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Ok I'll get into it briefly, above all remember that people's idea of comfort and what they need to survive and be happy is different for everybody. Some people can live very happy on very little, some people are miserable even with what most consider a lot.
>Buying a BoatThe cheaper your boat is, the more time you're going to invest in fixing it and making it seaworthy. You can get boats for free that may take a few thousand dollars to repair, but afterwards you have a fixed up boat worth $10,000 that you spent less than half of that on. Here's a list of cheap options, in order of least to most: YMMV
go to a few marinas and tell them you'd be happy to take an abandoned boat off their hands and fix it up while renting a slip there.
-Derelict or semi-abandoned:
Ask around and find somebody who has a boat where they're paying for a slip but never using it. They might be willing to let it go for next to nothing just to stop paying rent on it.
(what I did) shop around on craigslist and walk around marinas and find one in your price range, with features that you are happy with. This option frees you up a bit to decide what you'll be able to actually afford to fix on your own after acquiring the vessel.
MY COST: $1800
>Parking your BoatWhere are you going to keep it?
-Marinas: (Where I'm at Now)
Some marinas have minimum boat lengths to allow liveaboards, some don't allow liveaboards at all. Most require insurance. What I've found here in Texas at least, is that the cheaper the marina, the further out in the empty farmlands and fishing towns you are. Make sure the location suits your needs while fixing the boat up and learning to sail.
This isn't an option if your boat needs lots of repairs. Also it's a bad option IMO if you (like me) are just learning to sail. Really I'd say the only reason to do this option is when you are actually travelling.
I've seen advertisements for rich people who have big houses and a private dock on the water. They're never there because it's a vacation home, and figure they can make some extra money to pay the bills and have a set of eyes on their land by renting the dock out to a boat person.
MY COST: Currently $370/month but it's a super fancy gated marina with a yacht club, pool, restaurant, and all that rich people stuff. I stayed at one for a while that was $150/mo and did an overnight at another that was $200/mo.
I didn't do a ton of research, but Boat US is what I got and seems to be the best. Less than $300 for the full coverage this year that I already paid off and a $150 one time yearly fee for towing insurance.
MY COST: $450
>Living expenses and lifestyleThis one is where your personal comfort will come into play. I buy vegetables and grains, and then catch crabs and fish on my boat. It's healthy and cheap, and I love it. I installed solar panels for electricity, and right now water is free at the marina but several gallons for drinking every week when travelling won't significantly alter my grocery budget. For entertainment I sail, or kayak, or fish, or go to the beach. All of which are free! And I make hard cider on the boat for my alcohol needs.
-Groceries: $50 a month
-Stove Fuel: $15 a month
-Entertainment: $0 a month
-Gasoline: $5 a month
Then as far as repairs go, I bought a boat that I knew I could fix things on. It's got a simple outboard 4 stroke, and everything else involves simple sewing, drilling, electricity, and maintenance/cleaning. Nothing crazy expensive really. Including the Solar Panels I probably put less than $800 into repairs and the boat is great now.
All the old retired people on the cruisers forums and stuff bitch about cost because they can't stand to go without a marine grade refrigerator, air conditioner, automatic bilge pump, wall mounted television, full bathroom with a shower, and so on. You don't need any of that shit out here, so if you go without it you never spend money repairing it. In addition to that, I find a lot of the people who complain about how expensive owning a sailboat is are the kind of people who hire expensive professionals to do everything for them. It's not hard to get down in the water and clean your boat off, but the guys who come out with scuba gear and do it charge $70/an hour and take at least 2 hours.
Let's average an anticipated repair cost at about $100 a month, I think that's being generous considering I can go without most stuff if needed as long as the boat still floats.
Adding it up you can see I spend under $500 a month. The marina fee is 74% of that cost, so out on the journey I imagine bringing my cost down to $200/mo will be no problem. Just working hard every day to save extra money and learning to sail better for now, when I feel the time is right I'll be on that journey, on that budget, and we'll see if I was right!
If you are serious and wanted to do something similar, I'd say have around $5000 in savings and a confident way to generate at least $300 a month and you'll be fine, provided you aren't afraid to rough it a little and learn about yourself. It's an exciting challenge man.