Explore New York City: A Local-Led 5-Day Itinerary

I’ll come clean, I’d been to New York City four times, I felt like I’d ‘done’ it. Statue of Liberty: check; Empire State Building: check; Times Square: check; Central Park: check; Macy’s: check; Wall Street: check. And so on and so on, you get the idea that I felt I’d ticked all the tourist boxes. I loved the experiences, but I didn’t have a desire to return.

But then….. my daughter moved to New York City. I gave her a month or two to settle in to her new job, apartment and to explore her new home town. Then I booked my flight to JFK and was on my way to the Big Apple.

This time I was going to see New York, if not completely with a local (as she had work to go to), then certainly like a local armed with all her tips. And, by exploring the city this way I fell in love with it all over again.

Here I’ll tell you about some of the off-the-beaten-tracks experiences I had! So if you are in New York here is an itinerary written by a local – steal whatever ideas you want and add them into your New York adventures to explore the big apple like no other.

Summary

If you’re looking for what to do in New York City and want more than a rushed checklist of tourist attractions, this local-led 5-day itinerary shows you how to explore NYC beyond the classic tourist attractions.

• Neighbourhoods including Gramercy, East Village, Greenwich Village,& NoLita
• A balance of iconic sights, local cafés, parks, TV filming locations, food spots and free experiences
• Written from real, first-hand experience, guided by local insight
• Ideal for first-time visitors and repeat travellers who want to see a different side of NYC
• This guide is about experiencing New York the way locals move through it – slowly, curiously, and without trying to do everything at once.

Day 1 Itinerary – Walks, Rooftops & Parks

1) Manhatten, East Village

Mud Cafe, East Village

This easy, walkable route starts in Midtown and winds south through some of Manhattan’s most characterful neighbourhoods, perfect for a slow first day in the city.

I was up bright and early on Day 1 – that’s what the five hours time difference between the UK and the US does for you. After walking from Midtown to the Flatiron district to drop my daughter at work, I carried on walking along the route she suggested. This morning I was going to nosey through Gramercy, East Village, Greenwich Village, and NoLita.

These neighbourhoods are known for their residential streets, independent cafés, historic brownstones, creative energy and some of the most characterful corners of Manhattan, where everyday New York life plays out just as much as the famous sights.

First things first, some breakfast. My daughter recommended the cafe MUD in Manhattan’s East Village and it did not disappoint. It was very quaint inside, stained glass windows and lots of wood. But being August and HOT I enjoyed my pancakes in the seating area on the sidewalk outside. If you are looking for a wholesome, lovely cafe MUD is a perfect stop.

2) Tompkins Square Park

Fed and watered I continued walking to Tompkins Square Park and found myself on a film set! Tompkins Square Park is located in Alphabet City portion of East Village, Manhattan, New York City. 

Apparently scenes from American Love Story were being filmed when I visited. The clapperboard, director’s chair, the film crew and extras were all there and it was cool stopping to watch the goings on for a while. I loved this spontaneous New York encounter!

We also visited other neighbourhoods including checking out the NYU area near Washington Square, sitting down for a rest in beautiful Elizabeth Street Square in NoLita and checking out the building photographed on Led Zeppelin’s album cover back in the seventies in Alphabet City. I was down 30,000 steps by the time I returned to the hotel to freshen up for the evening, but I had spent very little money and had seen lots of parts of Manhattan I’d missed on past visits.

3) Gossip Girl Fans This One Is For You xoxo – Visit The Empire Hotel

According to my daughter the Empire Hotel features in Gossip Girl, the iconic New York-set series that follows the lives of Manhattan’s elite Upper East Side teenagers, narrated by an anonymous blogger who knows all their secrets. The Empire Hotel serves as Chuck Bass’s hotel and residence in the later seasons, making it a must-see spot for fans of the series.

The Empire Hotel also features in the TV show Dexter: Resurrected. Dexter is a cult crime drama about a forensic analyst living a double life, and seeing one of its New York filming locations added a fun, TV-inspired twist to our evening.

At the hotel we headed up to the roof for a cocktail, which seemed like a good plan. We had a great view of the rather cool hotel sign above us, as well as streets around the Lincoln Center below us.

4) Little Island

Next was Little Island, after a quick bite at Los Tacos No 1 in Chelsea Market. This park is new since I last visited New York, and is a great addition to the area with its panoramic views of the Hudson River, Lower Manhattan and the Statue of Liberty. This was a wow for me, and we wandered about for a while, seeing the city light up.

While there was lots that was familiar to me on this first day of my holiday – the skyline, the yellow cabs, the hustle and bustle and the general New York city vibe – I had also had the new experiences I had been craving, so it was thumbs up from me as I crashed into bed.

Day 2 – New York TV & Flushing Meadows, US Open

1) The Today Show

Day 2 was equally novel, beginning with me joining the audience of the Today Show to watch Role Model perform! Yes, the Today Show was filming outside my hotel and the bouncers were happy to let me in to cheer the American singer-songwriter on as he performed! I even got a pass to wear around my neck as if I was a VIP! Only in New York!

Once that was finished I popped in to St Patrick’s Cathedral to look around. I’d passed it many times before but had not realised that it is open to the public, and it is certainly worth seeing. 

2) Flushing Meadows, US Open & The Signature Honey Deuce Drink

Anyone for Tennis? Flushing Meadows, US Open.

If you love Tennis and visit New York in late August and early September, you are in luck. Every year the Flushing Meadows US Open commences.

And this time visiting New York we were lucky enough to have US Open tickets! It was pretty straightforward to get to Queens via public transport and my daughter and I decided to visit the very large Chinatown there before we headed to the stadium.

Flushing Chinatown is purportedly the largest Chinese cultural hub outside of China itself, and many locals say it is much more vibrant than its (smaller) Manhattan equivalent. We certainly had an amazing meal there, and by New York standards it was very reasonably priced. Stuffed full with noodles and dumplings we then headed to the USTA Billie Jean King National Tennis Center to watch the opening.

My daughter bought a personalised cap from the shop (personalisation done as we watched the tennis) and we tried the signature honey deuce drink as well as watching a couple of matches before heading back into Manhattan on the train. The atmosphere was amazing and it was another first for me that I probably won’t repeat, but I will have memories to last a lifetime of this iconic sporting event.

Day 3 – New York Theatres & Ramen from Ichiran

1) New York Theatres & Ramen from Ichiran

Day 3 saw us queuing for same day reduced price tickets at one of the Broadway theatres, but unfortunately they ran out just before we got to the front of the line! In better news though, my daughter had entered the lottery for reduced price Wicked tickets and discovered she had won that just as we were walking away from the theatre feeling crestfallen.

I had seen Wicked in Edinburgh a few years before, but nothing beats seeing a show on Broadway! We had some pre theatre ramen in Ichiran, though I was glad my daughter was with me as the ordering system was not one I was familiar with – queue and pay before sitting down, and customise every aspect of your ramen from noodle firmness, to broth spiciness and oiliness! There is also rather unique seating here, in individual chambers with your food appearing through the curtain. Great food and a memorable experience, with a short walk to our show afterwards.

Day 4 – IKEA In New York! ( Yep I’m Not Joking)

The next day was a Sunday, and we, along with many other Manhattanites took the free IKEA ferry to Brooklyn. Wherever you are in the world, what better to do on a Sunday than some furniture shopping! My journey to my local IKEA back home does not, however, pass close by the Statue of Liberty.

This was a lovely boat trip and after a little shopping we had lunch in Red Hook and headed to a bar which I was gobsmacked to find overlooked Lady Liberty. I was glued to the view rather than my drink! Other stops in Brooklyn included Valentino Pier for some key lime pie on a stick and  Marsha P Johnson State Park for uncrowded views of Manhattan, before heading back to Manhattan for pizza in the West Village. 

Day 5 – Art & History

Met Cloisters

My final full day was Labor Day, a US public holiday held on the first Monday in September. Originally created to honour American workers, it’s now widely associated with the end of summer, with many locals leaving the city for the long weekend, making New York feel a little calmer than usual.

We took a trip to the Met Cloisters. The Cloisters Museum and Gardens is a branch of the Metropolitan Museum of Art located by the Hudson River in Upper Manhattan. It is accessible by public transport from Midtown where I was staying, but it takes a long time so we grabbed an uber. It houses art and architecture from medieval Europe. I actually appreciated the building itself more than I did its contents, but for those interested in this period it would be pretty amazing.

Pop Up Bagels & Central Park

All that art made me hungry so a bagel stop was necessary. Our bagel shop of choice – Pop Up Bagels – was on the edge of Central Park so we took them to go and enjoyed a very busy Labor Day afternoon in the park. There were lots of bikers out, rowboats being hired, frisbee games going on, and children playing. It was fun and relaxing to simply people-watch, with the skyscraper backdrop. 

Final Verdict

New York City is often sold as a place you need to conquer – attractions to tick off, neighbourhoods to rush through, schedules packed from morning to night. This trip reminded me that the opposite approach is often far more rewarding.

However, I can appreciate that often, visiting New York is a one in a lifetime experience so there is absolutely nothing wrong with the original approach either, but if you do have the privilege to visit more than once don’t be afraid to give a try to the less touristy things!

By exploring New York by neighbourhood rather than by landmark, walking between areas, stopping for coffee, sitting in parks, hopping on ferries and embracing everyday city life, New York felt less overwhelming and far more personal. Some of the most memorable moments came from simple things: wandering unfamiliar streets, stumbling across a film set, or watching the city light up from a rooftop at the end of the day.

This local-led itinerary also proves that you don’t need an unlimited budget to enjoy New York City. Walking is free, neighbourhoods are endlessly interesting, and many of the city’s best experiences cost very little, or nothing at all.

If there’s one takeaway from this guide, it’s this: don’t write New York off after one visit. There are many ways to do New York so don’t be afraid to be a repeat visitor – I have my next trip booked already, and will be collecting more tips from locals and exploring more neighbourhoods not on the main tourist drag. This is a city like no other and I now know I will never tire of it!