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In yesterday’s post I wrote how we came to find multiple friends at anchor here in the USVIs. Last night we were able to meet up with two more couples who, like other friends of ours, have been here for some time. Why here? Because they are US citizens and have been working, refilling the cruising kitty. The friends that we shared some pizza with last evening (awesome pizza by the way) have all been here for at least a year and a half!

This whole work thing intrigues me. I think it’s the part about money going in to the bank account as opposed to only out of the bank account that is the attractive part, not the work itself. I did a little online digging to find out how a couple of Canadians could get in on this gig. For example, what if we wanted to run a charter boat here? From what I can gather, it doesn’t seem like I would be permitted to captain a US flagged boat in US waters, not being a US citizen. I could captain a foreign-flagged boat but in order to do so, I’d need to obtain a C1/D visa. What’s involved with getting one? It sounds like quite an extensive process. Have I mentioned how much I hate paperwork? If you’re gone through this process, please share your experiences.

Yesterday, along with our friends Shane and Steve, we hiked around historic Hassel Island. In less than an hour we plan to raise anchor and head to St. John, hopefully to do some more exploring. Perhaps that will get my mind off the whole making-money thing. 🙂

Charlotte Amalie Harbor. We’re in there somewhere.

The Shane’s-eye view.

Wasn’t that nice of them to leave this pole there for Rebecca to play on?

Someone other than us hamming it up.

More playground equipment. 🙂


  1. I think, if somehow you can infiltrate the large yacht charter trade with what you love to do (fitness) as work, you might find a very lucrative cash flow. I’m not imagining full time but something more in line with the charter company’s offering it in some way to their clients. I bet a lot of unfit people while visiting the islands, run through their minds over and over, “I wish I looked like that”

  2. I am interested to know other than Captaining a charter, what other work have your friends found to replenish the kitty?

    • Our friends who are not working on charter boats are still involved with the marine industry in some respect. I know one runs a ferry boat, one works in marine refrigeration repair and another works from an office, coordinating trips, etc.

  3. Dorsey Wallace with Wallace Marine Restorations - Reply

    Mike, I was under the impression u just needed a 6 pac license..I am interested in the same thing. I am getting all my sailing cert first, but want to get 6 pac, which is supposedly in the US anything up to 100k lbs and 6 guest. Does that sound right or am i lost 😉 ?????

    • USCG licenses are for Americans only, which we are not. If you search the word Yachtmaster on our blog you’ll find info on the British equivalent.

      • I live in the US and got my USCG 6 pack as a British National, although at the time I did have my green card.

        • True. Again, based on my research, US residents can get a 6-pack but you must be a US citizen to get anything beyond that (masters, etc.). It’s kind of a dead end unless you are a US citizen.

  4. I believe there are more rules, a foreign flagged vessel cannot charter between US ports (why all the cruise ships head to a foreign country, even the Alaska cruises have to stop in Canada), and even a US flagged vessel is prohibited if it is foreign built, like ours.

    Not sure if I want to return to the land of rules when it comes time to refill the kitty, or try and deal with another country’s rules!

  5. I’m guessing the “awesome pizza” was the Pie Whole? That place is so banging. Enjoy St. John’s! Also, there are a ton of people tending to the kitty in Ensenada Honda, Cubebra. It’s a bit cheaper than USVIs in terms of groceries and expenses. Fair winds,

    – CC

  6. Mike
    Just wanted to thank you for the pix of us on Journey — great way to remember a nice morn with you two. Sure wish we’d read your “Ready to Get Wet” book before we went to Dominica!

    Also, It’s no coincidence pageviews jumped pretty dramatically. My pageviews are doing ok; yours must really rock!

    We too had to emergency anchor due to our first-time engine failure, and it was less than totally smooth (understatement). Right after our breakfast with you! Like yourselves, we were on our way to gas (and propane & water) up, but so far it’s looking like that’s not the cause. We’re chipping away at it with some local help, but are still not sure the exact cause or cure and are stuck here just West of Charlotte Amalie until we sort it out.

    Enjoy St. John! We look forward to visiting there when we return to this neck of the woods someday. Look forward to using your photo tips when I have an underwater camera I trust for underwater photos.

    I’m sure you & Rebecca will find some brilliant way to refill that cruising kitty. You two do a first class job on anything you tackle.

    Smooth Sailing!
    Dana & Wayne of Journey

    • Thanks for the nice comment, Dana. Sorry to hear about your boat issues, especially as I know you were really ready to get out of there. Hope everything gets resolved quickly and with few boat bucks spent.. Keep in touch.

  7. If you want to hike in St John get the trail bandit guide/map. Well worth the 4 $. We have done almost all the trails in St John by now. Only one thing, there are no waterfalls. Everything else is fine.

  8. I just love St. Thomas, our daughter lived in French Town just across the channel from Hassle Island.

  9. Thats why you should go to BVI’s……With that said, I believe the USVI’s are exempt from the charter provision of Jones Act on Foreign Vessels, but double check….

  10. When our daughter was living in the USVI/BVI she worked on two different charter boats, one a US boat and the other a BVI boat with a US native as owner/captain. Both boats were licensed to take charters to any islands between St. Thomas to Tortola, Virgin Gorda and areas around there. She and a friend had checked into operating a ‘six-pack’ boat for fishing and snorkel trips and found that the rules and regulations were VERY strict. She said fishing in the waters around the BVI’s can be very risky also, as she witnessed people being arrested off the coast of Tortola.

    • I assume arrested for not having proper permits. If that’s the case, I wouldn’t call it risky. It would be illegal. If that’s not the case I’d love to hear why they were arrested.

      • If I remember correctly, he had a permit and had unknowingly drifted into waters his permit didn’t cover. He was an elderly man, and was arrested and then loaded onto a ‘police’ boat and hauled off to jail leaving his wife on their small boat drifting, not knowing how to operate the boat. A couple of the crew members from our daughter’s boat boarded the boat with the lady and took her to their island home, I think on St. John. Then she had to find a way to get the old man out of jail in the BVI’s. I think she said the old guy stayed in jail something like 3 days. Our daughter said their charter guests, 4 couples from Texas, kept up with all the details and even tried to help the old lady get the man out of jail days later.

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