Visiting New York City with Teens & Pre-Teens
Archived Q&A and Reviews
I'd like to take my 14 year old daughter to Manhattan for a day while we're visiting relatives in the area the week before Christmas. I grew up in a suburb of New York and love to visit the city, but I'm sure there are lots of new places since those days (the Disney-ized Times Square is one example, but a bit too young for my daughter). A Broadway show would be great, but even at TKTS prices, that's beyond my budget.
We visit NYC each summer with my daughter, who is now 16. Last summer we brought a friend of hers who had never been to New York. I asked my daughter what she would recommend and she said:
Walking around Central Park (visit the Alice in Wonderland statue at the sailboat pond, walk around the reservoir, if she's into John Lennon try to find Strawberry Fields etc.). Bring a picnic lunch. Or rent bikes and ride through the park. (Oops! I forgot that it's winter.)
Theatre -- if Broadway is too expensive, see what's playing off Broadway
American Museum of Natural History -- never too old for that!
Circle Line boat ride
Chinatown, Little Italy (walk through both, get dim sum in Chinatown then get gelato or cannoli in Little Italy) -- if she is into shopping, you can also hit some of the discount outlets on the Lower East Side
If she's into art, visit galleries in Soho and other hipper neighborhoods
In addition, here are some of my ideas:
The Ellis Island immigration museum is FABULOUS! If you have ancestors who might have come through there, you can look them up on their computers. Lots of hands-on stuff, plus a pretty boat ride that takes you past the Statue of Liberty.
NY Tenement Museum. I love this -- they have recreated several apartments in 1870-1920s style and give guided tours that show how immigrants lived. It's on the Lower East Side. You could combine it with Little Italy and Chinatown. Or you could have lunch at Katz's deli -- huge pastrami sandwiches, egg creams etc.
High Line. This is new and I haven't been there yet myself. There is an old section of elevated railroad on the far west side around 20th street that has been made into a park. You can walk along it for about ten blocks and peer into people's windows. It sounds very cool.
Take the number 4 bus all the way uptown to the Cloisters. It goes through a bunch of different neighborhoods (upper east side, Harlem, Washington Heights) and at the end, you get to see the Cloisters, a recreated monastery in which the Rockefellers bought pieces of medieval monasteries fromn Europe and brought them over here. It has the Unicorn tapestries. Ilana
The Metropolitan Museum is still pay what you will, has been renovated with an excellent cafeteria, and you could spend weeks there and not see everything. Daphne.
Hi - We may be able to visit NYC this summer, a first for the 11 year old. Does anyone have recommendations: where to stay, what to see/do, what to avoid? We may end up staying in Brooklyn rather than Manhattan - can anyone comment on the advantages/disadvantages of doing that? Especially desired - comments about reasonable (??), or decent, hotels. Thanks so much. Hope to visit NYC
We just did a short November trip w/our 11 and 7 yr. olds. Our 11 year old 'tween insisted on the Madame Tussaud's Wax Museum in Times Square and though it was pricey but we all actually had a good kitschy time. The MOMA was great (eat lunch in the cafe) and if we'd had more time would've gone to the Nat. History Museum.
We stayed right next to Grand Central Terminal, which is always exciting (at the Hyatt which has nice spacious rooms, by NY standards). The food market in Grand Central is like Market Hall.
Took the subway into the East Village for some fun shopping. Magnolia Bakery has a rep for being over-hyped, but we loved the cupcakes. Access NYC guide still seemed helpful to me, after being away from NYC for 20 years. Can't speak to Brooklyn vs. Manhattan though. Have fun. Tracy
I was in NYC in April without kids, but where I stayed was the Brooklyn Marriott. The subway station was right behind the hotel, literally, and I loved the location so much, I'm planning another trip with my kids (11 & 9 when we go) and we will stay at that same hotel. It was right by an outdoor mall that was pretty convenient (Macy's, a drug store, etc) and across the street from that was a small neighborhood store and a health food store, kind of a smaller version of Berkeley Bowl. Also, I could walk to Barnes & Noble. So this was the very best location for me to see everything I wanted to see and also where we were it would be easy to get to Manhattan (huge Toys R Us) or the Bronx Zoo. lena
I'm not sure what your budget is for staying in NYC, but there are some nice hotels on the Upper West Side (around West 80th) for about $200 or a little less per night (check hotels.com) including the Excelsior & On the Ave. It's a great location, because you are ON Central Park and all that has to offer, plus the Natural History Museum with its incredible dinosaur, animals, etc. collections, the Metropolitan Museum of Art, fantastic restaurants (of all price ranges), and of course markets (Zabars & Fairway) and H Bagels (you have to get these while you're in NY).
If you're looking for something much cheaper, you might be better able to find that in Brooklyn or New Jersey - and you can certainly take the train into city central. But, there is something about staying right in the city, in a nice, safe - fun to walk around neighborhood with places like the Mozart Cafe (a dessert menu of over 300 items) open (with a line) at midnight, fresh markets every block, and the sounds, life, and feel of the city itself.
Have a fantastic time! NYC native girl
We (me, DH, DD10 & DD 7) visited NYC in spring 2006. We had a fabulous time. We stayed at the Westin Times Square, so unfortunately, I don't have any Brooklyn accomodation recommendations.
Things we did: American Museum of Natural History--okay, much like the California Academy of Sciences in SF. The girls enjoyed the butterfly add-on but weren't impressed with the rest of it (they'd seen it before). Metropolitan Museum of Art--loved it. Huge, no way to see all of it. Egyptian Art/Temple of Dendur and Impressionist exhibits were our favorites. Top of the Rock--no lines (vs. Empire State Bldg), great photo ops of Empire State Building/Central Park. Staten Island Ferry--Statue of Liberty is a little distant, but it was FREE and fun. Visted/walked through Central Park, Grand Central Station, Chelsea Market. Broadway shows--Tarzan (not so good) and Lion King (great). Great fun exploring neighborhoods and eating/sampling a lot of food. They loved riding the subway--bought 7-day unlimited Metrocards. DD10 loved to be our guide--we'd pick a place (NYU for example), and she'd figure out what subway line to take, which way to walk, etc. If you have any questions, feel free to email me. I have a more detailed trip report I think I posted on fodors. holly
the washington square hotel in the village is nice has decent rooms for $145. it's at nyu and sees a lot of academic types come in and out. subway is a block away, so is a pharmacy and a health food store. central park is fun and the natural history museum is supposed to be a gas. the harold square hotel is midtown and cheap but not so nice. anon
I am looking for a list of fun things to do and great places to see in New York with my 10 year old son. We will spend 10 days over Thanksgiving (lucky us !!). Monika
New York is full of wonderful things for a 10-year-old! A few suggestions among dozens of wonderful museums: the Tenement Museum near Canal Street is housed in a 19th c. tenement, the Guggenheim Museum--modern art in a very cool spiraling building, and the Metropolitan Museum--the armor and corresponding weapons can take a couple of hours in themselves. Walking around Central Park--climbing rocks and statues and skating (go after the holiday weekend) is fun. If your son likes baseball, Yankee Stadium has a fantastic tour where you get to sit in the dugout and go into the locker room. Even if you are not so into baseball it's a great tour. For views, go to the top of the Empire State Building, take the tram to Roosevelt Island and back, go to Brooklyn Heights by subway and take in the view of Manhattan along the river, especially at night. There is also ice skating in Brooklyn's Prospect Park, which like Central Park was also designed by Frederick Law Olmstead and is beautiful. Go to FAO Schwartz's ice cream parlor if you are in midtown. Eat Ray's pizza. Travel by subway--the buses are too slow. Have a great time! Melissa
We just returned from a trip back East, including 4 days in New York, and I must say that our California fear of New York is not warranted! The subway was clean! Times Square looks like a movie set! If anything, the cleanliness was a little unsettling. What has Giuliani done with all the homeless people? At any rate, we stayed with friends on the very upper East Side, not the best of neighborhoods by any means, and it was just fine. Both our fellow passengers on the subways and the taxi cab drivers were very friendly and helpful. It really was kind of eerie - not the New York I remember from years ago. Our kids are much younger than yours, so I can't say what teenagers would like. A good guess would be walking around Soho - very atmospheric, cool shops; and Times Square. Try to see a show (but not Annie Get Your Gun - it was bad). The Museum of Natural History is astonishing. The Museum of Modern Art and the Met are stunning. If the Hitchcock exhibit is still at MOMA, I'd think teens would like it. Go up the Empire State Building and to the Statue of Liberty. Even the most hardened teenager has to fall for it.
I'm a native New Yorker from Queens, married to a Manhattanite, and we both will emphatically say - USE THE SUBWAY! I would try to get your hands on a copy of a subway map in advance and get familiar with the lines and likely routes you will be using. (Tip: Noah's New York Bagels shops invariably have maps on the wall. Check one out and see if there's an address or phone number to call for a copy.) It is a vastly more complex system than we have here (vastly more useful, too), and I've managed to get lost on it despite basically having grown up using the trains! Be prepared for a lot of humanity in your face at all times when travelling to NYC. Some of it will be pleasant and some of it will be rather unpleasant. Keep your wits about you at all times and don't ride too much after dark. There are loads of taxis that can take you wherever you want to go. (Though the taxi experience is often not as mild as you'd hope!)
As far as fun things to do - there are so many, it's almost hard to remember. Also, I'm sure a lot has changed. On my last trip home, I went down to Battery Park City a couple of times, and was really impressed with how nice it is. Especially at sunset, the views of the bridge and the statue of liberty were incredible! Try going to see something at Lincoln Center - that's always a special treat. I guess I'd get a good guidebook and sit down with your kids and see what everyone would like to do together. Have a wonderful time! Diana
When I was 16 I loved the South Street Seaport (and the Fulton Fish Market for lunch) -- on a day with sun and a breeze from the river, just being around these old ships took me to distant times -- you know what it _smelled_ like if you lie on a deck there with the tar and the lines and the sun-baked wood :-)
The fish market (starts right across the street from SSS) has a number of very fresh and rather quirky seafood joints. Good stuff! Also some very upscale stuff. In fact, the whole lower tip of Manhattan down there is pretty cool -- that's where (South Ferry) the ferries leave, it's where Wall Street is (very eerie early on a Sunday morning with NOTHING and NOBODY in the streets except a little wispy fog, and these narrow cobbled streets with huge sheets of glass rising from the sidewalk 60 stories into the air -- like wandering a lost city of great age and magic -- the glass, reflecting the sky, the walls of your canyon). There are, amid the canyons of glass, tiny ancient churches, some from the Dutch days, on their miniscule plots of grass, at least one complete with churchyard and ancient tombstones, I seem to recall. Wander! It's an amazing place, and so small -- you can cross the island down there and not even realize you're doing it. You'll wind up at the World Trade Center or Battery City if you go that far west, and be looking at the Hudson River. Both of these have many little shops and places to eat (WTC even has a cafeteria frequented by the building's employees on the 44th floor, which is the transfer point for the elevator system. There's also a hair salon and a deli there). The top of the WTC is a good place to have a lemonade or something -- there's a bar and a restaurant (expensive and in the evening packed with mating-dance yuppies).
Four blocks north of WTC (leave from the east side of the bldg) there's Job Lots Trading Corp and Syms (down a side street, but you'll see the sign), and a lot of other discount places have sprung up -- it's like a tiny spillover of Delancey Street, which is the original deep discount district (on EVERYTHING from clothes through furniture/upholstery/yard goods to you-name-it) farther north and east. ASide: Delancey is a place you want to get to first thing in the morning, and NOT on a Saturday. It is an intensely Jewish and traditional neighborhood (or was, last I checked), and while the owners want to make the first sale of the day and will haggle with you (that's the Delancey experience, you learn to haggle, and you learn what things are worth if you didn't already know) while trying to DO that -- a little superstitious, but so what -- many shops are either closed or do not have the owners in them on Saturday. Also, take the subway back out if you don't know your way around, or walk West and keep going until it looks pretty good again -- mornings are not an exceptionally dangerous time, but you're in some seedy areas on the lower East side and some rather blank ones as well, mugging is always a possibility. Generally, stick to crowded areas and prosperous-looking areas and you'll be fine. If a situation feels wrong to you, trust your gut and retreat, or go into the nearest business and if necessary explain what you're doing there. Don't wear gold chains or earrings or things that could be snatched, especially on the subway; it happens, _not_ all the time, but why push it? You will notice that the rules are different for some people. Accept it -- they are probably armed. :-)
Heading over to the eastern end of Chambers street takes you around city hall, the courts, and Chinatown -- now THAT is a cool spot, especially in the late afternoon/early evening. There are all these fascinating little stores, and thousands of restaurants in every conceivable price range... BTW, Don't get caught around the courts bldg well after closing, it's deserted and fairly high crime. Three blocks east and north, on the streets of Chinatown, the party rolls on late into the night, but with two kids I'd recommend eating early and retreating to an easier neighborhood. Where are you staying? Upper West Side, Central Park South, Central Park West, or down in the Theatre District?
Oh, yeah, another thing I enjoyed as a younger person: the Museum of Holography, in the south Village near Canal Street.
The Village itself: go to NYU, specifically, go to the park beside NYU, and you are near the north end of the Village, seen in virtually every movie with New York in it. There's a little arc de triomphe there, you can NOT miss it. The subway station is West 4th Street -- Washington Square. A couple of blocks east of the N end of the park is The Strand Bookstore, which has literally MILES of used and new books, messy but kind of a NY institution, for bibliophiles. There are jazz clubs and rock clubs and comedy clubs in the Village. You know all this, the Village is too famous for me to detail all this. BTW, if you get over into the tangled maze around Christopher Street, there are streets that intersect with themselves, and many many people on display -- that is the gay (mostly male) parade and cruising ground of the Village. Wonderful restaurants all over the place, but with the kids it might take on a wonderland aspect if you wander up there much. Many ebullient trans-everything people, at all hours of the day and night.
More Museums: I assume you are going to do the American Museum of Natural History, and maybe walk across the park (try to hit Belvedere Castle on the way, it's an oddity of Central Park, right next to the open-air Shakespeare-By-The-Lake theatre; also, Cleopatra's Needle is very close to the MMA) to the Metropolitian Museum of Art, and even possibly hit the Guggenheim or MoMA (not sure what you think of modern art). Just doing AMNH and MMA can take up a day. Hmmm, you might want to start on the East side, for logistical reasons -- good food is available within a few blocks of both places, but you'll probably pay less in the evening and still eat very well if you eat on Columbus at or south of the AMNH. Walk down as far as 73rd and Columbus and you will find (unless it's gone by now) the ORIGINAL Silver Palate, BTW, and it was tiny when it moved in! Anyway, lots of restaurants on Columbus between 79th and 72nd -- but if you want to try a great coffeehouse, skip dessert... Below 72nd, at 71st hang a left, and see if Cafe La Fortuna is open or whether they are taking their summer vacation (they take LOOOONG summer vacations). If open, they have the best schwartzwaldekirschetorte you have ever tasted, when it's in. Otherwise try a Rum baba or even the canolis. Yum!!! If not open, there's Cafe Mozart (or whatever it's called now) farther west along 71st (cross Columbus and head halfway to Broadway, it's on the S side of the street).
That neighborhood is safe (Columbus especially) a long way down. If you head down Columbus, you will pass ABC TV and the studios where the soaps are filmed (again, this may have changed but that's NY; my data on that area are older), and eventually you will run into Broadway and a large open area. Look diagonally right, and you will see Lincoln Center; the fountain, the Met, the NYState opera, and the concert hall. Want a weird factoid the tourist don't usually get here? There's an underground connecting all of these, and within it is a cafe called Footlights. The food I recall was not great, but you can still occasionally surprise performers in here catching a quick bite. On summer evenings there are often outdoor concerts in the bandshell beside the Met. Also, the Met sells standing-room tickets and you can convert these to seats at the first intermission when it's clear which ticketholders didn't use theirs tonight...
If you are musical, Julliard is here, just north of the Met attached by a pedestrian bridge over the street. Between Julliard and the Met is a small musical arts museum and gift shop. It may have grown since I was last in there. I found the book Cat by Kliban in there in 1973 or '72 (don't recall, but it was completely new); they seem to have a record of wise buyers! Also, musical puns -- a note pad for the fridge with staves and Ah, la mia lista across the top... Mid-manhattan: The Ford Foundation building is amazing. Lobby several stories high and it's a rainforest. Indoors. In Manhattan. There are waterfalls and trees, and people's desks on little platforms along the paths. Worth a drop-in! :-)
Or do Park Avenue. That is GREAT fun, especially starting at Central Park South and walking south. You'll recognize a lot, again. that's best at Christmas, though, because of FAO Schwartz' windows and Rockefeller Ctr's skating and giant Christmas tree and Messiah sing-along. Mid-manhattan has a lot of tourist locations and a lot of paper about it, I am assuming, like the Village. Basically, the island is only 12 miles long and about 3 miles across at the widest, you can walk all OVER it if you have good shoes. And you discover a lot doing that :-) Broadway crosses diagonally, but it is also the busiest and usually dirtiest. Try staying East of Columbus farther south than 59th street, although the Theatre District breaks that up. It used to be a 'bad'
neighborhood :-) You are familiar with Harlem's rep for crime, but if you want to go there it can be foundat the north end of central park. 110th street is a good place to avoid as a pedestrian. Columbia University's stop on the Broadway line (the 1 train only, NOT the 2 or 3 trains) at 116th is OK, but going father north could be a big mistake, if you look like a tourist :-) It's actually OK, especially during the day, to walk down Broadway from Columbia.
There is too much to talk about. Sorry the post has gotten so long! I'll write you if you send your email address, to avoid spamming the non-NY-interested.
To see where you are going before you get there, try this link (NYC subway system with clickthrough details about each station, so they claim :-) http://www.mta.nyc.ny.us/nyct/maps/submap.htm
To get directions to any destination station (why? you have a map!), try the NY Subway Finder: http://www.krusch.com/nysf.html
To find the cross-street for any address in Manhattan (only! and in some areas of the Village, not even), go here: http://www.ny.com/locator/
good luck! Heather
I grew up in NYC and now that I am a mom of toddlers/preschoolers I am not sure I remember what teens like to do, but here were a few of my favorite memories. Also, you don't say how long you'll be there, so some of this kind of depends.
Friday nights on the museum mile (from 80s to 90s on fifth avenue) -- live jazz and other music outside each museum, free admission, party atmosphere.
Opera in the Park -- pack a picnic and join the hordes on sheep's meadow -- sometimes they have fireworks after them, and its a really nice atmosphere of the kind that's best in NY, where people can adopt a kind of resigned hilarity in big crowds.
Jones Beach: an incredible beach, huge, and really great -- pack for the whole day, and barbecue there at dusk. The Atlantic is wonderful there in the summer, and they have great sand. Not accessible except by car (built that way on purpose by Robert Moses, and there's a whole book about it).
You can also go down to the meat market, fish market, up to the flower markets (all of them at the crack of dawn, unfortunately) and see the how much of everything comes into a city of millions (and the transport point for millions more). Those are kind of spectacular spectacles.
Some other secrets -- if you wait on line on the morning of the night you want to go, you can get into David Letterman (get more info on his website); if you go to the Vidal Sassoon salon in the fifties on 5th avenue on (I forget) Tuesday or Wednesaday at a particular time (11am?), they'll use you as a haircutting model and give you a free haircut, but you have to let them do whatever haircut they want to practice on your head, a risk; if you go to the TKTS office in the 40s on Broadway, you can get half price into Broadways shwos on that day. They might like the Rocky Horror Picture show down on 8th street -- that was where it all started.
We were in New York City a couple weeks ago with our 10 and 13 year olds and had a great time. Don't be concerned about the subways - if you're used to BART or any similar transit system you won't have any problem and you'll realize how much cheaper and more reliable they are too. Get a subway map from your hotel or a visitor center. You can buy fun passes at many newstands or visitor centers that cost $4 for an entire day's transportation on either subway or bus. Or you can go one-way on the subway as far as you want in one direction for $1.50! We never waited more than about 3 minutes to hop on a train, and never had any problem with crime, or even rude people. We also walked a lot, many sights are not far from each other. And we took a few taxis - very easy to flag one over and not really that expensive when you have four people in it.
In fact, we were amazed at how clean and pleasant New York was in general. It's cleaner and has fewer (obvious) homeless people than Berkeley. (We were however doing the tourist things and were mostly in the mid-town, Central Park, and Theatre District of Manhatten.) They have people out there picking up trash, the grafetti is gone, we didn't see a single person pushing a shopping cart, and were never asked for spare change!
With older kids I would recommend a Broadway show or two. We were lucky enough to have gotten tickets earlier for the Lion King, and we also got 1/2 price tickets (at the Times Square booth - be there by 3:00 for a show that night) for Ragtime. The Lion King was so creative and different I think adults and older kids enjoy it more than little ones. (Yes, the same Disney story, but with so much more - wonderful costumes, a magical stage and props, great choreography and puppetry.)
I was also surprised that my kids enjoyed some of the museums - the Cloisters and the Guggenheim are cool to begin with just due to their architecture. They really liked climbing up the Statue of Liberty (but be sure you get on the FIRST ferry in the a.m. or you'll have to wait much too long).
Also, we found a hotel that has free parking and a pool, and is cheaper than most (AAA discount)!! The Travel Inn on 42nd (?? - the same street the Disney Amsterdam Theatre is on). It's 3 blocks from Times Square, 2 from a subway stop. It does border on a not so great neighborhood and there is construction on the block next to Times Square, but I think it's a great family place if you don't care about a grand lobby or the Plaza type experience.
I'm not sure about activities for your 16-yr-old, but for the 12-yr-old I'd recommend the Museum of Natural History. Actually, for both, I suggest you try to find out if there are any children's performing arts events in the plaza at Lincoln Center, or anything else at Lincoln Center, for that matter (but the plaza stuff is probably free of charge). There's probably all kinds of stuff for kids because the city is usually teeming with culture, so sorting it out may be hardest part. As far as transportation goes, I myself wouldn't even think about using a car, and public transit is more more extensive than in the Bay Area. I'm not up on the current state of the subways, but I'd bet that there are probably lots of cops in the subways now. The last time I was there, they weren't especially clean, but they sure are fast! Buses are another option, but they have to deal with all the summer street traffic. It goes without saying, but definitely avoid the rush hours. Have a great time!
We just got back from NYC with two small children, but two things we did seemed like teens would be into them as well. The first, Ellis Island, is maybe obvious, but the second, the Tenement museum, is less well known. It's on the lower east side and is really well set up and interesting. The tenement has been restored to the state it was in during the heyday of European migration. So it's dark, dingy, cramped, peeling paint and very atmospheric. I highly recommend it.
I took my then 14-year old son to New York for a 4-day trip last year. Be prepared for a lot of that sounds boring, I could do that at home, why would we want to do that? But go ahead and drag them to all the usual places anyway. He couldn't believe I wanted to take him to the Natural History Museum or the Met, for instance, but luckily it rained and he loved both (remember, the Met's got a lot more than boring old pictures).
He was blown away by St. Patrick's, St. James, & the old church (particularly the graveyard) near Wall Street even though we're not in the least bit religious. He thought the boat pond in Central Park was very cool, didn't see much in the village (west or east) or Soho that he felt was special next to Berkeley or San Francisco, liked the World Trade Center view, was disappointed that getting out to the Statue of Liberty would suck up half a day and so we opted not to do it, found it great fun to be dumbstruck by the prices at Tiffany's and the grotesque lobby of Trump Tower, loved Times Square at night, enjoyed Katz's (? - deli on Houston) & walking from Wall Street through the lower east side to get to it, thrilled to eavesdrop on dinner conversations in Little Italy, and was disgusted but intrigued by the meat packing district in the west village (which was right next to where we were staying and so I accidentally walked him through it one time since he's never seen that type of area).
The afternoon at Yankee Stadium was like going to Mecca; if either of your kids is a baseball fan, plan on either Yankee Stadium or Shea depending upon what team is in town. If you're there on a Wednesday (I think), take them to Amateur Night at the Apollo, which is an absolute blast that I regret not being able to take him to because he would have loved it. And no, despite being in Harlem, when I went year before last it felt safe so long as we left with the rest of the crowd.
But what my son liked most of all was the graffiti, and so once I figured that out I asked an artist friend there where we might see some interesting stuff and that was what lead us on the Wall Street to Katz's (?) walk which proved interesting beyond the graffiti because you could see the overlay of several immigrant populations so clearly in the buildings and businesses. I'd recommend this walk only during the day on a weekday because it is one area that still felt a bit unsafe.
I also wanted to take him to the Tenement Museum in the lower east side, but our timing was bad. That's fascinating because what they've done is taken an old tenement house, researched about the families that actually lived in that house, and restored several rooms to the state in which those families lived during several different periods, in one case with actual items from the family that lived in that room. It's a guided tour, but only lasts about 45 minutes and so is within the patience limits of a teen.
Giving them some perspective helps--at first he was disappointed because he felt like it wasn't that different than San Francisco, but when I started pointing out the different scale of the buildings (the Bank of America building is the size of now inconspicuous turn of the century skyscrapers there, for instance), the natty easterner dress style (we were there for Easter & so saw some of the best of this), the accents & attitudes, the foods, etc. he started to get the hang of it and got very into noticing the ways in which people behaved differently from in the Bay Area--he noted at one point that a lot more people seemed to be reading, even the teenagers, which does seem to be true.
As for the subways, they're basically as safe as anyplace else if you take neighborhoods & times into account, they are usually the quickest way around, and to my mind are an integral part of experiencing New York. They do have the drawback of being underground, so use the buses too so you see things. And WALK--New York is one of the world's great walking cities and you miss a lot if you don't get out and beat the pavement. Some subway stations were pretty confusing last year because of reconstruction, and the easiest way to become a mark in New York is to look confused. So stride with purpose and if you blow it and end up on the wrong platform, well you're on vacation anyway, aren't you?
All in all New York is a much safer place than it used to be, so if you're thinking of a New York you knew 20 years ago be prepared to be shocked at how friendly people have become and how previously unsafe neighborhoods are now very safe--after meeting some friends at around 110th on the west side one evening that went much longer than planned, we found ourselves out on the street at 2:00 AM, and then took the subway back to the village without ever feeling threatened. The previous year I'd walked with my lover from Times Square to the village after midnight, again without feeling the slightest threat. I probably have a greater capacity for feeling safe in such situations than most people because I love walking at night & so have learned to do it safely, but the point is that even so I felt much more unsafe in New York when I was in my 20s than I do now in my mid 40s.
We had a blast & I'm sure you will too. I'd suggest keeping an open mind about what to check out, but having enough specific things in mind so they get exposed enough to start expressing what they like so that you don't get stuck in that jaded bored teen rut.
The funny thing was is we'd go through the naw, not that, I don't think so routine and then he'd say to me so, what are we going to do? Coulda killed him, but what was nice is that at times that would lead to moments where we'd just keep walking, turn a corner, and he'd suddenly be gapping at something like St. Patrick's and say What's that!?!?!
Also, one little thing I forgot: if you should happen to find yourself walking along the lower west side by the river where the Hoboken Ferry lands, there's a park just above that where there's a very cool series of brass sculptures among the chess tables that are a wonderfully goofy commentary on capitalism.
Another thing a lot of people have recommended but I've never done is taking a Circle Line tour, where you take a ferry around the entire island. They say it gives you a very good sense of the city right off the bat. Or of course the Staten Island or even the Hoboken ferry, which is kind of cool if you're a fan of On The Waterfront because you can stand there in Hoboken and look across the water to New York and suddenly realize how painful it must have been to be a poor working stiff in Hoboken with Oz so close. The restoration of the Hoboken Ferry Terminal's probably complete by now too, so you don't have to sneak in to see this incredible building like I did a few years ago.
And (there's always more to say about New York it seems...) St. James Cathedral (113th & Amsterdam, roughly) is really something even if not the most ornate or well-known cathedral in the world. I believe it is the largest cathedral in the world (because it was built later than most & thus could use better construction) so you have this absolutely huge interior space, and the alcoves feature secular themes like technology and sports so there are these great big stained glass windows with something besides the same religious themes you see in every church.
Enough! Clearly I've got to get back there again soon myself!
Have fun! Patrick