Re: First Timers Looking for a Short Trip..
If Stevo’s offer doesn’t pan out for you, I’d suggest just doing your ASA courses. You’ll get a feel for sailing over multiple days and it will be enough for you to decide if you’d like to invest in a boat for continuing the adventure.
Being in Missouri, you could do as my wife and I did, and sign up for an ASA101,103 and even 104 in Pensacola FL. We found a sailing school with a captain that only does couples. He prefers teaching couples as opposed to larger shared classes. We spent 4 days sailing in FL with one on one instruction, for about half the cost of a charter boat.
The experience gave us the confidence and knowledge to proceed with buying a small used boat, which we did, and now sail out of the same Pensacola area. The benefit of this approach is that you’ll get a taste for sailing, proper instruction, and a pass a certification all at the same time. Nothing wrong with crewing, but if your serious then spending $2000 on proper instruction is nothing. We would love to cruise full time, however now we have the means to continue improving our skills, learning, getting experience, and do some “commuter cruising” for a few years before taking off around the world. Like a “crawl, walk, run” approach.