An Itinerary for 5 Days in New York City

Whether you’re heading there for the first time, or a return visit then this itinerary for how to spend 5 days in New York City covers the key tourist sights, recommendations on where to stay, where to eat, things to do, and most importantly how to maximise your time to get the most out of your trip.

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As well as the tourist areas and must see attractions, I always think it’s important to try and sample a more local experience, so there’s some suggestions to try and achieve that too.

I’ve been to New York on quite a few occasions now, and I really believe that the more you visit the more you enjoy it and the more you get out of it. This is usually down to making mistakes and learning from them, becoming more familiar with your surroundings, and planning your time carefully.

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Be under no illusions that the Big Apple can be overwhelming, and the last thing you should do is turn up unprepared thinking that you can just head out and see what happens. Your feet will betray you before you’ve scratched the surface. By following this schedule hopefully you will feel confident at taking on one of the most amazing cities in the world.

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There are so many tips that I would give to first timers, so if you haven’t read it yet I would recommend you start here, with my tips for first timers to give you an idea of what to prepare for, and what to expect before you even get there. This itinerary covers from the moment you’re ready to head out and explore.

Where to stay in New York

For the type of visit that this itinerary covers, I would personally always recommend staying central Manhattan, so midtown. It will give you ideal, centralised access to everything you’re going to want to see and do, and all within as much walking distance as possible, or within reach of a subway.

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My preference is also the West Side of Midtown, somewhere between 6th – 8th Avenue, which covers hotels in the theatre district near Broadway, hotels labelled as close to Times Square (although I wouldn’t recommend staying on Times Square), and also near Central Park.

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I’m going to be honest, decent hotels here aren’t cheap, but if you’ve already booked New York you probably already know that. For a city like this it’s worth every penny, and with the amount of walking you’re going to be doing it really is beneficial. Rooms are likely to be smaller than you expect too. I’ve stayed at The Wellington, The London, and The Time.

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The following sections are broken down in to days, and are designed to make it easy for you to mix up the order if you need to, or select specific ones if you’re looking for a 24 hour, or 3 day itinerary too.

I approach planning days in New York by neighbourhood, to reduce walking or travelling extreme distances across the city, wasting valuable time and energy. I also target key tourist sights early in the trip, because if you’re visiting from the UK you’re going to be awake early, so it’s best to take advantage of the quieter mornings with smaller crowds.

Another bonus of approaching it like this is that you get some days later in the trip to relax a bit more without feeling like you’ve missed something and are running out of time.

Day 1 in New York City

Times Square, Rockefeller Centre, Broadway, 5th and 6th Avenue.

In my experience, travelling from the UK means you’re going to have been flying all day, but arrive early afternoon US time. By the time you get through customs, which is good prep for how busy and how much queuing you’re going to be doing, have got your luggage and get to your hotel with about a 40 minute to an hour transfer time, it will be mid to late afternoon.

After a quick freshen up get out and see your local surroundings. Pay close attention to where your hotel is using the New York grid. What avenue and street number cross road are you nearest, as that’s what cab drivers are going to ask you.

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Head to Times Square first, as it’s one of the closest and most iconic things to see, and stand on the viewing platform to really take it all in. There’s a reason people don’t stay here long, and it’s because it’s manic, but the bright lights make it feel like daylight even in the dark and it’s one of those things you just have to experience.

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From here, walk along to 6th Avenue, also known as Avenue of the America’s. Here you’ll see the huge concrete skyscrapers, and Rockefeller Centre. Again, Rockefeller is a tourist trap similar to Times Square, but it’s worth seeing, especially in winter with the ice rink and famous Rockefeller Christmas tree.

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Alongside the Rockefeller Garden displays which are decorated seasonally, as are the 6th Avenue fountains, you can also find the start of some of the amazing shopping opportunities, including Kate Spade New York, Tiffany, the Lego shop and across the road directly opposite – Saks.

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Rockefeller Centre is so big it spans right across the block, from 6th right through to 5th Avenue, and on your way over to 5th you will pass Radio City, and the TV studios where Saturday Night Live is held.

Our first day was a Thursday, and the queues were already beginning to form her for both the Radio City show, and SNL. This is one of the busiest parts of the city, crowds are controlled by NYPD, and it’s everything you imagine New York to be – fast paces, crazy, loud, sirens blaring, lights flashing, all against a backdrop of huge skyscrapers.

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From Rockefeller over to 5th, you’ll find yourself quite near the top of 5th Avenue, and again this iconic New York avenue is mesmerising. Huge designer and high street flagship stores can be found, and the top section towards the park includes Cartier, Gucci, Tiffany, Nike, Rolex and D&G.

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By now you’re probably a mix of knackered, and very hungry, and after a long flight time I would suggest you dive in to a good old fast food option. Choices are obviously endless, but I would recommend a Shake Shack.

This New York born burger and milkshake chain is frankly absolute heaven, especially after a long day, and the branch on 8th Avenue means you’ll have done a good loop of everywhere I’ve mentioned, but be on your way back to your hotel.

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Day 2 in New York City

For your first full day, when you wake up refreshed and ready explore properly, you’re going to want to see iconic New York. This route is also good if you just have one day to see as much as possible.

I can guarantee you’ll be awake very early, we were up and out the hotel by 7:30am every morning and that was trying to leave it as late as possible. As Manhattan brunch is a thing, resist the urge to eat a big breakfast early on.

Instead grab a coffee to go from Starbucks, your hotel if they offer it (The Time does), a street cart or any of the cafes around Broadway.

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5th Avenue

Head over to 5th Avenue, and basically start to walk all the way down it. Doing this early on means you’re going to see commuters, but there aren’t too many tourists about yet. It’s also a good time to see the Rockefeller Centre again minus the crowds.

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Your walk down the top of 5th Avenue will take you past even more shops, both designer, high street, and NYC sport team memorabilia shops, but as you continue down you will come across plenty recogniseable sights…

New York Public Library

One of the first stops you will come to is the New York Public Library. The impressive building is the scene of iconic movies such as The Godfather, and of course Sex & The City. It opens at 8am every day and is free to enter.

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Even if you’re not a fan of libraries it’s worth going in because it’s beautiful inside. Most areas are accessible to the public, including one of the rooms from which you can see the Empire State Building framed in the window.

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Empire State Building

From here come back out and continue down 5th Avenue, where you will also come to the Empire State Building. Despite losing it’s crown as the tallest building in New York, it’s still very impressive and one of the most recognisable. If you’re wanting to go up it I would suggest you plan to do it early.

Tickets are usually $39 but it is free with a New York City Pass. I’ll leave it up to you if you think a pass is worth it, full details can be found here. Personally I’ve never bought a pass yet. I’ve paid to do specific things, but if you want to do a lot of attractions then costs do add up so it could be worth it for you.

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When it comes to the Empire State Building, I’ve never gone up it. Instead I prefer the Top of the Rock, as the view from up there has the Empire State centre stage. Obviously for some it’s one of those bucket list items you might just have to do.

The next stretch of 5th Avenue as you continue down doesn’t have much to see, so pick up the pace until you come to Madison Square Park. Half way down the park as you walk past you’ll see the Flat Iron Building up ahead of you.

Flat Iron Building

I really love this iconic building, and the giant gold clock that stands in front of it. 5th Avenue opens up a bit here and Flat Iron Square has some great photo points that allow you to get some good shots of the Flat Iron Building.

As it sits in the middle of the road, when facing it take the left side of the road fork, which you will realise is actually the bottom end of Broadway. You’re in the Flat Iron District now, and heading more towards the East Village of this lower Manhattan area.

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Union Square Park

You’ll come to Union Square next, which is both a park and a pedestrianised area often filled with market stalls. The skyline of the park itself is pretty impressive, surrounded by office and apartment buildings.

Down on street level as well as the market you’ll find shops, restaurants, cafes, locals running about, street performers and artists and protestors.

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Brunch at Clinton Street Baking Co.

From here you’re going to head to brunch, as you’ll be pretty hungry. There are so many places on offer in the East Village that I’m sure you can find and research, but personally I would recommend Clinton Street Bakery.

It’s up to you how you get there, you could continue to walk, or jump on the subway. For us we chose to walk as it was such a nice day, and it’s definitely the more scenic route.

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The Bakery is on Clinton Street, which is just off East Houston Street, and it serves the most amazing pancakes, waffles and milkshakes. Again I’ll refer you to my Manhattan brunches blog post for full details. Katz Delicatessen is also very close by if you prefer a sandwich to go.

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The nearest subway is Delancey St, so once you’re finished brunch head there, and get the subway to Wall Street. If you choose to walk you will pass through the famous NYC Chinatown, and while it’s impressive to see, we chose to skip it on this visit to head to Wall Street quicker.

Wall Street and the American Stock Exchange

You’re now in Downtown Manhattan, in the financial district, and the main thing to see is the American Stock Exchange. It’s just next to Wall Street, which is pretty underwhelming as far as streets go, but obviously it’s famous and so there’s plenty of people about snapping photos.

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Make sure you pay ‘Fearless Girl’ statue a visit, she was recently moved to outside the Stock Exchange representing a more gender equal environment.

There isn’t really much else to see here, once you’ve seen these things, and of course the Wall Street sign, so next up is the Charging Bull.

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Charging Bull

Many think that the iconic bronze bull is located on Wall Street but he actually isn’t, he’s not far away though on the very bottom of Broadway. It only take a few minutes to get there from Wall Street.

You can’t miss him, he’s always surrounded by crowds of people taking photos of and with him, and the queue at the rear is of people waiting to touch his balls for luck! Historically, doing this was meant to bring a good day on the stock market.

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Battery Park and the Statue of Liberty

As you’re now right at the bottom of Manhattan, you’re very close to Battery Park, and the Staten Island ferry terminal. If you wanted to either go to, or sail past the Statue of Liberty on the free Staten Island Ferry now is the time.

Like most things, I’d probably try and pre book, as the queues can be huge. If you’re wanting to save this for later in the trip, or skip completely, then you can still see the Statue of Liberty from this coastal point.

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A walk through Battery Park, and along the Harbour House pier is both pleasant and gives a great view of both the Statue of Liberty and the American Merchant Mariners Memorial.

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Freedom Tower and the World Trade Centre

Ground Zero, the Freedom Tower/World Trade Centre, and the 9/11 Memorial Museum are very close by from here, so it makes sense to go there next.

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The Freedom Tower is incredible, as are the 9/11 memorial fountains themselves. It’s so unbelievably hard to comprehend what happened here, but the site is so tastefully done and it’s a very sombre, emotional experience.

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The names of all the 9/11 victims are written around the fountains, and roses are placed by their names when it’s their birthdays. It’s very respectful, and really worth spending some time here.

Again, the queues for the museum are often big, so worth booking in advance – details here.

Refreshment and Relax

After all this, you’re going to be ready for more refreshments, and probably a break from walking, or time to gather yourself after the 9/11 memorial.

There’s an amazing Irish Bar not far away called Trinity Place, you could always go back for a Katz deli, or pay a visit to McSorley’s Ale House where Abraham Lincoln used to drink.

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Or you could do what we did, and get the subway from the World Trade Centre up to West 4th Street, and get a slice of world famous Joe’s Pizza on Carmine Street.

About $3.50 a slice, and with famous faces on the wall of visitors like Leonardo DiCaprio, you know the pizza is going to be good. The crowds outside munching on the enormous slices tell you the same.

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Once devoured, and after what has been a very busy day with a lot of walking, jump back on the subway and head back up to Midtown to your hotel for a much needed rest.

All of these things can be fit into one day easily. Despite sounding like a lot, many of the buildings/sights I’ve mentioned are just to be seen. Things like going up the Empire State, or going on the ferry to Statue of Liberty are going to add much more time into your day so may need to be done at other times, or planned to precision.

An evening out in NYC

In a city this size, trying to give you suggestions or recommendations for where to eat, and which bars to drink at would mean I’d be here forever. The best thing I can suggest you do is research the types of food, bars and music scene that you like, and research well.

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Your options are endless and include areas like Chinatown, Soho, Little Italy…but each neighbourhood has gems of it’s own.

I can tell you what we did on our first evening, we went to an Italian on the Upper West Side that I was recommended, called Pomodoro Rosso. It’s family run, and absolutely delicious. The staff are so friendly, it’s reasonable, and the food was excellent.

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There are also a number of relaxing but sophisticated bars very close by, so it was a great choice for us after a tiring day. We got cabs there and back, and enjoyed some cocktails in our hotel bar too.

Day 3 in New York City

Central Park, Grand Central Station, Chrysler Building, Brooklyn, and New York Knicks at Madison Square Garden

Central Park is so vast, and with so many miles of footpaths to wander it’s probably a good idea to have specific things you want to see and do in mind. We just wanted a wander through, and the perfect time was early morning when surprise surprise, we were awake early again.

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The park has so many choices when it comes to activities, the boating lake, ice skating in winter, the zoo, pavilions for food and drinks, cycle and jogging routes, Gapstow bridge, horse and carriage rides..the list goes on.

You can spend as much or as little time getting lost here, simply enjoying the beauty of nature amongst such a busy city.

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Once you’re done, exit the park on the bottom corner, right on 5th Avenue, you should recognise the Park Plaza Hotel, made famous of course by Home Alone.

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Grand Central Station and the Chrysler Building

Head down the top of 5th Avenue, but branch off anywhere between East 45th and East 43rd Street, and Grand Central will emerge in front of you. You can also get the subway if you don’t want to walk, but I think it’s much more impressive seeing it from outside first.

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It’s obviously enormous, and from right outside the front you can get a great photo of it with the pretty Chrysler Building in the background too. Go inside and you’ll find the main concourse, with old fashioned ornate gold trip, sweeping staircases, and that fabulous ceiling.

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The old ticket booths are still there and in use, albeit more modernised, and you can see the old fashioned lifts and postbox too. There’s so much more to the station than just the trains and platforms themselves.

There’s a shopping concourse filled with American brands, a very posh oyster bar, and a huge food court underneath too. Perfect to grab a coffee or small breakfast before you, of course, head off for a proper brunch soon.

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You’re in the perfect spot to get the subway from here to wherever you choose to go for brunch. I’d suggest the West Village, as it’s FULL of amazing places. I’d scoped out the Old Rose at The Jane Hotel as the place I wanted to go on the Saturday, so we got the subway across there to West 34th Street (the same one you got to on Day 2 for a slice of Joe’s pizza!).

Friends building

A walk through the West Village on your way to brunch is always going to be fun, a neighbourhood full of things to see, beautiful boutiques, cute cafes and inviting bars.

You can also find TV hotspots such as the Friends Building, located at 90 Bedford Street, and Carrie’s apartment stoop from SATC. This borough is my absolute favourite, and I’ve wrote an entire post on it here. I have planned a lot more time here on Day 4, but you might as well make the most of your time walking through on your way for food!

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Old Rose for brunch

This was one of my most favourite meals of our trip, and the Old Rose is gorgeous, perfect for a more classy brunch. The food is amazing, especially the eggs and the pizza, and so are the Bloody Mary’s!

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Definitely don’t rush your brunches, the point of them is to relax, enjoy the environment as well as the food, and it’s a great scene for people watching. There’s a lot more detail and photos on the Old Rose specifically in my brunches in Manhattan blog post here.

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Brooklyn Bridge and Brooklyn

Again it’s up to you if you prefer to get the subway back Downtown to Brooklyn Bridge – City Hall station, or if you prefer the scenic route to walk off your food. Either way I’d suggest you walk over Brooklyn Bridge from Manhattan to Brooklyn rather than the other way round.

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Brooklyn Bridge is further to walk than it looks, and also higher than it looks, but it’s a great walk albeit busy and bustling with tourists. Turning back to see the Manhattan skyline is amazing, and at every point you look it just gets more and more impressive.

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Once you reach the other side, I would suggest you get some of the tourist spots out of the way first, so that you can then make the most of exploring some of the areas deeper into Brooklyn if you wish.

From coming off the bridge walk through DUMBO to Front Street, and as you get to the cross section of Washington Street, you’ll see the famous view of the Empire State Building framed under the arches of the Manhattan Bridge. You know you’re in the right spot if you’re surrounded by other people taking photos too.

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Brooklyn Bridge Park itself is another amazing photo opportunity, right down at the river front. Brooklyn Bridge and the New York skyline are stretched out in front of you, so pull up a seat on one of the park benches and take it all in for a while.

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Further into Brooklyn you’re going to find such an interesting, artistic, and different experience to Manhattan, and one that I’ve only seen a small glimpse of. I really wish we had spent longer there, as from research it sounds like an amazing area to discover, but basically we spent way too much time gazing at the view.

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I have previously eaten at Fette Sau barbecue place in Brooklyn, and would strongly recommend it if you like meat. It’s basically someones garage, but the food is unreal. For other Brooklyn recommendations and suggestions from someone who is a lot more in the know than I am I’d suggest giving this blog post by Pin the Map Guide a good read.

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Really discovering Brooklyn is on my list for my next visit.

New York Knicks at Maddison Square Garden.

It’s a very long way from Brooklyn back up to midtown Manhattan, and at this stage of the day the subway will be your best friend. The F train Uptown will take you quickly right back up where you need to be to get back to your hotel.

Our Saturday night was spent at Madison Square Garden, watching the New York Knicks play the Brooklyn Nets. It’s something I’d always wanted to do and so many people had recommended we do it, even people I know who aren’t sports fans.

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I can totally see why, it’s a great atmosphere and experience, completely different to British sports events, and the hot dogs and popcorn are pretty good too! If you can attend an American sports game of some sort, I absolutely would. The night itself is cheap, but tickets aren’t really. We purchased ours in advance through Ticketmaster.

It’s not a quick event, but it is very casual and a lot of fun. There’s plenty bars nearby afterwards as well if you can stay awake to enjoy them.

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Day 4 in New York City

The High Line, Chelsea Market, West Village, Top of the Rock, dinner and a Broadway Show.

Day 4 is going to be slightly more chilled out, starting with a lie in, as sleep will be catching up with you and you’ll be getting more on the right time zone. When you are up and out, head for the High Line, or the garden in the sky as some call it.

High Line

The High Line is a 2 mile stretch of old disused railway line that runs from West 30th Street, right down to Gansevoort Street right on the border of Chelsea and the West Village. To keep this day more chilled we got the subway down to West 23rd Street, and joined the High Line at that point.

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In the summer the High Line is busy, and the incredible city views, sun loungers, and modernised public spaces are the reason why. In winter, it might be far too cold to sit, but a walk in the fresh air taking in the views and street art is still very much worth doing.

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There are often art projects, renovations, book stalls, and open air markets happening at various points along the High Line, so it is really interesting.

Chelsea Market

Exiting the High Line at West 16th Street means you can also explore, or shelter from the elements at the Chelsea Market, which is in an incredible old factory that once produced Oreo’s.

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It’s an urban shopping and food court in the quirkiest of settings, and it’s a pretty cool place inside. Sarabeth’s Bakery is a good one to pick up a coffee while you have a look around.

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West Village

If you’re going to dedicate any day to being in the West Village, rubbing shoulders with the locals, (brunching like a New Yorker, shopping like a desperate housewife of New York etc) then make sure it’s a Sunday.

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Brunch at the Spotted Pig is an absolute must, and again I’ll send you back to this blog post for full details on why. You could spend hours here, it’s just so good.

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Once you’re fully fed and watered spend the afternoon roaming the streets, darting into independently owned boutiques, drink in the bars, lust over the brownstone townhouses that you could never afford, grab a cheesecake from the Magnolia Bakery on Bleecker Street, and cuddle puppies at Citypups.

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Here’s my full guide to exploring the West Village and how to make the most of your time there.

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Top of the Rock at sunset

I’ve saved this for your last night in New York, because it is an amazing experience. If there is one thing worth queuing up for, buying tickets ahead of time, and planning into your trip at some point it is Top of the Rock.

Pre booking your tickets means you’ll skip the waiting queue, and you’re fast tracked into the lift that will take you up 70 floors to the panoramic views of the observation deck at the top.

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You’ll see Central Park on one side, and Manhattan and the Empire State building centre stage on the other. I’ve done this three times, and I’ve found that sunset is unbeatable. Depending on when you’re going, the time of sunset is obviously going to vary, but in general that’s the time I would aim for.

You can read my full post on what to expect, how to get tickets, and other info on Top of the Rock here.

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Dinner and a show

Your final evening deserves a fine dining, slap up New York meal, I would say, and whether or not you want to add a show on there afterwards too is up to you.

Our ideal last meal in the big apple was a New York steak, and while the options for this are endless, we went to Del Frisco’s on 6th Avenue as it was so close to our hotel, and has a reputation for being up there as one of the best.

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It didn’t disappoint at all, and everything from the surroundings, the view out onto 6th Avenue, the service, the wine and the food was perfect.

Another place I’d really recommend is Blu on Park, also a steakhouse but with a wider menu if steak isn’t really your thing.

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Day 5 in New York

Upper East Side

Chances are if you are traveling back to the UK it will be overnight, so your last day in New York will also mean you have checked out of your hotel. If there’s anything you haven’t done or seen now is the time to do it.

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We had done pretty much everything that was on our radar to do, so we decided to have a walk through Central Park, and then up into the Upper East Side. You might have noticed that museums aren’t a heavy feature of this itinerary at all, but if you want to visit them the Upper East Side is where you’ll find them.

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It’s also where you’ll find Madison Avenue, home of an even better shopping experience than 5th Avenue, including the flagship Ralph Lauren that has the most adorable little cafe too.

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The Upper East Side is where the mega rich and the famous live, but don’t let this put you off. It’s an area that really surprised me, and like Brooklyn is somewhere I would love to see more of on a return visit.

I’ve wrote a full post dedicated to the Upper East Side here.

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However you spend your final day in New York, whether it’s going back to your favourite spot, ticking off the things you hadn’t done yet, or simply wandering around a new neighbourhood, enjoy every minute of it because a trip like this just goes by so quickly.

Leave enough time to grab one final American fast food meal (Shake Shack, Chipotle…) before you travel and head back to your hotel for one last cocktail in the bar to toast what will have undoubtedly been an amazing trip of a lifetime.

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Other posts you might like and the full list of all the ones mentioned in this post:

Tips for First Timers Visiting New York

Planning your Christmas trip to NYC

3 Amazing Brunch Spots in Manhattan

Welcome to the West Village

Exploring the Upper East Side

Top of the Rock and the Rockefeller Centre

The Time Hotel, New York

The London Hotel, New York

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  • Laura
    8th March 2019

    Absolutely love this, especially as I know you’re a NY vet, we managed to tick off the majority of the things on this list on our last visit. Next time you should check out Joanne’s (Gaga’s dad’s restaurant) and Ellen’s they’re both great in their own ways! Your photos make me want to go back!!!!

  • Smita
    9th March 2019

    That’s so much information. I don’t think I’ve done half as much the times I’ve been to NY. And Joe’s Pizza is amazing

  • Pia
    9th March 2019

    That´s such a great post! I´ll be back in New York in April and I have a lot on my wishlist which I´d like to see and visit! Great ideas and the pictures are stunning!

  • Stacey
    9th March 2019

    This is a great post!! I feel like I need a month in New York. Those views are everything!

  • Brooklyn
    9th March 2019

    Now I’m missing NYC! Also, that pizza looks delicious, yum! You have beautiful photos.

  • Chloe - New Girl in Toon
    15th March 2019

    Oh wow Steph! Thank you! This post is absolutely amazing – probably the most useful and detailed review of NYC I’ve ever read. Don’t be surprised if we literally copy you and plan our entire trip following in your footsteps! So many great tips on how to make the most out of our time!

  • March 2019 Monthly Round Up | Stephanie Fox Blog
    3rd April 2019

    […] was pretty scarce in March, but I am proud of the main post that I did manage to finally finish. My 5 day itinerary for New York City was about five years in the making, over about 6 different trips. It covers advice, tips on […]

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