My NYC Itinerary: Planned vs Reality | A Visitor’s View (Part 2)
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After a month of planning an NYC itinerary, analyzing maps, and going slightly crazy while making the itinerary, here’s how my 3-day NYC itinerary turned out, how the trip actually unfolded, and what went according to plan, what didn’t, and everything I learned in between.
If you haven’t already, check out Part 1 to discover why I visited New York City and how I planned my trip!
Planned NYC Itinerary
Day 1 – Midtown & One Vanderbilt
- 12 pm: Arrive at hotel, drop luggage
- Explore Grand Central, NYPL, Empire State, Bryant Park, Rockefeller Center
- 7 pm – 10 pm: Summit One Vanderbilt (arrive 15 mins early)
- 10 pm: Times Square and dinner in Midtown, then rest
Day 2 – Downtown & Liberty Island
- 10 am – 3 pm: Liberty Island
- 4 pm – 8 pm: Downtown sightseeing, Friends Building, SoHo, Little Italy, Chinatown, pizza spots, 9/11 Museum, Oculus, WTC Memorial, City Hall, Seaport, Wall Street, Pier 11, Brooklyn Bridge
Day 3 – The Met & Central Park
- 9 am – 2 pm: The Met (specific galleries), Levain Bakery, check out of hotel
- 2 pm – 5 pm: Central Park stroll
- Evening: Pick up bags, head to the station for departure
Day 1 – Downtown & Summit One Vanderbilt
The Flight & First Impressions
The flight from Toronto was really short, only being around 1.5 hours and I sat at the left window seat, which gave me a stunning view of Manhattan. It was surreal. For the past month, I’d been obsessively researching NYC by studying Google Maps, planning by area, memorizing where everything was, and suddenly, I was seeing it all from above. It felt like the map I’d been staring at for weeks had come to life. I could spot everything instantly: “Oh my god, that’s Uptown. That’s Midtown. That’s the Empire State Building! That’s Central Park!” I knew exactly where to look, like I’d known the city forever. Seeing it all unfold beneath me was one of those rare full-circle moments that make all the planning worth it.
I met my friend at the airport, and thankfully, I’d planned our route into Manhattan ahead of time. This is really important because some people don’t plan how they’re going to get into the city from the airport and that ends up costing you a lot. If you don’t have a lot of luggage and people with you, the train is your best bet. Don’t get stuck paying $100 for an Uber when a train will get you there for $12.
Halfway through our train ride to Manhattan, we realized we were sitting in the wrong train and ended up wasting half an hour because of it, so make sure you always ask people around you for directions as well. We arrived at the hotel in Midtown and were surprised (and kind of annoyed) when they asked us to pay a ‘destination fee’ of 17 dollars per day. On the other hand, we got an early check-in, which was a win, and stepped out around 1 pm. Instead of heading to Midtown right away, we decided to explore Downtown, since we had lots of time to spare and could always hit Midtown later at our leisure, as our hotel was in Midtown.
The August Heat Reality Check
Our first stop was the Friends Building. Honestly, it’s just a building, but it’s fun if you’re a fan. I’m not the hugest fan but I still wanted to go just to cross it off my list, which I realized later was a mistake because that’s when NYC hit me with its August heat. We had planned to walk fifteen minutes to SoHo but it felt like an eternity. I was literally melting away – I know 15 minutes seems like a short walk but in New York’s heat even a short walk will completely humble you. I didn’t realize how hot it could get. So rather than going to SoHo directly, we ducked into a café, grabbed drinks, and rested for 20 minutes. The moral of the story is that the heat will humble even the most ambitious itinerary. Bring sunscreen, sunglasses, a hat and be prepared for August heat. My friend brought along a portable hand fan, which really came in handy.
SoHo, Little Italy & Chinatown
SoHo itself was…chill. Not the grand spectacle I imagined. It was mostly boutique stores and long dressing room lines. But it was nice just exploring and going into different stores. I think if you’re more into shopping this would be the spot for you, but since I was going there to cross it off my list, I didn’t spend too much time there. After wandering a bit, we headed to Little Italy and split a pizza, which was delicious. Then, a quick stroll through Chinatown, which reminded me of Toronto’s version. Planning my itinerary by area really helped, since we were able to see most of what I wanted downtown.
Even though I made the itinerary, my friend was the one who helped execute it by figuring out subway routes, keeping us on time, and making sure we didn’t get lost. It was such a good balance; she made navigating New York so much easier while I kept us on track with the plan. Thankfully, both of us were flexible as well, which made the whole experience feel smoother. We worked in sync, me with the schedule, her with the logistics and somehow, it all just flowed.
Grand Central Magic
Next, we headed back to Midtown for our slot at Summit One Vanderbilt. Since it’s right next to Grand Central, we took the subway there first. Sitting on the iconic Grand Central floor, just watching people rush by felt surreal, like one of those quiet, cinematic moments where you’ve seen this place in a hundred movies, and suddenly you’re living it. It reminded me a lot of Union station back in Toronto. It honestly looked like a museum and I couldn’t believe people used this stunning building for their daily commute. I even made my tote bag touch the floor which felt like an achievement somehow. We sat there for a while, people watching, just soaking it all in.
Packing Lessons from My Friend
Also, a quick lesson about packing: I’m the type of person who literally brings everything and I make lists, write everything down, and overpack just in case. My friend, on the other hand, is the opposite. She’s been to New York before, so she doesn’t think she needs half the things I pack. Turns out, she forgot her eye drops and had to spend almost $25 on them at CVS! That really drove home the point: pack the essentials. Otherwise, you’ll end up spending unnecessary money, and trust me, it’s not fun when you realize you could have avoided it so easily.
Summit One Vanderbilt
After the eyedrop chaos we made our way to Summit One Vanderbilt. That’s when I realized I’d made a mistake. Everyone says to arrive 15 minutes early, and they’re right. I hadn’t, and it was a problem because I’d booked the sunset slot (and paid extra for it). The lines are long, at least a 30-minute wait so definitely plan ahead if you’re going during peak hours. We were booked for 7:30 p.m. but only got there around 8:00 p.m., which thankfully worked out fine.
The wait was absolutely worth it. The view was breathtaking. Glittering city lights, endless skyscrapers, the skyline stretching out in every direction. It really did feel magical. They even play soft, dreamy music in the background, which adds so much to the experience. For a moment, I couldn’t believe I was really there, that my dream of seeing New York City had actually come true.
But at the same time, I caught myself expecting a life-changing, cinematic epiphany. It was gorgeous, but not transformative and that’s okay. I realized that New York, for all its magic, is still just a city. It’s about the experience, not the fantasy. So, I reminded myself to just enjoy the moment.
The sunset view was beautiful, but if you’re looking to save money, you can honestly skip the extra $12 and visit either in the morning or at night. For photography, the second floor has the best light; the first floor’s lighting can be tricky. Oh, and skip the heels. You’ll have to wear shoe covers anyway because of the glass floors, so comfort is key. And definitely don’t wear skirts because the floors are reflective.
We spent around two and a half hours at One Vanderbilt before heading out for dinner. Unfortunately, our plans for a nice restaurant didn’t pan out. We were completely exhausted by then, and my legs were on strike. Thankfully, I’d saved a bunch of spots on Google Maps, so I quickly looked up what was nearby. Joe’s Pizza popped up, it’s been hyped up all over the internet so I was kind of excited to see what it was all about. When we got there, the line was massive and there was no way I was waiting an hour for a slice when I was already so exhausted. Instead, we went for a classic New York halal hot dog from a nearby food truck instead. Simple, quick, and surprisingly satisfying. By the time we got back to the hotel, my legs were screaming. I checked my phone and realized I’d hit 20,000 steps without even noticing. I crashed out immediately.
What I Learned from Day 1
Day 1 was all about learning how to pace yourself in New York. I realized that cramming too much into one day doesn’t make the experience better and it just makes you tired. The key is balancing sightseeing with breaks, planning by area (Downtown, Midtown, etc.), and having a realistic idea of how to get to your hotel from the airport. Saving places on Google Maps and using it for subway directions is a lifesaver. August heat will humble even the most packed itinerary, so schedule shaded or indoor breaks and be prepared.
Day 2 – Liberty Island & Rainy Midtown
Day 2 started a little slower. Honestly, we were tired after Day 1. I kind of wished I’d woken up earlier to “seize the day,” but sometimes you just need rest, right? So, we slept in, grabbed breakfast, and got ready for the cruise to Liberty Island.
Liberty Island & Ferry Tips
The Statue City Cruises departs from Battery Park, so we made our way there first. Tickets were about $23, and yes, it’s mainly the island and the Statue of Liberty. Save time by booking the tickets online and keep in mind that there’s only one official website and cruise for Liberty Island, so don’t get scammed. The time that you book on the site is essentially the time that you wait in line and not the time the ferry departs. . Also, on the website itself they do warn you about the heat, so make sure you dress up accordingly and take water with you!
I was initially not too keen on going to Liberty Island, and I was just doing it for my friend, but the views of Manhattan from the water were gorgeous, and I actually did have fun on the island. If you want an iconic photo with Lady Liberty in the background, Liberty Island is the spot.
A few highlights: Liberty Island has some food, so I grabbed a panini (honestly, pretty average) and a lemonade which was 10/10, highly recommend. The lemonade kept me refreshed throughout the walk on the island, and makes for a good souvenir too.
Ellis Island is included in the ticket, but we skipped it because we wanted to go to the other spots in downtown.
When Rain Changes Your Plans
After the ferry, we had planned to do downtown sightseeing like the Financial District, 9/11 Memorial, Charging Bull, and a few other spots. But as soon as we got back, it started raining. Instead of forcing it, we decided to skip those stops. Honestly, I didn’t feel too bad because none of these were on my “must-see” list. The lesson I learned here? Always have a few indoor activities in mind just in case the weather doesn’t cooperate. I hadn’t factored that in this time, but hey, you live and learn.
My friend and I ended up relaxing at Battery Park, talking about life and soaking in the chill vibes. As the rain picked up, we returned to our hotel and rested until around 8 p.m. We watched a horror movie, which wasn’t on my agenda but was actually so much fun and it’s nice to just enjoy the hotel you’ve spent so much on. That’s when I realized it’s perfectly okay to veer off your schedule.
Times Square After Dark
Once the rain eased, we wanted to head to Times Square for a few photos and then wander around the city until 2 a.m. I’d been looking forward to this all day – walking the streets late at night, soaking in the New York energy. My friend had done it on her previous visit, and I was so excited to experience it myself.
Times Square was… intense. Bigger and crazier than I’d imagined. I started to understand why many New Yorkers avoid it. It’s visually striking, yes, but there’s not much to do besides take a few photos. Still, it was fun to stare at the massive billboards and watch the city lights reflect on the streets.
Then, things got a little sketchy. Costumed characters started approaching us and I knew from YouTube videos I’d watched that these people sometimes try to charge for photos, even if it’s accidental. My friend said, “We might have to go now,” and we decided to leave. Safety first, and I was glad I had prepared by watching those tip videos.
If you want good photos, I’d recommend the area near Madame Tussauds instead as the lighting is perfect and the shots come out amazing. What I did enjoy about Times Square was the affordable souvenirs. You can pick up postcards or keychains for a dollar or less, which makes it a fun place to grab something for friends and family back home.
Safety & Street Smarts
Around 10 pm, we were both pumped to explore the city. We wandered around Midtown, near our hotel in Hell’s Kitchen, but things started to feel off. People were acting a little strange, and my friend began feeling uncomfortable and was getting stared at and hit on in some souvenir shops. She suggested we head back, and even though I was quite sad and heartbroken to cut the night short, I agreed.
Later, talking to a New Yorker confirmed what my gut had been telling me: Hell’s Kitchen can feel unsafe late at night, especially for two women alone. It’s always better to be safe than sorry. It might sound cheesy, but trust your instincts because if something feels wrong, it probably is.
And honestly, awareness shouldn’t just be a nighttime thing. Even during the day, especially when you’re on the subway or walking through crowded areas, it’s so easy to zone out or scroll on your phone. But in a big city, things can shift quickly, and you never know what might happen. Try to stay alert, take out your earphones, and just be aware of your surroundings. New York is amazing, but it’s still a massive city, and it helps to stay switched on wherever you go.
What I Learned from Day 2
Day 2 taught me a slightly different lesson: it’s okay to let go of strict schedules and priorities. I learned to distinguish between must-see spots and “nice-to-see” spots and that it’s completely fine to skip the latter, especially when the weather doesn’t cooperate. Veering off your planned route can lead to unexpectedly charming experiences, like wandering down the wrong street or stumbling upon a cozy café. Even a wrong turn can be surprisingly wholesome. The best memories aren’t always the ones on your itinerary; sometimes they’re the small, unplanned moments, like sipping lemonade while gazing at Manhattan from Liberty Island.
It was also a reminder to trust your instincts, especially when navigating crowded areas like Times Square or late-night neighborhoods and being situationally aware at all times.
Day 3 – Central Park and Met
The Elevator Chaos & Cookie Saga
Day 3 started off a little rough. The elevator in our hotel wasn’t working and it was starting to get a bit frustrating. My friend had enough and decided to fight for our rights and told them that having an elevator not work is literally a fire hazard and we needed some sort of compensation. After a lot of back and forth, we got that destination fee reimbursed. But we still had to lug our suitcases down 12 flights of stairs and by the time I got to breakfast, I was already exhausted. The breakfast was decent – bagels, cream cheese, pancakes, yogurt, fruit; but it was a shared seating setup, and honestly, some people seemed a little snippy.
Then came the iconic Levain cookie incident. My friend had ordered it to our hotel because we weren’t able to go to the store in person, and how can you leave NYC without trying them? The cookies had arrived and were delivered at the reception, so I thought I’d finish breakfast and go and pick it up. But as luck would have it, by the time I went to pick up the cookies around 15 minutes later, they were gone! I panicked because my friend spent $30 on it, and I felt absolutely terrible. The reception helped me track down where it was placed through the DoorDash photos, and I found two girls sitting at the table where the delivery guy had left it. But there was no bag.
My first instinct was to assume they’d taken it, but my friend told me to approach them nicely. I did, using Google Translate to communicate. Turns out, it wasn’t them but it was a lady in a purple shirt who had accidentally taken our cookies, thinking they were hers. She returned them, profusely apologizing. The lesson I realised was not to judge anybody too quickly, and tact goes a long way.
A Shift in Mindset
The best part of day 3? My mindset had totally shifted. I’d finally let go of trying to take perfect photos or see everything. I focused on soaking in the vibes. We had planned Central Park and the Met, keeping it simple with one morning and one afternoon activity which is a strategy I highly recommend. I’d initially thought of doing The Met first and then walking around Central Park but I realized you can walk to the Met through Central Park, and the walk is wonderful.
Central Park & The Met
Central Park in the morning was peaceful. We strolled to Bethesda Terrace and enjoyed the greenery, taking everything in at our own pace. From there, we walked to the Met. We got lost a bit in the park trying to figure out which way the Met was so we decided to ask people for directions and they’re usually happy to help. We spent two hours exploring Roman art, American Wing, stained glass, Egyptian collection, Van Gogh, and Monet. You could spend the whole day here just looking at the iconic artwork, but unfortunately, we didn’t have the luxury of time. The good news is that since we had planned out which exhibits we wanted to see beforehand, we left the Met not feeling like we missed out on anything because we’d seen what we wanted to see. Quick tip: Plan exactly which exhibits you want to see in the Met, especially if your time is short.
Accidental Detours & Hidden Gems
We tried to hit the New York Public Library but accidentally went to the wrong branch. At first, I was slightly annoyed, but it turned out to be a lovely detour. This little West Side library gave me a sense of what “real” New York feels like. Sometimes the detours are where the magic happens.
The highlight of the day was an impromptu detour to the Kinokuniya near Bryant Park. I don’t even know why, but I loved it. As a bookstore nerd, this place was magical with tons of merch and books to explore. My friend had been there before, so she knew the spot. Honestly, that random detour was one of my favorite memories of the trip.
The Perfect Ending: NY Public Library & Reflections
At long last, we finally made it to the correct New York Public Library branch. It was gorgeous, exactly as I imagined, and a perfect way to close our trip. We grabbed one last pizza to go before heading to our buses. Pro tip: New York pizza is incredible even at random spots, not just the famous joints like Joe’s. The bus ride back to Toronto was calm and relaxing. I spent the time reflecting on everything I’d learned.
Having a flexible plan made all the difference and it kept me organized without taking away the joy of spontaneity. Looking back, I realized my trip went almost exactly how I planned; most things did happen, just not always on the day I expected them to. And honestly, that made it even better. Sometimes the best way to experience a city like New York is to have a plan, but also let the city surprise you a little. My biggest takeaway? Keep a rough itinerary, but leave room for the city to lead you somewhere unexpected.
Actual NYC Itinerary
Day 1 – Downtown & One Vanderbilt
- 10 am – Landed in New York City
- 12 pm – Arrived at hotel and checked in early
- 1 pm – 5 pm – Explored Downtown: Friends Building, SoHo, Little Italy, Chinatown
- 6 pm – 7 pm – Visited Grand Central
- 7 pm – 10 pm – Went up Summit One Vanderbilt
Day 2 – Liberty Island & Times Square
- 12 pm – 4 pm – Took the ferry to Liberty Island and enjoyed the Statue of Liberty
- 8 pm – 10 pm – Explored Times Square
Day 3 – Central Park, The Met & Midtown Detours
- 10 am – 12 pm – Strolled through Central Park
- 1 pm – 3 pm – Visited The Met
- 3 pm – 7 pm – Went to Kinokuniya, New York Public Library, and Bryant Park
And that’s my New York City itinerary! Check out Part 3 where I cover what I wish I knew before visiting.
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