...I don't mean to sound like an advertisement by saying "conveniently located." (I got really spooked by the lengthy warning to posters about NOT ADVERTISING anything...)
In other words, it's a nice short walk from the Windward House to both the beach and the pedestrian mall.
And there are a lot of interesting collections to look at all around the house, including a glass-enclosed case full of ceramic "nudie" statues! :0)
I've stayed at the Windward House several times. Unlike most other B&B's, they serve a hot entree for breakfast, along with other goodies. (I recall egg-and-sausage bake, raisin French toast stuffed with cream cheese, and egg-and-cheese souffle.) Sherry in the parlor is available in the afternoon and evening. It is conveniently located halfway between the pedestrian mall and the beach, on lively Jackson Street. It's across the street from The Ebbitt Room.
Wow I had a weird experience there recently. The bus boy musthave gotten mixed up and threw out our leftovers after we asked him to wrap them up. The wervice was kind of shoddy as well. It was a later dinner and the waitress kept disappearing. Finally our desert tiramisu as so tiny, a sliver as opposed to full piece and covered in whip cream to hide the small portion.