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One of our favorite lines is “How hard could it be?” When it comes to trying something new, perhaps that’s the secret, just believing that things are possible in the first place? It’s what we did when we bought a boat without really knowing how to sail. It’s what we did when we left Canada for parts unknown. And it’s what we did when we decided to become a charter crew. In the latter example, with only our desire to learn and be the best charter crew out there, we had a couple of stellar seasons (until you know what happened).

While we’re now on another path altogether, there is a real need for quality charter crews in the Virgin Islands, to do exactly what we had been doing. How do I know this? Because we have very good friends in the industry that, on a regular basis, keep asking us “Can you recommend a good crew for us? We need good crews, several of them!” Note that I said crews, not boats. Our friends have the boats… large, nice catamarans. What they need are Captain/Chef teams who are eager to work, make money, and have fun in the process. Think you have what it takes to do this? Comment here and I’ll pass your names along to our friends. For the right couple, it can be a great gig, and like I said, “How hard could it be?

  • UPDATE AUGUST 2, 2015: Please see this important followup post.

PS: I guarantee you won’t be working with “that guy!


  1. Hello 🙂
    I was actually looking for an opportunity to crew on a
    Catamaran. Cleaning,chef and hosting guests would be right along my alley. I have lots of experience with hosting guests on a caramaran and some sailing experience (basic) on a catamaran. I’m single and happy to work with other people. I’m in Toronto at the moment and can fly over to meet the owners of the catamarans if required.

    My profile on Facebook is Bhavna bhikajee ad I have been following your page for ages. Please drop me a private message on Facebook if you have questions.

    Thank you.


  2. I am a recreational sailor, with dreams of leaving the race behind and sailing to the USVI. I’m planning my get away and a large part of that is being able to sustain the life. I would love to crew and possibly captain a charter cat. I’ve sailed and lived on boats seasonally, but haven’t found the right opportunity. Perhaps this is it…,

  3. Thanks for sharing this – I’m happy to hear that there is, in fact, a need. While we haven’t headed off the docks quite yet, if we need to re-fill our kitty at some point, charter work is certainly on our radar. Good luck to those searching, and to you guys on your up-coming adventure! We will continue to follow along, as always.

    – Jennifer

  4. Mary Beth and I are interested!

  5. I’m curious to know. What’s an average that a crew can earn doing chartering like this? Can anyone share a ballpark guestimate?

  6. Yes Please! Hey Mike, Janet and i still looking for a cat to work in the VIs this season .. Please throw our name’s in the hat when you get inquiry’s.
    Thanks, Steve and Janet

  7. My wife and I would live this opportunity, our sailing experience is limited with a monohull. I’m a retiring firefighter captain up here in Chicago. Our plan was to purchase a catamaran as a liveaboad down there. This would definitely help in this process and give us some cat experience. We were taught how to sail by our friends who were competitive sail boat racers. Yet it’s been a few years since we have been on a boat, since they retired a few years ago and moved away. We would love to help crew and get our sea legs back and help in our transition to living aboard a catamaran. At his moment I haven’t even talked to my wife yet, so hopefully she’ll be in, if they are willing to help make this dream a reality.

  8. My husband & I have been looking for a way to get jobs in the VI. He is currently unemployed (downsized) so this would be good timing for us. Where can we find more info on qualifications etc?

  9. Mike, we a very interested! We’ve been saving $ and trying to decide when to put our own home on the market. We are currently both Realtors in Phoenix, AZ & empty nesters as well. This would definitely speed up our timetable on coming down full time. We’ve been shopping for cats, just lacking the funds not the desire. Please pass our information along & hope all is going well with you & Rebecca with your new journey.

    Doug & Serena

  10. Oh shit Mike! See what you started,,, lol 😉

  11. I would love the opportunity!

  12. Damn! I’m going to have to step up the search for Sparky’s new mom.

  13. I would love to be considered for a charter chef positions! I am a business owner, Masters in Social Work and mobile social media manager with a passion for cooking and pleasing one’s pallete. I fell in love with the VIs last year when we chartered a cat for 10 days. My buainess schedule allows for breaks of time that would make me perfect for this opportunity. In my business, I provide boutique concierge customer service and would love to provide the same for charter customers.

  14. Experienced licensed captain already in the Caribbean a lot and have beautiful 1st mate that can make them smile captain also plays guitar , sings and does live shows on board featuring island music please send info. Thank you

  15. My husband and I would be interested. We currently live in Michigan and own a monohull, we are in the process of learning to sail, well we know the basics and a bit more but are not seasoned sailors as of yet by no means but we both love it and my cooking is not to shabby. Could you tell me more details or is this somrthing for sailors all ready in the area? Thanks for the info and Fairwinds

    Nicole and Richard

  16. Bhavna meet Travis… Travis meet Bhavna!

    In all seriousness, please share ballpark $$ range…
    Naturally lots of variables (# of weeks / size of tips, etc)

  17. If the guests will eat poutines everyday and are willing to stay docked Ren & I are in.

  18. I’ve been boating all my life and have my 50 ton USCG Near Coastal Masters with commercial towing endorsement. My dream is to own at least a 45′ or larger cat. The Lagoons have really caught my attention. I’d love to know more about the opportunities you write about.

  19. Hello! Cecil and I would definitely be interested. This has been our goal for the past few years. We have both been following your adventures for some years now. He has owned several boats…the last being a monohull. He has spent many a winter down island on livaboards and sailing the islands. I am an experienced cook/ hostess as both a profession and privately. We both have been self employed as well as have worked for someone. We understand the ins and out of each. He ran a very successful outfitting business for 18 years. Lead trips, hosted events, dealt with customers. I have extensive customer service background. We have extensive experience travelling together and living in small spaces. I am an avid diver/snorkeler. Love kayaking,paddleboarding, yoga and bodyweight workouts. He has years of experience diving throughout the islands, leading trips to following the grey whale migration in kayaks. Please feel free to forward opportunities to us or our information to those looking for a crew. We know it isn’t necessarily easy but also can be exactly what you want to make it. Thanks for the confirmation that this is a viable goal. We have enjoyed your blog and being along for the ride through your adventures.

  20. Damn this competition is getting fierce! Ok, so here’s my serious post.

    Captain 50 ton inland/OUPV near coastal, with sailing and towing endorsement. Hopefully doing an early upgrade to 50 ton near coastal. About 3-1/2 years experience running my own business, mostly running day trips on a 34′ cat, but I do have some charter experience on a larger cat as well. Mostly around the Keys.

    I’ve been diving for years, and have experience as a snorkel, kayak, and jetski guide (I know, we all hate jetskis). Getting freedive certified in about 3 weeks and may getting SUP instructor certification next month.

    We’re just missing the cook. And the little furry guy may be a deal breaker. He does actually help attract more business, though.

    Is this a work the boat all season and live aboard and sail the boat south for hurricane season like you were doing? Or do most of these boats generally give you a the off season off…minus any repairs, maintenance, refitting that needs to be done?

    I need to decide if I need to sell a certain boat, put her in storage, or move her to where I’d like to cruise during the off season.

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