do a breakfast or brunch here ( the chopped liver is one of the planets great delights)....
http://shop.russanddaughters.com/

Get yourself two documents which I cannot recommend highly enough:

http://www.stanfords.co.uk/New-York-Everyman-Mapguide-2016_9781841595672 - the most user friendly pocket size map and guide books I have found. The city is split into fold out easy to use maps. It has served us well for about six trips.

https://shop.herblester.com/products/how-to-find-old-new-york-city-guide - just like London, a lot of the old characterful places have been swept away, this little maps lists a host of interesting old bars, shops, diners and restaurants where vestiges of old New York still endure. We've ticked off about two thirds of them now and they're all winners in their field.

Get yourselves MetroCards for the duration of your visit, which allow you to ride, subway, buses and urban trains - and cane them to death!

Go up a tall building and take a view of the city. The World Trade Center 2 view is best but the Empire State is more evocative. Book up in advance as the queues are enormous.

Take the free ferry to Staten island and back for views of the harbour and Statue of Liberty.

If you like to walk, see where John Lennon got rubbed out at the Dakota Building on the Upper West Side, then walk across Central Park to the Upper east Side and see Frank Lloyd Wright's masterpiece the Guggenheim Museum - an extraordinarly wonderful building.

A few random highlights:

Grand Central - have a drink at the Cambell Apartments then a meal at the Oyster Bar.

Eisenbergs Sandwich shop near the Flatiron - huge sandwiches as you might guess and obscure soft drinks like Egg Lime Rickeys, which are mixed up in front of you.

MOMA - Museum of Modern art if you have time.

McSorley's Old Ale House - supposedly the oldest bar in the city, which didn't admit females until 1970, it was the subject of Joseph Mitchell's book 'McSorley's Wondeful Alehouse'. A bit of a tourist hangout TBH but still very atmosperic.

JJ Hat Center on 5th Avenue - great hats and staffed by real gentlemen.

I'm sure you'll really like it, contrary to popular belief, New Yorkers are extremely polite and helpful.

Thank you all for your suggestions thus far. I've extrapolated everything and am working it all into a google map. Three things occur to me thus far, which are somewhat relevant - firstly, I am travelling with my elderly Mother. For the most part she's pretty willing and able but she did have nearly half a lung removed earlier in 2017 and is therefore unable to walk any great distance, so the ability to trot from one location to the next is sadly somewhat hindered. Secondly, I abhor fish, it's a long story but I never eat the stuff and I'm no great fan of Offal either, so whilst the suggestion for Russ & Daughters and the Oyster Bar is appreciated, I'm ruling it out! Thirdly, heights scare the bejesus out of me, I went up the Eiffel Tower a couple of years ago and had to be assisted down due to having a panic attack, so I won't be seeing any city views from on high sadly!
The good news however is I now have had the flight details and our flight timing means we actually wind up with very nearly a full extra day in town. Our flight doesn't depart until 2215 on Monday and although the airport is a couple of hours away (we're travelling Dublin - Newburgh Stewart & vice versa) we won't need to leave town until 1700 or so on Monday evening.

I'll see if I can manage to attach my map here somehow!

/\  Tim you are still going to have a great time, there are ways to work around these issues, like hiring a driver for a couple of days and making sure you're staying in a room on a low floor, etc.

instead of seafood and organ meat why not try to have a lovely porterhouse steak at Peter Luger or another great chop house?  Berkeley's suggestion of a ferry ride is a good one, and you can also arrange a cruise around the island ....

I was also going to suggest packing a lunch of lobster rolls and eating them on a helicopter ride to the roof of the Empire State Building where you could do some bungee jumping, but that's out now I suppose .....

Last edited by The Laird of Enfield (2017-12-31 14:34:57)

Around Manhattan on a guided boat tour is very good.

There's an Alden store on Madison Ave. They're sold other places but I'd check the actual Alden store first.

I've never run across any Ivy/trad-specific thrift store names for NYC, though I'm sure some are better than others. Most good thrift stores will cater to the hipster set, but if you aim for the right area (more $$$) you'll probably find some good stuff if you have time to shop around a few... Maybe others will know more than me. There's also J. Press - they let you peruse there even if you don't buy, and it's worth it.

When are you thinking of being here? First trip to NYC is a really exciting time. Nice to have someone who knows the ropes along, too. If you want to see what un-gentrified, neighborhood NYC looks like, come on up to Inwood, I'll buy you some Mexican food.

Philadelphia is worth a train ride over to, spent a lot of time there, having a lot of friends there in my 20s. More friendly than NYC.
Vintagewise in Philly,  http://www.briarvintage.com is good, but are now only open Saturday's or by appointment?