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Ok, I'll break it down large, I want to see you out here.
1978 Bayfield 29, $11,800 (2018) cash cash, envelope full of bills. I put about another $10,000 into it since in upgrades. Larger anchors, chain, lines for everything, new standing rigging, upgraded electrical, home built LifePo4 batteries, GPS, AIS-B, LED lights, solar, wind, blah blah blah.
My dingy is a 2015 Riviera 12' fiberglass $1500. My outboard is a 2009 Yamaha 2stroke 15hp $1600.
My rent is approximately ZERO. I pay jack shit to fuck all. I "live on the hook". I have about $1600 in my mooring (3 anchors, 150' G4 3/8 chain, crane swivel, floaty thing, two lines to the boat from the swivel).
If I was going to live here forever I would need to plan on replacing the chain, swivel, and the connectors every 3-5 years, just to be safe ($1500 just to be safe). I'm leaving after hurricane season but because I have a mangrove swamp I can hide in up to a Cat3 storm I'm here until Thanksgiving.
I have 550w of solar, a Honda eu2200i generator, a 400w wind generator, and live off of 400 amp hours of 12v batteries (2x200ah). Home built at less than half the cost of prefabs in 2020. I love them so much.
New sails will be about $4-6K. My sails are 8 years old and I'm fully expecting to get at least 5 more years from them. I've taken good care of them.
My car is a 2002 Toyota Echo that was $1000, I pay $100 a month to park it about a 1000yards from the public dingy dock, which 99% are free in the US. Down island is a whole other thing, lots of places charge.
I don't have Starlink. If dickhole ever sells his interest in it, I'll have it the next day.
You absolutely can do this, but you will need to become radically self-sufficient. I haven't been to a slip or a dock ( other than fuel) in six years. I haul water by hand, I'm my own electrician, mechanic, sanitation worker, plumber, electric company, you name it. And paradise can fucking suck.
I dont have an oven, don't have a toaster, I don't have any heating or air conditioning. I do have some fans. I don't have hot water unless I put a 20 l can in the Sun. Living this lifestyle is as much about sundowners sunset, bikinis and fun as it is about what you're willing to fucking endure.
Marina's will run you from $300 - $3000 a month. They are hot, noisy, you're crammed RIGHT next to others and they are expensive.
If you want to get an idea of actual prices, take .25 up to .5 off the asking prices for pretty much anything under $80k. Search Tempest for Craigslist, search Florida.
If you decide yeah.... I'll absolutely help your effort and happy to answer any more questions you have.
[edit] Maintenance runs between $2-6k a year. If you preventative maintenance the living shit out of everything, you'll spend a lot less a year. I do 90%+ of the work myself. I purposely bought a small boat because small boats are small problems with small bills comparatively speaking. And also when traveling to communities that are less fortunate than most Americans financially at least, it's easier to interact with the locals on a small boat than it is on a large boat because they will accept you much faster than if you show up on a 50-ft plus.
What do you do for work? Your costs are low, but they aren't zero. I imagine it's nearly impossible to get work if you have to go out to your boat every day or you don't have reliable internet.
Also, is it possible to get/run AC on a boat your size? Florida sounds like hell without AC. I don't think I could manage living there for long without it. I guess you can get in the water to cool off pretty easily though.
Now that it looks like a storm is forming, I'll be moving and securing vessels for the actual wealthy, and I charge a flat rate of $100/hr. (I'm the blue dot). There's money to be made, you just have to hustle.
After 25 years in tech I'm starting to look for my "out". I have a ton of experience with electrical (signals/rf too), plumbing, mechanical, woodworking, finishing, engines, etc There isn't much I can't fix. As far as nautical experience goes, I'm a novice but I recently went through a small boat certification course and planning on being a "trailer sailor" for a couple years or more to build up experience. I grew up near Charleston SC harbor, and I think the ocean is calling me back.
A couple of questions; how do you find work or how does work find you? Do you have a home base where your tools are located or are you doing these jobs in "random" ports you travel to? (You can message me if you don't want to share your industry secrets publicly 😉 )
/edit Found your blog so I got some reading to do.
Work comes around by asking and telling. Once people know you can do something well you'll get more work. You'll have to diversify and lean into your strengths.
Guard your professional reputation with jealousy because once you get a bad name it'll spread around like wildfire and you won't get any work at all AND people will avoid being your friend. Oh sure other shit heals will be your friend but the respected people won't. Water Folk fucking hate shit bricks.
Every single populated anchorage has "A Guy/Gal" who knows the lay of the land. You absolutely don't want to piss them off and you for god damned sure don't want to take work/money from them, so you don't offer what They offer .... Get it? If they scrape and clean boat bottoms, you don't. This person or these people will be able to facilitate you getting work but you got to be on the good side and you cannot dirty their name.
Working In foreign ports without a work permit is illegal, It absolutely doesn't matter who you're doing the work for. The exception to that is if you're a remote worker working over starlink blah blah blah. But if you're turning a wrench or a screwdriver or a spanner chances are you're working illegally, and you're taking money from the pockets from land-based businesses, so you better fly under the radar.
So given the above, 95% of the work you're going to end up doing is going to be for other cruisers. Because you're not out here already, you probably don't know that there is not a group of people on this planet that can pinch a penny harder and faster than the cruisers. So you're going to have to offer work they either can't do or they don't want to do at attractive prices better than what's available on land/in port.
Home base is where my cat sleeps. I have no permanent address anyplace on Earth.
The REAL answer you are looking for isn't the answer you want. The real answer is, you have to get over your fear of not having a paycheque. You have to throw yourself into the flow of life and hope for the best. After living a life of steady, reliable income jumping into The Flow and hoping you don't drown is pretty fucking scary. Your success out here depends on you managing and overcoming this fear.
My blog sucks, and I am sorry about that. My contact info is readily available if you look for it and if you want to text or call me feel free. I would be more than happy to help you in any way I can other than giving you money. :)
[edit] If you want to read a REAL blog, There is a guy named Alex Dorsey who runs a website called Project Bluesphere. He hasn't really written anything in the last 10 years but everything prior to that is still relevant information and he did an absolutely outstanding job. I highly highly recommend it.
Any book written by Fatty Goodlander, especially, Buy Outfit and Sail, and he has another book that's more technical called Creative Anchoring.
I definitely appreciate your words and completely understand what you're saying. I finished reading your blog and like your "raw" perspective. You should update it with an "where I've been, where I am and where I'm going" post. It feels like a short story, over the span of several years, but you have a bit of a cliff hanger there 😉
I had a bunch of other stuff written but I removed it because it was scatter-brained and all over the place. I may in fact reach out to you for conversation. While our bearings might not be the same, I think there's a lot to learn and I like your style.
Thanks man. You're right, I should.