Captains’ Club Spotlight: Capt. Les Annan

21 November 2023 By Lauren Beck
Capt. Les Annan

Lauren Beck is the former editor of Dockwalk and was with the publication from 2006 to 2023. At 13, she left South Africa aboard a 34-foot sailing boat with her family and ended up in St. Maarten for six years. Before college, she worked as crew for a year, and then cut her journalistic teeth at Better Homes and Gardens and Ladies’ Home Journal online. She loves traveling, reading, tennis, and rooting for the Boston Red Sox.

The BOAT International Captains’ Club now welcomes more than 170 superyacht captains in its ranks. The idea behind the club is to help facilitate contact and the exchange of information and experiences for superyacht captains. This issue’s Q&A features Capt. Les Annan as he shares his journey to becoming a captain, favorite destinations, plus his top tip for captains.

How did you end up a captain?

I got my dive instructor’s certification when I was 18 and I was teaching in Colorado in the lakes. We also did trips to the Caribbean and a dive shop in St. Thomas was looking for instructors. Just two weeks from my initial contact, I sold everything, bought a one-way ticket, and moved to St. Thomas. I did a season with a dive shop there, and then thought that a liveaboard dive boat would be better. I ended up on a boat called Tropic Bird for a year. And then I did 10 years with trimarans on Cuan Law and Lammer Law. And of course, I figured out really quickly that you can’t make a living diving, but you can make a living being a captain.

What would you be doing if you weren’t a captain?

I would probably be doing some scuba instruction. I’m a Triton submarine pilot too, so I’d probably try to do something with that as well.

Where is your favorite destination for cruising?

The Galapagos. I spent a year there — I took a charter sailing yacht there and then trained the locals on how to operate it.


Where is still on your yachting bucket list?

I’d love to go back to the Galapagos. It’s fantastic. I’ve never been to Cocos Island, so I’d like to go there. It’s the closest point of land to the Galapagos, and it’s just a fantastic diving with big animals.

Where is your top spot for snorkeling/diving?

The Galapagos and the BVIs. The BVIs is really good because it’s so protected and there’s a lot of variety.

If you were marooned on a desert island, which crewmember would you want with you?

I’d probably have to say my wife, or I would get into trouble.

What is your best trick for keeping guests entertained when the weather is poor?

That’s always a tough one. It depends on the charter guests, because if they drink, then it’s pretty easy. But if they’re not drinking, then you’re going to have to try to whip out some games or something. I had a BVI charter once where it started raining the first day, first hour they stepped on the boat and it rained the entire charter, until about five minutes at the end of the charter. They dived and they had fun, but none of them got out in the sun because there was no sun.

What has been your most memorable moment on board?

When I got my submarine pilot’s license. I’ve done 220 dives at this point.

Biggest crew challenge you deal with as captain?

Crew these days are more sensitive. They’re more demanding and less experienced. I just say that the new crew are just a bit more demanding and squishy and soft. I mean, we have six different types of milk in our refrigerator.

What is your one top tip for other captains?

Just be as professional as you can. Don’t create personal relationships with your crew. Be friendly but I don’t recommend any kind of personal relationship with them as it just gets very, very messy. Be honest and have a moral compass — there are some captains out there with some very bent moral compasses.

This artcle was orginally published in the July 2023 issue of Dockwalk.

The BOAT International Captains’ Club membership is currently open to active captains of sailing yachts and motor yachts longer than 24 meters LOA. For more information about the Club and how to apply, email


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