New York Itinerary – what to see and do

New York Itinerary

New York itinerary planning is a wise thing to do. Firstly it allows you to do and see what you want. Secondly you can use your time there in the best way.

I visited New York the first time with my now husband who consequently proposed to me on the ice rink in Central Park. A whole other story. We managed to fit in so much on that visit but, not everything. This time we filled the extra gaps with new experiences. As a result, we planned our New York itinerary well. People say that New Yorkers are rude and impolite. We found the opposite to be true. The people we met were very friendly, helpful and approachable.

New York Itinerary – what to see and do in four days

On this trip we decided to pay a trip down memory lane. Choosing to go in February was a gamble. Although the weather was cold, super cold, we still had a wonderful time.

Organizing the packing list was easy for this New York itnerary. Sweaters, comfortable shoes, jeans or similar were fine. All very casual.

Dress as you like in New York

New York is a real melting pot of people. Some dressed like a scene from Sex and the City. While others are totally dressed down. It is a place where you can pretty much wear what you like despite what you read or hear. Above all, dress for yourself.

Wearing the wrong shoes has the potential to spoil your holiday. Let common sense prevail in what to pack for New York in winter. In addition, everyone is busy seeing the sights and as a result not paying attention to what you are wearing. They don’t care, why should you?

New York Itinerary

Questions to help you pack for your New York itinerary in winter

  • What season is it? Dress and pack accordingly
  • Do you want to enjoy every minute of your vacation? Be comfy!
  • Is feeling relaxed and comfortable more important than being overly dressed? It is possible to look stylish and still be casual
  • Can you walk for long periods in the shoes you have packed?
  • Are you dressing for yourself or to please someone else?

Mistakes made on our first New York itinerary

On my first visit to New York, I was foolish because I convinced myself high heels would be okay. Consequently, I discovered this was a big mistake.

The second day was spent shopping for more appropriate footwear because my feet were sore and unhappy. Definitely, lessons learned. Painful feet and walking around New York is a recipe for disaster!

What is the best time to visit New York?

There are different opinions about the best time to visit New York. Summer can be very hot and sweaty. Other times of the year can be busy. February worked for us for many reasons, one of them being the great deal we received from Bliss Travel.

Most days the sky was clear and blue. One week to departure there had been heavy snowfall, therefore we had some concerns. Do the research and take the gamble that there may be snow.

Another advantage of visiting at this time was fewer queues. In addition, streets are quieter, therefore it is easier and quicker to move around the city. With so much to see and do, and a short time to do it, the last thing you want is to be standing for hours in a long queue. 

Transport from La Guardia airport to New York City

There is no need to stress about this because the taxi rank is directly outside. We were in the City within an hour. The fare is set so you know exactly what you are paying. We had no problems at all.

If you are travelling on a budget and want to save money, then public transport is inexpensive. Follow the directions to the link bus, and hop on the subway line you need.

New York Subways

Like most cities, the New York subway is cheap and easy to navigate. In addition, there are signs to direct you, therefore little chance of getting it wrong.  Do make sure you know where you want to go.

With that in mind this was the itinerary for our visit:

Times Square

The hotel was in a great location in the fabulous, famous, hustle and bustle of Times Square. The area is alive with never-ending activity. Full of neon light flashing billboards, street performers, shops, restaurants, and street hustlers, a real hive of non-stop action. In other words, be prepared to have a jolt to the senses. A complete sensory overload.  

New York itinerary

How to get around the city on your New York itinerary

On arrival, we purchased a ticket for three days on the hop on and off bus. Shop around and go for the best. Like everything there is good and not so good. It is also possible to book this online.

The New York pass is popular. In addition, a search on the internet will provide plenty of information to help you plan your own itinerary.

New York City is walkable and taxis plentiful, however jumping on and off the bus gives you the chance to do both and therefore is useful in planning your days.

Statue of Liberty and Ellis Island

This is a must-see for everyone’s bucket list. Make sure to include this on your New York itinerary. A well-known icon in itself. There is an option to take a free ferry that sails past the Statue of Liberty. Many people opt to pay for the ferry that goes direct to Liberty Island, consequently, we opted for that. The history of Ellis Island is captivating because history reveals the City’s heritage. Arrive early because queues build up quickly.

Statue of Liberty
Statue of Liberty

The 9/11 Memorial

It is impossible to forget the horrible event that took place on that fateful day.

Three hours spent here passes quickly. In addition, we made sure to do something uplifting after because this is such a deep, emotional experience. 

Built to honour the people who lost their lives that day, a very moving memorial. The fountains are beautiful with water cascading down into the area where the towers once stood. Names of the people that died are engraved in bronze on the sides of the fountains.  Roses are placed on the names and this itself is very moving.

The Empire State Building

Views over the city are magnificent from here. Built 1000 feet above the ground with an observation deck on the 86thfloor.  Above all make sure to take your camera to take some great shots. Security is tight. However, don’t let this put you off because the queue moves fast.

Central Park – a must do on any New York itinerary

Central Park is one of my favourites for so many reasons. A peaceful space, away from the hectic buzz of the City. Full of paths, and local enthusiastic joggers and walkers. I particularly enjoyed the benches that line the park. Gifts and commemorations engraved on the benches. There is even one from Donald Trump to Melania (or it could be the other way around). Eventually, we reached the ice rink where my husband proposed eleven years ago. Special memories indeed.

New York
Central Park

Each part of Central Park has a different vibe and energy, similarly there are great views from many areas within the park.

Bikes can be hired which is a fun thing to do. We decided to take a romantic horse and cart ride. Although pricey it was certainly worth it.

New York
Ice rink

Remember to visit Strawberry Fields The John Lennon Imagine Mosaic is here. Intended to be a peaceful resting spot to reflect and contemplate. This is true if you arrive before the crowds. Later it becomes busy with people jostling to take selfies kneeling or sitting on the mosaic, as a result, it gets loud and noisy.

Museums of New York

New York has some great museums:

The Guggenheim which is full of fabulous art

The American Museum of Natural History. A great educational experience. With 45 exhibition halls, there is much to see. When the weather isn’t great, it is possible to spend a good few hours here.

The Museum of modern art. Also known as the MOMO which also houses a beautiful art collection.

Greenwich Village

Washington Square Park

Greenwich Village has a great vibe. Known to the locals as “The Village”. Stroll around and stop at one of the trendy cafes or restaurants for a bite to eat, and enjoy watching life pass by. We liked Washington Square Park with its very French looking Washington Square Arch. I enjoyed the quirky shops and boutiques here. For art and museum lovers you will find the Rubin Museum of Art, the Grey Art Gallery, and the Children’s Museum of Art.

The Brooklyn Bridge

We took the night tour over Brooklyn Bridge, therefore the lights at night were beautiful. This was a free tour on the hop on and off bus. An unexpected bonus.

Include some shopping on your New York itinerary

Of course Macy’s and shopping was in the itinerary, however, with the exchange rate not being great I didn’t give in to temptation.

There are so many great shops and brands in New York. Designer shops, small boutiques, and huge department stores, therefore something for everyone. Some shops open 24 hours a day, however most open from 10am to 9pm through the week and 11am to 7pm on a Sunday.

New York
Shopping New York

Outlet Malls

Great deals are to be had in the many outlet malls. Sales offer big discounts and as a result, you go home with fabulous bargains (if the exchange rate is in your favour). In addition remember to pay attention to the customs rules of what and how much you can take home.

Fifth Avenue

Fifth Avenue is well known throughout the world. Similarly the biggest brands such as Armani, Dolce Gabanna, Hugo Boss and more are found here.

Book a show on your New York itinerary

New York is famous for its shows and theatres. With around 40 different venues, you are spoilt for choice. Radio City, Cirque De Soleil and Rod Stewart was on our list, and we were not disappointed. Shows and concerts can be booked online well before you arrive. This way you may be able to choose the seats you want.

The Rockefeller Centre and Top of the Rock

Also known for its artwork such as the bronze Prometheus, Atlas and many other pieces of artwork. Therefore, if art is something you love and enjoy, factor in time to spend here. 

New York
Rockefeller Centre

In my opinion this offers better views than the Empire State Building. A huge building that also has an ice rink. No more ice skating for us on this trip. There are options to take a tour of the centre however, we chose to go straight to the Top of the Rock. With three levels of viewing with the top giving incredible views of the New York skyline, therefore that’s where we headed. We got some great photos of the Empire State building and Central Park from here. 

In conclusion, I wasn’t sure if I would enjoy New York as much as the first time. I was proved very wrong.  On this visit the exchange rate was not in our favour. Consequently, it was a costly visit, therefore check exchange rates before you leave. However, it did not spoil our holiday and would certainly go back again. 

If you enjoyed this New York itinerary article, feel free to read about other destinations on the Blog.



  1. March 27, 2019 / 1:06 pm

    I am actually going to New York this weekend for the first time and I really enjoyed this article.

    • Isobel
      March 27, 2019 / 5:30 pm

      Hi Laura. Have a fabulous time, it’s got such a great vibe. Thank you for commenting on the Blog.

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