I am a regular visitor to NYC, but thought I would plug a few cool things we did on our last trip (mid-May).
As usual, stayed at Cambria Hotel New York Chelsea, located on W 28th St between 6th and 7th Ave. This is a Choice Hotel, located in the flower district, so it's quiet, and also really nice when you walk outside with all the plant and flower shops. Rooms are huge, bathrooms are ridiculously small, but - it's quiet. Really nice rooftop bar, but not one of the party-bars. Half a block to the 1 subway on 7th Ave, a bit more to Penn Station. Pretty reasonable for midtown - I usually pay $320-350/night on average. I am often there on my own and feel quite safe as a senior-ish ;) female.
We did a boat tour around Manhattan with Classic Harbor Line, ran about $95/pp for a 2.5 hour tour (note: NOT a 3 hour tour lol) which included a complimentary drink (full bar and snacks available for purchase). Smaller "yacht" completely enclosed by windows so you have great views regardless of weather. Our tour had an architectural focus, which was really interesting. Great views of Manhattan, Statue of Liberty, Brooklyn, and the northern parts of the island you rarely see - and all the bridges!
We also went to the Starbucks Reserve Roastery in Chelsea, which was completely unlike any Starbucks cafe you have ever been in, i.e. it was amazing. They have classes, and "experiences" - but we opted to have a cold brew flight and an origin (brewed) flight. I also had a tiramasu latte (yum). The sandwiches looked so good (I know - not the usual reaction at a Starbucks!) we had lunch there, and would definitely do that again. Pastries also looked fantastic, need to sample those next time!
On the less touristy agenda, we went to a performance at Jazz at Lincoln Center (beautiful venue), walked the Highline (elevated train line converted to a park), wandered around Fort Greene (brunch at Saraghina Cafe - very good!) and met friends and relatives for dinner at Soccarat (OK), Portale (excellent), and Gage & Tollner in Brooklyn (often makes a top 100 restaurant list and it shows -soooo good).
Also helped that the weather was great!