I’m lucky enough to have visited New York City three times in the past 19 months.
Growing up, it was always a dream holiday destination and having seen it on so many films and TV shows, it already felt like a close friend.
The first visit was in December 2024 for my honeymoon and seeing the city in the run up to Christmas was magical.
Mrs Molloy and I visited again for my 32nd birthday back in February and while still a great trip, it failed to live up to the incredibly high expectations set by that first experience.
It felt like there was a little bit of unfinished business there, so when my mum very kindly offered to pay for the three of us to go, I jumped at the chance.
Having now been three times, here is how I’d recommend spending 96 hours (or four days) in the Big Apple.
Where to eat
This seems as fitting a place to start as any and some of these won’t come as a surprise if you’ve read my New York food and drink bucket list post.
Beginning your day with a good breakfast is a must, especially if you’re battling jet lag at the start of your trip, but don’t overthink it.
Simply grab a bacon, egg and cheese from your nearest bodega or, if you fancy a bagel, my pick would be Ess-a-bagel; my go-to order is an everything bagel with Nova Scotia salmon and scallion cream cheese. They really don’t scrimp on the fillings so this will set you up really well for all the walking you’re going to be doing.
New York is famous for its pizza and I’ve tried some of the bigger hitters in Joe’s and L’Industrie but my favourite remains a classic cheese slice from Scarr’s in the Lower East Side. That being said, the fig jam and bacon slice from L’Industrie is also very good.
Another New York institution is Ukrainian restaurant Veselka in the East Village and for good reason. Their exceptional fried pierogi (in flavours such as braised beef and cheese) are the perfect mid-afternoon pick-me-up. Wash them down with a tangy lime rickey and thank me later.
Staying with small plates, the adobada tacos from Los Tacos No. 1 are one of the few ‘viral’ New York foods worth the hype.
I’ve also previously been effusive in my praise for the iconic Katz’s Deli and I would definitely recommend trying their ridiculously huge (and priced) pastrami sandwiches at least once but it can be extremely messy, quite overwhelming and take an age to get served so bear that in mind.
When it comes to sit down meals, I’ve got a couple of options that serve different purposes.
Despite loving steak, it took me until my third trip to visit a steakhouse and after visiting Gallaghers, I regret not doing so sooner.
Gallaghers has been open in Midtown Manhattan since 1927 and when you walk through the front door, it’s like stepping back in time. Back in the Prohibition era, it was a speakeasy for ‘colourful’ characters to hang out and almost 100 years on from opening, it still feels like something from Goodfellas with its red leather and dark wood interiors.
Despite only going for the lunch menu (3 courses for $34) it was perhaps the best restaurant experience of my life in terms of both food quality and the atmosphere. I paid the $22 supplement for the 8oz filet mignon and also had a glass of malbec, which took the bill to considerably more than $34 but it was worth every cent.
The steak was seasoned and cooked to perfection and is only closely rivalled by the one I enjoyed at Y.O. Ranch Steakhouse in Dallas a few years ago. Both sides – mashed potatoes and creamed spinach – were absolutely delicious and I could have eaten a full plate of each.
Both the caesar salad starter and cheesecake dessert were ample in size considering the relatively modest price point and, if I lived in New York, I’d be at Gallaghers for every special occasion.
Or, if you’re just in the mood for some hearty soul food cooked with love and served with a smile, Amy Ruth’s in Harlem does the best fried chicken I’ve ever had the pleasure of eating. (Bonus tip: ask for the grape Kool-Aid).
If you have a sweet tooth, then you can’t go far wrong with Magnolia Bakery and their famous banana pudding (I NEED the recipe to recreate it at home).
Where to drink
I have to admit that I’ve never actually had a ‘night out’ in New York in the same way as I’d have one back home (i.e. drinking about 10 too many pints) as I want to savour every minute in the city and not waste a whole day being hungover.
That being said, I still have a surprising number of recommendations on this front.
Speakeasy Attaboy, in the Lower East Side, has a particularly fascinating concept in that it doesn’t have a menu in the traditional sense. Instead, you tell the bartenders what you’re fancying or what flavours you like and they’ll make something that they think you’ll enjoy.
For example, Mrs Molloy told the bartender that her favourite cocktail is an Aviation and ended up with a Sunflower (gin, elderflower, Cointreau and lemon juice), while I said I fancied something creamy like a White Russian and got a cocktail made up of spiced rum, coffee liqueur and salted caramel cold foam.
Both were utterly delicious in very different ways; the Sunflower was refreshing, light and citrusy, whereas mine felt like a darker spin on something I already loved and a perfect dessert cocktail that I wish I could recall the name of.
To get in, you have to knock on a very inconspicuous door (it’s very easy to miss) and then wait for someone to answer. There’s also a CCTV camera looking at you in a way not too dissimilar to the eye droid at Jabba The Hutt’s Palace in Return of the Jedi but don’t let this put you off.
If you like your cocktail bars a bit more light and airy then famed celeb-watching spot Dante in the West Village is an institution for a reason.
I’ve previously noted my love of The Dead Rabbit in the Financial District. The Irish bar pulls off the winning combination of lethal cocktails, delicious pub grub and an atmosphere that feels like home. It’s out of the way from most of the other places in this post but definitely worth a trip if you fancy a drink or three.
If you just need somewhere with cheap beer and a quick snack to go alongside it, then it’s hard to go wrong with a pint and a hot dog for $4 at historic dive bar Rudy’s and if you’re a bit of a vinyl buff (and/or love karaoke) then Turntable LP in Koreatown is a very cool place to have a couple of drinks.
Alcohol of course isn’t everything and there’s plenty of cool coffee shops – Do Not Feed Alligators and Devoción are two of my favourites. Alternatively you can pop in your nearest 7/11 and create a ludicrously sized custom coffee and choose from a whole range of delicious creamers for a few dollars.
What to do
Eating and drinking your way round the city is very fun but there is obviously so much more to do than that.
If you’re flying into New York from the west (as is the case from the UK) then you’re probably going to have some early mornings, courtesy of jet lag.
Don’t see this as a bad thing though. It just gives you the perfect opportunity to tick off some ‘must-do’ attractions off the bucket list before the city wakes up they become super busy.
Central Park is probably my favourite place in all of NYC. There’s something almost magical about such a huge and beautiful green space slap-bang in the middle of hundreds of skyscrapers and seeing these hulking buildings framed by the park’s trees is quite something. It’s incredibly peaceful and tranquil first thing in the morning and you could genuinely spend hours wandering around and getting lost in it. If you’re into running then I would also highly recommend an early morning run around it – it’s a great way to cover ground!
Another strong contender for first thing in the morning is trying to catch the sunrise from Brooklyn Bridge. Aside from being an iconic landmark, it allows fantastic views of both Manhattan and Brooklyn, and like Central Park is very much something you can do at your own pace; you can take your time to soak up the scenery and get plenty of pictures or if you’re in a rush, you can probably get across in half an hour.
Something that I’ve never really fancied but now wish I’d done sooner is the Staten Island Ferry. As well as amazing views of the Statue of Liberty and Lower Manhattan, that sea (or harbour) breeze hitting your face first thing in the morning really blows the cobwebs away. It’s also completely free. I can’t imagine it’s very pleasant in the winter months, however.
Naturally, not everything in NYC is free and some of the more touristy activities cost a bit of money so be prepared.
With so many skyscrapers dominating the skyline, there’s a multitude of observation decks to choose from but if you’re not scared of heights there are some stunning views to be had. I chose Top of the Rock during golden hour and although it was far too busy, seeing landmarks such as the Empire State Building and Central Park from that vantage point was breathtaking.
Whether you’re a die hard fan of musicals or don’t really care for them, I’d still recommend taking in a show on Broadway. During our honeymoon, we watched the hilarious ‘Death Becomes Her’ and on our most recent visit, we saw the likes of Samantha Barks, Matt Lucas, Killian Donnelly, Bradley Jaden and Philip Quast in ‘Les Misérables: The Arena Spectacular’ at the very grand Radio City Music Hall (shout out to the waiting room outside the men’s bathroom, which is reminiscent of the Black Lodge from Twin Peaks).
If you’re not all musical’d out then Ellen’s Stardust Diner may be kitschy but it’s also really fun, with some extremely talented musical theatre performers in their own right serving the food (which also happened to massively surpass my modest expectations). The ensemble performance of ‘Be Our Guest’ that concluded my visit ended up being one of the standout moments of my entire trip.
Paradoxically, when I’m anywhere other than New York, I absolutely hate shopping but some of my best days there have been spent wandering in and out of shops, which brings me on to my next section…
Where to shop
We love starting in the Lower East Side and working our way up towards the East Village. There’s plenty of fun, little trinket stores in both these areas with A Shop of Things and Pillow-Cat Books (extra points for having an actual cat in-store) being a couple of our favourites.
As you get closer to the East Village, you can stock up on snacks from across the world at Economy Candy and pop into Old Friend Photobooth for a memento.
There are tons of vintage stores to choose from but my absolute favourite is L Train. On my first trip I picked up a burgundy corduroy Calvin Klein shirt for around $18, on my second visit, I managed to get an Adidas track jacket, long sleeve Adidas top and a really smart GAP shirt for under $40 and most recently I got four designer jackets for just over $100. Bonus tip: bring cash and you’ll save yourself some money.
Loads of other fun and unique shops are dotted around the city and there are plenty of indoor shopping and food markets as well, with Chelsea Market probably being the best of the bunch.
Then there are the iconic department stores in Midtown Manhattan such as Saks Fifth Avenue and Macy’s, while toy shop FAO Schwarz is a must regardless of whether you have children or are just a big kid yourself.
When to go
If you have the money or you’re only ever planning to go once, then I would say December. NYC is a pretty magical place as it is but seeing the festive window displays of those last three stores and the huge ‘Home Alone 2’ Christmas tree at the Rockefeller Center is awe-inspiring.
February was cheap (in relative terms) and much quieter but also deathly cold, without the Christmas magic. While on the other end of the scale, August was probably too hot, bearing in mind how much you’re on your feet. Saying that, the city – and Central Park in particular – is absolutely stunning at that time of year.
I definitely want to go back in December, possibly once I have kids so I can experience that wonder through their eyes. I can also imagine it’s very pleasant in Autumn and Spring if you don’t fancy either extreme.
Where to stay
In a similarly boring answer to my last question – if this is a once-in-a-lifetime trip then I’d recommend staying in Midtown in the heart of the action.
On our honeymoon, we stayed at the wonderful Library Hotel and feeling as if everything was on our doorstep made the experience less overwhelming and easier to navigate, for me personally.
But if you’re making a repeat visit then you can probably stray a little from the beaten track.
You may have sensed from this post that one of my favourite places is the Lower East Side so, for my birthday, we stayed nearby at the CitizenM New York Bowery.
Considering a king-size room for four nights was just over £500 (including taxes and all other hidden charges), I was absolutely blown away by how stunning it was inside but it did feel a little ropey outside after dark.
Most recently we stopped at the Freehand New York in the Flatiron district. I’ve never really explored this part of Manhattan but I loved it. It felt just far away enough from the chaos of Midtown that you could wind down after a long day but close enough that you could get around the city really quickly and easily on the subway. There’s also quite a bit to do around and see around there, so I’d highly recommend it.
What’s on your New York bucket list? Let me know in the comments.
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