rush, I filled my last day with exactly what I wanted. Swimming, planting myself in a lounge hair, sipping on rum, and just generally soaking in the afterglow of the much more active days that had come before.

You get where this is going – the day was relaxed. (Spending it at Bellavista Bed & Breadfast made it all the more so.) And the night was more of a victory lap than a last-ditch effort to wring the last drops of Caribbean adventure out of my trip.

I awoke to the sound of roosters greeting a new day. And as some of you may know, I love sunrises, so naturally, a dallied a little — gazing at the brightening sky over Charlotte Amalie, St. Thomas.

The ride to the airport was quick and uneventful as the island woke up around me. In fact, the airport opened just as me, and my fellow early birds arrived. Security was fast and lacked the usual mayhem of the afternoon crush.

But the best part came after we took off.

Flying over the Caribbean at first light is stunning.

Seriously, the light is perfect.

Taking off from St. Thomas this morning, the light was angled in precisely the perfect way. The steep hills appeared majestic with their long shadow capes. The already beautiful turquoise of the surrounding waters, positively brilliant.

Sailboats between the BVI’s looked like they were hovering.

The lush green landscape of Puerto Rico’s east coast was radiant.

I was floating in the most beautiful drone footage you’ve ever seen. Forehead glued to the window.

This was all thanks to the time of day.

Your next Caribbean travel hack?

Now, I realize there aren’t a ton of early flights out of the Caribbean, but you can find them (St. Thomas plus new options in Antigua come to mind), and I’ve got to say, this is one Caribbean travel hack I’ll be using to guarantee the most pleasant exits from the West Indies.

So, what do you think?

Will you rip off the band-aid at the end of your next trip, or draw out the pain?

Last updated by Patrick Bennett on .

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