Amy, I remember hearing about Windjammer Barefoot cruises back in the 70's. That always seemed like it'd be so much fun. I was sad to hear they'd gone out of business. I'm kind of looking for that kind of thing now. If Island Windjammers is the new version of that, (and why do I remember the Mandalay? Was that one of the barefoot company's boats?), I think that's likely where I'll end up. A lot of it has to do with itinerary and dates. Working within my spouse's work and vacation schedule makes it difficult to go when the time is right. And I'd lose my head if I went by myself.
Windstar definitely has the edge on luxury accommodations and such, which is also a plus. I think I would enjoy both types of cruises.
To be honest, the more rustic hand-on approach really appeals to me. I can navigate, read charts, and I know my way around sails, sheets, and capstans. I have decided snorkeling on Bonaire is a new bucket list thing, so any cruise I take needs to stop there. My recent snorkeling day on Cozumel reminded me of how much I enjoy being in the water. I want to do more of that sort of thing.
First world problems, I know. LOL!
Dave