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Come to NYC
Too many things to list for NYC. It’s fun just walking down the street and seeing where the day takes you (do this every Saturday)
Chief
I think they paused it due to Covid, but DL had an oddball PIT-CDG route that would be fun.
Otherwise, assuming you’re vaccinated, come to New York. Don’t stay in Times Square. Do check out a show. Definitely get a bagel at Ess-a-Bagel and walk around Central Park. Check out some cool bars (Employees Only, Proletariat, PDT if you’re a masochist) and restaurants (pizza at Roberta’s or Lombardi’s, steak at Keens, dim sum at Nom Wah or Golden Unicorn, anything at Gramercy Tavern, cheesecake at Junior’s, Jewish deli at Pastrami Queen). Take a ferry ride and enjoy the views (Staten Island ferry is free). If you like beer, check out Other Half in Domino Park.
Sarasota and then explore siesta key too
Cancun. Stay at the ritz and have them bring you buckets of beer and quesadillas by the ocean