First, I want to thank you all for the recommendations in my original thread here: http://chowhound.chow.com/topics/809803. It was very helpful.
As it turns out, a very full evening only allowed for 3 stops. We had a great time, and my husband really enjoyed it...and was quite surprised by my plan. I booked a driver with an Escallade, which was quite comfortable for the 2 of us.
Our first stop was Craigie. We got there a little after 7. I think we lucked out, because 2 seats opened up at the bar only minutes after we arrived. We thoroughly enjoyed sitting at the bar at Craigie, perhaps even more than eating in the dining room (something we've done only once and it was over a year ago). I didn't catch the bartenders name, but she was a friendly, young blonde woman. I ordered an Ardoise, which is sort of a sage infused vodka gimlet. My husband ordered a whiskey based drink, whose name I've forgotten. We snacked on grilled octopus and fried pigs tails (boy, that sounds awful, but those bits of fried pork are very, very tasty). We had a second round of drinks, he had a sazerac, that being his current favorite cocktail and something he wanted to compare at different bars. He declared this one absolutely perfect. I asked the bartender for a recommendation, and she mixed me a pegu club, which is a gin drink, quite tart, that comes out tasting of grapefruit, although I don't believe it had any grapefruit in it. It was delicious.
It was probably nearly 9 by the time we got to stop number 2, which was Clio. Clio was very nice, but not quite as much fun as Craigie. For one thing, we had to wait quite a while to get bar seats (a table would have been easy...the bar was crowded with folks going to Uni, Clio did not seem all that busy). For another, the bartender was too busy to be as friendly and entertaining as the one at Craigie. And finally, the bar seemed rather hot and stuffy, just not that comfortable. On the other hand, the drinks were terrific. We decided to try something odd off the bar menu. My husband had a charred old fashioned, made with bourbon infused with charred cherry wood, and mixed with fruit that had been torched on a little hibachi on the bar with a hand held blow torch. I had something called a Cinnamon Smoke. This was fun....the bartender takes a cinnamon stick, and puts it on a piece of slate on the bar. then he lights it on fire. Once its flaming, he blows out the flame, and quickly puts my cocktail glass upside down on the now smoking cinnamon stick. While the glass is smoking he mixes my drink, which was somewhat sweet and rum based. Then he pours it into the smoky glass. He explained that the smokey scent actually confuses your taste buds into thinking the drink is not as sweet as it actually is. Its a very strange effect, Not something I would do everyday, but it was interesting and entertaining. With our drinks we had some tempura vegetables, and corned beef banh mi sliders. My husband did also order a sazerac here, which he declared excellent, though not quite as good as Craigie.
By this point, we needed some fresh air and a walk, so we decided to walk the couple of blocks up to Eastern Standard. It was 11PM at this point, and i thought with the large bar at ES we'd find seats....silly me...it's 3 people deep at the bar here, and we won't get anywhere near a seat. So we go next door to Island Creek. Which is fine, because my husband wants an oyster fix, and he loves the Wildwood they mix here. I've had enough to drink, but rooibos tea and cider donuts is the perfect way to top off my evening.
Afterwards we called our driver, and snoozed all the way home :)
I wish we'd had the time or energy to include Rendezvous, or Green Street, or Citizens all of which made my list. Perhaps I will have to do this again sometime.
528 Commonwealth Avenue, Boston, MA 02215
280 Green St, Cambridge, MA 02139