Advanced NYC tourist has specific questions!
I've learned not to ask questions like "I have 2 days..where should I eat?" so here go some specifics:
1. We LOVE Prune for brunch on Sunday. But since we only eat a few meals a year in NYC (if we're lucky) I feel I should branch out. Please suggest something similar in tone and cuisine to Prune, downtown, and opened at least by 10:00 on Sunday am.
2. Staying at the Tribeca Grand, are there any gems in the area? Not necessarily for dinner, but maybe morning pastry, after dinner drinks, desserts, etc?
3. I'll be there on the last day of restaurant week...Fri Aug 1st. I looked at the list of restuarants, and the names that stood out to me were Morimoto and Del Posto...do you think either of these would be great bargains for lunch on Fri? Any others I've missed?
4. It's been a LONG time since I was in NY in the summer...although the best food is always the most important thing, if there are al fresco options w/ stellar food, please clue me in. (We like almost everything, particularly French and Italian)
5. Bouchon Bakery : worth the trip uptown? How do their doughnuts compare to the Doughnut Plant?
6. I've become obsessed w/ salted caramels...name your favorite source.
7. My husband loves John's Pizza. We were quite disappointed by Lombardi's last year. With that knowledge, how do you think he will like Otto?
Re: 6 - Not salted caramels, but if you like salt in sweets, the smoked salt chocolates at Kees (which is on Thompson in Soho) are wonderful. A reasonable walk from your hotel.
2. Bouley Bakery Market has the morning pastries and desserts. I also like Petite Abeille if you'd like to sit down for breakfast or a simple meal--great waffles. For after dinner dessert, you could also try Blaue Gans--great Austrian pastries.
7. I haven't been to John's or Lombardi's. I personally like Otto a lot, but be warned that their pizza is not authentic Italian or Italian American style. It's sort of its own breed with a very thin, crackery crust and nice topping combinations. I'm not sure if your husband would appreciate that. That said, the small plates, some of the pastas, and the gelato might be worth going for even if you don't try the pizza.
2. If you're staying at The Tribeca Grand I'd be remiss if I didn't point out Pepolino just around the corner - excellent fresh italian. There's also an amazing little sandwich shop on W.broadway called Columbine (don't be thrown off by the name). It truely is a hidden gem - fresh made/ baked sandwiches/cookies/cakes every day. You'll be in line for about 15-25 minutes if you go at lunchtime - and it's pretty much takeout only - most people take out and eat it the park down the street.
3. I'd skip Del Posto for reasons too numerous to get into here.
7. If he's particular about pizza I'd pass on Otto. Instead you may want to take him to Una Pizzeria (12th & 2nd) - it's true pizza napolitana (not NY style), they make their dough every morning and close up as soon as they run out. It's no frills, and very few options - but it's a mecca for pizza purists.
Drinks in Tribeca - B Flat has some excellent "high-end" cocktails (former Angel's Share people) and I think is across the street from your hotel.
I'd also consider Anthos for restaurant week.
Del Posto is somewhat disappointing I think when you go with 2; it seems the best dishes are some of the giant meat items that are for large parties. Morimoto is pretty solid, actually much better than I expected. I would also consider giving Anthos a try for a RW dinner.
Barolo (in Soho, fairly convenient to your hotel) has a huge al fresco dining area. I like the food at I Tre Merli, which they also own, and I think it's also a restaurant week place, so you could try that and kill two birds with one stone. Anyone else have comments on the food?
Outdoor dining + good food seem nearly mutually exclusive in Manhattan. The restaurants know they'll be packed because they have a sidewalk cafe, so the kitchen doesn't try very hard at all. The exceptions are more notable. A few off the top of my head are are Nice Matin, Pastis, Morandi, Chinatown Brasserie, 'inoteca.