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Same! I looked into it myself, and it’s nearly impossible to pull off. Since I have no experience sailing, it would take me at least 2 yrs of training. I’d have to start off by volunteering as a hand on someone else’s sailboat. I’d also have to get a dingy to practice on.

Eventually, I’d need to find a reliable person that would also like to try this adventure out, is dedicated enough to develop the skills necessary, has the financial means to pull it off, and isn’t tied down by other responsibilities (eg house, family, etc.). We’d also need to get along extraordinarily well since we’ll be together for ~2 yrs in a small space and deciding where to go and what to do jointly.

Then, we’d need to drop ~$80k on a sailboat and another ~$20k on renovating it. Once that’s completed, we’d have to take a few shorter trips to test it out, such as sailing around the Caribbean.

Lastly, once underway, things could still get pretty bad. Mechanical issues aside, we’d have to worry about safety out in the open ocean. There could be violent assailants or storms. There could also be political unrest of unwelcoming area where we dock and resupply.

Basically, this adventure is really difficult to pull off because it’s not just sailing and living on a boat. There’s a lot more to consider.

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It’s easier than you think! You can get your basic keelboat certification in about a month at a training place. Usually only takes four weekends. Once you have that under your belt, you’ll be able to rent at places and get some experience. The fundamentals of sailing don’t change, though with a bigger boat you will need to exercise some caution.

You can do it!

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Thanks for the encouragement! I keep an eye out for opportunities and let people know I’m interested in case something shows up ⛵

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Sailing is a liberating and exhilarating experience. I love it very much, and I’m sure you will too.

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Look up Wilfried Erdmann, he was a famous single sailor who has circled the world a couple times. He has books on the matter where he speaks about the experience as well as the preparation and what kind of yacht he used. Very well written and interesting if you’re into that topic.

It shows that you can do it alone easily enough and that you don’t need some crazy high end yacht.

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As a more manageable and not quite as expensive option: a shorter sail might be most of the adventure you need.

I live in Boston and at one point joined a sailing school/club out of Boston harbor. They had mostly 35’ boats but a few up to 49’. It was so much fun learning to deal with open water, complex boats, crew cooperation.

However the one thing I wasn’t in a position to do …. They organized cruises on the bigger boats: form a crew and sail to the Caribbean! While it’s nowhere near around the world, something like this is a couple weeks at sea and seems like a really cool adventure

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Good idea! I have been at sea for over a month at a time, but that was with the Navy, so definitely not the same as sailing for pleasure. I know I really liked the peace of the sea. I can’t imagine how much nicer it is with the freedom to go anywhere there is a shore.

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