Helicopter ride up/down the Hudson at night is pretty cool.
( See post # 5 )Here's a romantic night you will never forget......
Take the subway out to the bronx.....get out and walk around in some really seedy neighborhoods.....run in to some "gang bangers".
Next run for your life, as the hoods chase you through Manhattan and into Brooklyn.......(a la the movie "WARRIORS").
Talk about something both of you will remember for the rest of your lives (if you live, that is).
The carrige ride, boat ride crap is BORING.....try running for your life ! (very romantic and thrilling !)
Grand Central Terminal / station and Penn Station very late at night are likely spots to find bums a/k/a winos a/k/a homeless people.My wife and I searched for a wino lying in the gutter with a bottle wrapped in a paper bag. We finally found one in the Bowery.
The old NY is slipping away but you can still find it if you look hard enough.
Went there last time we were in NYC.I don't know what your wife finds romantic...but if she has a sense of humor I would suggest Katz Deli in Soho. They are famous for their pastrami but what makes this romantic is that this is the place where that famous scene in "When Harry Met Sally" that Meg Ryan got so excited with was filmed. They even have a sign above that very table. Not your typical romantic but it is fun and different - and you will LOVE the pastrami.
Not sure about your budget, but for my wife's birthday I rented a suite at the Plaza. Had the chef come up and make us a personalized meal and we were served in the suite. Also did there afternoon tea and did some shopping and saw a show. When all was said and done I think it cost around 5K but she said it was the best birthday present I ever gave her.
Not sure yet, but that one was her 40th. For her 39th, I rented the Tappan Hill in Tarrytown, and had a surprise party for her and invited all our friends and family.That's setting the bar pretty high, what do you do for the next birthday?