Re: Boston By Air
I vote Legal Seafood for seafood -- specifically go to their Legal Harborside location (they have several restaurants throughout the city, this is the one on the water with the amazing views).
If you want steak, I say go to Morton's. Best meal I ever had.
The little speed boats look like a lot of fun, and I would totally do that. I don't think they'd be dangerous if you're reasonably competent. Nothing in life is without risk...
I think you should visit the USS Constitution, if she's still there. This morning they took her out into the harbor for some unannounced purpose (not even a story in the paper for a notice in the LNM), so it's possible she's drydocked now or something, I'll know more when I get home.
I'm a huge fan of the Isabella Stewart Gardner Museum. It's a great art museum, but the building itself and the courtyard in particular is the real draw for me.
You should definitely visit the harbor islands. Georges is my favorite for going ashore, but Peddocks is my favorite for picking up a mooring and swimming/grilling/taking in the sights.
The Sam Adams brewery tour is a lot of fun, but I think the Harpoon tour is better, and it's even near the waterfront. I think many people would say Harpoon is the best local beer, at least the best of the big brands. There are so many tiny breweries you can't even count them.
A lot of people seem to enjoy the duck tours, but I haven't been on one since I was a kid so I can't comment on that. If you do take a duck tour, make sure you go with the classic duck tours (they have the ex-military duck boats). There's another company offering Super Duck Tours which are like someone tried to waterproof a schoolbus -- they look very unsafe, and always ride in the water with a significant list to one side. The Super Ducks are the only ones that go into the harbor proper, the regular duck tours stick to the Charles River. It's odd to me that the more seaworthy one would be the one in the more protected water, but that's the way it is.
I agree with a previous poster who commented that most of the "sailing" harbor cruises do not in fact sail. Adirondack III is one of the few who appears to sail most of the time. I think Liberty Clipper sails most of the time too. I have never seen Formidable under sail, and it actually looks really sad... it's a small boat (not a tall ship by any stretch) built in the style of a galleon and it looks like a toy or B-grade movie prop. It does have a cannon, which is a plus, I guess. Most of the harbor cruise boats congregate at the USS Constitution every evening to witness her fire a cannon at sunset, and Formidable often fires back.
Good luck and have fun!
1979 Gulfstar 37 Laissez Faire