January 21, 2020 by James Kell

22 Gear Tips for a Caribbean Sailing Vacation

After some gear tips for your next sailing vacation?

Looking at a week sailing in the sunray-bending warm waters of the Caribbean (or the Mediterranean)? Earlier this year we wrote a piece offering gear tips for skippers. Following this post we were asked for tips for crew and non-skippers who are about to head out for a week on a boat in the Caribbean. Below are some suggestions in no particular order. For brevity the clothing suggestions are all for men (sorry). Nevertheless it should provide a decent enough guide for women. If any of you have tips please leave them in the comments section below. Please note this is not for the hard-core, cold weather sailing. This is blue-sky, vacation stuff.

1. Sunglasses

Cheap sunglasses may damage your eyes. So get a decent quality pair. Polarizers take out the glare. Yes you might have to lift them to read your phone but on balance they are worth it. There are plenty of different brands around. Persols are what I use and are expensive but awesome. Oakley, Ray Ban, they’re well known and all good. Dot Dash if you are on a budget but still want something decent.

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2. Shorts

You can look at some specialised sailing shorts like these bad boys from Zhik or just buy some great basic shorts like these from J Crew. I love those J Crew shorts. They get even better with sun, salt and age (until they get shredded after you've worn them every day for a season). Get a size under your normal size (I’m talking about the J Crew shorts - they are sized a bit larger).

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3. Shirts

Again you can go gear-freak and buy fancy wicking material if you like. However for those of us who are not Volvo racers and spend our time sailing in warm weather a simple cotton t-shirt usually suffices. Some skippers love the merino wool long sleeve shirts. These don’t smell, last for ages, are cool(ish) in the heat and warm when it’s chilly. Here is a link to Icebreaker if you shop Amazon and here at Backcountry (the brand Icebreaker is the original and the best, from NZ). They ain’t cheap but it’s quality you are buying here.

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4. Shoes

There are two types of sailors: those who wear shoes and those who actually sail where it is warm. Shoes are for shore. Even then it's optional. Yes you might stub a toe every now and then but then you know that part of the boat a whole lot better. A simple pair ofSperrys is hard to beat. If you’re thinking flip-flops/thongs/jandals, try a pair of Havianas. They are basically Australia’s national dress (even though they’re from Brazil. Whatever. They’re awesome.)

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5. Hat

A subtle disclosure here, we happen to sell the coolest sailing hats everrrr. You can get yours here

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6. Rain Jacket

We’re talking summer sailing here. In the Caribbean it tends to pour rain for short periods. They are usually pretty warm showers. Only the serious blue water sailors would need proper sailing foulweather gear. I live in the Caribbean and find I need a rain jacket only a few times each season. A light jacket like this from Mountain Hardware (here is the women version) and if you have more to spend, this from Arc’teryx is excellent. These are light and multi-purpose.

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7. Reef-friendly Sunscreen

Most sunscreen is apparently bad for coral reefs. Make sure you get some that is OK. Here is one made in the US and made from natural ingredients.

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8. Bug net

If you can bring a little bug net with you your evenings on the dock will be much more pleasant. It might take a little innovation to rig up a system. But it's worth it (and you won’t be swimming in chemicals as you try to sleep). Here is one designed for travelers. 20 bucks well spent.

9. Kindle

"I just like the tactile nature of books". Says nobody who has read their first book on Kindle. Want your entire library in your carry-on? Want the instant definition of “estivation”? Hear of a book during your travels and want it, now? Get a Kindle, the Paperwhite is fine.

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10. Bluetooth speaker

There are plenty of decent speakers available nowadays. Ultimate Ears (UE) are the best we've heard (better than Bose even). Sound is awesome. Waterproof, shockproof. Very handy on a boat. Mine fell overboard while we were out sailing once. We turned around, did an MOB on it (yes they float), rinsed it with fresh water and it was good as gold. If you're not convinced about the sound quality head to a comparison site. If you bring two speakers you can pair them so you get bigger, fuller sound.

11. Freediving gear

If you're chartering a boat there is a good chance they will provide snorkel gear. However if you'd like to try a bit of freediving while you're there, either bring some freediving fins and decent snorkel/mask in a kit like this from Cressi (and if you’re serious, a rubber weight belt like this) or buy them when you arrive. Incidentally you can pre-train the freediving component of your vacation with help frm an app. Get into the AppStore or Google Play and search for freediving apnea or just apnea - it will point you in the right direction. Here is one example for iOS. Here is another for Android. If you're after a bit of harmony with nature, freediving is the *best*. Scuba is the equivalent of powerboating. Whereas freediving is the equivalent of sailing. Hence my bias. :)

12. Strange integrated mask/snorkel thing

We have seen this around. It is great for kids as it avoids the separate snorkel piece which can fall out of their mouths causing issues. It doesn’t fog up either. Clever, if a bit odd. Check it here.

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13. Collapsable duffel bag

You shouldn't need to bring too much stuff. It is good to have a bag that can fold into one of the little compartments that boats have. Here is one example.

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14. Cup-sized Inverter

Some boats only offer 12V power. Pick up a little cup-sized inverter and you'll be able to charge your devices no problem. Here is one for thirty bucks. One is fine for your whole group.

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15. Solar Powered Battery Pack

These things used to cost $100. Now they’re $20. SO good. Nice backup should there be issues with your inverter. Here is a link.

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16. Slackline

OK we confess this is a bit of a luxury. We're starting to add weight to your kit here. However if there are a few of you then it can be great fun for one of you to bring a slackline. There are plenty of coconut trees and sandy bases in the Caribbean. One of the best, healthiest ways to chill out on land. Play some music, find some shade and take turns slacklining. Gibbon is pretty well known in this area.

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17. Hammock

It’s hard to beat swinging on a hammock in the Caribbean warmth, sound of waves lapping nearby. You can get this lightweight variety or if you’re into a heavier cotton feel (that’s cheaper and not as strong), this. We’d recommend the lightweight one shown in the image below.

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18. Waterproof case

If you're sensible you will have some sort of specialised waterproof case for your device. If you're like me you make do with zip-lock sandwich bags. I've crossed oceans with the trusty ziplock and never had an issue (my saying this means of course that I will, probably later today). Nevertheless here is a link if you like the sound of a more specialised case. :)

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19. Airbed Sofa Thingy

This is awesome. We have one on order. They retail for $100 but you can usually find one for half that. Check it here.

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20. Multi-tool

If you're handy with things, bring a multi-tool like this from Gerber. If you're not handy, bring a nice smile, some charm and get someone else to fix it.

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21. Headlamp

If you have seen our tips for skippers post you will have seen this (plus a few of the other tips) before. Nevertheless no matter what your role on the boat, a little headlamp can prove to be very handy at night. If you’re just a passenger for a week or two keep it cheap and cheerful. A headlamp like this comes well recommended and will cost you less than $15. A bit more can get youthis - probably worth it.

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22. Ron Zacapa 23 (and Don Julio Añejo)

Our tip for excellent rum (the only rum we sip) is Ron Zacapa 23. It’s awesome.While we’re on topic, if you haven't tried Don Julio Añejo you haven't actually tried tequila. Just sayin.

Conclusion

You really don't need much sailing gear to enjoy a week sailing in the Caribbean. In this post we list essentials and also share some "nice to haves" so you can enjoy your sailing vacation that little bit more. Most of them use our affiliate links. Same prices for you, we just get some love if you click on them that's all.

Author James Kell started Sailing Virgins early in 2016. Sailing Virgins offers sailing courses between November and July in the Virgin Islands. In one week (if you have experience) or two weeks (if you don't) most people sitting a fast-track course will be able to become a sailing skipper. See https://sailingvirgins.com for more information and to check out courses.

Thanks to Jens Werenskiold, Xavier Strawson, Michael Crisp and Matthew Ross for helping out with this list.

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