I'm looking for some help from someone in the Boston area that can map out a great drive for us. I'd like to end up at Fire and Ice but I don't think there is enough parking to accommodate a bunch of Elises. Thoughts?
Parking isn't ideal, but it's doable. You may find that many don't want to leave their car in a lot which is the only choice I can think of. If you really want to go to Fire and Ice, you have a couple parking options depending on whether you go to Harvard Square or the Back Bay.
I don't know how much you know about the restaurants, but Harvard Square is the original location and tends to have more energy. When the owner built the first restaurant, he tried keeping the bar and the grill near each other to make it more social but it was too congested. Back Bay on the other hand is too spread out. He redesigned the Harvard location a little and it's much better. Also, the area around Church St. in Harvard Square is more active than St. James Ave. in the Back Bay. Although if you wanted to walk around the Back Bay after, Newbury St. and other busier areas aren't far off.
For the Back Bay, I would drive into the city and park at the Boston Common garage which you can see on this map. It's $10 for the night and you can usually find open spaces near each other, especially on a Sunday night. We could come in on 93 or 2 to Storrow Drive and we would spend very little time circling around the city streets.
For Harvard Square, you could park at Alewife and take the red line to Harvard Square. (No, you can't park in Hahvid Yahd. A friend of mine did that once and almost got towed.) That would spare you driving into the city and reduce the chance of running into traffic. It may just be me, but I think the cars would be safer at the Boston Common Garage. It more enclosed/isolated and drunk kids take the trains. If we parked there, we could walk over to the Charles Street (nice area a lot of tourists miss) stop and take the red line from there.
Speaking of tourists, if there are any in this event there are a few things we could throw on once in the city. For that, the Back Bay or at least parking at Boston Common would be a better choice.
As for drives, the city is too congested. We meet in the city as a starting point for events all the time, but quickly reach escape velocity. Storrow drive is actually a fun road when it isn't packed with cars or flooded. Potholes are unpredictable. Generally all events I plan are outside of 495. To keep it accessible to the Boston-NY corridor there are plenty of routes we could follow that are closer by. Here's a suggestion which is a modified event we did a while back. I added some backroads from 495 to 95 and followed Storrow Drive into the Boston Common garage.
Point B is Lilly's Lilly's on the Pond Restaurant & Pub which makes a great lunch stop. They open at 10:30. Those who choose to continue on for dinner in Boston may want to eat light since it's all you can eat at Fire and Ice.
If we leave point A at 10:00, we'd be at Lilly's for lunch. Leaving plenty of time for lunch (1200-1330) and breaks in Peterborough and Kimball's ice cream stand in Westford (which could also serve as the end point for those not going into the city), we would then be in Boston around 17:30.
Is that roughly what you're looking for? We could iron out the details or take a different approach.