I am 19, been on boats all my life, and will be purchasing a Columbia 8.3m next summer out of Manitowoc, WI (on Lake Michigan). I'll be spending the entirety of next summer on the boat, learning it, bettering my sailing skills, and exploring Lake Michigan. The following summer I'll be graduating college, and would love to charter sailboats on the Great Lakes (it may take awhile for me to be able to live more than driving or sailing distance from Chicago). I saw a few people who do mostly day sails, at a rate of $150/hour, and didn't have prices for longer trips on their website. This price makes it possible for me to purchase a Catalina 30 or similar, which has two cabins to make longer crewed charters possible. However, I have a few questions which I hope some more experienced members may be able to answer.
First, I see that all the charter companies (sailing and fishing) have captains with a coast guard license. How hard/expensive is it to get said license, and is it helpful legally, or just to inspire confidence in possible customers?
Second, how much is insurance on a boat that is to be chartered?
Third, does anyone have a knowledge of what the sail-chartering market is like on Lake Michigan? I see fishing charters everywhere, but it took a full three hours of searching to find a crewed sail charter.
Fourth, it's hard for me to ignore inexperienced people's thoughts that this is not a possibility for me. If anyone has done it, on the Great Lakes or otherwise, please help bolster my confidence.
I know the basic costs involved with keeping a boat, and can do the math, but if anyone has any insights into things I may not be thinking of, don't hesitate to interject. Thanks for all your help.