20 people in search of wedding venue
Congratulations! My fiance and I just finished our search for our wedding later this year, which is also going to be pretty small (25-30 people) and it's really tough to find a venue. For us, we wanted something that was more full service so we didn't have to deal with multiple vendors - like we didn't want to rent a small loft and then bring in the tables/chairs, caterer, etc. I'm not sure your price point but we were trying to stay around $175 per person, all in, which is not easy either.
We looked at Craftbar and Jane and both had really nice packages in terms of food and drinks (though we heard the food at Jane for dinner is just okay) but in the end the rooms felt a little too cramped. We also looked into 'inoteca but our party would have been just a little more than their capacity, and we considered Lupa at one point too.
Originally we thought we'd have a 20 person guest list, and realized quickly we needed to increase that number. We also looked into the Harrison and Market Table - I think both places have a 20 person capacity for this kind of thing but I can't remember off the top of my head now since we looked at so many places.
We ended up booking Frankie's 457 on Court Street in Carroll Gardens - they have a great private space which is actually a converted brick stable that is separate from the restaurant. It's really cozy and the setting was just what we were looking for.
Good luck with your search and have fun with your planning!
Check out City Winery, which recently opened. While they have a private dining room in their wine cellar downstairs, the elevated dining area, which they already have the abiltiy to curtain off - in a really nice and tasteful sort of way, was what really caught my idea.
They have a fantastic wine selection, and although their menu is very geared toward small plates, I would not hesitate to ask what they could do for you to the tune of several courses.
This place is the latest event space that I'm obsessed with. Good luck!