Let’s start with a reality check. You’re headed for a bareboat charter someplace wonderful, you’ll have a luxurious yacht at your disposal and a multitude of coves, beaches, resorts, pubs, and eateries to explore.

Do you really need more? Does a hot fudge sundae need an extra dollop of whipped cream? If so, read on.

We’ll talk about what water toys you want to take in a second, but first, I have one word for you: rent. Yes, you love your kayak at home or your stand-up paddleboard (SUP). And yes, dedicated surfers ship surfboards to faraway waves. But not easily. The point is to slip through TSA, customs, and foreign entry as effortlessly as possible so that you’re not paying extra or risking spending your vacation dealing with lost or damaged belongings. (Here’s another reality check: 27 x 21 x 14. That’s the size in inches of the duffel bag that most airlines will accept. And it can weigh no more than 50 pounds. Overweight at American is $30, at Delta it’s $100.)

Take the kayak, for example. Nearly every charter company has kayaks for rent, and they’ll even lash them down on deck before you arrive. For example, the Moorings in the BVI partner with Caribbean Divers, and as easy as checking a box on your Moorings charter form, you can have a one- or two-person kayak for a week for about $200. They deliver and pick it up, so you don’t even have to wash it down. Same price for a SUP.

Also consider fishing gear though again, rent, don’t take it unless it’s one of those little reels of line with a sinker and hook. Every charter base is ready for you with better rentals. Don’t forget the fishing license for the BVI.

While we do take our own snorkel gear, we draw the line at dive gear. The merest idea of toting regulators or weight belts in my suitcase gives me the willies. Businesses like Caribbean Divers have it all for rent, and they even have boats to take you to better dive sites than you can venture to with your boat.

So, smarty-charterer, that’s a lot on the “rent” list. What are you bringing?

At the top of my list, as mentioned, is a mask, snorkel, and fins for everyone. Sure, the charter companies have a box of beat-up snorkel gear, but (ewww!) I don’t want that snorkel in my mouth, and their fins always raise blisters.

We’ve also added a pair of webbed hand fins à la “Man from Atlantis,” which are fun for everyone. Go to a big box store, try on snorkel gear, and bring it with you. It’s not all that expensive and well worth the effort. Besides, the suitcase volume-to-memorable-experience ratio is very much in the favor of snorkel gear.

We always carry reef runner shoes for walking around on rocks or ironshore. Again, big box stores will have them.

If we have kids aboard, we take a Reef Tourer underwater viewing bucket. It gives kids a clear view into the delights of a reef without scary snorkeling; you can also use it to check your anchor while staying dry. And it barely takes up any space in your suitcase, especially if you shove your socks inside.

Never leave home without underwater cameras, and make sure everyone has one. I’m partial to my GoPro Hero 12, which shoots high-res images (27mp!) and video with stabilization (about $300 everywhere). But I’m a pro, so I want the best. You can find a multitude of great waterproof cameras, both still and video, for $80-ish with features like selfie screens on the front and underwater flash. Check the depth rating; some don’t promise anything past 11 feet. We buy these beforehand and pass them to anyone who’s in the water, which provides an interesting documentary of our adventure. Add a couple of expanding selfie sticks for maximum effect.

Speaking of cameras (and no, this isn’t a water toy), think about bringing a drone. They can be surprisingly affordable, take amazingly good pictures, and provide an entirely different angle on your adventure. Just be sure to check the regulations for drone flights before you leave the charter base and practice ahead of time to make sure it doesn’t go swimming.

Another absolute take is a pack or two of plastic (not paper) playing cards. These saved us during what the locals call a “soft afternoon” on a San Juan Islands charter when we were cabin-bound. We’ve stopped carrying them after the youngsters aboard slaughtered us at canasta, but that’s our problem, not yours. Cards are fun, and though the last thing you want to think about when planning for your tropical getaway is crummy weather, it pays to have a backup plan. A travel set of Chinese checkers and Bananagrams are also good options for curing boredom.

If you’re more of a relaxed charterer, picture yourself floating on an inflatable air mattress in a quiet cove. You can get one of these from Walmart that weighs just over a pound. But you don’t want to mess with folding up and packing a soggy lump post-charter, so give it to your dock crew so that someone else can benefit from your packing foresight.

So, that’s the basics. To add some whipped cream to your charter sundae, plan to either rent it; take it and toss it; or give it away. But only after you ask yourself the all-important question: Do I really need it?

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MHS&P Winter 2025