Boat Men of the Caribbean

March 10, 2023 6 min

Everything works a little bit differently in the islands. From driving on the left with a left-side steering car, having your third beer of the day by 10 am and finding that all the grocery stores or fuel docks are empty, simply because the containerships filled with essentials have been delayed due to weather, or possibly for no reason at all. Everything is on island time, and locals and seasoned cruisers just know that there is nothing else to do but go with the flow.

Cruising websites and forums are filled with tips on how to deal with these little everyday annoyances and inconveniences that inevitably crop up as you live the island life. But there is one such ‘annoyance’ that just seems to literally keep popping up over and over and leaves everybody divided –boat men.

What are Boat Men?

If you have ever been anywhere in the Caribbean, you are sure to have come across these quintessential island entrepreneurs, colloquially simply known as boat men or boat boys.

These are the sometimes helpful, sometimes annoying and always present floating island entrepreneurs that race up, viciously paddle or awkwardly sail towards your boat as you come close to entering an anchorage or port. These boats are usually a bit rickety, and sometimes they are nothing more but a couple of kids on a paddleboard selling French baguettes in Bequia or a highly decorative barely floating tiki- hut-looking little skiff selling local fruits, jewelry or conch shells in Dominica. Or the over-eager army of little skiffs trying to help you tie up to a mooring in St Lucia.

The cruising forum Noonsite is a wash with sailors dived on both sides of the fence on this topic, with some users calling them a “protection racket” implying that if you don’t pay the boat men for their services, you are sure to “accidentally” lose a dingy or get ripped off when you go to shore.

Other cruisers and vacationers find them helpful in places like St Lucia, where they offer help to tie up to a mooring ball for a mere $5. This might seem unnecessary to most, if not all of us, but just remember, everything works differently in the islands-especially in the poorer parts of the Caribbean that see fewer tourists- and what’s pocket change to you is someone else’s livelihood.

So, what exactly do these boat men offer? Besides making you part with your money for services or goods, you might not actually need?

Your Local Concierge

The best way to look at the little skiffs enthusiastically making their way to your boat as you get ready to pull into an anchorage or port, is to think of them as your own personal island concierge. And if you help them -financially -they will make your visit to any island a more pleasurable experience.

And yes, it can be hard to see the bright side of what seems like a billion little boats and arguing Caribbean men and boys screaming and vying for your attention when you have just sailed hours with screaming kids, a seasick wife and an overly drunk great uncle that thinks that going full sail in 30+knots of wind is a good idea, but breath in the fresh salty island air and remember, everything works differently here- just go with the flow!

In places like Anegada in the British Virgin Islands, you will be inundated with men racing up to get you to eat “the best lobster” on the island at their establishment, followed by several more claiming the same. But you know what? All the lobsters in Anegada are great and if you get an “island concierge “to help you, they will make your reservations for you, take your orders to place at the restaurant beforehand and they will make sure that you get treated like royalty at their cousins’ bar or get a better deal on renting scooters from their sisters-brothers-uncles place. So, that little annoyance and frustration will be well worth your while to make your time on the island more enjoyable.

In other cases, a well-organized group of boat men, like Dominica P.A.Y.S. (Portsmouth Association of Yacht Services), may offer safe moorings, security patrols, and a single point of contact for the best local services. The Dominican model is one of the most successful and helpful boat man cultures. Instead of dealing with a swarm of boats jostling for position, you’re met by a single boat. PAYS boat men take turns and divide the incoming boats fairly. The approach is organized, simple and low-stress for visitors. PAYS members are typically polite, friendly, and very well informed.

But this is not the case in other islands, and although the process can be somewhat frustrating and overwhelming, using one of these informal island concierges will help you get anything you want, from dinner recommendations and reservations ashore to arranging tours to getting your laundry done. If you want fresh fruit or commemorative t-shirts, let him know, and he’ll bring something out to you, find the right guy to get it, or give you tips on the best market days and stalls to find what you want.

In a place like Dominica, the boat men work through an extensive network of family, friends and business contacts to meet your needs. They’ve got excellent local knowledge and can make your stay a whole lot easier and more convenient, and even score you better prices ashore. Some boat men can even arrange fantastic eco-tours of the island, sometimes leading the expedition themselves.

The boat men usually collect payment for the goods and services they deliver. They rarely mark up those costs and fees because, like a travel agent, a boat man typically makes money on the other end. It’s customary, however, to give a good-sized tip before you leave.

If You Take Care Of Them, They’ll Take Care Of You

So, what might seem like a complete nautical nuisance at first, is quite a blessing in disguise, and will ultimately help you have a better experience exploring the islands.

Here are a few tips to keep in mind when dealing with your island concierge to make sure everyone involved has a pleasant experience:

• Put some fenders out as soon as you’re in an anchorage as to avoid dings and scratches from eager little boats vying for your attention

• Have a game plan before your reach a concierge-laden anchorage. Decide in advance what (if any) services you require. This way you will avoid feeling frustrated, overwhelmed and confused at all the commotion.

• Don’t necessarily take the first offer. But also make it clear to other sailing salesmen that you have found your chosen concierge that’s dealing with your needs.

• Negotiate a fair fee for any service in advance and make it clear what you are looking for in terms of services and goods.

• Be honest and polite in all your dealings. Everyone is just trying to make a living!

• If you pick up a mooring, check whom it belongs to, and pay for its use. Check that the person you pay is the owner or person responsible for the mooring—not just some chancer. It’s a good policy to dive on any mooring to check its condition—what you can see at the surface may not be representative of what’s down below!

• In St Lucia, if your concierge helps you tie up ashore, do go and check it as soon as you can. It may be subject to chafe, tied up to a weedy-looking sapling or secured with an if-you-can’t-tie-a-knot-tie-a-lot situation.

• Some of the worst-looking local fruit is actually some of the best tasting. Companies can’t export ugly fruit, but the boat men know what’s good! Don’t be put off by looks, and try it!

• And if you’d like to become part of the solution, consider joining one of the sailing and conservation charities that work with local communities such as Oceanswatch.

And just remember, this is island life; everything works a little bit differently here. And what is mere pocket change for you is someone else’s livelihood. So, whether you love them or loathe them be kind to your local sailing salesmen and just go with the flow -unless that flow is your drunken great uncle going full sail into a nasty squall!