Your Guide to a First Trip to NYC: A Local-Approved 5-Day Itinerary
The more I travel the world, the more I continue to realize that there really is only one city of all cities – and that is New York City.
View of downtown NYC from Hudson River Pier 45; November 2025
Many people plan to take an exciting first trip to New York City to discover the bustling and alluring chaos they have seen in movies all of their lives – but as a result, it can be overwhelming to plan a first trip to NYC and know exactly how to pace yourself as a tourist in the Big Apple for the first time.
As the daughter of a New York who has spent all their life taking both long and short trips to New York City – I’m going to share with you all of my super-secret tips to make the most of your first trip to New York City, including my local approved 5 day NYC trip itinerary to optimize every second you’re in the city that never sleeps.
Is 5 Days Enough for a First Trip to NYC?
Yes, 5 days is actually a great amount of time for a first trip to NYC – as you won’t feel rushed and will be able to see all of the city’s major attractions at a fair pace while also being able to enjoy the culture, food, and under-the-radar neighborhoods.
Spending five days in NYC is enough time to see everything and stay excited during your first trip to New York City while still leaving mystery and enough time to explore more things the next time!
In 5 days in New York City, you’ll easily be able to see several iconic monuments and places in NYC like:
🗽 Iconic Places to Visit in New York City 🗽
🗼 Empire State Building
One of the most iconic skyscrapers in the world, offering panoramic views of Manhattan. A classic NYC experience — especially magical at night.
💼 Wall Street
The historic heart of the Financial District, home to the New York Stock Exchange, Charging Bull, and some of the oldest streets in the city.
🌆 Times Square
Bright lights, giant billboards, and nonstop energy. Overwhelming for some — but undeniably a must-see at least once.
🌳 Central Park
A massive green escape in the middle of Manhattan. Perfect for walking, picnicking, people-watching, and seeing the skyline from afar.
🏘️ West Village
Charming, tree-lined streets with cafés, brownstones, and boutiques. One of the most picturesque and livable-feeling neighborhoods in NYC.
🗽 Statue of Liberty
A symbol of New York and the United States. Best seen by ferry — or admired from afar for skyline views and photos.
View of Manhattan from Hudson River Pier 45; November 2025
What Should I Prioritize Seeing on a First Trip to NYC?
On a first trip to NYC, you should try to cover all of your basis first but still leave some time to explore iconic neighborhoods and try the incredible food New York City has to offer – this includes making time for Times Square, Central Park, Rockefeller Center, the Empire State Building, but also fun neighborhoods like Chelsea or the West Village.
Personally, I find things like the MET, High Line, and Brooklyn less important for a first trip to NYC – those can be done on return trip once you’ve already familiarized yourself with the city.
NYC is also big on food, and while in the city you’ll want to be sure to try:
🍽️ Iconic Foods You Have to Try in New York City 🍽️
🌭 New York Hot Dog
A true NYC street food classic. While you’ll find hot dogs on nearly every corner, Nathan’s is hands-down the best — especially if you find yourself near Times Square or Coney Island.
🥨 Pretzel
Honestly? You can’t really go wrong here. Any soft pretzel from any street cart is good — salty, chewy, and perfect for eating on the go while exploring the city.
🥯 Bagel
New York bagels deserve their reputation. My personal favorite — and absolute kryptonite — is Tompkins Square Bagels. Perfectly chewy, generously topped, and worth the hype.
🍕 New York Slice
TikTok isn’t always telling the truth. While Joe’s Pizza is popular, Ray’s Pizza feels far more like the classic, no-frills New York slice locals grew up with.
🍰 Cheesecake
If you only try one dessert in NYC, make it cheesecake. Junior’s on 45th & Broadway in Times Square is the best — rich, creamy, and iconic for a reason.
🥪 New York Deli
A classic New York deli sandwich is a must. Think towering stacks of pastrami or corned beef, tangy coleslaw, mustard, and rye bread. A proper Reuben is pure New York comfort food.
As a whole, my itinerary will provide a jam-packed but not overwhelming itinerary for first timers in NYC who love to walk and see as much as they can when they travel.
Is NYC Worth Visiting for a First Trip?
Yes, NYC is absolutely worth visiting for a first trip – as it’s inspirational and forward-focused atmosphere can ignite people to either travel more or even pursue their own individual goals once they get home.
Who Should Visit NYC?
NYC is perfect for people who love big, energetic cities like London, Tokyo, Cape Town, and Sydney who enjoy exploring on foot, and are attracted to loud big statements –because after all, that’s what New York City is at the end of the day!
Who Might Struggle on a First Trip to NYC?
I’m not going to lie to you, as a native New Yorker – I have taken several people to NYC for either a single day-trip or for up to a week, and have seen them struggle to keep up with the pace of the city.
Travelers who tend to gravitate toward smaller, quiet, and approachable places to visit will have hard time during a first trip to NYC if they aren’t properly motivated to see the city.
If you tend to gravitate towards calm cities in places like Switzerland or New Zealand, then New York City is going to be the opposite of what you’re used to. For instance, if you think of Paris or Amsterdam as a “big city” – you’re going to find yourself struggling to keep up in New York City.
View of Empire State Building at night in NYC; November 2025
Where to Stay in NYC for a First Visit
I find the best neighborhoods for first-time visitors in NYC to be Flatiron, Herald Square, or Korea Town – as all of these areas are equidistant between upper and lower Manhattan and can make walking on a first trip to NYC easier. This is because these neighborhoods are close to 5th, 6th, 7th, and Broadway – making them easier to navigate for those on a first trip to NYC.
Should I Stay in Manhattan or Brooklyn on a first trip to NYC?
Without a doubt, you’ll want to stay in Manhattan while on a first trip to NYC. Native New Yorkers call Manhattan “the city” for a reason – this is the stuff you’ve seen in movies, books, and media your whole life, so trust me when I say you’ll want to be here in the middle of all the action.
Staying in Brooklyn can be fun, but it will make it challenging to see all of the classic NYC tourist spots you’ll want to hit during your first trip to NYC – as these can be very far away depending on how deep you stay in Brookyln.
Where Should I Not Stay on a First Trip to NYC?
On a first trip to NYC, I would stray away from hotels in the both the West or East Villages, up in Central Park, the Financial District (FiDi), or anywhere all the way on the West or East side – like Chelsea or Tudor City.
This is because of these locations are more isolated and further away from “tourist central” Manhattan – and I could see a first timer quickly becoming agitated with not knowing which direction to head in when leaving and returning to their hotel every day.
The overview cards below will help you to choose some places to stay on a first trip to NYC:
🏨 Where to Stay on Your First Trip to NYC
🚶♀️ Low Walking Tolerance / No Budget
Aim to stay in Herald Square or Flatiron. You’ll be extremely central and won’t have to walk far to get anywhere — think 20 minutes max to most of the things on your NYC to-do list . This is the most convenient option for first-time visitors.
🚶 Medium Walking Tolerance / Save a Little
Neighborhoods like Hell’s Kitchen, the Garment District, Kips Bay, or Murray Hill are great middle-ground options. You’ll still be between 30th and 40th Streets, but slightly east or west — meaning a bit more walking, with better prices.
💰 High Walking Tolerance / Budget Stay
To really save money on a first trip to NYC, consider staying further outside of Midtown — neighborhoods like Hudson Yards or even Chinatown. These areas are still safe, but noticeably more inconvenient for tourists compared to central Midtown.
Getting Around NYC (What First-Timers Need to Know)
As a whole, NYC is a very walkable city and relatively easy to navigate – especially in midtown where tourists tend to spend the majority of their time while on a first trip to NYC.
How to Use the Subway in NYC
Honestly, even growing up visiting the city with my Brooklyn native mother – we always ended up walking or grabbing a cab if it was really too far away to walk. That being said, I have taken the subway in recent years with friends – and although it is still a confusing system at times, the subway is functional and clean for tourists to use.
My advice on a first trip to NYC is to avoid buying any of those day passes, as my full-proof and local planned itinerary will allow you to see the majority of the city on foot. The machines for the MTA New York City transit are confusing, similar to the ones in Paris – meaning you can accidentally buy the wrong pass and end up wasting money.
Personally, I wouldn’t bother getting a pass for the NYC subway – as you can now pay on Apple Pay like in London. Trust me, this will make your life easier while juggling all the other tickets, hotel keys, and reservations you’ll have to handle during your first trip to NYC.
Subway in midtown in NYC; November 2025
When Should I Take the Subway vs. Walk in NYC
Honestly, New York City is made for walking – I personally avoid taking the subway unless I am all the way across town or over in Brooklyn.
In truth, I truly walk every in New York City – all the way from the Bowery to Midtown unless I am in a different borough or needing to get to the airport. I often find tourists making the mistake of getting on the subway when walking would be faster, or paying for a yellow taxi cab when an Uber would be cheaper.
The overview cards below will help you realize when to take the subway or to walk:
🚇👟 When to Take the Subway vs. When to Walk
🏙️ When it’s under ~25 minutes on foot
If Google Maps says it’s 10–25 minutes, walking is usually the move — you’ll actually see the city, avoid transfers, and it often takes about the same amount of time door-to-door.
📍 When you’re staying in one neighborhood
If you’re bouncing between nearby spots (cafés, shops, museums), you’ll save time by staying above ground instead of going down into stations and back up again.
🌤️ When the weather is nice (or you want a “reset”)
Walking is perfect when it’s not raining — plus it breaks up your day. If you’re feeling overstimulated, a walk can be the easiest way to regroup.
⏱️ When it’s 30+ minutes walking (or you’re crossing the city)
If the walk is 30–60 minutes (or more), take the subway — especially if you’re crossing from one side of the city to the other and want to protect your energy for sightseeing.
🥵 When you’re tired, hot, or it’s raining
On high-heat days or in bad weather, the subway is your best friend. It’ll keep you moving without arriving drenched, sweaty, or exhausted.
🧳 When you’re carrying bags or on a tight schedule
If you’ve got luggage, shopping bags, or a timed ticket/reservation, take the subway — it’s the most reliable way to avoid arriving late (or already annoyed).
The Best 5-Day NYC Itinerary
Day 0: Travel Day & Arriving into New York City
Most NYC guides will start at day 1, or your first full day in the city – but I’m starting at the very beginning: when the wheels hit the pavement in the great state of New York.
When arriving in NYC, you’ll likely be landing in either JFK, LGA, or EWR.
The overview cards below will reveal how to get into the city from each of these airports and how much it usually costs:
✈️ Getting Into NYC From Each Airport
✈️ Newark (EWR)
Newark is actually one of the fastest and easiest airports to get into Manhattan from.
The NJ Transit train from EWR takes around 25 minutes and drops you directly at
Penn Station.
💰 Cost: Around $17 USD.
✈️ JFK
JFK is further out, but still very manageable thanks to the AirTrain connecting to the subway.
Expect about 45–60 minutes total travel time into Manhattan depending on your final stop.
💰 Cost: Around $8.50–13 USD (AirTrain + subway).
✈️ LaGuardia (LGA)
LaGuardia doesn’t have a train, but it has a shuttle bus that can connect to the subway quickly.
Travel time is usually 30–45 minutes into Midtown depending on traffic.
💰 Cost: Around $16–20 USD using public transport.
What is the Best Airport to Fly Into NYC?
My personal favorite airport in NYC and severely underrated is Newark Liberty International Airport (EWR) – as it’s usually way cheaper than flying into JFK and much, much closer to the city than both JFK and LGA.
For the first half day or night in NYC, I would suggest settling in, picking a restaurant not too far from your hotel (think a 20-minute walk max), and just taking in first impressions of life in New York City.
This is exactly what I did when I took my (now-ex) Portuguese friend with me to NYC for the first time!
Check out her first trip to NYC (where I planned the whole itinerary) in my travel vlog below:
If you have the energy, you can try to get a first taste of something nearby your neighborhood – like the Chelsea Market or Madison Square Park, but be sure to not exhaust yourself, get a good night sleep, and save your energy for tomorrow!
Day 1: Midtown Classics & First NYC Impressions
This first full day in NYC will be full of many of the classic monuments, streets, and first impressions of the most charmingly chaotic city on Earth.
Day 1 NYC Morning
Start with either breakfast at your hotel or hop to the nearest bagel shop. Tik Tok will tell you to head over to Pop-ups, but trust me – what you want is a bagel sandwich from a place like Tompkin’s Square Bagels or Grabstein’s.
After fueling up, be ready to take charge of your first morning in NYC to see the most iconic sights.
Here’s the order I recommend visiting each, presuming you start in lower midtown and work your way up – but feel free to reverse the order to make the last location closer to wherever your hotel is!
☀️🚕🍎🌭 Midtown Classics Morning Checklist
🕒 16 minutes
📍 0.6 miles / ~1 km
Now is the perfect time to break for lunch, and if need be – another coffee. If you want, you can head back over to the west side near Times Square and try Joe’s Pizza (Tik Tok trend, but go for it if you must) or Junior’s (incredible food and cheesecake) – but there are a lot of amazing places between 37th and 38th street and 6th and 7th avenues.
My personal favorite spot for lunch in midtown is Beyond Sushi!
Day 1 NYC Afternoon
⛅🚕🍎🌭 Midtown Classics Afternoon Checklist
🕒 1 minute
📍 ~0.1 miles / ~0.2 km
Day 1 NYC Evening
By now, it’s probably early evening – making it a great time to either catch an early dinner before seeing a Broadway show or checking out a rooftop bar in Midtown.
I’ve personally been to Wicked and On Your Feet!, and my brother and mother have seen Back to the Future!, Great Gatsby, Book of Mormon, and more. At the end of the day, you can’t go wrong with any show you see on Broadway.
However, if you’re not too into musical theater – you can opt for a rooftop bar before heading to dinner in Midtown such as:
🍸 NYC Rooftop Bars — Dress Code + Price Range
🏙️ Peak
Peak is an elevated, “special occasion” vibe — think polished outfits and a more upscale crowd.
Typical drink range: $18–$28+.
🌃 Overstory
Overstory isn’t as strict, but it still has a “put-together” expectation — you can’t roll in looking like you’re going to the gym.
Typical drink range: $18–$26+.
🥂 Monarch
Monarch is similar to Overstory vibe-wise — a great rooftop for photos and skyline views, but still expects you to look presentable.
Typical drink range: $16–$24.
✨ Nebeluz
Nebeluz is the most “dress up” of the bunch — it’s very much a cocktail bar moment, not a casual rooftop drink.
Typical drink range: $20–$30+.
Day 2: Lower Manhattan, History & Neighborhood Wandering
Perhaps my personal favorite day to relive over and over again every time I return to the city is this one, and the parts that many first-time tourists in NYC miss – which is all the lovely neighborhoods in lower Manhattan.
Here’s my local approved lower Manhattan itinerary, presuming you’re starting from closer to Midtown, but again – feel free to reverse the order heading back to your hotel!
Day 2 NYC Morning
☀️🥯☕🌳 Lower Manhattan Morning Checklist
🕒 10–15 minutes
📍 0.7 miles / ~1.1 km
View of NYC skyline; November 2025
Day 2 NYC Afternoon
By this point, it’s late morning or early afternoon – and I have two suggestions.
First, you could head over to the East Village to visit MUDSpot – which has incredible food and coffee. On the other hand, if you’re still in the mood for Pizza – head over to Ray’s Pizza next to Astor Place.
Either place you choose, we’ll head over to the West Village from here.
⛅🥯☕🌳 Lower Manhattan Afternoon Checklist
🕒 61 minutes
📍 2.8 miles / ~4.5 km
View of buildings in SoHo in New York City; November 2025
Day 2 NYC Evening
By now, it’s early evening – you have three options:
🌆 NYC Night Plan — 3 Great Options
🌅 Sunset Views
Sunset views at either Hudson River Pier Park or Two Bridges.
🍝 Dinner Downtown
Dinner in Little Italy, Chinatown, or NoLita — as SoHo is more about shopping than eating.
🎭 Broadway vs. Rooftop Bar
Or if you opted for a Broadway show over a rooftop bar the other night — you can head back towards Flatiron to head to a rooftop bar: I love 230 Fifth or Sandbar Rooftop.
Day 3: Central Park, Museums & Upper Manhattan
On the third day of your first trip to NYC, it’s time to go a bit deeper and explore places like Central Park and nearby Museums.
Once again, here’s my itinerary for day 3 in NYC – starting in Midtown and working your way up!
Day 3 NYC Morning
🎨🚣♀️🚲 Central Park & Museums Day Morning
🕒 26 minutes
📍 1.2 miles / ~1.9 km
By this point, you’re right near the southeast entrance to Central Park – which is where we’ll head next.
Central Park in New York City; November 2024
Best Things to See in Central Park
Central Park is huge, spanning a whopping 843 acres – and lots of tourists often try to see and do too much in the park when it’s virtually impossible.
The overview cards will provide the best things to see in Central Park, in order, working from closest to the Plaza and Columbus Circle closer to the MET:
🌳 Central Park Highlights — From Midtown to The Met
📸 Gapstow Bridge
One of the most photographed spots in Central Park — lots of TikTok and Instagram pictures are taken here, with skyline views peeking through the trees.
🎬 Bethesda Terrace
A Central Park classic you’ve likely seen in movies and TV, including Gossip Girl, where Chuck and Blair get married.
🌉 Bow Bridge
One of the most romantic bridges in the park, perfect for beautiful photos and wide, peaceful views across the water.
🏰 Belvedere Castle
A whimsical stop that feels like a little taste of Scotland and Ireland right in NYC, offering elevated views of Central Park.
Gapstow Bridge (lots of Tik Tok and Instagram pictures are here), Bethesda Terrace (seen this in movies and TV, like Gossip Girl where Chuck and Blair get married), Bow Bridge (for beautiful pictures and views of the park) Belvedere Castle (for a little taste of Scotland and Ireland in NYC!)
If you’re in NYC during Christmas, now is the perfect time to go ice skating at Wollman Rink if that’s the place you’ve decided on ice skating – and then you can break for lunch after working up an appetite shredding the ice!
Day 3 NYC Afternoon
After lunch at your place of choice (which could very well have been a hot dog from a cart or some other place in the park), now you can head to one museum of choice – such as the MET or MoMa. On a first trip to NYC, I suggest going inside MoMa and only seeing the MET from the outside – but the choice is ultimately up to you!
Personally, I really do enjoy MoMa – and I find the MET to be prettier and more “iconic” for photo purposes.
The overview cards below will breakdown the differences between the MET and MoMa to decide which one you might prefer:
🖼️ The Met vs. MoMA — Which NYC Museum Is Right for You?
🏛️ The Metropolitan Museum of Art (The Met)
Vibe: Grand, historic, and encyclopedic — perfect if you love classical art, ancient civilizations, and wandering for hours.
Highlights: Egyptian Temple of Dendur, medieval armor, European masters, American decorative arts, and rotating exhibitions.
Time needed: Easily 3–5+ hours (or multiple visits).
Price: $30 USD (pay-what-you-wish for NY residents).
Hours: Generally open daily, usually closing around 5–6 PM.
🎨 Museum of Modern Art (MoMA)
Vibe: Modern, sleek, and fast-paced — ideal if you prefer contemporary art and a more curated experience.
Highlights: Starry Night by Van Gogh, works by Picasso, Warhol, Monet, and major modern photography.
Time needed: About 2–3 hours.
Price: $30 USD (free on select evenings).
Hours: Often open later than The Met, sometimes until 7–9 PM.
Bryant Park at sunrise in New York City; November 2025
Day 3 NYC Evening
Following your museum visit, it’s likely late afternoon or early evening – and you can then choose to explore either the Upper East Side vs Upper West Side. As a whole, I tend to find both of these areas primarily residential and not have a ton to offer tourists besides local coffee shops or restaurants – but these places have regained momentum on Tik Tok.
As an NYC local, these are some of the places you may want to explore on the Upper East or Upper West Side and breaking down the differences between the two:
🏙️ Upper West Side vs. Upper East Side — What’s the Difference?
🌳 Upper West Side
The Upper West Side feels more grounded, relaxed, and approachable.
It’s home to places like Lincoln Square and the
American Museum of Natural History, making it a great area for
culture, families, and quieter neighborhood vibes.
This side of Manhattan feels lived-in and comfortable — perfect if you want
easy access to Central Park and museums without the polished intensity.
✨ Upper East Side
The Upper East Side is noticeably more polished and refined.
It’s home to iconic institutions like the Guggenheim Museum
and sits along Museum Mile.
The vibe here is more upscale and classic — think elegant buildings,
quieter streets, and a more traditionally “luxury” New York feel compared
to the West Side.
Plan to have dinner anywhere you like tonight, whether it be a restaurant you’ve had saved in your phone for the longest time or just heading back to the room for an early night.
Day 4: Brooklyn & a Different Side of NYC
When people visit New York City for the first time, they often stick to staying in Manhattan (as they should), but if it’s possible – heading over to Brooklyn (even just the neighborhood right across the Brooklyn bridge) can offer a different shade of NYC for first time tourists.
Best Things to See in Brooklyn On a First Trip to NYC
🗽 Best Things to See in Brooklyn on a First Trip to NYC
📸 DUMBO
DUMBO is a Brooklyn neighborhood gaining popularity for its trendy cafés, waterfront views, and iconic cobblestone streets. It’s one of the most photographed areas in NYC and a must-see on a first trip.
🌅 Pebble Beach
My ultimate favorite spot in Brooklyn. I love sitting here at either
sunrise or sunset, having a little picnic and watching Manhattan
from afar.
It’s absolutely stunning in person and truly needs to be seen with your own eyes —
and honestly, it offers a better view than walking the Brooklyn Bridge
from the Manhattan side.
🍂 Prospect Park
Prospect Park is known to be a favorite among NYC locals and is often said to be even prettier than Central Park — especially in the fall. It’s calmer, more local, and perfect for a relaxing break from sightseeing.
Day 4 NYC Evening
Upon heading, back into Manhattan in the late afternoon or evening, this is a great time to see a couple of things you may have missed earlier (depending on where your hotel is) – such as either the High Line and Chelsea Market or Gramercy Park.
Heading to Chelsea on your fourth night in NYC works well if your hotel is closer to the west side – as you can walk the High Line and then grab dinner at the Chelsea Market, while also catch Artist’s & Fleas nearby. Personally, I find the High Line to be a bit overrated – as all it leads to is Hudson Yards (a sterile, commercial shopping mall) and a big modern building, but tourists seem to love it: so I won’t stop you if your heart is set on seeing it.
However, a more alternative option is to head to Rose Hill and Gramercy Park. While the actual park is private and reserved for residents, it’s a beautiful place in the city to see the infamous NYC walk ups with your own eyes.
I always think of the quote from that Zac Efron movie That Awkward Moment when I’m here,
“I know that I’m romanticizing the idea, but…come on, that’s kind of my dream. You know, to have the key to Gramercy Park… [New York’s charm is you’re surrounded by things you can’t have]… New York’s charm is it makes you think you can have them.”
Day 5: Free Day in NYC: Shopping, Food & Final Favorites
Your last day during your first trip to NYC should be reserved for all of the things that you still really want to do, not trying to cram in last minute common tourist activities simply because you want to check them off of a list.
Here’s an idea of some of the things I recommend doing on your fifth day during your trip to NYC:
🗽 Ideas for Your Fifth Day in NYC
🏘️ Revisit Neighborhoods
If there are any neighborhoods you wanted to see more in depth — like Harlem, Chinatown, Nolita, the Bowery, or the Villages — today is the perfect time to do it. Take things at a slower pace and really explore each neighborhood’s culture and cuisine.
🛍️ Shopping
NYC isn’t just the city that never sleeps — it’s also one of the best cities to shop in (re: Sex & the City and literally every movie you’ve ever seen about New York). I recommend 5th Avenue for window shopping, but since that’s out of most of our price ranges, try heading to SoHo or Flatiron, both of which have great chain stores and more affordable individual boutiques.
🥯 Best Last NYC Meal
Personally, every time I leave NYC, my perfect last meal is a bagel from Tompkins Square: cream cheese, tomatoes, capers, red onion, lox — the whole deal. And then I wash it down with a Blue Bottle oat milk latte.
🌿 High Line & Chelsea Market
As I said earlier, I find the High Line to be a bit overrated — the views on the walkway aren’t that nice and aren’t likely to appeal to tourists. Chelsea Market can be nice, but I wouldn’t say it’s the best food hall in all of Manhattan. That said, there are a few vendors (especially bakeries) that are worth seeing.
🌳 Revisit Central Park
The tour I gave you earlier for Central Park is a highlight reel. There are several other gardens and pathways you could return to and easily fill most of the day with if you want a more relaxed pace.
🗽 Ellis Island & Statue of Liberty
This is much better in the spring and summer when the weather is warmer and a boat ride on the Hudson is more enjoyable — but if you’re up for it, it really is worth seeing the Statue of Liberty up close. You’ll head down to Battery Park and take your ride to our gift from France.
🕊️ 9/11 Memorial
A beautiful memorial downtown, this really is a special thing to see — but prepare to feel emotional or stirred by it, even if you weren’t affected by 9/11 directly.
🚠 Roosevelt Island Tramway
This spot has gained massive momentum on TikTok, but honestly — as a local — I don’t think it appeals much to tourists. It’s all the way on the east side, and you won’t see iconic monuments like the Empire State Building or One World Trade Center from the views.
⛪ St. Patrick’s Cathedral
Most people walk right past St. Patrick’s Cathedral without going inside, which is a huge miss. This stunning cathedral feels like a little piece of Europe dropped right into the middle of Midtown. It’s free to enter, peaceful compared to the streets outside, and absolutely worth stepping into — even if just for a few minutes.
View of Brooklyn Bridge and Manhattan at Pebble Beach in New York City; November 2024
What to Book in NYC in Advance (and What You Can Wing)
In New York City, it’s always better to book things in advance – even if you think you’ll be able to get last minute tickets to places, events, or shows.
Back in the day when I was a teenager in the 2010’s, you could in theory have stood outside the TKTS booth in Times Square and have scored seats to a Broadway show that night – but with everything done online and on phones now, it’s been harder for those things to prove reliable.
Here’s what you should book advance in NYC and what you can probably wing:
🗽 What You Can Wing vs. What to Book in Advance in NYC
⛸️ Ice Skating
I would book tickets in advance if you’re going to Rockefeller Center or Wollman Rink. I have seen tickets for Bryant Park last minute, but if you want to be safe – do it all online before traveling to NYC, especially if you come during peak Christmas time.
🏙️ Top of the Rock
I’ve gotten tickets to the Top of the Rock last minute, but I went on a weekday in March when it was quiet. On the other hand, I have been in late November in 2024 on a Saturday and it was full to the brim. For this one, it depends on the time of year you go – if it’s shoulder season, it could be okay, but not during the peak of Christmas or summer.
🍽️ Restaurants
NYC isn’t like Paris as in you don’t usually need a reservation to be seated, but if it’s something on the fancier or more expensive side – it’s a good idea to make a reservation before your trip to NYC.
View of Times Square at night in New York City; November 2025
Common Mistakes First-Time NYC Visitors Make
As someone who has taken many people to NYC for the first time, I know exactly what mistakes they made and what I wish they would have listened to me say in advance before we left for our trip.
Over Packing
First off, I have had friends bring far too fancy or far too many clothes to NYC. There’s really no need: New York City isn’t like walking the runway in a European City – a lot of us are dressed more on the functional than upscale side, as we are constantly walking everywhere and want to be comfortable.
Leave the stilettos at home. No need to wear $100 pants out sightseeing. The most important thing is to bring a great jacket in line with the weather and time of year you’re visiting, and your most comfortable pair of walking shoes. Bring basic tops and bottoms, and please – don’t go over the top when packing for NYC!
Not entirely sure what to pack for your trip to NYC? Be sure to check out my article on what I pack in my carry on and also my favorite amazon travel essentials for solo female travelers.
Falling for Tik Tok Trends
As a part-native New Yorker, I often cringe at the trends I see on Tik Tok about traveling to NYC – and always know that when some random place that has been quiet for years suddenly has a long line outside of it, it’s because of Tik Tok.
This includes a million Tik Tok videos on Joe’s Pizza… when no New Yorker would ever suggest that to you. Same thing when my foreigner friend asked if we could take a boat ride on the Hudson after she saw it on Tik Tok, not understanding that it was winter and it was going to be freezing – and that most of us would only consider doing that in the summer.
If you want to know about great food, advice, or views in New York City – I implore you to stay away from Tik Tok and ask someone who has actually lived there.
Being Scared to Ask For Help
On my most recent trip to NYC, my mom and I were walking in Midtown – and I heard a couple who wasn’t sure if they were walking the right way and trying to zoom in on their phone for the map. I chimed in, asking which ice rink they were heading to – and my mom and I both confirmed it was straight ahead.
When I lived in New York City, there were tourists who were very shy to come up and ask me or someone else for help with directions – but we always helped them in the end.
There’s a stereotype that New Yorkers are rude, which is why first time visotors may be scared to bother us – but don’t be! I promise, we’re not rude – we’re just busy and will talk to you like we’re in a rush (because we are, it’s the city where dreams are made of because we’re working really hard to achieve them!)
Additional mistakes I see first timers in NYC do includes:
🚕 Common Mistakes First-Timers Make in NYC
👟 Underestimating the Walking
Underestimating how much walking they’ll do while in NYC — hopefully my guide (as these locations often go in order of what’s next to each other to maximize time) can help to reduce that — but be prepared for thousands of steps a day, even if you don’t think you’ll walk that much.
🗓️ Trying to See Everything
Trying to see everything in a few days, which is virtually impossible. Pick what’s most meaningful to you and plan a return trip in the future — NYC will always be here, and it’s much more enjoyable when you don’t rush it.
🏘️ Ignoring Neighborhoods
Almost all local New Yorkers will tell you one of their favorite past times on a weekend is to pick a neighborhood for the day and just explore. There are so many to choose from — be sure to read my best neighborhood guide in NYC for more.
🗽 FAQ First Trip to NYC 🗽
| 🛡️ Is NYC safe for first-time visitors? | Yes, NYC is very safe for first-time visitors — especially as the areas you’ll visit will be surrounded by other tourists and locals alike. |
| 💵 How much money should I budget for 5 days? | New York City is one of those places that can be as expensive or as cheap as you want it to be, but if you want to plan on the safe side — I would plan for around $100 per day in spending for food, extra activities, and souvenirs. |
| 🚶♀️ Is NYC walkable? | Yes, NYC is one of the most walkable cities in the world — far more than Sydney, Tokyo, or London. In this sense, Paris and NYC are very similar — and you’ll be able to see a lot of NYC on foot. |
| 🎄 Best time of year for a first visit? | Personally, I think the most magical time to visit NYC for the first time is during Christmas — although the days are shorter, the city is even more lit up and alive than usual. Plus, you’ll avoid summer crowds and muggy heat — both of which I find make for an unpleasant first trip to NYC. Shoulder seasons can also be nice, but I would choose autumn over spring. |
My Honest Advice for Your First Trip to NYC
When visiting NYC for the first time, don’t focus too much on hitting every single place on this checklist or itinerary – but taking a moment to really immerse yourself in the unique energy that is New York City.
NYC is truly the city that never sleeps, meaning – it will always be waiting for you to return again, with an endless list of things to do.
Looking for more information on NYC as you plan your trip to the Big Apple?
Click here to discover more, as I have several articles like this to help you plan the perfect trip to NYC.
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Last updated: January 17, 2026