I agree with Jamaica being a disappointment - dozens of people with their hand out contantly hounding women to braid hair and men for donations - not very enticing. Any number of Caribbean Islands are better.
I don’t agree with Vegas on the list, one poster complained about the Luxor after spending $50/night...really? You get what you pay for and you paid for nothing more than a campsite.
I’d recommend Boston over NYC every day of the week. Boston has character, NYC has concrete. Boston you can drive, great restaruants and sight seeing, rooms aren’t cheap but can be had for what you would expect.
The best boots I ever owned, I bought in Boston in 70s.