We haven't been on Windstar in a couple years, but no one ever checked our bank account statement. Unless things have dramatically changed (and I highly doubt that) what you will find is people who love to travel and enjoy a relaxed sailing experience. Windstar spoiled us for mega ship cruising really. Our favorite "shows" were the crew show where they perform their local dances and songs and of course, the watching the stars.

There is (was) a certain general elegance and sophistication of many of the cruisers, but that has nothing to do with jobs or money. If you are friendly and enjoy your vacation, you will fit in great.

My Windstar experience was over 10 years ago (Costa Rica, 1 week), but since there aren't many replies, let me just echo what Golfergal said.

There definitely was some serious wealth on-board (e.g., late in the cruise, other folks told me the (I forgot if it was the CEO or Chairman) of GM was on-board (and that was before GM went bankrupt!)), but as Golfergal said, no one was checking back accounts, everyone was friendly, and there was a pretty wide range of passengers, many of whom with very interesting back stories, so it was very fun to mingle and meet people. And it's not like everyone was fantastically rich and famous (or poor and anonymous -- I shouldn't presume which direction of "fitting in" the OP is wondering about! )

I'm not a big cruiser, but the three I have done have felt VERY different (Windstar, big ship Caribbean (RCI I think it was Liberty), and an Antarctic "research vessel" (Akademik Ioffe)). I definitely enjoyed the Windstar more than the RCI ship (better food, no crowds, better more personalized service, the "certain general elegance and sophistication of many of the cruisers", etc.) but there wasn't nearly the variety of activities and amenities of a big ship.

It's Windstar and Windsurf, cruises of choice, for us. There will be a mix of peole, most are early 40's I'd say, with some young ones and a few elders who are fit. All nice people and kind, never met a snob. A few times we have met people we didn't care to know any better, and we just avoided them..Food is excellent, you can get into places that the big ships never dream of, no long lines, no tipping frenzy, nice public spaces and great crew. What's not to like.

We are taking the Athens to Istanbul cruise on the 20th of this month. We certainly are not CEO's of anything . I will report back for you on the "fitting in" concern. I have had some of the same concerns myself. This cruise has been highly recommended to us but the friend who did so loves to hob nob and we don't so we will see.