Here's an offbeat suggestion. For Christmas get him a guide book with lots of pictures (Insights?). Tell HIM to come up with what he'd like to see or do. I suspect that if he's typical of most 16 year old boys, there's nothing YOU could suggest that would make him happy, so have him find what HE suggests.

You may want to check out the PGA museum on West 57th Street (near Carnegie Hall, where the Russian Tea Room used to be). He might enjoy that.

Pressed post too soon. The suggestions are great - especially the Blue Man Group and the auto show - he does love cars. ESPNZone also sounds good - he lost interest in sports after middle school, but video games always work. He does enjoy looking at girls, but I don't think I want to go there this trip

PGA museum right across from our hotel - definitely a winner!

Donna, thanks for asking this question! We have a teenage boy just like yours, and NYC might be the site of our spring break, too. I'm loving everyone's answers.

As much as I'd hate to encourage video games in NYC, last I knew, there was a place called Bar Code in Times Sq. that was a big arcade. I think the upstairs becomes 21+ at night and turns into a club. There's also some sort of laser tag thing right around the corner from there.

There's a heated driving range at Chelsea Piers that I think is open year round. There used to be an indoor place where you could play the best courses in the world (virtual golf) but I can't find any info about it on the web. Maybe it closed.

Do not give up hope that he is enjoying/absorbing more than you think. Our 17 year old son also grunts, eats Italian food and BBQ ribs, plays computer games and hangs out with his friends. I knew some of our travels had sunk in when we spent one night in Las Vegas last summer on way to some national parks and he pointed to the hotels featuring Venice canals, New York and Egypt pyramids and laughed, stating he had seen all those places in real life and so had no need for imitations!

Although NYC is expensive, for this or future trips, consider taking a friend for him. Also, remember that although we may seek the family time together vacations bring, spending 24 hours/day with parents is not something most 16 year olds brag about.

Although it may scare you to death, consider letting him go off to a planned destination alone - whether wandering in a vintage record store, funky shop or part of a museum. He'll enjoy bragging about it to his friends later. Also, I have found if we let our son have a large say in where and what we eat, he speaks more and grunts less.

Try to balance the desire to have him absorb NYC and the goal of having a pleasant family trip - if he wants to play computer games while you see "boring paintings", consider letting him do that. Presumably he has decades more to re-explore NYC. Also, don't force him to get up early if he is like most kids and hates that. In fact, I remember as a teenager thinking it was incredibly cool to go someplace to eat in NYC at midnight and finding places open.

And as a postscript - don't give up on the video game obsession - our son is headed to college in the fall studying computer animation.

As few years back, my mom, teenage brother and I went to NYC (he went begrudgingly) over Thanksgiving weekend. We stayed in Times Square at the Marriott Marquee which was directly across from a huge Virgin records store and ESPN zone and next to MTV. He loved it. Plus he loved all the street vendors and came back with 2 fake rolexs and an NYPD hat and shirt. He also loved the Village.

Take the little slacker to CBGB, the (in)famous punk club, located on Bowery at Bleeker. (Going south, Bowery is what 3rd Avenue turns in to; Bleeker is a little south of 6th Street). Don't go during the evening, of course, but no harm in stopping by during the afternoon. Open the door and explain to whomever is sitting inside that you're from out of town and could you please look around for a few minutes...they're very nice people and will most likely say yes. Make sure you go all the way down towards the stage, past the stage and down the steps to check out the restrooms. They're famous -- you'll see why. Take you camera and don't fear the reaper -- you're perfectly safe.

I always take my out-of-towners there. Guarantee the kid'll like it.

I think he'd like a store on Broadway at 12th Street called Forbidden Planet which appeals to no one but boy slackers, it has to do with comic books, old comic books, esoteric comic book lore, etc. It's near Union Square.

If he reads or looks at books, or if you do, combine with a visit to the Strand bookstore, 12th & Broadway. Or you go in there whil he visits Forbidden Planet. Biggest used bookstore in the world, etc. (Strand).

Not having a teen myself, I'm not as experienced as others, but I wonder if you'd get more words and less grunts if you tried an "interactive" dining experience. I'm thinking along the lines of Shabu Shabu (where you "cook" the food yourself in the middle of the table) or dim sum (where the ladies walk by with carts of these little bites and each one is an adventure) or even family-style dining like Ruby Foo's (which has cool decor anyway).

He likes video games? Put him IN one...kinda.

See if the Beast is running. It's a 50-60 mph boat ride down the Hudson and around the Statue of liberty. It mixes an adrenaline rush with a view of the city/harbor that can't be beat.

Loki's post (above) is a good one and can be combined with CBGB. Your kid will be in slacker heaven.

FYi - Bar Code in Times Square is closed

Wow - what great suggestions you guys have given! I can't wait to show this thread to my son. Even he will have to get more enthused for the trip. We may get him out of that hotel room yet And letting him sleep in is also a great idea - my husband and I can get some great alone time and a great walk in the Park. We are also taking our 23 year old son - but that is a totally different kettle of fish. I am not concerned about entertaining him!

GC's idea is a good one, The Beast is a fun, 40mph speedboat with two hairy, rock'nroll types manning the boat, telling stupid funny jokes and blasting rock and roll up and down the Hudson. Unfortunately, it doesn't start until the weather warms up - and you don't really want to do it until it's at least 80 degrees anyway!
As I said, Chelsea Piers' driving range is actually a very cool 5 story building, cut open - with 8 or so driving spots on each floor. You drive the ball across the pier toward the Hudson River - a very cool view. check out the website.

In Times Square, the other good Arcade is on 42nd St. just east of eighth - on the north side of the street. I forget what it's called but it's huge and pretty fun.

You don't drive the ball over the water. The driving range is enclosed with mesh so that you won't hit a passing boat. You just drive the ball at a big net.

I thought the USGA was trying to get out of the Russian Tea Room. I passed by it recently and it's still closed despite the logo.

Beware, Chelsea piers golf is expensive. Something like $25 for 75 balls and the place is mobbed on weekends. It is interesting to go very early and watch the oceanliners go by and the morning light. And if your son is a good golfer, tell him the net ends at 200 yards. Not very far out indeed. Still worth a visit, but it'll probably be brief. The bowling alley next door might be interesting.

Donna, I went through the same thing with my 17 year old nephew this summer when I took him on his first trip to NYC.

Honestly, instead of trying to coddle him, I laid down the law. I told him, "we are doing xyz and you can participate or you can not participate, it is up to you".

He did everything the rest of the family did and we had a blast.

Grayline Bus Tour
Walked Brooklyn Bridge
Staten Island Ferry
Metropolitan Museum of Art
Central Park
Times Square

Manhattan is SO stimulating, it is impossible to be a slacker there. It is an assault on your senses.

Don't worry, he won't lay around the hotel room.