New York: A Three Day Itinerary for New York City

Start researching a trip for New York City and you’ll be inundated with different options and itineraries. There’s so much to do in New York that any short break won’t seem long enough, yet it remains a popular long weekend destination because there is so much that you can fit into a short space of time. We had three nights in New York, and with it being our first visit to the city there was a lot that we wanted to see and do. However, we also didn’t want the entire trip to feel rushed so we chose a few key things we wanted to fit in (I’ll share my first timer’s guide to New York shortly) and then decided to take everything else as it came. I really enjoyed what we did, and thought it was a good way to see different parts of the city so I’m sharing it here as a three day itinerary.

Day 1 – Exploring Downtown New York

We were staying in Downtown Manhattan, just off Wall Street, and so it made sense for us to explore our immediate surrounding area first.

Walk across Brooklyn Bridge

Brooklyn Bridge is an iconic site which has been used in countless films and television shows. Knowing we were within such a close proximity to the bridge, it was the first place we visited after walking a short way along the waterfront. We walked all the way across the bridge, and if you can I’d recommend doing the same. The crowds thin as you walk across, and there are some great views across Manhattan from the centre of the bridge. This is where we caught our first glimpse of the Empire State Building. We continued on into Brooklyn, to look at the Downtown Manhattan skyline from across the water. In comparison to the limited amount of New York we had seen by that point, Brooklyn felt quieter, calmer and had some lovely houses that we walked past. It’s an area that I’d love to explore more if I return to New York City.

After a short time watching the world go by, and noticing the number of helicopters which seem to travel around New York, we walked back across the bridge to keep exploring.

See the 9/11 Memorial

From Brooklyn Bridge, we walked towards the One World Trade Center, the tallest building in the United States. I’ll be honest, when you’re standing next to it you can’t really tell that it’s the tallest building as everything you’re surrounded by seems to reach ever further upwards. However, it is quite an elegant looking building and is worth going to see, even if you don’t go up.

Next to the skyscraper is the 9/11 memorial, which I found really moving. It felt very peaceful is very cleverly designed the way the water completely drops out of sight. The names of those who lost their lives are engraved around the edges of each part of the memorial, and their are white roses next to those whose birthday it would have been. The survivor tree is also visible on the memorial ground and felt like a strong symbol of both resilience and hope.

Eat on Stone Street

We were recommended a number of places to eat that evening, and all of them were on Stone Street which had a great atmosphere. The street was filled with people eating outside under bunting and gazebos, enjoying the end of the working week. We opted for the Route 66 Smokehouse BBQ and shared a platter of different meats with some sweet potato fries.

Take the Staten Island Ferry

I’d highly recommend taking the Staten Island Ferry for the simple fact that it is free and it runs for 24 hours a day, every day of the year. We decided to take the ferry at night, using it as an opportunity to see the Manhattan skyline lit up from a distance. It was quite spectacular! The ferry also takes you past the Statue of Liberty, meaning that we saw the statue from reasonably close quarters, despite having decided not to visit the island. When you arrive on Staten Island you do have to leave the ferry, but can run round and join it again to ride back immediately if you don’t wish to stay there. I really enjoyed taking the boat at night, but I imagine the views you’ll get are just as impressive by day.

Although we actually fitted this into an afternoon and evening by the time we’d arrived, you could easily lengthen it to take a full day by spending longer in Brooklyn, going into the 9/11 museum, or heading across to Liberty and Ellis Islands.

Day 2 – Enjoying the Sunshine in New York

We were really lucky to wake up to cloudless blue skies and bright sunshine on our second day in New York. Given that heavy rain was forecast for our final day we knew we had to make the most of it and crammed in as much as we possibly could.

Central Park

Central park was top of both our lists so was the first place we headed after breakfast. We could easily have spent all day there if we hadn’t been trying to fit so much else in. It’s vast – certainly big enough to forget momentarily that you are in a huge city, and it feels surprisingly tranquil. When we first arrived I was amazed by the vast numbers of runners and cyclists, but it was good to see that there will still pockets of quiet in the park. It felt a little bit like being in a film set as parts of it were so recognisable.

5th Avenue

After eating a picnic lunch in the park, we headed up 5th Avenue – you can tell we were trying to go to as many iconic locations as possible! We went into Tiffany’s and Saks, and I no doubt amused anyone near us by announcing the names of all the fancy shops we walked past. One thing I hadn’t expected was the number of neo-gothic style churches which appeared on 5th Avenue, looking entirely out of place among the shiny tall buildings.

Top of the Rock

As the weather was so good, it seemed a shame not to go up a tall building and see New York from above. We decided to go to the Rockefeller Center and up to The Top Of The Rock. It was the most expensive thing that we did whilst we were in New York, but it was one of my highlights as the views were amazing. From one side we could look out over Central Park and marvel at the large rectangle of green that was carefully placed in the city. From the other side, we had a great view of the Empire State Building, and out over lower Manhattan. We could even see the Statue of Liberty because it was so clear.

I thought we would have made a mistake by not pre-booking, but it appeared that we were there at the perfect time (the 3:15pm time-slot if you are interested) . There was no queue to purchase our ticket or head up in the lift, and then we managed to avoid the queue heading back down as well. We probably spent about an hour in total at the top, wanting to make the most of the view and seeing how much we could spot.


Once we’d headed back down to earth, we had a quick Ben and Jerry’s banana split at the bottom to fortify ourselves for the next lot of exploring. I really wanted to see the New York Public Library, and I’m so glad we made it even though we had very limited time before it closed. It was a beautiful building, and we were able to go in to see the atrium and reading room which were lovely. It certainly puts the British Library to shame!

Grand Central Station was next, and looked every bit as grand as I’d hoped. I’d recommend heading over to The Whispering Gallery, just outside of the Oyster Bar. You might get some strange looks from passers-by, but it’s pretty special standing at opposite corners to the archway and speaking into the corner, to be able to hear the person you are with as if they are are whispering in your ear. For such a busy and bustling place, it’s amazing how clear the sound was.

Walking the High Line

Not quite ready for dinner, we spent the early evening walking along the High Line, a public park which was built on an elevated, disused railway line. I had heard quite a lot about it, and so was curious to see the space, knowing that it would be interesting to see parts of the city from a different level. Along the walkway were plenty of plants, some art installations and places to just sit and watch the world go by. I really liked it, and probably wouldn’t have visited that section of Manhattan otherwise.

Chelsea Market

Coming off the High Line, we went in search of food and ended up in Chelsea Market. It was one of the few places that we visited which I hadn’t read about, so it was nice feeling more like we’d stumbled across it. Through the winding indoor space were a number of different shops, bars and eateries. Some offered street food to take away, whilst others looked more like restaurants for a proper meal. The taco stand had a huge queue and is clearly a favourite with visitors!

Times Square

Having missed it out in the day time, assuming we wouldn’t see the full impact until night, we headed back to midtown to see Times Square. It was every bit as busy, flashy and overwhelming as I’d expected. I don’t think I’ve ever seen such walls of advert screens anywhere! It was amazing how much the different adverts affected the space as well. There was one which was quite dark and you didn’t really notice until the next advert played with a white background and the whole area was flooded with light. I was also very impressed with the Disney Store (mainly because they actually stocked things in adult sizes!).

We saw a lot of different theatre shows advertised whilst we were in Times Square, and the only thing I feel like I missed out on was seeing a show on Broadway. We decided we didn’t really have the time, and it was quite expensive, however it will be top of my list if we ever return.

Day 3 – A rainy day in New York

Natural History Museum

What do you do when it’s raining in New York City? Go to a museum! But don’t expect it to be quiet because everyone else will be doing exactly the same… We decided to head to the American Museum of Natural History and were feeling pretty downhearted when we saw the two huge queues to get in. Luckily a third entrance was opened as we were walking past, allowing us to join a third and, more importantly, indoor queue. My top tip would be to keep an eye out for a self-service ticket machine. Despite the large queue to get to the ticket desks, nobody was using the machines so once we spotted them we left the queue and purchased our tickets that way. You’ll have to pay the recommended fee rather than “pay what you wish” but it was worth it to actually get on with seeing some of the museum.

The sections with the animals in were my favourite part of the museum. I’m not really a fan of taxidermy but painted dioramas made the landscape look very realistic. The dinosaur hall was also great, with one dinosaur skeleton actually too long to fit in the room, so its head poked cheekily out of the door. We paid slightly extra to go to the T. Rex exhibit which was on at the time. It was quite interesting, and is the first time I’ve seen a feathery baby T. Rex model.

Even though we were there for hours, we still didn’t see everything so do expect to spend the best part of the day there. We’d (foolishly) thought we might be able to fit in seeing the Metropolitan Museum of Art but it was closing by the time we’d finished with the natural history museum.

Exploring Bookshops

I love a good bookshop so whilst the weather outside wasn’t particularly pleasant, it seemed like a good excuse to go and explore a few. First stop was Barnes and Noble, a retailer I’d seen referenced in different novels. I guess it’s best described as an American equivalent of Waterstones but I still really enjoyed it. There was a fantastic selection of books, stationery, games and magazines which was all really nicely laid out. It felt like there was plenty of space, and there was also a cafe.

For something a little more independent, I’d recommend heading to The Strand which was where we went next. An independent retailer which claims to have 18 miles of bookshelves, I’d spotted The Strand mentioned in our guidebook and decided it was worth a visit. Given their claim to fame, I was actually expecting the store to be larger, but the shelves were quite crammed in and very tall. It seemed to have a particularly large art section so worth checking out if that takes your interest.

Dinner at a Diner

For our final night in New York we decided to have dinner in a diner, so found ourselves in a booth in Big Daddy’s Diner looking at a very jazzy menu. It was quite cheesy, but we both enjoyed it, particularly as I was on a mission to have as many ‘American’ experiences as possible throughout the trip. James had his first hotdogs of the trip, and I had a mac n cheese burger with tater tots (think mini croquet potatoes). Needless to say, we were both very full afterwards!

A street in Downtown Manhattan

For the amount of time that we had in New York we decided to pay the extra and stay on Manhattan island where most of the things we wanted to see would be easier and quicker to access. We managed to find a reasonable deal for The Club Quarter’s Hotel, just off Wall Street which I’d really recommend. We had a much bigger room than I expected, and the staff were really helpful. It was located close to a subway stop and we could walk around most of Downtown so found it pretty convenient.

I left New York on a high, having thoroughly enjoyed my time in the city. I was pleased with the amount that we’d been able to fit in, and wasn’t too disappointed by what we’d missed. I’d already decided that we’d probably be returning to New York at some point!

Have you been to New York? What would you recommend in a short trip?

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