>>249251I'm in the same boat(LEL!) as you
Always had the desire to take a year, couple years, rest of life off and sail the ocean. Being from MN, I've never been on an ocean going boat before.
My plan is as follows:
>buy a truck with a hitch(something cheap but reliable)I've got a car now. I'll probably sell it for ~$3k or so, fork over another couple grand and get a early 2000s Ranger or F150.
>buy a small ~14" sailboatLearn to sail. Minneapolis has three decent lakes for sailing(perfect spot to bring a lovely young lady and a bottle of booze). Take the occasional trip up north to one of the many glorious lakes we have in this state. Bring fishing gear along too.
>Buy a slightly larger sail boatBring this on bigger lakes, and Lake Superior.
Continue using both boats until finances and life is order where it's feasible to finally move to the coast and buy a ocean sailboat.
If I'm tied down by family or job at that point, hell, I'd still have two sailboats to use in MN.
The hardest part of the sailing dream is obviously finances, particularly finding a source of income during a long sea excursion. I've also got the obstacle of not living anywhere near a coast so it likely isn't going to work out. All I can really do is continue the 9-5, live cheaply, invest, learn a skill that can generate income with an internet connection, spend my free time sailing and generally being /out/ and /trv/ing, and hope it works out. I hope it works out for you too