Taking Mrs. Smails to Boston in late September for a 4 day weekend. I've been several times mostly for work but haven't done a pleasure trip there. We'll do all the historical stuff + North End dining, Mike's etc. Also Steelers are in town that Sunday so will try to score some tickets to the Patriots game. If my fellow FBG's have any great recommendations for activities, food, drink, culture etc that would be great! Staying at the Renaissance in Seaport.
With the idea in my head that Mrs. Smails is a foodie:
Ken Oringer is one of the best chefs to come out of Boston, check out Coppa (patio dining!), Toro, and Uni.
In the North End, home of the cramped Italian restaurant, make a reso at Forcella in the enclosed patio in the back. Best table in the North End, IMO.
An OG Italian food spot there is Terramia, as well.
The Beehive for live jazz and cocktails.
Dubliner if you wanna do the Irish pub thing, and they have live Irish bands as well.
Speaking of live music, Grace by Nia, walking distance from your hotel, and a very cool scene in the Seaport.
There are 10 good seafood places near your hotel, please don't go the North End and stand in line at Neptune. The bar at Ocean Prime is a nice upscale buzzy vibe.
Essex Rooftop. Small bites with a view