Background: myself and my boyfriend are going to New York in mid-September, my third trip (previously in June 2001 & February 2010) and he spent a day in Manhattan about 13 years ago. So this is our first trip together and we can't wait. We both have a few things we want to do and see, but don't want to over plan and take away from the experience.
Plans so far: we arrive in the evening on a Wednesday and will get a taxi from JFK to our hotel near Times Square, check in and just be in New York! On Thursday we plan to walk over the Brooklyn bridge and have a tour booked at 5pm in the Brooklyn Brewery, followed by dinner. I also have somewhere in mind for dinner on the Saturday night, just need to book first!
Request: below are the things we want to see, do and eat, and I'd be much obliged if anyone has any suggestions as to which things go well together, are located close to each other, or any ideas on what days are better or worse to go. I'm aware some places do freebies, but that they get pretty busy, so would probably prefer to pay $20-25 in that case, but I'm not adverse to saving $$$ either!
The Lyric diner (http://www.lyricdiner.com) - I went here 2/3 times in 2010 as I was staying close by, and need to fit in a proper diner breakfast of pancakes, bacon, maple syrup and endless coffee.
Shake Shack, Madison Square - burgers in a park, and himself wants a hotdog!
A Broadway show - I've been keeping an eye on the TKTS app, and hoping for Matilda..
Empire State (by night)
The Metropolitan museum of art
Magnolia bakery maybe?
Some sort sort of boat trip?
Open to suggestions, food based ones are especially good.
Thanks in advance.