What to do on your trip to New York
I have written here about how the idea for our trip and our itinerary came together, but for us, the first stop on our journey across the United States simply had to be New York. When it came to NY itself, whilst the sites themselves were obviously a huge draw, we were also hugely excited about the food & drink side of things, specifically the chance to seek out some of the typical, traditional and historical foods and places that are so much a part of the popular imagination when it comes to New York. In fact, we enjoyed this side of things so much that I have detailed this in a separate article about some great places to eat and drink in New York.
Billions of words must have been written about New York City and whatever your tastes or whatever you want to get from your time there, New York will have something for you. This is not therefore written as a definitive guide, but rather as an attempt to give you a sense of some of the options that you have in structuring a few days exploring the Big Apple.
Day 1 – Arrival, Midtown, Central Park, Upper West Side & Upper East Side
Arrival
Having landed at JFK just after midday on the Friday and succeeded in passing through immigration, Covid checks and baggage collection relatively smoothly, we took one of New York’s iconic yellow taxis to our hotel in Manhattan. With the hotel being based in Chelsea and having looked into the various public transport options, we decided that the ease, convenience and (marginal) time saved by using a taxi outweighed the slightly higher cost. The drive also gave us our first glimpse of the Manhattan skyline and took us across some of Manhattan’s famed avenues (including Madison, 5th and Lexington) for the first time.
An early check-in at the hotel allowed a quick change of clothes and meant that we were ready to pound the asphalt, start exploring (and start eating) by 3pm. Given that it was a warm spring day, it felt as if we had a good chunk of the day ahead of us.
Midtown
Almost immediately we were thrust into cinematic New York. As we picked our way through the Midtown sites familiar from a countless number of films and TV shows, the only real questions were where to go first, where to go next and how to get there. Yes, it’s familiar and of course it is a cliché, but an exploration of this iconic area is essential.
As we usually do, we decided to walk as much as possible in order to take in as much as we could and to avoid simply popping up next to each point of interest and then disappearing back into the subway. Despite starting the exploration part way through the day, we still managed to take over 30,000 steps that day as we meandered our way through Midtown, Central Park, the Upper West Side and the Upper East Side.
In addition to sating our appetite by grazing our way through some incredible places (which you can read more about here), we passed Madison Square Garden, before walking up Broadway and through the much-maligned Times Square to Central Park, taking in the Empire State Building, Radio City Musical Hall, Carnegie Hall and myriad other sites along the way.
Amidst everything, we also witnessed some pretty intense telephone conversations (“I will put you in the ground #@1*”) and the odd street altercation. What was clear from the start was that this was a real place full of real people – in short, everything that we imagined and more!
Central Park & Upper West Side
We were already aware of the scale and popularity of Central Park, but what really struck us was the diversity of its landscape and the importance that it clearly plays in the lives of so many New Yorkers. In addition to the tourists and dog walkers, the park was packed with people doing everything from picnics to baseball and rollerblading.
If anything, I had underestimated just how pleasant and varied Central Park was. After taking in the Bethesda Foundation, Belvedere Castle, Cherry Hill Fountain (the inspiration for the Friends fountain) and of course the John Lennon memorial, we strode off into the famed and mostly residential Upper West Side to have a quick look around and have another quick pit stop for food.
We then crossed back across the park, visiting the Shakespeare Garden before exiting Central Park at The Met on 5th Avenue. Unfortunately given the time of day and the fact that a proper visit would no doubt take a whole day, we had to content ourselves with taking in its imposing (and familiar from the screen) façade.
Upper East Side
With evening approaching and a cold wind starting to replace the baking afternoon, it was then time to press on into the gilded Upper East Side. After strolling down the fabled Park Avenue, which was in its spring blossom pomp, it was time for our first sit-down meal in Manhattan. I had earmarked the long-established upscale burger joint J.G. Melon as somewhere that we were keen to try, and after a long day of travelling and walking, it really didn’t disappoint.
By this point, it was time to seek a relatively early night and after initially starting to walk the 50 odd streets south to our hotel (seduced by the seeming simplicity of just walking in a straight line towards somewhere that you could see), we sensibly opted to jump in a taxi for the remainder of the way home. The upshot being that we still had some energy in our legs for the following day.
Day 2 – Gramercy, Flatiron, Greenwich Village, West Village, Hudson River Greenway, Meatpacking District, Highline & Midtown
Gramercy, Flatiron, Greenwich Village, West Village, Hudson River Greenway, Meatpacking District, Highline
Saturday morning gave us the chance to head South from our Chelsea base. Getting up and out relatively early on a bright weekend morning meant there was a lovely relative calm and stillness to this area of Manhattan. We enjoyed a lovely stroll down through Madison Square Park and Union Square, where there was a terrific farmer’s market, before walking down past the NYU buildings and spending some time in the appealing Washington Square Park.
The second part of the morning took us through Greenwich Village and the East Village and then to the Hudson River Greenway. The more varied street pattern of Greenwich and the East Village made a great contrast to the other bits of Manhattan that we had experienced up to that point. With a plethora of cafes, restaurants, bars and galleries together with a very evocative cityscape, this really felt (budget notwithstanding!) like it would be our choice of places to live in New York.
After lunch in the Meatpacking District near the Witney Museum of American Art, we took in the views by walking the very popular Highline (with a pit stop at the Chelsea Market) before heading back across to the Eastern side of Midtown to visit some of the sites that we hadn’t been able to the previous day.
Midtown (again)
A real highlight was the New York Public Library on 5th Avenue. Although it wasn’t possible to visit the Rose Main Reading Room on that day, the rest of the building is also stunning and the chance to be able to read and write in such an environment must be incredible. Being able to unwind in the sunshine in the adjacent Bryant Park provided an opportune breather and refreshment. At this point, we started to see more and more of the Chrysler Building, my favourite of New York skyscrapers.
From there it was a short walk up to the historic and fabulous Grand Central Station. Here, we kicked off our evening in earnest at The Campbell cocktail bar before heading out for dinner and drinks at the Old Town Bar & Restaurant. After a final nightcap at the historic and buzzing Pete’s Tavern, our second night in New York had come to an end.
Day 3 – Brooklyn, Wall Street / Lower Manhattan, Staten Island, Chinatown, Little Italy & The Lower East Side
Brooklyn
Despite ‘refreshing’ and ‘enjoying’ ourselves thoroughly during our Saturday night in Manhattan, we rose at a (relatively) reasonable hour, forsook the underwhelming hotel breakfast and hopped on the subway to Brooklyn (York Street Station). First stop was breakfast (or maybe brunch by this point) at the Time Out Market in the shadow of Brooklyn Bridge. This wouldn’t typically have been my first choice – I have previously visited the Time Out Market in Lisbon, and whilst there is undeniably some fantastic food there, the venues are inevitably quite sanitized and tourist heavy. However, when you are feeling seriously hungry, have no real fixed idea of where to eat and you find out that it has another branch of Ess-a-Bagel, then such reservations do tend to melt away.
After an incredibly filling bagel (filled with cream cheese and jalapenos for full disclosure), it was time to kickstart our exploration of Brooklyn and to get a proper look at Manhattan from this side of the East River. In truth, the leisurely amble down through Brooklyn Bridge Park was a real highlight and a change of pace. Much like New Jersey on the other side of the Hudson, it seems as if a completely new skyline has emerged further up the East River in Long Island City.
It was amazing to see the range of sporting facilities at Pier 2, and I was slightly envious of the surroundings within which people were playing basketball, handball and particularly, pickleball, which I was only vaguely aware of previously and which seemed to have really taken a hold on people’s imagination here.
A walk through the elegant Brownstones of Brooklyn Heights was another indication of the variety the city has to offer. By this point, the fabulous weather of the preceding two days had quite suddenly given way to a strong and bracing cold wind. Having spent a good deal of time next to the water, we made the reluctant decision to forgo the walk across the Brooklyn Bridge in favour of a return metro journey from Borough Hall to Manhattan, and specifically Lower Manhattan.
Wall Street / Lower Manhattan
Now was the time to if not worship at the Temple of Mammon, then to at least have a good look around. In other words, it was time for Wall Street and the financial district. Given that it was Sunday, the budding (and actual) masters of the universe were thin on the ground (or well disguised). Whatever your take on Wall Street, there is no denying that this is a place that has played, and continues to play, a central role in shaping both America and the wider world.
One disappointment was that the National Museum of the American Indian was closed – my visit as a teenager had stuck in my memory, but alas a return visit will have to wait for another time. We contented ourselves with the obligatory photos of the area, giving as wide of a berth as possible to the tourist scrum around the famous bull statue near the New York Stock Exchange, before embarking for our third borough of the day.
Staten Island
The Staten Island Ferry really is a marvel. In a time when everything has a price (and normally a high one) the ferry remains free. Given the prices charged by private boat trips into NY Harbour, this is even more incredible. Long a hidden gem of any visit to New York, it seems that the social media age means that more and more people are discovering the ferry, but that does nothing to diminish the value and enjoyment of your free round trip.
Now the Manhattan skyline is an impressive thing. It may be often imitated by newer, sometimes taller and sometimes gaudier challengers, but for me it remains something special. Often imitated, but never bettered if you will. For sure, part of this is due to its own self-perpetuating mythology (aided valiantly by the twin titans of film and television), but it remains a truism. And nowhere is the view better or more iconic than from the middle of New York Harbour, and ideally from the Staten Island Ferry. Having done the journey during the day and at night, it is really splitting hairs as to which is best. My advice – if you have time, do it twice!
The only footnote I would add is that the emergent cluster of skyscrapers on the New Jersey side of the Hudson River means that the Manhattan skyline now seems a little less distinct when viewed from the ferry. Whereas previously it had very much appeared as an island of unfathomably large buildings surrounded by buildings of a more human scale, this is now less evident.
Lower Manhattan, Little Italy, Chinatown & The Lower East Side
After a short stopover in Staten Island, it was back to Manhattan and time to track down some more of its typical and historical culinary offerings. From the towers of the financial district, our walk north from the ferry terminal took us past some of the imposing landmark buildings of another era including New York City Hall and the New York County Supreme Court.
By this point, we were spoiled for choice with Little Italy, Chinatown and the Lower East side all looming ahead of us. When we travel, we often opt to share meals and snacks when possible so that we can try a wider range of foods and places. Even with this strategy in place though, it was clear that some difficult decisions would have to be made.
Having concluded that there wasn’t enough time for a trip to an old school red sauce Italian in Queens or the Bronx, we were clear that a visit to a typical New York pizzeria (ideally in the shrinking Little Italy) was a must. With a trip to the legendary Lower East Side Jewish deli Katz’s having also long been on my hitlist, it was clear that all other temptations would have to be resisted. Again, our thoughts on these places have been detailed here.
Day 4 – Departure: Next Step New Orleans
Monday morning, and it was already time to leave New York via an early flight from La Guardia to our next stop of New Orleans, which you can read about here. Other than our taxi driver incurring the wrath of a very serious man with gold teeth driving what looked like a military-grade SUV, this was a nice opportunity to drive through another part of Queens and also to visit New York’s ‘other’ airport. Post-remodel, La Guardia was actually a more than adequate place to wait for our plane, and an airport outpost also allowed us to check one more item from our culinary to do list!
PS. Given the short timeframe, there was so much that we were unable to fit in. Included on our (ever expanding) list for our next visit are Harlem, the Bronx, Williamsburg, McSorley’s, an old school ‘red sauce’ Italian, digging deeper into Latin New York and succeeding in crossing the Brooklyn Bridge on foot!
The Considered Journey is a travel blog focused on travel reviews, travel tips and travel guides, all focused on travel inspiration with a view to helping you make the most of your trip and maximise your travel time.
Having travelled across Europe, Asia, South America, North America, and parts of Africa, we have a host of experiences to share with you. As our focus is on helping you make the most of your trip and maximise your travel time, we highlight the best things to eat, best things to drink, best places to go, and best things to do. In addition, we have written a range of airline reviews, hotel reviews, airport lounge reviews and credit card reviews, and also cover topics such as travelling as a couple, career break travel and sabbatical travel.
We understand that circumstances vary from trip to trip, so we cover everything from luxury travel to some more budget travel options, and the traditional to the modern.
Comments