I've done the Delmarva a number of times in a boat no larger than yours, and with similar amenities (Stiletto 27). I became so enamored of the expereince, hopping in an out of the inlets, that I wrote a detailed guide book that I sell through Alibris and my blog, below.
That said, you've drawn a big challenge. No engine on the Bay is workable, but it's going to make the tidal inlets a hazardous proposition, unless the wind an tide are just so. Time is a problem too. Why rush the experience? It took me 8-10 sailing days each time, with shorter days in some cases, but that's on a boat that could motor at 10 knots and sail faster. It is about 450 miles, and given some headwinds, no winds, and bad days, that's a bunch! But I won't say that you can't do it - I do suspect some long days and a few evenings.
Read "Eastern Shore - Western Wind" for a wonderful account of the trip in a small boat. I think it was 24 days. There is also information on my blog. I hope you make the trip, but allow a little more time, I think, so that you can drink in the expereince. Your classic boat deserves that.
(when asked how he reached the starting holds on a difficult rock climbing problem that clearly favored taller climbers - he was perhaps 5'5")
"Well, I just climb up to them."
by Joe Brown, English rock climber
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