My wife and I will be in Boston next weekend (Oct30-Nov1) and we've both been there before -- so I'm looking for your suggestions for "seasoned" travelers.
Also, regarding trasnsportation -- when I've gone in the past, it's been for business and I usually take a taxi from BOS into the city. Since this is a personal trip, I'd like to be a little more economical. It appears there is a shuttle that runs from the airport to the station which if I recall is about 10 minutes or so.
We're arriving at 11pm. Would it be better to just take a cab? Our hotel is near Fanueil Hall.
The taxi is far more expensive than it should be, but at that hour I'd absolutely take a taxi. Just make sure that the taxi driver takes the Sumner Tunnel. There is no shortage of taxi drivers in Boston who will take you through the far-less-convenient Ted Williams tunnel to try to run up the fare.
How about this -- any recommendations for drinks at a bar with a view? For example, we've visited Banyan Tree in Bangkok and Park Hyatt in Tokyo (and of course, since we live in Chicago we've been to the Signature Room at the Hancock Building)
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re: Top of the Hub
I wouldn't go there for dinner, but I think it's a very good choice for lunch, especially on a clear day. Lunch is half the price of dinner (so it's only very badly overpriced, instead of preposterously overpriced), and the view is a lot better. And FlyerTalkers should appreciate the terrific view of BOS that you get.
Specifically for the OP and others who are somewhat familiar with Boston but looking for the special places that are outside of the standard tourist itinerary, I'd put the Mapparium at the Mary Baker Eddy library very close to the top of the list. Not so coincidentally, the Mapparium is just a few steps from Top of the Hub. Or, if you're a serious or semi-serious baseball fan, it's a 10-minute walk over to the Bleacher Bar on Lansdowne Street, where you'll see Fenway Park and its former flag pole very up close.
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Top of Hub
I also agree the top of the hub is not worth it for dinner, but if you want a view and drinks, I would highly recommend going there after dinner.
They have a $24/person minimum, but their scotch is very reasonably priced, so you can go there for the view, and enjoy a glass or two with dessert. I believe they also have live jazz music.