When A Guide Named Sue received a request for a 6 AM custom tour the next morning through AnyGuide that included Central Station and Madison Square Garden, she responded with several questions, checked on a few things, came up with a proposal and the next morning we left my guests' hotel in the West 30's at 6 AM. The tour was a bit (less than an hour) longer than expected because of unexpected events that enhanced the tour.
The Starbucks barista may have been a bit rude to the guest who asked for restroom directions without ordering (her friend ordered for both of them). However, the early morning security guard at the Empire State Building let us in to have a look around the lobby when we were peeking through the window.
Yes we passed the Drama Bookshop, the Times Building, Madison Square Garden, and Macy's. We saw many sleeping arrangements for the homeless and those who end up scammed by an apartment rental.
We saw Madison Square and the (where's that building that looks like a ship) Flatiron building and met the police in the Union Square train station near the Sept 11 memorial and said hello to Tom Otterness sculptures at Eighth Ave and 14th Street. Not knowing when the restrooms would be open on the Highline, we stopped to use the facilities at a beautiful hotel on 16th Street. Chelsea Market stores were not yet open but the guard allowed us to walk through the space en route to The Highline.
My guests hadn't heard about the Highline until I suggested it. At 7:30ish after a recent snowstorm the Highline was beautiful and empty. We managed to end at Grand Central terminal and my guests returned to their less mobile family. I went on to volunteer at a Senior Center (did I mention that Shake Shack had no line early in the morning and they have very good breakfast sandwiches)!