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A 5 day New York itinerary to help you plan your perfect trip and honeymoon

Alright, I will admit that when we started planning our honeymoon in New York, it wasn’t our first thought of destination. I mean in an ideal world we would have been snorkelling in the Maldives or getting cosy in a ski chalet in Switzerland. But as usual, time and money came into play and so we settled on New York (and let’s face it, NYC is a pretty amazing city to have to settle on). Literally every blogger and their dog have been to and written about New York, so we thought we would add a hint of romance and write about the city from the eyes of two people on their honeymoon….us. This is our 5 day NYC itinerary.

5 days in New York – Is it enough

We planned our honeymoon in New York as part of a bigger trip around the USA. We ended up only having 5 days in New York, and you might be wondering is that enough? The short answer is no. But that is because it feels like no amount of time spent in New York is ever enough. But if you only have 5 days then it is a good amount of time to get to grips with the city and explore. You just have to make sure you plan things in advance. We didn’t get to see everything we wanted, for example I really wanted to visit Coney Island, and Dave wanted to go to a baseball game, but due to the time of year we visited and other constraints we had to sacrifice. Oh and in case you visit NYC when it rains, check out this guide

5 day NYC itinerary in a nutshell

Here is our 5 day New York itinerary in a nutshell. I have to say that the first day was a complete write off because we were so tired from our red eye flight from Vegas. 

Day 1

Times Square, Hells Kitchen (and a whole lot of sleep)

Day 2 

Top of the Rock, Central Park, Greenwich Village

Day 3 

Empire State, The High Line, 9/11 Memorial, Wall Street, Brooklyn Bridge, Chinatown

Day 4

Cronuts, Liberty Island, Williamsburg, East Village

Day 5

DUMBO, Katz’s Deli, Museum of Modern Art 

5 day New York itinerary in detail

Day 1- The Write Off

Someone (I am going to have to take the blame here) thought it would be a brilliant idea to get the red eye from Las Vegas to New York. The rationale being that it would save us on accommodation costs and it would give us a whole extra day in New York as we would land early in the morning, Things didn’t really go to plan. We were tired. Really tired. We sat red eyed (we now understand the meaning of red-eye flight) on the steps in Times Square, watching the world go by. The noise and the hustle and bustle were the only things that kept us awake at this point. We dragged ourselves around 42nd street and counted down the minutes until we could check into our hotel.

The moment we could check in, we got to our room, threw our suitcases onto the ground, closed the curtains and went to sleep. The day was a write off and definitely not the romantic vacation we had in mind. We slept through two alarms and woke up at 7pm. In a panic we got out of bed and tried to make the most of the rest of the evening. We were staying in the Hells Kitchen area so we visited some Irish bars (much to Dave’s delight).

Day 2- Let the honeymoon begin

With some sleep behind us we were ready to face the day in New York City. First stop, Top of the Rock, which is the observation deck from the top of the Rockefeller Centre.

Top of the Rock

One thing we did right in our sleepless stupor the day before was purchase tickets for Top of the Rock. You generally cannot show up and expect to head up the tower straight away, so don’t forget to purchase your tickets in advance. The visits here are timed so you need to be here for your time slot. The good thing about this is the queues aren’t too bad. Before you know it you are admiring the views across the city. It is crowded at the top and you do get pushed around a bit but seeing New York from up above is a
must!

Central Park

Another NYC must is of course visiting Central Park. To get here from the Rockefeller Centre we had to negotiate the subway. We arrived at the subway station like proper tourists, who had no idea what they were doing. I foolishly thought it would be wise to ask one of the people at the ticket booth if they had a 4 day ticket. She pointed to a sign and mumbled something inaudible. I guess not. She looked irritated so we went for a 7 day pass because we were confused and felt rushed. Never mind, tickets in hand we made our way to Central Park.

To me Central Park was exactly what I imagined from the movies. There were horse drawn carriages and families rollerblading and laughing as they tried not to fall. This was what I wanted for our honeymoon. We strolled around the park stopping to purchase some over priced ice creams from the various vendors stationed on the corners.

Central Park is huge, and we did not have enough time to explore everything, although we made sure to visit Strawberry Fields and the Lake.

Strawberry Fields

In memory of John Lennon’s life and talents a 2.5 acre area was dedicated to him and was named Strawberry Fields. It is located adjacent to the Dakota Building, which is where John Lennon was living when he was shot returning home on the 8th of December 1980. In the centre is a mosaic with Imagine written across it, where you will find keen visitors trying to get photos taken.

The Lake

The iconic Central Park Lake, where you can rent paddle boats was another must see for us. It’s such a beautiful place to sit, take in the skyline and the calming waters before you. Alongside the row boats we also saw a random Gondola which was confusing but oh well it’s New York right?!

Honeymooning can be thirsty work so we found the coolest bar around Central Park, The Dead Poet. Cocktails here are named after famous writers and poets, which made the afternoon drinking feel a little more cultural.

Greenwich Village

Keeping with the cocktail theme (because honeymoons right?) we made our way to the always trendy Greenwich Village for some more afternoon drinks. One of the best bars we found was Employees Only, a prohibition style bar with some really creative cocktails. It’s sort of hard to find and there is actually a psychic doing readings near the front door, which can throw you off. Once you are inside though the atmosphere is bustling. Expect to have to queue to get in! We also had some really good Mexican Food a couple of blocks away and got to walk around and admire the beautiful streets in this area.

Day 3- A fear of heights

Despite the fact that we both hate heights we decided to head up the super iconic Empire State Building. I mean what says you are on your honeymoon more than getting pushed around in a crowded space whilst looking out at New York City?

The Empire State Building

We bought tickets through our hotel concierge and could use these tickets at any time. Because of this the queues are quite intense here. I sort of feel that this might be one of the most overrated tourist attractions in the world. I mean it was great being there, especially as the building is a New York City icon, but it was so busy. We ended up just getting pushed around and waiting patiently for a space to open up where we could look out without our view being impeded by someone’s head. Still the Empire State Building is a classic New York attraction and we just had to do it.

The High Line

Moving on we made our way to a newer city attraction, the High Line, a 1.45 mile elevated park on a disused train track. For us this was a lovely place to sit and just chill out. It was still pretty busy, but it’s a nice break from the so called concrete jungle, and it gives you an opportunity to appreciate some greenery. From here we decided to make our way to the Brooklyn Bridge via the September 11 memorial.

The 9/11 memorial

This was genuinely a sobering moment that I am struggling to put into words. For my parents the question of their generation was “where were you when Kennedy was shot”? For my generation it’s more where were you when the twin towers fell. I was only 13 when it happened and couldn’t really understand the full magnitude. There is a memorial at the base where each of the twin towers stood. Water rushes down into a centre that you cannot see and the names of all the victims are etched around the pools. It is both beautiful and terribly heartbreaking. There is also a museum you can visit which has more information about that day.

Brooklyn Bridge

After visiting the memorial we decided to head over to the Brooklyn Bridge. I am going to be honest walking across the bridge was actually a terrifying moment for me. We walked across the Manhattan side, and I didn’t even get to the middle before I freaked out. Architecturally it is a pretty awesome bridge, so for me I did feel disappointed that I couldn’t walk across the whole thing.

When you get to a certain point on the bridge you can actually look down and it dawns on you that the only thing holding you up are some wooden slats. You can also see the water below through the gaps in these slats. That is a big nope from me. At one point a jogger came past and I swear the nail in the wooden slat was loose and it shook. This was certainly too much for my fear of heights. Fortunately we got some nice pictures before departing.

Chinatown

After calming down we went to Chinatown for some evening drinks and food. We got off the subway and made our way up Canal Street, which is a shopper’s dream. When we reached the back streets of Chinatown however it was actually like being transported to somewhere in Asia. It is definitely a foodie’s paradise with so many dumpling and noodle shops, with a few bars mixed in for good measure.

Day 4- Typical tourists

This was actually one of our favourite of our 5 days in New York because we got to see Lady Liberty herself! We woke up early though in search of another New York icon though, the Cronut. With high hopes we set off to the Dominique Ansel Bakery. We genuinely thought the line would be insane and we would be spending the whole day waiting to eat this incredible creation. So we were pleasantly surprised to find that after a mere 20 minutes of standing in a queue we were ready to devour the Cranberry and Pumpkin flavoured pastry.

The pastry was great, but the flavour wasn’t my favourite. I should note that you only have the choice of one flavour, and this does change each month. You also have a 2 cronut minimum per person and you should get in early in case they sell out!

Full of sugar we decided to be even bigger tourists and went to Liberty Island.

Liberty Island and Ellis Island

So just to clarify the Statue of Liberty is located on Liberty Island and the famous immigration centre is located on Ellis Island. To get to both you need to pay the $18.50 per person and hop on an overcrowded ferry full of fellow tourists ready to elbow you in the face to get that perfect shot of the statue and the NYC skyline from the boat.

If you are planning to do this you should set a full day aside. It is super busy and you will spend a lot of the day just waiting in line. We were short of time so we only managed to see Liberty Island to get a few close up shots of the Statue. It is a wonderful experience and we would really recommend it. Alternatively you could get the Staten Island Ferry for a glimpse of Lady Liberty herself, but you certainly don’t get as close as you do on the tourist boats.

Deciding that we wanted a bit of a break from tourists (I know pot…kettle) we headed over to Williamsburg. We really wanted to explore some New York neighbourhoods and delve a little deeper than your typical tourist activities.

Williamsburg

Initially we had one of those “we’re not in Kansas  err I mean Manhattan” moments and held our bags a bit tighter. But in all honesty Williamsburg is full of super hip bars, trendy shops, and some chic restaurants.  It is a great place to explore. There is also some really cool street art that will keep your camera busy.

The East Village

Another trendy area we decided to explore was the East Village. There are a lot of cosy bars and super cool restaurants.  Some of our top picks though were:

Drinks- The Immigrant – a cosy and intimate bar which is a great place for people watching.

Food- Veselka – I might be biased here because of my Ukrainian heritage, but this was honestly the best food we ate all trip. Veselka is a 24 hour Ukrainian style diner with all the best food from my childhood. We feasted on Borsht (a beetroot soup which tastes better than it sounds) and Veraniki (dumplings filled with potato or whatever you want really! and served with fried onions).

Entertainment- Rue B a really unpretentious bar that has live jazz music every night from 8.30pm. The cool thing is when we were there the owner of the bar got involved and sang during some of the numbers.

Day 5- The mad rush

This was our last of our 5 days in New York and we panicked. There was so much more that we wanted to do but so little time. Wanting to checkout some more neighbourhoods were headed over to DUMBO in Brooklyn.

DUMBO

DUMBO is short for Down Under the Manhattan Bridge Overpass, and is another trendy neighbourhood in NYC you need to explore. The best thing is you can get some amazing shots of the Brooklyn Bridge here.

Katz’s Deli

Once we had overloaded our camera with enough photos of the bridge we headed off to Katz’s Deli. This was an absolute bucket list thing for me. I know it is a total cliche but it had to be done. It was really made famous by that ahem scene in When Harry Met Sally, but the food here is good enough even without the Hollywood connection. When you first walk in it is chaotic and confusing. We had no idea what was going on, but somehow managed to wedge in to a spot at the counter to order. We ordered a pastrami sandwich to share because these things are not only huge but also over $20.00 per sandwich. Ignoring the price it is an experience you cannot miss.

Museum of Modern Art

With our 5 days in New York nearing an end, we desperately wanted to take advantage and visit one of the city’s amazing museums. We eventually settled on the Museum of Modern Art. It houses works from artists such a Van Gogh, Dali, and my personal favourite Andy Warhol.

We were actually really disappointed during our visit. For starters half the exhibits were closed due to maintenance. I understand that this has to be done, but it’s kind of frustrating when you are paying full price and not really getting the full service. One of the reasons I wanted to visit was because I read it was home to Andy Warhol’s Soup Cans. We spent a good while looking for them to no avail. When I asked one of the staff members where the Andy Warhol stuff was she looked at me like I had threatened her first born. “It’s not stuff” she spat and pointed me in the general upward direction. Still no soup cans. We eventually realised the exhibit was undergoing maintenance so we left.

Honeymoon in New York – should you do it

This was probably the perfect destination for us. Neither of us are the types to want to sit on the beach and do nothing, not for long periods of time anyway. We love exploring and New York is certainly the place to do it. Our only gripe was that we needed more time but I guess that is always the way. 5 days in New York was a good amount of time, but it really did leave us wanting so much more. New York we will be back! 

 

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  • Fred
    January 10, 2018 at 6:16 pm

    Thanks for this travel guide.I really liked it.

  • Edoardo
    January 11, 2018 at 4:13 pm

    You probably won’t believe, but for Italians, NYC is one of the top honeymoon destination. And as you have found out on your experience it offers a lot for a young couple curious to discover the city with an active mood. NYC is one of my favorite place in the world, I would dare to say that NYC is not properly the USA, but a reality apart. The museums are something of amazing, I loved the MoMa and the Guggenheim, and the underground cultures and art happening; Is a city that holds most of the cuisine in the world in just an island, and for a glutton as myself what is better than having so much choice in a few miles? At every time of the day or the night, the city is lively, and you can catch the different souls of this metropolis. There are so many people, so different and coming from so many different countries with different culture, that if you never experienced the melting pot, well that is the place to be!

    • [email protected]
      January 11, 2018 at 4:48 pm

      Oh wow I had no idea! But I guess it makes sense. And I agree it feels so far removed from the rest of the USA!

  • Leona
    January 15, 2018 at 9:26 am

    OMG I love Katz’s deli. It must be on every itinerary! Looks like a fantastic honeymoon

    • [email protected]
      January 15, 2018 at 5:03 pm

      Thanks! Katz’s is so good although so busy!

  • sarah ricks
    January 15, 2018 at 8:17 pm

    Wow, you packed a lot into your 5 days in New York. I lived in Manhattan for 7 years and visit every couple of months. But I’ve still never made it to the 9/11 Memorial or Katz’s Deli, and it’s been years since I took the Staten Island Ferry. What a whirlwind honeymoon you designed! Good guide for us regulars too.

  • Jessica Norah
    January 16, 2018 at 12:51 am

    I am happy to hear that you had such a great honeymoon (well except for Day 1)! As an American, I don’t really view NYC as an ideal honeymoon destination, but I think it is for a lot of people living elsewhere. Looks like you covered lots of the top attractions and must-sees for a first time visit, New York has a lot of offer and there is always something new!

    • [email protected]
      January 16, 2018 at 7:36 am

      It’s funny how you view your own country isn’t it! I would feel the same about England but then some people do come over for their honeymoon and love it!

  • Punita Malhotra
    January 16, 2018 at 4:44 am

    I loved two of your captions…the write-off and the mad rush. It really is a great idea to ignore Day 1, so that one can start fresh and rejuvenated. And I can relate so well to the panic of the last day 🙂

    • [email protected]
      January 16, 2018 at 7:35 am

      Haha oh my gosh yes the last day panic is the worst 😂

  • Amanda Kendle
    January 17, 2018 at 7:03 am

    Beautiful! I actually spent a few days of my honeymoon in NYC too but it’s a few years ago now, Love your gorgeous pictures and as i’m always plotting a way to get back to NYC for a longer stint I always like to read more about it!

    • [email protected]
      January 17, 2018 at 7:42 am

      Aww thanks so much! Yeah I’m trying to work out how to get back too! X

  • wanderlustvlog
    January 18, 2018 at 6:02 pm

    I am not actually a honeymooner, but I guess I can take the trip anyway? 🙂

    A really good 5-day-NYC-trip! And some amazing pictures to illustrate it!

    • [email protected]
      January 18, 2018 at 7:24 pm

      Aww thanks so much for your kind words 😄

  • Medha
    January 19, 2018 at 9:29 am

    I’m glad NYC suited you guys as the perfect honeymoon destination. To be honest, it’s not my idea of a honeymoon. I love beaches and mountains and I’d probably choose a more out-of-the-city, quiet place in the middle of immensely beautiful landscapes rather than the busy, bustling city of New York. Having said that, I do love the vibe of NYC and your recommendations are perfect for anyone travelling there, on a honeymoon or not 🙂

    • [email protected]
      January 19, 2018 at 10:32 am

      I think if we had the money we would have gone to the Maldives or somewhere exotic! But still it worked out ok. I agree though we would have loved someone less bustling 😄

  • Lori
    January 19, 2018 at 7:57 pm

    You’re right, it’s an interesting choice for your honeymoon, but such a great city isn’t it? You certainly hit all the tourist hotspots, grabbed THE sandwich from Katz’s, hit the Highline and Chinatown (for dumplings, I hope?) and even met some real New Yorkers (rude subway lady)! I think it was an awesome choice for a honeymoon, but all that REALLY matters is who you’re with, right? Congratulations!

  • Kelly Dunning
    January 20, 2018 at 5:14 am

    It’s funny when you say that New York wouldn’t be your first choice for a honeymoon – as it certainly would for Lee and I! There’s just something about the city that is so romantic and captivating! The Dead Poet sounds like a cool bar – I would have enjoyed the cocktails named after writers. The Brooklyn Bridge looks great, but I would have also felt uneasy if a jogger went by and shook the slats!