I spent a summer doing this around the Caribbean while in college

11/10 experience, would do again

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*no one is going to just let you rent a boat and sail off into the sunset without a captain's license, nor would I want to tbh

lots of things can go wrong and you want someone around who knows how to sail through storms, fix an engine, navigate without gps, read a depth chart, set an anchor, etc.

captains are great

I just found a guy who needed help bringing his boat north to avoid hurricane season and flew to meet him. You can do something similar if you want to really dig in but if this is a vacation trip then chartering a boat (and its captain) is the best way

It's pretty affordable tbh if you get a group together

no way, congrats

do you have any tips on getting a crew together, finding boats, planning the trip?