NYC Virgin
September 9, 2007 2:36 PM   Subscribe

New York for a virgin?

I am taking my GF (from rural Ireland) to New York for her first time in October. We arrive around 7pm and are staying in the East Village.

What would you recommend doing on the first night to give her that jaw-dropping, big city, NYC experience?

Had thought, yellow cab to Times Square, Pizza at John's and a late night trip to the top of the Empire State Building / Rockefeller. But maybe a bar crawl of the Village?? We dig Jazz so hoped to hang out till 4am (God bless your licensing hours) somewhere hep ;)

Or what?

Super Bonus points for Sunday brunch in the East Village suggestions also!
posted by brautigan to Travel & Transportation around New York, NY (25 answers total) 27 users marked this as a favorite
Walk across the Brooklyn Bridge.
posted by grumblebee at 2:41 PM on September 9, 2007

Sunday brunch in the east village at Cafe Mogador or Cafe Orlin.
posted by milarepa at 2:46 PM on September 9, 2007 [1 favorite]

Broadway show?

For jazz, go to Greenwich Village... see what's going on at the Blue Note, Fat Cat, Vanguard, Smalls, Sweet Rhythm, or even just hop from place to place. Here's a calendar.
posted by miss lynnster at 3:02 PM on September 9, 2007

What would you recommend doing on the first night to give her that jaw-dropping, big city, NYC experience?

If you get into Manhattan before sunset (which is a close thing in October): take her out to Staten Island on the ferry, and make sure she doesn't look back until you've got there, turned around, and start heading back.

If you don't, then head over the Brooklyn Bridge and do the ferry the next day. The aim of both is to get just far enough away from Manhattan to get a sense of its scale.
posted by holgate at 3:15 PM on September 9, 2007

On the Brooklyn side of the Brooklyn Bridge, you can have wonderful New York pizza at Grimaldi's followed by ice cream right on the water under the bridge. Great views.
posted by Bookhouse at 3:36 PM on September 9, 2007 [2 favorites]

Brautigan, email me for a jazz venue recommendation that I'm trying to keep secret so it doesn't get so popular I can no longer get in. I promise you will both have your socks blown off.
posted by CunningLinguist at 3:36 PM on September 9, 2007 [1 favorite]

don't want to be the one to rain on your parade, but just a word of warning that lines for the empire state building are usually very long. it also costs a bunch of money.

a cool alternative (still costs money--- everything in this city does) is top of the rock. amazing views, less (but still) tourists. also, the elevators are f'n cool.

you'll be near central park then, and the met. the met at night is breathtakingly beautiful.
posted by modernsquid at 3:57 PM on September 9, 2007 [1 favorite]

7 p.m. New York time is midnight in Dublin. Maybe you should just plan on a night's sleep?
posted by Carol Anne at 4:01 PM on September 9, 2007

Empire State at night is a good call. It's a bit of a wait in line to get to the top, but the view of the city is pretty awesome.
posted by altcountryman at 4:09 PM on September 9, 2007

I read somewhere that you can reserve tickets for the top of the Empire State Building ahead of time. It's a couple bucks more, but probably worth avoiding the wait. I believe it's open late night, but that may be a seasonal thing.
posted by Frank Grimes at 4:13 PM on September 9, 2007

BIG ditto for Grumblebee - take the 4 or 5 trains to Borough Hall, Brooklyn, and walk back to Manhattan over the bridge. Takes about an hour, best done at dusk. I recommend it to everyone I know that's visiting NYC for the first time.
posted by deadmessenger at 4:19 PM on September 9, 2007

Taking the A/C to High Street will get you much closer to the bridge. If you take the exit at the front of the train, you just have to cross the street, go diagonally across the little park, and climb the stairs in the underpass (on your left). Then you will be right on the bridge. Though really I would recommend walking from Manhattan and spending some time in DUMBO or Brooklyn Heights (depending on your tastes). New York isn't just Manhattan, and while Manhattan is neat in some ways, Brooklyn is awesome and has a lot of the charm that high rents and too many Duane Reades has driven from the City.
posted by dame at 4:38 PM on September 9, 2007

Mmm, make that the back. I am used to coming from the other direction.
posted by dame at 4:39 PM on September 9, 2007

For brunch in the East Village, you must go to Prune.
posted by TryTheTilapia at 4:54 PM on September 9, 2007 [1 favorite]

If you like hamburgers, go to the Shake Shack. There will be a line -- it will be worth the wait.
posted by spilon at 5:00 PM on September 9, 2007

Take the Roosevelt island Tram to Roosevelt Island and back into Manhattan around sunset. It feels like you're floating into the city.
posted by the jam at 5:11 PM on September 9, 2007

Mmmmm Shake Shack. Seconded!

The Bridge is also the right call.
posted by rokusan at 6:24 PM on September 9, 2007

Get on some of the underground mailing lists for New York events. Nonsense is one of the best, mine isn't as active these days (but will be again...)
posted by lupus_yonderboy at 6:56 PM on September 9, 2007 [3 favorites]

Taking the A/C to High Street will get you much closer to the bridge.

This is true, but if you take the 4/5 to Boro Hall, you can walk through Brooklyn Heights (my hood) to the Brooklyn Promenade on the way to the Bridge. Awesome views.
posted by Bookhouse at 7:41 PM on September 9, 2007

7 p.m. New York time is midnight in Dublin. Maybe you should just plan on a night's sleep?

Nah. If you're flying west to the east coast, staying up till US bedtime is the best way to get your body clock sorted. (4am is pushing it, though.)
posted by holgate at 8:34 PM on September 9, 2007

First off, you must read this Flyertalk wiki on Getting to Manhattan from various NYC airports, where it's broken down into what's easiest versus fastest versus cheapest. will give you point A to point B subway directions for anywhere you want to go, taking into account service changes (construction, etc).

As for seeing the city right...
- Top of the Rock over Empire State Building (shorter lines, view that actually includes the Empire State Building, facilities are newer, you're exposed to the elements as opposed to being in a big glass box, it's not crowded at all). Don't forget your camera. No tripods are allowed but you can stay up there as long as you want. I like to time my visits for just before dusk. You can see the city in the daylight, in the sunset, and at night. (If you do go to the Empire State Building, buy tickets online at, buy the fast passes, and look for info about the passes to get to the 102nd floor. It will be about 100 USD, but worth it if you want to feel like a VIP. Oh, and call to find out how long the wait is, visibility, etc. 1.877.NYCVIEW)
- Rockefeller Center, Museum of Modern Art, Times Square, Grand Central, and a peek at the exteriors of the Chrysler Building and New York Public Library (most of these can be combined into one or two days but MOMA will take a few hours to get through.)
- Central Park, The Metropolitan Museum of Art. These can be combined. You'll never see 100% of either in one day, so get a taste to satisfy yourself.
- Don't go to South Seaport. It's a giant outdoor mall with bad food.
- Be forewarned that a visit to Ellis Island and the Statue of Liberty will be time consuming, involve many lines, and both attractions can be very crowded. It's nice, it's interesting, it's not jaw dropping. If you do go to the Statue of Liberty, reserve a monument pass in advance! They do sell out. This pass lets you go inside the Statue. You are only allowed to ascend up to the viewing platform nowadays. Nobody gets to go inside the crown and torch.
- If you do go to Shake Shack (gourmet burger/hot dogs/fries stand in Madison Square Park), go on a weekday around 11:30am or 4:30pm as the lines are long these days. From the park you can also site around admiring the Flatiron Building and Empire State Building.
- Additional activities: walking through the Union Square Green Market, gawking at Church of St. John the Divine or Grant's Tomb, taking a walk down St. Marks Place, wandering around the West Village (say a stroll down Bleecker St.)
- But don't forget to schedule some down time with some good bench-sitting and people-watching!

See also:
New The Basics
How to Visit NYC: The Basics
NYC: The Must Sees. Essentially: skyscrapers, museums, Grand Central.
What You Can Skip.

Make sure you click over to, it's my indispensible resource for what's going on in NYC.

See also:, New York Times' UrbanEye, Flavorpill, New York Magazine's Agenda, Manhattan User's Guide. Offline, I'd also look through the New Yorker's highly curated event listings (grab a copy of this week's magazine and flip through the first dozen or so pages); Time Out NY has a larger listing. The NY Times also does a few decent ones. Here's also a citywide events calendar from city government. also does a regular "Pencil This In" entry that lists that night's events, oftentimes free.

You can also find many self-guided tours of NYC, both online and in book form. I like City Walks: NYC if you go the book route; it's actually pack of fifty-some cards. NYC government maintains an NYC for Free list that has some free, guided tours of places of interest.

If you're into food, I also like this Lower East Side noshing tour.

For brunch: Best brunch in the East Village (that I've found so far) is at Prune (also mentioned earlier). There will be a wait; it opens at 10am, so get there at 9:45am. On the same level, a little walk away is Clinton Street Baking Company, which is barely on the Lower East Side and could be pretty close to where you're staying. It also opens at 10am; there will definitely be a wait, get there at 9:45am.

Also very good: Five Points (technically Noho), 9th Street Market, and Westville East. Cafe Mogador and Cafe Orlin are good and on the inexpensive side, but I wouldn't recommend them to people who want to be impressed by NYC brunch.
posted by kathryn at 9:50 PM on September 9, 2007 [30 favorites]

If you land at 7 pm, expect to get to your hotel and check in around 9; I base this on general airport issues (particularly at JFK or EWR, which are the two that are furthest away from Manhattan), collecting luggage, travel time, etc. At that time of night you will have little traffic from any airport and should be able to see some nice views on your way in.

Depending on where you are, you may be able to just go up to the roof of the hotel (provided they have roof access) and see some nice skyline views. I'd probably skip Times Square and all that the first night. Wander around the East Village. Hit St. Mark's. There are a ton of bars there - try Grassroots Tavern for a semi-divey feel.

For brunch: when I lived in Alphabet City I liked Life Cafe on 10th and B. Now that I'm nearer to Stuyvesant Park I like Galaxy Global Eatery on 15th and Irving (Irving is in between 3rd Ave and Park). Bonus is that it's a block from Union Square so you can walk over, check out that area, and then hop on the subway to almost any other part of the city, since Union Square has so many different trains.
posted by bedhead at 11:10 PM on September 9, 2007

Heh. The title struck me as a "my kingdom for a horse" type question.
posted by wile e at 5:32 AM on September 10, 2007 [2 favorites]

A few more things:
- You can always grab a subway map from a booth in the station. They give them out for free. Sometimes they run out. You might want to check out one of the city's official tourism centers. They will also have free subway maps.
- NY Times Jazz listing for the week of 9/7. When you come in October, look for the updated one. I'm sure there's other NYC Jazz gig listings.
- If you are coming in early October, you may make it in time to attend events put on by the New Yorker Festival (tickets required for most, a good number sell out the day tickets go on sale, which is this Saturday, at noon ET on
- See also Open House New York for some out of the ordinary sights and tours (like places not usually open to the public). Their web site is kinda confusing so make sure you visit on Sept 28 when they put up the big PDF brochure (reservations required for some tours, usually the more behind-the-scenes ones with limited capacity.
- My favorite places to eat in the East Village
posted by kathryn at 7:12 AM on September 10, 2007 [1 favorite]

Well if she's a virgin, whatever you do, don't take her here.

also, buy your ESB tix online and you can skip most of the line when you get there
posted by allkindsoftime at 7:23 AM on September 10, 2007

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