New York City: My Amazing First Solo Trip to the Big Apple + How to Plan Yours

 

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Have you ever wanted to take a solo trip? Have you just not been taking that first solo trip because you’re skeptical? Skeptical of, well, everything? Safety? Where to go? What to do? You know…everything? I hear you, this was me! Although not targeted as a solo trip, I wound up inadvertently taking my first solo trip to New York City this past February. And you know what? I had a blast and it is now one of my most favorite trips! Hopefully, my amazing first solo trip to the Big Apple will give you an idea of how to create your own!

So like I said, my trip wasn’t supposed to be taken alone. There was an event I wanted to attend in NYC and none of my traveling friends could go. So, I decided I would go anyway. I will admit that I have been to NYC several times before, but I purposefully tried my best to look at it from a first timer’s point of view (however, there are a couple of places where I reference I’m not a rookie).

Why is New York City the best place for a first solo trip?

I’m so glad you asked! 😜

1. Easy Navigation

NYC is a walking city so you do not need a car. In addition to the convenience of walking, there are multiple other transportation options as well. Uber is my favorite as you will see!

2. Cultural

Is it another country you’re ideally wanting to travel to solo but want to try your hand a little closer to home for that first time? NYC can just about be turned into any culture you’re looking for. You can find all types of authentic food, hear all different languages, and have all kinds of different experiences here. You can even get lost in the middle of Central Park to simulate a nature trip!

3. Populated

There’s safety in numbers. Keeping in mind obvious, standard rules, you can pretty much pick a time of day you want to go somewhere in the city and chances are, thousands of your fellow travelers will be right there with you. 😉

4. Adventure

There is anything and everything you could possibly want to do in NYC. Pretty sure I don’t have to elaborate on this one for you. But just in case, in addition to the iconic activities, you might want to discover NYC’s hidden gems as well. 

5. Iconic. It’s NYC. Why not?

Ready to plan your own NYC solo adventure but are overwhelmed and not sure where to start? Here’s my planning process and how I spent my five days in the city that never sleeps!

Plan

To start my planning, I took care of the two biggest parts of a trip: transportation and accommodations.

Transportation

How to get there? Most of you will have to or at least want to fly to New York just like I did. I always fly the same airline because I have built up status and Skymiles with them, but Skyscanner is a great way to compare prices and get the best deals on flights. And, if your best option is flying into Newark, be sure to read these tips on traveling between the Newark Airport and Manhattan.

If you want to get views like this as you fly in, read my guide on why the plane view matters!

Accommodations

Where to stay especially in New York City is truly a personal preference. Some people swear by getting out of midtown and staying in an Airbnb with more of a local feel. I think that’s a great idea if that’s the purpose of your trip. However, wanting to stay convenient to the action, I opted for midtown (plus I love it there).

Okay great, midtown. That narrows it down to just a few places…or a million. After some research, I narrowed it down to a boutique hotel and a hotel chain I have points with. I thought about what I was going to do in New York and since I scheduled two nighttime activities, I wanted to stay in close proximity of both since they would end later in the evening. I also had one very early morning activity and therefore didn’t want a long commute for that.

The hotel chain won this round and so I stayed at the Hilton Garden Inn Times Square. It was not actually in the middle of Times Square, just in the area and therefore convenient to my plans for a Broadway play, a concert at Radio City Music Hall and a morning talk show on the Upper West Side.

Note: This is not the same Hilton Garden Inn that offers views of the Ball Drop on New Year’s Eve. If you are looking for that hotel, it is the Hilton Garden Inn Times Square Central and you can read about my stay at this hotel and how we watched the ball drop without the crowd!

Big Ticket Items

After flights and accommodations, book the events and attractions that require tickets. For me on this trip, that included a Broadway play, a concert, a morning talk show, One World Observatory, Top of the Rock, a food tour and purchasing the New York CityPASS to cover other attractions.

Once you have the tickets to these attractions bought and have a concrete idea of when you are going to visit them, you can then fill in the gaps with sightseeing that doesn’t require a ticket.

Now make a list of these things. My list looked like this: Times Square (day and night), Central Park (including a list of things in the Park like Strawberry Fields), the exterior of United Nations, Rockefeller Plaza, Carnegie Hall, NYC Public Library, Grand Central Terminal, Chrysler Building, St Patrick’s Cathedral and a bunch of yummy places to eat!

Get Ready…

Watch the weather so you know what to pack (NYC packing list for winter coming soon) and how to schedule your activities. Because I promise you will hate yourself if you don’t look at the weather and you end up having to go to the One World Trade Observatory on a rainy day because you assumed since it was sunny the day before it would be that day also. You do NOT want to miss these views!

Make sure you leave your flight and hotel information with someone back home for safety reasons. If a passport is required for this trip, make copies of it. Leave a copy with someone back home and carry the other copies with you.

Finally, get excited because the fun times are about to begin! 🙌

GO!!!

Have an amazing time and enjoy the rewards of all your hard work planning your adventure!

Amazing Adventures in NYC

If you want to follow my actual itinerary, then your trip will look a little something like this (especially if you are making a long weekend out of it):

Day 1

Arrive in NYC and go straight to the hotel to check-in or store your luggage if you’re too early for check-in.

I then headed to One World Trade Center.

I visited the sites and memorials to both towers and took photos of the new Freedom Tower.

If you are using the CityPASS, you can use it to enter the 911 Museum. I had already seen this so I passed this time.

Location: 285 Fulton Street, New York, New York 10007

Make sure you see Oculus before you leave the area. It’s one of the newest masterpieces from the Spanish (and my favorite) architect, Santiago Calatrava. It’s a 78,000 sq ft retail and dining space in the center of the World Trade Transportation Hub.

Location: Church Street (across from the intersection with Dey Street), New York, New York 10006

Trinity Church-see where Alexander Hamilton is buried. You can see the grave from the street (albeit through the bars). If churches are your thing when traveling, check out this tour (with tips) of the best churches in NYC!

Location: 75 Broadway, New York, New York 10006

Hit up NYSE and the Charging Bull (you must exercise extreme patience here to be able to get a photo without someone hanging on the bull’s horns. Or from other unmentionables on its, ahem, back-end. 🙄)

Locations: NYSE-11 Wall Street, New York, New York 10005
Charging Bull-Broadway & Morris Street, New York, New York 10004

Now would be a great time to do the Staten Island Ferry if you decide you have enough time. It is free and you can get incredible views and photos of the Statue of Liberty and Manhattan. For reference, I was going to do the 2:15 pm ferry, but because it was February and the sun sets early at that time of year, I decided to head on up to the One World Trade Observation deck. But, if you are there during the summer, go for it!

Location: 4 Whitehall Street, New York, New York 10004

One World Trade

At One World Trade, priority access zipped me right on up, bypassing the line (which was out the door). I was through security and on the elevator faster than the next person in line could buy their tickets.

I was able to take amazing photos on this beautiful, sunny day in New York. It’s just a gorgeous city!

After I took my daytime shots and admired the cityscape, I grabbed a pepperoni flatbread pizza from the restaurant. There are a variety of options, but pizza just sounded good to me at the moment. Upon finding out that I could take the food anywhere I wanted, I walked around and settled onto one of the comfy leather benches where I could people watch and see out the floor-to-ceiling windows.

Make sure you catch the sunset behind the Statue of Liberty. It is one of the prettiest sunsets I have seen and I felt a surge of pride. We aren’t perfect by any means, but I am definitely proud to be an American!

I then parked it on the north side to obtain this time-lapse video looking uptown (with a few dozen others doing the same thing). It just might have been my first ever time-lapse and I might have, well okay, I did fall in love with them! I also fell in love with watching the Big Apple wake up for the night!

I finished up my time on the 102nd floor with incredible night views.

Location: 285 Fulton Street, New York, New York 10007

And with that, I finished up my first night in NYC at the Snowflake Spa (a Thai massage place with amazing prices 1/2 block from my hotel) and a pair of beef buns with duck sauce at Kung Fu Kitchen (right across the street from my hotel).

Locations: Snowflake Spa-324 West 49th Street, New York, New York 10019
Kung Fu Kitchen-610 8th Avenue, New York, New York 10018

DAY 2

Ray’s Pizza (Times Square) for an early lunch.

Location: 736 7th Avenue (between 48th & 49th Streets), New York, New York 10019

Grab photos in Times Square-I was there in February and this is leftover confetti from New Years. Watch videos from my Instagram Stories of the countdown and the confetti coming down from my New Year’s trip 2017!

Side Note: This is the first time in probably 3-4 visits to NYC that I have not seen the Naked Cowboy in Times Square!

The New York Public Library is really impressive inside. The hallways, stairways and the actual library rooms just blew me away!

TIP: They have one library room you can take photos in and one where no cameras are allowed.

Location: 476 5th Avenue, New York, New York 10018

While shooting this time-lapse, I literally heard someone mutter “it’s like Grand Central Station in here!” Um…🤣🤣🤣

You have to walk into Grand Central Terminal to at least say you were there. If you love to people watch, this is a great place to do it!

Location: 89 East 42nd Street, New York, New York, 10017

From here, my walking plans took me to these next 4 places:

Chrysler Building

United Nations and Flags

St Bartholomew’s Episcopal Church (St Bart’s)

Waldorf Astoria

St Patrick’s Cathedral is iconic in NYC and you must go inside! The Neo-Gothic style architecture in this Roman Catholic church is absolutely gorgeous!

Location: 5th Avenue, New York, New York 10022

Rockefeller Plaza-be sure to see the ice rink (if you are there mid-October to mid-April) and the spot where the Christmas tree stands every Christmas (or the tree itself if you are up there in December).

Location: 5th Avenue (between 49th and 50th Streets and through the Channel Gardens), New York, New York 10112.

Right after the Plaza, head up 30 Rock to Top of the Rock! It also is an option on your CityPASS. This is another one you must do early enough to get some daytime photos and watch the sunset. It probably offers the best views of NYC (when the weather is good) because you can get uptown (with Central Park) and downtown (with the Empire State Building and, in the distance, Freedom Tower and the water).

Location: 30 Rockefeller Plaza, New York, New York, 10112

Radio City Music Hall is a great place to catch a concert or show. If you are up there during Christmas, the Christmas Spectacular featuring the Rockettes is fabulous! However, if it isn’t the holidays, try to catch a concert there for an iconic experience. I went for the LA X LOVE LIVE concert to see Luis Fonsi and J Balvin in February and had a blast!

Location: 1260 6th Avenue, New York, New York 10020

Times Square Diner (across the street from my hotel) for a late night snack!

Location: 807 8th Avenue, New York, New York 10019

You might also like: NYE IN NYC: WATCH THE BALL DROP WITHOUT THE CROWD

DAY 3

Bibble & Sip-for mid-morning lavender latte

Red Eye Grill-lunch. Their sushi burger is delicious!

Carnegie Hall is across the street. I walked into the lobby to take photos even though it was early afternoon on a Saturday and no event was taking place. This is a special place because I played onstage Carnegie with my wind ensemble in high school. Epic experience!

Location: 881 7th Avenue, New York, New York 10019

Uber to Pier 83 for a Circle Line Cruise. This is an option on the CityPASS and I chose the Landmark cruise. This cruise leaves on the Hudson River goes by the Statue of Liberty and up into the East River, under the Brooklyn Bridge and back. It was rainy, foggy weather on the day I went so it wasn’t ideal for photos, but on days with better weather, you will have fantastic views of some of New York’s most iconic landmarks!

TIP: With the CityPASS, you don’t have to have tickets in advance, but the lines can get long especially during peak season so you do need to arrive early (30-45min) to be guaranteed admission for your chosen time and to get a good seat!

Location: Pier 83, West 42nd Street, New York, New York 10036

Uber to Serendipity 3 for dinner. Remember to check out my NYC restaurant list!

Location: 225 East 60th Street, New York, New York 10022

Rich Rodgers Theater for Hamilton! I can NOT tell you how excited I was to finally be able to see this production. I’ve waited for a few years for availability and for prices to go down and finally!! I can’t recommend Hamilton enough. This very modern take on history has something for everyone!

TIP: There really isn’t a bad seat in the house. I was sitting in the upper balcony 3 rows from the top on the extreme right-hand side and the photo above was my view. I went here to see the views from different seats and it helped me decide!

Location: 226 West 46th Street, New York, New York, 10036

DAY 4

I began the morning exploring a little of Chelsea Market before my scheduled food tour. Chelsea Market is located in the old Nabisco factory and is home to TV shows such as Iron Chef and Rachel Ray as well as to companies like Google, YouTube, and MLB.com. It also houses the longest indoor walkway in NYC at 800 feet long!

Location: 75 9th Avenue, New York, New York 10011

Food Tour

Clockwise: Fried Oreo; Salted Caramels, Chocolate, and Dried Blood Orange; NYC style Margarita Pizza; Buttermilk Biscuits and Marmalades

Foods of NY Tour-I wanted to do a food tour, see Chelsea Market and the High Line and needed a rainy day activity. This company had a tour that fulfilled all three! While you do have to go outdoors, some of the tour took place inside the Market which was really cool. I loved the foods that were offered and the 3-hour tour was absolutely amazing!

Museums

I really did go timelapse crazy this trip!

Uber to Metropolitan Museum of Art, another inclusion on your CityPASS. Since it was raining, there was a ginormous line. But it went lightning fast and I was inside in only 5 minutes! They’ve done this a time or two I think!

TIP: If you aren’t a huge museum fan (I’m not except for certain things) and just want to hit the highlights, then my recommendations are the Great Hall, The Denial of Saint Peter, Death of Socrates, the Temple of Dendur and its Reflecting Pool (celebrating 50 years in 2018 since President Lyndon B Johnson gifted the temple to the Museum), and the Sphinx of Hatshepsut.

Location: 1000 5th Avenue, New York, New York 10028

Walk a few blocks north (about 7 min) to the Guggenheim Museum, also an option on your CityPASS. Look up at the dome from the ground floor, walk the famous circular ramp and see the exhibits along the way!

Location: 1071 5th Avenue, New York, New York 10128

Uber to the Empire State Building. I have seen the views during the day and wanted to see them at night. I actually arrived in time for sunset, but the weather was so cloudy and foggy that when I arrived, they warned me there was “no view”. No view. Different than limited view. I elected to go up anyway because my CityPASS covered it and it was my last night in New York.

I’m so glad I went up! I got this gorgeous photo of the city below as the clouds cleared for a few seconds only!

Bonus: No one was up there with me. NO ONE. 

TIP: Although the Empire State Building is an option on the CityPASS, I could argue a good case for VIP skip-the-line tickets. If you’re going in the offseason or on a questionable weather night like I did, stay with the CityPASS. However, if it is peak time/season or you have a time crunch, I would recommend skip-the-line tickets (no waiting)!

Location: 350 5th Avenue, New York, New York 10018

Sticky’s Finger Joint-dinner. Highly recommend the salted caramel chicken fingers!

Location: 598 9th Avenue (between 42nd & 43rd Streets), New York, New York 10036

Snowflake Spa-Thai massage, take two. I couldn’t resist the prices!

DAY 5

Live! Kelly & Ryan

I love Ryan Seacrest and so I wanted to catch a taping of Live! Kelly & Ryan. I had a great time, got fantastic photos and even scored a free copy of the movie Coco since one of its stars, Gael García Bernal was a guest that day!

TIPS: This is another reason I chose to stay at the Hilton Garden Inn Times Square. It was close to the studio on the Upper West Side. I took an Uber since it was early in the morning, left the hotel at 6:40 am and arrived at the lineup location at 6:52 am. Also, these free tickets will need to be obtained in advance (priority is better than general) and you need to arrive early to try to be as close to the front of the lines as possible for the respective ticket types. They do allow the use of cameras and cell phones!

Location: 7 Lincoln Square, New York, New York 10023 (but lines form on the corner of West 67th Street and Columbus Avenue)

American Museum of Natural History

American Museum of Natural History-This is an easy walk from the Live! studios and also included on your CityPASS. I love Natural History museums and this one is my favorite. I’ve been before, but I love seeing the dinosaurs (particularly the T-Rex)! If you’ve seen the movie Night at the Museum, this is the museum it is based on!

TIP: Take a cool, unconventional Museum Hack tour!

Location: Central Park West and 79th Street, New York, New York 10024

Central Park

Explore Central Park. It is much bigger than you realize and you likely won’t get to all of it, but you can start with Strawberry Fields, a 2.5-acre section of the park that pays tribute to John Lennon. Be sure to see the mosaic “Imagine” at the center of Strawberry Fields!

Balto!

Other things to see and do in the park are Bethesda Fountain, the Loeb Boathouse, carriage rides, children’s zoo and Balto, a tribute to the hero sled dogs of Alaska who mushed through a blinding blizzard 674 miles to deliver medicine during a diphtheria outbreak!

From this point, you are on the tip of the eastern side of the park. Exit the park and walk south, and you will pass:

The Arsenal

The Plaza Hotel

and then head over to the Burger Joint for lunch. You will definitely want to read my food post for the story of this interesting secret!

Location: 119 West 56th Street, New York, New York 10019

I spent the rest of my time meandering back to the hotel seeing attractions such as the fountains at 5th Avenue and 55th Street, St Thomas Church, Museum of Modern Art (MoMA), Radio City Music Hall (again), and The Tonight Show with Jimmy Fallon.

Arrive back at hotel, pack up, head to the airport.

Departing

NYC is one of the prettiest cities to fly in/out of and one of the easiest to photograph from the air!

Still on my NYC Bucketlist: Brooklyn Bridge, Staten Island Ferry, SoHo, West Village and more!

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I always hate leaving NYC because I have such a great time every time I go. But this trip was just extra special as it was my first solo trip where I carefully planned everything I wanted to do *just for me*. With no time restrictions of anyone or anything except the ones I placed on myself.

Do you travel solo? If so, do you remember your first solo trip? Where did you go and what did you do? If you haven’t traveled solo, where would you like to go on your own?

‘Til next time…

Trimm Travels,

Heather