Why New York City?

The real question wasn’t “why New York?” but“why not New York?” I’ve always been a city girl, and what’s the best city in the world if not New York City? From the skyscrapers and yellow cabs to the iconic buildings on every corner, the city has always felt larger than life. I’ve seen that skyline in almost every movie and TV show, and it somehow always looked too cinematic to be real.

For the longest time, I’d fantasized about walking those streets and seeing those buildings in person. It felt like a faraway dream, like one of those things you talk about but never actually do. I mean, is the city even real? How can a place look so vibrant and dazzling? How do you plan an NYC trip? Every time I’d see an Instagram reel with “New York, concrete jungle where dreams are made of” playing in the background, the urge to go only grew stronger.

Everyone who’s lived in New York says it changes your life, and I wanted even just a little glimpse of that. My close friend and I (both women in our 20s) had been talking about visiting New York City for ages. I’d always say, “We should totally go,” but it stayed hypothetical for years until this summer.

Making a Decision

While I was in Toronto, I finally had a choice to make: LA or NYC? Both are equally dazzling, but for me, it came down to one simple fact which is: I don’t drive. California is gorgeous, but without a car, you’re basically stranded. New York, on the other hand, was built for people like me. You can walk, hop on the subway, or grab a cab. No license required.

Safety was something I did think about before going. It was just me and my friend: two women traveling together, so of course it crossed my mind. But after reading so many travel blogs and Reddit threads from women who said it’s absolutely doable if you stay cautious, I felt reassured. New York is busy, walkable, and safe for the most part.
That said, as I’ll mention in Part 2, it’s still important to stay aware of your surroundings, not just at night, but even during the day. The city has its moments, and a few experiences definitely reminded us that staying alert is key, no matter the time.

Another big reason I chose NYC was the food. The halal options are endless, from street carts to upscale dining. I knew I’d never run out of variety, and for me, that’s something that’s important.

The only thing that had stopped me before was the cost. New York is expensive. But this time, my friend agreed to split the hotel with me. Suddenly, the trip went from “maybe someday” to actually happening. Honestly, splitting accommodation in an expensive city is the best hack ever. It makes going somewhere like New York actually doable.

So here’s how I planned my first trip to NYC.

Who I Traveled With

I went with one of my really close friends from college. We’d been planning this trip for over a year, but our schedules never aligned. Finally, one day I just said, “Let’s stop overthinking and just do it.”

She’d been to New York a few times before, so her experience was invaluable. I wouldn’t have been nearly as confident figuring out the subway or navigating neighborhoods without her.

Why August

Going in August was honestly pure timing. My friend was free, weekday flights were cheaper, and I had the time too. Did I think through the fact that August in NYC feels like living inside a pot of hot soup? No. Would I rethink that next time? Absolutely. But hey, at least we didn’t have to carry jackets.

NYC Travel Planning: Travel Logistics & Budget

Everyone knows NYC is expensive, so I wanted to save where I could. I ended up mixing travel types to balance comfort and budget.

Flights: I took Flair Airlines to NYC for $170 one-way. I did the free seating option so I didn’t get to pick but I ended up getting a window seat on the left side and got the most stunning view of Manhattan as we descended. I also paid extra for 10 kg of luggage because cramming three days’ worth of outfits and essentials into one backpack was not happening. It was one less worry off my head. Sometimes it’s just worth it to spend that extra money.

Return: I took a FlixBus back to Toronto for $90. It was a nine-hour ride, surprisingly comfy, and honestly a fun little post-trip cooldown. I listened to podcasts, scrolled through photos, and just stared out the window replaying the trip in my head. Sometimes the slower route isn’t just cheaper: it’s more memorable.

Hotel: Manhattan vs. New Jersey

When it came to accommodation, my first instinct was to save money and stay in New Jersey. But my friend immediately vetoed that idea. She said we’d waste too much time commuting, and she was right. For a short trip, time is more valuable than money.

So we splurged (a little) and booked the Holiday Inn Express near Times Square (39th Street West). Two nights came to $440, which we split ($220 each). For me, it was all about the location. I wanted to be able to walk everywhere, and this spot was perfect for that.

I’ll be honest with you, the hotel was fine. The elevators were broken half the time (dragging suitcases down 12 floors became our new workout), and the “destination fee” was the most annoying surprise ever. But the staff were lovely, the location was unbeatable, and the memories were worth it in the end. I always like to think that the imperfect moments are the ones we remember the most.

Maximizing Days

I booked an early morning flight to arrive around 10 a.m. and a late-night bus back at 9 p.m on the last day. That gave me three full days in the city with no wasted hours on travel. If you’re doing a short trip, this is the best way to make the most of it. Time management is everything. 

How to Plan an NYC Trip: Planning Style & Considerations

Transport? Subway all the way. People did warn me about the subway and said don’t even step foot in one you’ll regret it, but I decided to risk it because how else would I save money in a city like New York? Plus, transport in NYC is so well connected that it just made sense.

Safety? Be aware and trust your instincts. Coming from Toronto, I’m used to big cities, but if you’re from a smaller town, stay alert.

I’m a “must-see” traveler. My goal was to check off Uptown, Midtown, and Downtown even if it meant shorter stops. Food came second and honestly you have options everywhere so I didn’t even have to go out of my way to research restaurants that much.

Different Travel Styles

This brings me to something very important which is travel styles. It’s crucial to travel with someone whose travel style matches yours, or at least to set expectations early on. Otherwise, you’ll find yourself arguing over whether to take a cab or risk the subway at 10 p.m. and that’s not the vibe you want on a trip you’ve spent so much money on.

I didn’t even realize there were different types of travelers until recently. There are Adventurers, Luxury travelers, Cultural travelers, Family travelers, Solo travelers (and so much more). The real trouble starts when you and your travel partner belong to opposite categories.

Take me and my friend for example. I need to have my exact schedule planned from A-Z. My friend, on the other hand, is a full-on “go with the flow” person. Once I booked the tickets, my inner Type A planner went into overdrive. I had spreadsheets, schedules, and alarms. Meanwhile, she was like, “We’ll figure it out when we get there.” You can imagine how that went.

At one point, during a call, I got frustrated and (accidentally) said, “You’ve been there so many times but you don’t even know the areas?” which, in hindsight, was rude. She got quiet after that, and I could tell I’d stressed her out. 

Then I came across a YouTube video that said, “Don’t overplan your New York trip.” That line hit me hard. I realized I was trying too hard to make the trip perfect instead of letting it be fun.

A couple of weeks before we left, we finally talked it out. She thought I was mad at her, and I explained that it was just my stress showing. We apologized, laughed it off, and decided to meet halfway. I’d plan the structure, and she’d bring spontaneity. And that balance? It actually worked out perfectly.

The Itinerary for NYC

When I started planning, my mindset was very much, “I need to cross everything off my list. I have to see every part of NYC.”

I even posted my draft itinerary online for feedback and someone commented, “What you’ve planned isn’t exploring, it’s just walking through so you can say you’ve been there.”

At the time, I was really annoyed with the person and tried to justify myself. But later, I realized they were absolutely right. I was so focused on checking off boxes that I forgot the whole point was to actually enjoy the city. This is why the mindset you go into a trip with matters just as much as the plan itself, as I will explain in the next part when we actually executed our itinerary. 

When it came to planning with my friend, this was where things could have easily gone wrong. Everyone has a different travel style, and it’s really about meeting each other halfway. We decided we’d both make our own lists first. I’d note what I wanted to see, she’d do the same and then we’d hop on a call to merge them into one shared itinerary.

For me, it was about covering all the major areas like Uptown, Midtown, Downtown so I’d leave feeling like I’d really seen New York. I also wanted to squeeze in Brooklyn and at least one observation deck (because those skyline views are unmatched). After a lot of research, I decided on Summit One Vanderbilt, which is expensive, yes, but I really wanted to go there. I mean, I’m in New York and I had to see the skyline from up there. I also started getting a little overwhelmed when I realised I was trying to see all of NYC in 3 days, so I slowed down a little and decided to make a list of places that are a priority to see versus things I’m okay with missing out on in case there wasn’t enough time. 

When me and my friend finally got on a call to finalize everything, my heart sank a little. I wanted to explore Brooklyn, but she wanted to visit Liberty Island since she’d missed it on her previous trips. I’d read online that it wasn’t worth the time, and it would easily take up half a day, which meant rearranging everything I’d already planned. But that’s where compromise came in.

NYC’s Must Sees vs Optional Stops

Remember how I’d made a priority list of “must-sees” versus “it’s okay if I miss this”? That came in handy. Brooklyn wasn’t a top priority, so I agreed to skip it and add in Liberty Island for her. It wasn’t just me compromising though because when it came to Summit One Vanderbilt, she wasn’t that interested and thought the ticket price (around $75 for the sunset slot) was too steep. But she still agreed to come along because she knew how much I wanted to see it. That’s the key to a good travel partnership: give up one or two things so that you both enjoy the trip instead of silently stewing over who “won” the argument.

I’m the kind who loves building an itinerary from scratch like maps, routes, the works. My friend, on the other hand, was more of “go with the flow” and was happy to let me take the reins. She shared her preferences, trusted me with the rest, and honestly, coming up with the itinerary was easier than I thought it would be. 

If we’d both been planners, we’d probably have spent half the trip debating whose list to follow. But because she was chill and I was organized, it turned out to be the ideal mix. I’m an 80-20 traveler, basically 80% exploring, 20% relaxing and she was the same. So even though our approach to planning was different, our travel style matched perfectly.

To keep it manageable, I planned by area (Uptown, Midtown, Downtown) and limited it to two main activities per day which is enough to see a lot without feeling like I was on a marathon.