New York City: A Planning Guide


First things first, I am not a New Yorker. I am a New York City enthusiast. Of all the places I’ve been, New York holds a very special place in my heart. I don’t know it all, but that’s part of magic NYC has. The opportunities seem endless and around every corner there is a new adventure just waiting. (omg! I love it and I can’t wait to go back!)

Now, I’m sorry if I’ve disappointed you, but I’m not going to tell you what to see in New York. That my friends is another tale for another day. I am however, going to share with you what I’ve learned about planning your NYC trip.

How are you going to get there?

Where are you going to stay?

How are you going to make the most of your time?


These are all questions and concerns we are going to address in this post. And yes, many of these skills can be transferred to other trip planning situations.

When is the best time to go?

It’s a no-brainer that traveling in the spring, summer or fall is easy. Clothes tend to be lighter, weather is less variable, but nobody ever talks about the magic that happens in New York during the winter. There is so much to see in New York during holiday season. Somehow this already magical city is transformed into a whimsical christmas paradise. For the most accurate weather, you may want to consider last minute planning. If you’re stuck, make the most of it! In my experience, NYC weather tends to have a quick turn around.. unless they’re calling for a snow storm.

New York’s attractions are not hindered by winter weather. However, there are some “outdoors-y” adventures which are better left to the spring and summer months. Visiting Ellis Island and the Statue of Liberty, sailing toy boats in Central Park or riding your rented bike across the Brooklyn bridge! These are activities better suited for the warmer seasons. Regardless of what season you choose, there is so much to see and do.

After you’ve decided what kind of NYC you would like to experience.

Next, we must start planning your escape to New York.

I’m lucky. I live close enough to the big apple that I have a few transportation options:

Flying - The most convenient, but also the most expensive way to get to the city. This is the best mode of transportation if you’re short on time, not fond of travelling solo or you’re uncertain about road conditions. Flight time varies from 45 minutes - 1 hour. You will honestly spend more time at the airport, than you will on the airplane. If you’re flying with friends try flying from Buffalo  International Airport. You can often find some excellent travel deals.

Driving - My boyfriend’s personal favourite. The most cost effective, yet comfortable way to travel. If you’re travelling with more than one person, you have a confident and reliable driver or you really just enjoy a good road trip. Turn up the tunes! And start the car! It will take you approximately 7-9 hours of driving time, depending on how many stops you make. Things to think about: Where will you park? How are the roads? Who is the best city driver?

Trains / Buses - My least favourite. Hopping on a bus is a relatively cheap alternative, but it is not comfortable. Unless this is the only option, I am never doing this ever again. Taking the train sounds a little more comfortable, but it is also more expensive. Both will take you ~10-12 hrs to get you there.

Moving along: Where are you going to stay?

This is a very tricky topic because it depends solely on your personal preference.

Staying close to attractions is convenient. Let’s take for example, Times Square. If it’s your first time in New York, staying in Times Square sounds awesome. It’s a short walk to the Rockefeller centre, Central Park, 5th avenue etc. However, hotels in this area are a tourist trap. They are loud, busy and significantly overpriced.

There are hotels everywhere! A multitude of price ranges and styles to fit your needs.

There are also options which offer the whole “live like a New Yorker experience”. Although, this is a relatively new concept. Renting out an entire apartment gives you more options in terms of food preparation and downtime. If you are planning a longer stay in New York, this may be an option you want to consider. The prices are comparable to hotels, sometimes even more affordable.

My favourite hotel area is located on Lexington ave between 52nd and 47th. I enjoy this area because the hotels are established hotel chains, while still being reasonably priced. It’s close enough that attractions are still walkable. If I feel so inclined I can go for a 15-20 minute walk to Central Park, passing Times Square along the way.

If you’re a NYC veteran and love this city as much as I do. You probably have your favourite neighbourhoods, in which case I would love to hear where you stay when you visit!

Now that we know when you are going, how you will get there and where you will stay; How are you going to pack everything NYC has to offer into a few short days?!

The answer is: you’re not.

This will not be your last NYC visit. You’re going to fall in love with this city and you’re going to want to come back. So for this trip, you need to narrow it down. What are your interests? What are your priorities? Start by making lists. Is this primarily a shopping trip? Is this adventure geared towards food? or Photography?

If you’re going for a weekend; Choose 5-10 attractions that are MUST sees. Tours are an easy way to see quintessential New York City landmarks. Because they are guided; It can reduce the amount of navigation you have to do, but they are also longer. Over a weekend, you might have time for 2 tours, a quick trip to a museum, the top of the empire state building and a few other little things. (just to give you an idea) Check the prices for each attraction and take a step back. How much will it cost you to see everything on your list?

If the price is over your budget you may need to rethink your itinerary. You may also want to look into a new york city pass. These passes allow access to a long list of attractions. Depending on what you plan to do, it may be a cheaper alternative than paying for each event separately.

Now how are you going to make the most of your time?

Planning your meals - There are so many delicious and instagram-popular restaurants in New York. Unless, you’re planning a food trip, don’t get to specific about where you want to eat. Make a list of restaurant options in the areas you will be venturing to. (Don’t forget to check their reviews and menus beforehand) If you get hungry while you’re out and about, you have plenty of nearby options. Instead of having to double back. If there is a place you’re dying to try, please make time for it.


Transportation - haha … you thought were were done talking about transportation! Walking is fun, but it is not always practical. Getting from point A to point B can be made much easier using those fun yellow taxis or the more daunting public transportation. Now, if you have the money (that I wish I had), feel free to taxi everywhere! I usually reserve this option for I-am-wearing-heels-and-don’t-want-to-die nights and the rides to and from the airport. There are also ubers, which tend to be a little more wallet friendly.

  • I feel like I belong when I take public transportation. I love the subway! It looks super complicated, but as long as you have a map (there are offline subway map apps) and you remember if you’re travelling uptown or downtown, you’re going to be fine.
  • Buses, although less convenient, allow you to see above ground. This can significantly reduce the amount of times you get very lost. It also allows you to sight see as you travel, so you can scope out the landmarks you might have forgotten.

We’ve made it through all our talking points! I really hope you enjoy your time in New York. Let me know how it goes :)

This was a really lengthy post. Thank you so much for sticking with me through it. If you made it through the end… *high-five*. Until, next time…

Always, Khristine