FutureMrsReilly: It’s really hard to find a place in that area that can accomodate that many people without charging a room fee at lunch time that isn’t a chain or corporate restaurant. I live just outside of the city, but have lived in and worked in the city for over a decade. I bartend and FI is in wine industry, so we know a lot of places to check out. But what you are asking for is tough.
I like Parish Cafe on Boylston St. They prob can’t accommodate all of you, but you could always put in a to go order and have 30 sandwiches ready to be picked up. It’s near the park and the library, so you could have a little picnic.
There is also Mooo, on Beacon Hill, by the statehouse. It’s a steak house, but they have prix fix lunches and a private dining room that looks into their wine cellar. It’s $$$$ but the food is awesome. The day chef has been with the company for years. He cooks a steak better than anyone else I know. Legit.
Legal Seafood is also near you, and they are open for lunch.
Beyond that, unless you do a chain restaurant or something in the hotel, you will be shelling out $$ for 30 people to dine together at lunch.
FI and I are restaurant “industry” people and have pretty much gone to any restaurant worth going to in the city. I would be more than happy to make a few recommendations as to where to find the best whatever, and anything else off the beaten path.
The South End is where all the smaller haute cuisine/ farm to table restaurants are. I LOVE the Salty Pig, the Buttery, and the cocktails at Coda a great. The North End is overrated, as is Mike’s Pastry. I think Modern Pastry across the street is much better and they have smaller lines (cash only). Giacomo’s is my favorite italian spot and Neptunes is the best seafood. Avoid Fanuiel Hall. Nothing worthwhile beyond sight-seeing (although the Holocaust memorial is heartbreaking and moving). The bars over there are always packed with college kids, too.
If you want a super-dive bar, I like the 21st Amendment on Bowdoin St. on Beacon Hill. It’s an interesting mix of lawyers, suits from the state house, and college kids from Suffolk. It’s my watering hole. No. 9 Park is also on Beacon Hill and that is where I am having my wedding reception. It is fine dining and quintessentially Boston. The Seaport area is new- an initiative by our former mayor the rebuild the area. It’s booming with restaurants and business. If you want fancy, pretentious-but-good cocktails, go to Drink. There isn’t really a sign for it on the building, so make sure you get the address and look for it.
If you and the ladies want some fun the night before the wedding, go to Jaques to see a Drag Queen show. Quite possibly the most fun I had with my girls ever!
The T is super easy to use and Boston is a small city. I’ve walked from one end of the city to the other in just a couple hours. Wear sneakers- the cobblestone streets in the older parts of the city are brutal- and you will want to walk a lot. If there is any museum you need to go to it’s the Isabella Stewart Gardener Museum. It’s breathtakingly beautiful and where FI proposed to me. The American Wing at the MFA is spectacular, as well.
Also, don’t discount Cambridge. There are 7 restaurants that I can name off the top of my head that are easily the best restaurants in all of Massachusetts; three of them have been my top dining experiences I have ever had, in any city, ever. (Bondir, Salts, Oleana). If you go to Harvard Square, the best falafel in the city is at Falafel King. Also, Tasty Burger serves beer in their downstairs. That’s my go-to late night burger joint.
Downtown crossing is sketchy at night, but not as bad as it used to be. I used to love JM Curleys when it opened because it was a hot industry spot, but they raised their prices and so out of principle I stopped going. Their burger is pretty awesome, though. It’s a fun bar to drink at, too.
Everyone LOVES Eastern Standard in Kenmore Square, but I’ve never been. It’s well-respected and a hot spot in the city, but I hate the name and I met a bigwig from there once who irritated me to no end when he sat at my bar. So I haven’t and probably won’e go because of personal reasons.
Don’t go to Southie. There are better places to visit in your short time. There’s nothing but the airport and working-class families in East Boston.
Let me know if there are any questions!