Just got back from 6 days in Manhattan and wanted to share my experiences because such posts and your advice were so helpful in planning our trip:
1st night - Jane http://www.ctrnyc.com/JANE/index.html - This wasn't a pick off the board, it's kind of a sentimental spot for us from our first visit to NYC a few years ago, so it's a 'must go' every time we're there. I know it's a restaurant belonging to a 'group', not an individual owned/chef run kind of place, but the food is so good and the prices are a bargain by our standards. I had the calamari to start/boyfriend had the gnocchi with the cream sauce he dreams about all year long until we're able to get back. He then had the filet mingion, I had the hanger steak, topped off with a bottle of a Barolo. We had a corner table, the music was good, the service was casual and not intrusive. For the total meal bill (with an $84 bottle of wine and dessert) of around $200 this is SO worth it.
2nd night - Picholine. WOW. It was a huge change from Jane, very old money/old school kind of place, everyone was quite dressed up. But the food, OH THE FOOD, was unbelievable! It was the kind of food where you take a bite and swoon, so good you don't want to talk, just close your eyes and focus all your energy on the taste and textures and making it last. I had the Sheep Milk Ricotta Gnocchi to start/bf had the wild mushroom risotto. Then the mains came and we were further impressed. I had the Halibut, he had the Wagyu beef. The flavours were so soft but so full. The best part of the evening was when the cheese specialist came out and selected a plate for myself for dessert (as well as a gorgeous 20 yr tawny port to match) - I couldn't stop smiling, what an experience - such wonderful cheeses based on my preferences. The service was wonderful, unobtrusive and refined.
3rd night - Well we were SUPPOSED to go to Di Fara's in Brooklyn, but after a long story/work commitments/general exhaustion and having to get up at an ungodly hour to set up trade booths the next morning, we ended up at the hotel restaurant we were staying at - Etrusca - http://www.hilton.com/en/hi/hotels/di... - which was certainly not a pick off the board but a last minute/no internet access sort of choice. It was a comedy of errors and the food was merely adequate.
4th night - Vice Versa. A pick off the board. Perhaps we'd been spoiled by Picholine but this was very average. Don't get me wrong, the food was good, the room was nice and the service was good - but it wasn't anything very special. I was disappointed because some of the menu items were subtly different in actuality (I know, not a big deal but I was really looking forward to the fried sweet basil), so I had the calamari tart to begin and the bf had the lobster salad. The lobster was kind of hard/stringy, but the calamari tart was great. We moved on to the salmon for me and the veal medallions for him. As I said, both were good, but in retrospect I would have preferred to sample Degustation in Vice Versa's place,or left it out for something else and I wouldn't have felt I missed anything special.
5th night - Gramercy Tavern. Beautiful room, spectacular meal. I would definitely go again. Nice area to walk around in before and after. He had the Pappardelle to start, I had the Tagliatelli, then moved on to the sirloin/braised short ribs and the lamb. I would say this was the second best meal we had, and make an effort to go if you are visiting New York. The ONLY thing I didn't like about the restaurant (and this is being picky) was the wide eyed/happy, kind of intrusive service we had. At a nicer restaurant I'm used to something a little more refined, but again, that is being picky. Food and room were beautiful.
One last place - I had an hour to wait for my tour to begin at the Tenemant Museum (which you really must go to, it's absolutely wonderful) and went for lunch at the l.e.s. sandwicherie. BEST SANDWICH OF MY LIFE. Great lemonade too. http://www.lessandwicherie.com/