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I guess it's just me but I think it's funny when someone asks if a 21 foot Whaler is enough for the Chesapeake Bay. I grew up going out on the Bay. Mostly the western shore of the middle Bay from point lookout to Sandy point. I've been all over the Bay but mostly those areas.

I have been out on everything from a kayak to a skiff to a CC to a DC to a bowrider to a Downeaster. I had a good time on all of them.

The Bay can be glass or it can turn to stringy green snot. I've yet to die. Now comfort is another discussion. How many people, how much gear, what you expect amenity wise. Those are deciding factors. If you use common sense, you can enjoy the Bay with any craft.

I know plenty of guys who would kill to have a 210 outrage for the Bay. If you can afford it, and it makes sense, go bigger. You certainly wouldn't regret it.

Best of luck with your purchase, no need to over think it.