Hey! Traveling to the Caribbean whether it’s to a resort, a charter boat, or an Airbnb comes with it’s own unique packing strategy. Below is a list of things/websites we’ve used while traveling the Caribbean and we want to share them with you! Many of the links below are affiliate links, which means that we’ll get a small commission if you click through the link and make a purchase. We’re hoping that you’ll use these links anytime you need to make a purchase! These small commissions help us stay stay afloat and bring you more Caribbean content! ???? We would never recommend anything we don’t personally use and think is valuable!

Let’s start with bags because we love bags! Probably a little too much.


Endurax ShellX P01

This is the bag I (Ryan) am currently using for my camera gear. I can hold my camera, drone and accessories, the DJI Osmo Pocket and accessories and all the charging cords and craziness. It has a laptop slot which was key for us, plus it’s water resistant and has an additional rain cover. Can’t let the gear get wet! It has a quick access top and body and it’s super durable with good zippers which was important. We are loving it so far and highly recommend it!

Earth Pak- Waterproof Dry Bag

We tend to spend a lot of time on boats when in the Caribbean and boats can be wet. So we always bring a along a good dry back along to keep essentials like phones, cameras, wallets, and things like that dry. Sometimes you have to swim up to the beach and you’ll be sorry you didn’t have a dry bag!

Wrangler 20″ Smart Spinner Carry-On Luggage With Usb Charging Port

Crystal and I love our current hard-sided carry-on luggage, but it’s coming to time upgrade. Our current roller roller bags are covered in stickers from different islands and beach bars, but they are starting to show their age. This Wrangler carry-on is what we have our eye on now because of it’s USB port and handy accessory holder. You will need to get a power bank, but everyone should have one of those anyways when traveling!

Foldable Duffle Bag with Shoes Compartment

This is what we typically use for a shorter weekend trip. It has a ton of pockets (which we love!), holds a ton of stuff and packs away easy for storage. Also great boat charters, any soft-sided bag is really, because space is at a minimum on boats.

Colorful Beach Bag

Crystal lovers her brightly colored pineapple beach bag. She is in a pineapple phase. You’ll see her in lots of photos and videos rocking pineapple hats!

Okay, on to some of our favorite clothing items that are packing essentials.

Clothing Essentials

Crystal’s Favorites!

Sunshine & Rum Shirt

Crystal loves to fly in this shirt because it’s long sleeves which keep her warm as she tends to get cold in airports, but it’s still fun and says, I’m ready for the islands!

High Waist Yoga Pants with Pockets

Crystal loves pockets! So when it comes to comfortable yoga pants, these are what she is always wearing.

Ryan’s Favorites!


When on island, I live in these things. You never know when you are going to jump into the water, go for a hike, or go for a boat ride. Boardshorts keep any guy ready for the island life. Some of my favorite brands are Billabong, Hurley, Rip Curl, and Tunaskin. The first three you can find on Amazon buy clicking the Boardshorts link, and for Tunaskin you will need to visit their website. They are a local southwest Florida company and we always love to support local, plus their stuff rocks!


The Jellypop Women’s Dallas Sneaker

Crystal loves to make a splash with the red Jellypop Sneakers!

Madden Girl Women’s Baailey Fashion Sneaker

Another one of Crystal’s favorite shoes. Great for travel, casual exploring and walking around town.

Crystal’s Keen Sandals

We think these are an absolute must when doing some island exploring. Great for the beach, hiking, and just about anything else. They can get wet, dirty and clean up easy. They are packed ever single time!

Ryan’s Keen Sandals

Again, simply an absolute must when traveling to the islands. We like to do a lot of hiking and off-the-path exploring and these Keens can do it all. They easily stuck to slippery rocks when exploring natural pools on Aruba and I even climbed a volcano on St. Kitts in them!

OLUKAI Men’s Ulele Flip Flop

I am a HUGE fan of Olukai footware. I switched to them because the Reef brand that I had worn for years was just too thin of a sole and had poor arch support. Olukai’s are rugged, comfortable sole and look great. The have ones that are nice leather for going out in and ones that are waterproof and perfect for the beach.

Hey Dude Men’s Wally Sox Loafer

Hey Dude is my new absolute favorite shoe brand. I have 7 pair now! They are super cool, but they are the most comfortable shoe I have ever worn. They are lightweight, casual and perfect for just about any type of outing. They have dozens of colors and styles to choose from. You’ll love them.

More coming soon!