OK, I'll start, because we have to start somewhere...
SALEM MA PIMPAGE!
The thing about Salem is that it’s got historical buildings, shops, restaurants, wharfs, pirates, witches, antiques, a world class museum, and is very centralized and walkable. I just love walking around and looking at the buildings. The Peabody Essex Museum offers tours of the houses from various colonial periods, as well as the Yin Yu Tang House. It also holds some amazing art exhibitions.
The train station to Boston is walkable to downtown Salem as well. NOTE: The frequency of trains to North Station, Boston is less during the weekend, so some planning and attention to time is key for Boston excursions. It’s a half hour train ride from Salem to Boston. You can find the schedule here: [link]
I think that Salem would be perfect for a F2F because it’s low key enough that people can just chill without the pressure of having to Do Stuff all the time, yet, it has cool stuff to do in its own right, PLUS it is a train ride away from Boston. (they also have a new Salem-Boston ferry) It’s super cool!
Also, the Salem Willows has an old school boardwalk, arcades, skee ball, etc. and you can wander, buy a slice of pizza, some cotton candy, and fried dough. There’s also a couple arcades there geared for young children. The Peabody Essex also has some cool kids’ activities. You are also close to various beaches on the North Shore and the legendary Woodman's in Essex or the Clam Box in Ipswitch.
One potential issue would be transportation to/from the airport. Going on public transportation is a bit of a haul (lots of legs), though certainly possible. I think there are also some busses that go to and from Logan to Salem Depot as well. But as I move ahead in my discussions with the various hotels in the area, I can see if they offer any services with regards to that issue.
Peabody Essex Museum
House of Seven Gables
PIRATE MUSEUM
Plus many tours, and the various witch museums; lots of stuff to be found here: [link]
Restaurants:
A bunch listed here with websites (including one of my faves, Finz)
Also:
The Grapevine
The Lyceum
Cilantro
Bella Verona
Bankok Paradise
Lots of options.
Bars/Pubs:
In a Pig’s Eye
Salem Beer Works
(both have food as well)