Saying goodbye to the land life and sailing off into the sunset seems dreamy, and it is, until the bank account starts getting low. Then you are forced to face a bit of reality again.

Sailing takes money.

Boat parts break, beach bar drinks require cash, and mouths still need to be fed. There is no escaping those facts. You may find yourself standing around saying, “How Can We Afford To Sail?” But just because the cruising kitty needs a top up doesn’t mean that you have to move back to hard ground or sell your kidney on the black market.
There are a many work options out there if you are resourceful and willing. It is worth checking into work visa requirements, work permits, and laws for each country as they each differ and you don’t want to get pinched working somewhere you are not allowed to.


Here are some of the ways we ourselves have made money along the way, and some ways we have witnessed friends’ of ours pad their cruising account.

  • If you have a good sewing machine (one that can handle thicker boat materials), learn to use it. Learn it well. Take classes, watch tutorials, and perfect your craft. Because sewing a pair of pants and sewing a sail are two very different things.

    Eben was taught to sew as a kid, a skill that not many young men possess. He, and his brother Jair, have taken their sewing skills from just stitching stuff together creating.

    The first time we “made money” while sailing was in the Bahamas. Eben had pulled down our sail to repair a tear. He was using the beach as his “sail loft” and soon people were lining up to see if he could help them with their sails next. There aren’t many sail repair shops around, so he was in popular demand. From there he has gone on to create our bimini and dodger, our indoor and outdoor cushions, and to sew these same things for other people (for money!).


  • Having rebuilt our boat from the hull up Eben has amassed a huge gamut of skills. If you are like him and like to collect skills, and are good at them, you could prove handy in certain locations. Because, lets face it, not all the islands have the skilled labourers needed for certain boat jobs. So if you can fill a job gap let it be known to everyone around, and you may find work.


  • Crewing/Captaining boats. If you have the right certification/training there is a huge demand for crew and captains in the USVIs. This is a vacation hot spot that caters to people wanting to come charter boats. There are work positions for day charters (which consist of sight seeing, fishing, snorkelling, scuba diving, etc for a few hours each day) or term charters (which consist of sailing the Virgin Islands where you captain, cook, and serve for guests aboard for an average of 6-14 days). If you are considering charter work though, it is the service industry, so be prepared to serve, happily. Don’t be one of those grumpy waiters that hate their job.For more on this check out our friends’ blog Zero to Cruising, who spent some time doing term charters in the VIs. Remember, the USVIs are part of the States and so you need to make sure your certification is valid here and that you are allowed to work here.
    You can also use your certification to do boat deliveries. If someone’s boat is in one spot and they would like it brought somewhere else but do not have the time, confidence, or experience to do so themselves, they may hire a captain and crew to deliver their boat to said place. These are usually more “one off” type jobs, but they can be quite lucrative.


  • There is also the possibility of getting work on land. I used to teach English as a second language, and although I have not used my training to teach while we have been sailing, in my younger years I had spent 2 years doing so in Southeast Asia. Now I am content with teaching our daughters!

    But outside of teaching, if you are in a touristy enough area there are many jobs available in the tourism and service industry. Do keep in mind that depending on what country you are in, you are up against the locals trying to get a job, and so local salaries may apply, sometimes it is not worth working for pesos!Our friends’ from Where the Coconuts Grow made some money last year working in the food service industry, on the water!, when she got a job working for Pizza Pie. It was fun work, where days consisted of being covered in flour while in a bikini, and the pizza is stellar.


  • If you are floating around somewhere for long enough, like for hurricane season, and you have some sort of specialized training, you can offer to give classes to other boaters that are “waiting out the season” as well. Once a week yoga classes, sewing tutorials, cooking classes, weather classes, etc etc. You can make these “paid” classes, or offer your knowledge for free. And by word of mouth maybe a job will come looking for you.


  • Online money. If you have a “land job” that can be done from home, from a computer, well you are golden! Take that job and start sailing. But this also means that you will most likely be requiring internet every now and again, so make sure to plan your sailing destinations around that. Internet can be a little tricky in some islands, but on average with a good data plan you are fine. A great blog to check out about online opportunities is Saving to Sail. Melody uses her skills to do all sorts of jobs. She writes, she does web design, she monetizes her blog, and she even sells stuff online (by running her own jewellery business and selling golf clubs on Craigslist!).


  • If you are “in the know” with social media and can keep up with all the new online fads, there are job opportunities as a Virtual Assistant. Or if you are a writer some magazines will pay for articles, as well as buy pictures. You just need to seek them out, learn the style of writing/pictures they look for, follow their guidelines and submit your work. And ff you are a blogger there are ways to monetize your blog, with ads, affiliate links, sponsors, paid posts, etc. I am not the best at bringing home the bacon in this department, but I am sure you can find plenty of tutorials online about this subject as I know some people ACTUALLY manage to make a living off of their blogs. 


  • Can you make something worth buying, then do it. We have had plenty of people tell us that we should start selling the shell necklaces that Eben makes, or the salt scrubs that I have made. And I swear one day we will get around to doing it. But this is another way to make a small income. You can start your own website, or sell on sites like Etsy, or even seek out local shops that might be interested in selling your goods (for a cut). If this is the route you choose make sure your stuff looks nice and professional, because you can’t just slap a shell on to a string and hope to make bank.



There are plenty of jobs out there that can keep you afloat, probably way more than what I have mentioned here. But at least this is a start, possibly a glimmer of hope for some, knowing that suburbia is not the only place to make money.