Caribbean Packing List: Travel Essentials We Learned the Hard Way
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As we roll our suitcases out the door and load them into the truck, I remind my husband and teenage son that whatever happens from this point on is all part of the adventure.
Sometimes that means peacefully sipping a fruity drink in a beach chair.
And sometimes that means sleeping on an airport floor.
Travel is messy.
If you approach a Caribbean vacation with the expectation that everything will go exactly as planned, you’re setting yourself up for misery.
When you leave your front door on a new adventure, don’t forget to pack your patience, curiosity, and—most of all—your sense of humor.
When things go awry far from home, it’s easy to panic. It will happen. But step back, take a breath, and remember this: the calamities that happen on your trip often become the best memories—and the best stories—once you’re home.
When Things Go Sideways
On our last trip to Belize, we spent a phenomenal day on the water with Tuff E Nuff Tours. We snorkeled the Hol Chan Marine Reserve and Shark Ray Alley. Our knowledgeable guides made sure we saw all kinds of marine life, learned their names and habits, and understood the ecological significance of the largest barrier reef in the Northern Hemisphere.
Above water, they shared stories, played music, served food and drinks, and made sure we had a perfect day on the water.
Until the boat broke down on the way home.
Most of the other tourists didn’t realize what was happening, but my husband—who is training to become a captain himself—noticed the crew struggling with the engine and felt the tension shift. It was getting late, and we were still moving (slowly), but we had a long way to go.
John gently reminded the crew to keep the atmosphere light and keep the party going. No one panicked. No one complained. We all continued soaking in the island vibes until a rescue boat arrived to tow us home.
It was a memorable day.
We take everything in stride. The biggest problems can turn into the best memories! Real travel is full of surprises, mistakes, and mishaps. We’ve had our share.
Keeping It Real: Our Travel Mistakes
With full transparency, this travel family has…
Booked Embassy Suites at the Portland, Oregon airport instead of Portland, Maine
Tried to sprint for a short connection in Atlanta, not realizing it’s the busiest airport in the U.S. (Not a chance—even with the train.)
Forgotten to reapply sunscreen on the water and spent the rest of the trip hiding in the shade
Packed everything except one essential clothing item
Had a pair of Tevas stolen (our fault because we left them in a golf cart overnight)
Booked “cheap” Delta flights for an upcoming trip and now can’t select seats together. (Other airlines allow seat selection later—fingers crossed I can work some magic at check-in.)
And then there are the mishaps that were completely out of our control…
Getting very sick from resort food or water
Sleeping overnight in the Philadelphia airport on a solo trip to Jamaica after endless delays
Sitting in an unbolted back seat of a tour van in St. Lucia and then getting rear-ended in the jungle
Helping a tour driver change a flat tire en route to an excursion
Booking a “half-day” tour on our last day in Punta Cana, expecting to be back by lunch and returning after dinner instead
But even those moments turned into fond memories.
In Punta Cana, although I was hungry and frustrated about missing our last beach afternoon, the tour unexpectedly included an incredible indigenous dance performance and a local chocolate tasting party. We brought home the best hot chocolate I’ve ever had and shared it with family at Christmas that year.
Learning how chocolate is processed in the Dominican Republic.
Preparation is Key
You can’t prevent every problem, but preparation can smooth the edges.
We’ve learned a thing or two from our misfortunes, mistakes and conversations with other tourists. It helps to have the right gear and the right supplies for the unexpected. There are plenty of Caribbean packing lists online that cover the necessities—sun hats, sandals, swimsuits, etc. They usually contain things you would probably think of on your own, but having a checklist is helpful when you’re in the middle of the stress of packing.
If you enter your email at the bottom of this page and click Sign Up, I’ll send you my Free Caribbean Vacation Packing List. It contains items to keep you safe, comfortable, relaxed and joyful. It also has a short list of what to leave at home, such as camouflage clothes (sign up for the checklist to find out why!)
What’s more, I’ll also send a checklist version of The 12 Caribbean Travel Essentials We Learned the Hard Way detailed below: things you won’t always find on those “ultimate” Pinterest lists. These are the essentials we’ve learned the hard way-through experiences, mistakes and trial and error.
Affiliate Disclosure: This post contains Amazon affiliate links. If you make a purchase through these links, I may earn a small commission at no extra cost to you. I only recommend products we personally use and love, and I hope they bring joy and ease to your next trip.
Caribbean Travel Essentials You Might Not Think Of
Comfort & Health
Benadryl (tablets and cream)
On our first trip to Barbados, my husband befriended a couple and noticed the woman was suffering from terrible sand flea bites. When she skipped dinner due to her discomfort, John offered her husband some Benadryl cream from our room and some tablets he was able to get from another couple. She came to breakfast the next morning incredibly relieved and grateful.
Since then, we always pack both. In the Caribbean, you’re exposed to new foods, plants, insects, and humidity, and your body doesn’t always react the way you expect.
Apple Cider Vinegar
Imodium and Pepto are travel essentials for your first aid kit. Digestive issues are one of the most common Caribbean travel problems, especially when adjusting to new food, drinks, water, and schedules. But when discomfort is just starting, apple cider vinegar can be a chemical-free alternative. It’s helped me recover from stomach issues both abroad and at home.
Now, I’m a picky eater and do not enjoy the taste of apple cider vinegar, but there are ways to make it more palatable. We bring an apple cider vinegar tonic from a local farm here in Union, Maine. Our favorite is infused with elderberries, ginger root, and cinnamon for immune support. Check out the Elderberry Tonic from Herbal Revolution and other flavors here on Amazon.
Bonus hack: Apple cider vinegar also helps relieve stings from some species of jellyfish.
Motion Sickness Wristbands
This is one of my favorite Caribbean travel hacks, especially for island driving, planes and boat days. Island driving can feel like a roller coaster—with oncoming traffic and goats. I avoid medications like Dramamine due to side effects, so I rely on these acupressure wristbands. They work every time, even if I do look like Wonder Woman wearing them.
Electronics
Power Bank
Electronics are easy to overlook on a Caribbean packing list, but they can make or break a travel day.
Taking lots of photos and videos while on tour drains phone batteries fast. Your phone is your lifeline—boarding passes, directions, confirmations. Once, in NYC with my 10-year-old, I received a flight cancellation text—and then my phone died.
Never again. I don’t travel without a portable charger. Click here to view the power bank that works for me.
Charging Station / Travel Adapter
Some islands use different outlets (Grenada, the French side of St. Martin). Skip the cube adapters because hotel outlets are often hidden behind furniture.
Look for one with a long cord and multiple ports instead. The night before traveling home, I love that I can power up all of my electronics at once because there are plenty of plugs and USB outlets in my charging station.
Waterproof Phone Case
You don’t need an underwater camera for snorkeling. These cases capture great photos and video and keep your phone dry.
I’ve found that once my hands get cold underwater they become less sensitive for taking photos. The solution—just press video record above water before you dive in. I’ve used these Seawag cases for most of my underwater videos.
Nightlights
Since our son was little, we’ve packed two—one for the bathroom and one by the bed. Blackout curtains + unfamiliar rooms = nighttime hazards.
Ring Cameras (At Home)
Not something you pack—but essential for peace of mind.
People often wonder how we travel when we have alpacas at home. Well, they are easier than dogs, only take about a half hour a day for care, and are in good hands with our farm sitter (thanks Drew!). A camera in the barn makes travel easier knowing everything is okay back home. I have an outdoor Ring camera so I can check on them whenever I miss their fuzzy faces. We use Ring cameras to check on our alpacas, cats, and front door while we’re away.
Beach & Adventure
Dry Bag Purse
My dry bag purse has been a life saver on catamaran trips when we needed to swim to shore. It’s larger than the underwater phone case, so you can bring along essential items such as keys, cash, and sun block! I also used it when we visited public beaches and did not feel safe leaving all of my valuables on shore when my whole family was in the water.
Bonus Hack: A dry bag backpack makes a great watertight beach bag.
Hammock Float
Our favorite space-saving float rolls up small and fits easily in a suitcase. It sits low in the water so it’s great for relaxing and snorkeling. This 4-in-1 Hammock float we purchased from Amazon rolls up to the size of a paper towel roll and is perfect for the pool or calm Caribbean sea.
Snorkeling Swim Buoy (Our #1 Recommendation)
If you plan to snorkel in the Caribbean, a swim buoy is one of the most important safety items you can pack. A dry bag, safety float, and visibility tool all in one. It keeps valuables dry, helps boats see you, provides flotation when you’re tired, and makes it easier to spot your family in the water.
Documentation
Passport & Document Holder
Worth every penny. Keeps everything organized and accessible during security and boarding. Choose a bright color so it’s easy to spot in your backpack if you’re a compulsive passport checker like me.
Final Thoughts
Bring both international credit cards and enough cash for tips and emergencies! We once met a couple who did not bring credit cards or cash and whose debit card was shut down. Luckily, we were at an all-inclusive so they could still eat, but they were scrambling to get a hold of their bank so they would have money for the journey home.
Also consider packing:
A sunblock stick for your face (sprays + saltwater = burning eyes)
A handkerchief for dust if you plan to go on a 4-wheeling tour
A portable carbon monoxide detector for your hotel room, especially if you are staying in an older hotel or rental.
A pen for customs forms—not all islands are fully digital
Also, download your movies and music to a device at home because not all streaming apps work internationally.
You can’t always plan for the unexpected, but you can pack smarter for a Caribbean vacation. With the right mindset, preparation, and flexibility, travel becomes less stressful and far more memorable.
With each Caribbean adventure, I hope you’ll learn, adapt, grow—and laugh along the way.
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