My wife and I managed to fit a lot of eating into our approximately 48 hours in Milan last month; we enjoyed the city and its food and drink very much. We drank cappucinos and macchiatos at all the usual tourist suspects - Cova, San Ambroeus, Marchese, and Peck; they were all good, of course, but the winner for coffee and ambiance was the strong, properly hot macchiato (priced at one euro!) at the somewhat faded Marchese and for food was Peck's delicious wholewheat croissant and squeezed to order Sicilian blood orange juice. Lunch both days was Luini's panzerottis, well worth the inevitable 10-15 minute wait in line to get them to go. We tried both the fried and baked varieties, and much preferred the former, which were reminiscent of a wonderful savory doughnut, filled with either tomato and mozzarella or ricotta and spinach. We were fortunate that the sun was shining so that we could take our panzerottis down the street and eat in front of Il Duomo.
We had two excellent, very different dinners, both of which seemed genuinely Milanese to us in entirely different ways, as PBSF had commented in his/her response to my original post looking for advice. Antica Trattoria della Pesa was perfect for our first night, when we were a bit jetlagged: the casual atmosphere (we were seated across from each other at a table for six with another couple occupying the other end of the table), delicious, straightforward food (including wonderful, copious osso buco and risotto milanese vey fairly priced at 30+ euros and a decadent, eggy, sweet, boozy zabaglione for dessert), and friendly, relaxed service from the proprietor and his assistant were just what we were looking for.
Il Luogo di Aimo e Nadia was also very special, albeit completely different: much more formal room and service, with headwaiter, sommelier, and several waiters to look after the eight, well-spaced tables. We opted to eat a la carte, rather than getting the degustation, and were very impressed by almost all of the very sophisticated dishes. I enjoyed the pigeon and duck liver pate I started with more than any cold foie gras preparation I can remember, including Per Se's; the gaminess of the pigeon complemented the unctuous foie perfectly, and the accompanying toasted brioche was delicious. My wife's swordfish was tender and tasty, and my succulent but not too fatty roast pig was the best pork I've had since the maialino at Maialino. The amuse of pancetta and deep fried olive properly whetted our appetites and the complimentary cold, thinly sliced octopus appetizer was delicious. The only (mild) disappointment was our shared pasta course of overly al dente, underseasoned fettucine with tomatoes and pepperocino. Aimo patrols the room in his pristine chef whites, lapping up the praise from his delighted patrons, while Nadia appears at the end of the meal from the kitchen to bid all a warm farewell. Perhaps most remarkable were the wines by the glass that the sommelier matched to my meal and stated preferences for an amazingly reasonable 86 euros (I can list them here only because he was kind enough to record them for me): Riesling Auslese 1989, Lauer; Galea 1999, Clivi Zanusso, a wonderful tocai from Friuli; Paleo 2006, Le Macchiole, which retails at over $100 a bottle in NYC and went wonderfully with the pork; and Solaria Jonica 1959, A. Ferrari, an extraordinary portlike wine that I had never heard of. The sommelier not only provided very generous pours, but enjoyed my excitement over his selection so much that he gifted me a small glass of Barbaresco 1982 from Oddero to pass the time between the Paleo and Solaria! The elegant room, delicious food, formal but not at all stiff service, and amazing wines made it a memorably hospitable evening, well worth the 300 or so euros for two.