http://boston.citysearch.com/review/...20___review__1

We ate at Spire a few weeks ago and found it wonderful. Our wait staff was great and the food fabulous and we had a lovely bottle of wine - we have eaten many times at Rialto and love it there too - Jody Adams is highly thought of chef and more often than not has walked thru the restaurant chatting with customers. I also like L'Espalier, but if he's been, maybe you want to try and choose somewhere else. Sounds like your boss has enjoyed good dining and if he likes good wine, he won't mind "adding to the certificate" for it - while I like Abe and Louise I find it can sometimes be loud and crowded nad I don't find it a "special" or romantic type place. Anyone eaten at Torch lately? We had a lovely meal there several years ago, it was different (small but cozy) and the found was excellent - and they also have valet maybe take a look at their menu/prices on line. ANY of the choices mentioned, anyone would be delighted to get a gift certificate to !! I dont' think you could go wrong with any of the suggestions given -

I would recommend...
Davios (Boston on Arlington)"Menu offers a more sophisticated take on Italian and steakhouse classics."

75 Chestnut (Back Bay/ Beacon Hill)"Best described as having an upscale American, bistro-style menu, 75 Chestnut succeeds in every aspect--presentation, freshness and flavor. This charming restaurant and bar in a converted townhouse has become one of the premier dining destinations in its neighborhood."

Mamma Maria (Ask for Table 33)
Mamma's kitchen churns out noteworthy Italian and New American dishes featuring seasonal, local ingredients.

Favorite, Aujourd'hui (Four Season's; Request window table.)might be too pricey. "Timeless culinary landmark sets the New England standard for inventive, modern French cuisine." Amazing service.

We had a great meal at Davios.
Aujourd"hui was very good, however, everyone in our party of 8 left hungry,even after dessert. The portions were so small, and it was very expensive.

Mantra was spectacular, as was Excelsior. They offer two very different types of ambiance, so it all depends on what your boss is into.
Also, I know it's not as grand scale as some of the others mentioned, but Hammersley's is one of THE best restaurants in Boston. I have only been there a few times, but my boss goes there at least a couple times a month.
Good luck!

Thought I'd give you an update. I decided to go with Grill 23 and was pleasantly surprised to find out that the same restaurant group also owns Excelsior and Harvest in Cambridge. So he can choose any of the 3, he was very happy.

I love it when someone lets us know what finally happened !!! So glad it all worked out, 3 great restaurants in our town for him to choose from. Now your boss knows what excellent taste you have, if he didn't already!