Lupa - What to order !
Last time I was there (Father's Day) there was a spectacular steak and watermelon special... perfect for summer. Cubes of meat and melon skewered together then topped with a pile of mint/cucumber/chili flakes/herbs I can't identify. I think about it at least twice a week.
Never had their gelato but if you don't feel like knocking back that grapefruit-sized tartufo, Emack & Bolio's is just a few blocks away... and they serve kiddie cups.
don't miss the tartufo. i'm not a big sweets person, but i could have eaten half a dozen.
the beets, artichokes, and eggplant caponata are my favorites from the veg antipasti. if there is eel or pork shoulder as a special, go for it. the duck and the lamb sausage from the daily special menu are both excellent as well, and i loved the grilled asparagus and braised escarole we had as sides recently.
The gnocchi! The only good gnocchi I've ever had outside of Italy.
Any of the special pastas (agree with above about the orecchiette. Ravioli also very good.) Avoid the cacio e pepe -- uninteresting.
The fishes can be surprisingly delicate, if someone doesn't feel like pasta.
Batali also makes the only real gelato west of the Atlantic, so have gelato.
I won't be surprised if you get different suggested dishes with each response. It's simply a can't miss place. When you're there, just go with your gut instincts or try their version of dishes that you've had elsewhere.
Be that as it may, and just so I can have something to recommend, if they have the orrochiete pasta special, you'll definitely have to order that!
I have never had the tasting menu, but the people next to me did and it looked nice.
I create my own tasting menu by splitting pasta dishes which Lupa does not mind doing.
I have always enjoyed their oxtail alla vaccinara, beets, fennel, gnocci and pasta specials. The last time I was there that had a trippa pasta special that looked really good.
Oh and housemade limoncello.
You're in for a treat. I would definitely order as many of the antipasti as you can handle. The seafood is especially good. For the pastas, I would go with the Bucatini or the Cacio e Pepe although all the pastas I've had there have been great. They also now offer a $60 6 course tasting menu which I've had a couple times which is delicious but a huge amount of food. The wines are also quite affordable and they recommend very good bottles. Enjoy your dinner!