After having lived in New York City for the past 10 years, I have helped countless friends and family generate itineraries for a weekend in New York City.  Rather than allow these plans to rot in the vast nothingness of my Gmail outbox, it would be a crime for me, a travel blogger, not to share some of them with the general public.  I have done countless flavors of a weekend depending on who is coming, but this is a budget-friendly first time weekend in New York City itinerary.  

When people come to visit for the first time, I’m typically asked for a mix of sightseeing the major attractions along with a few local off the grid recommendations.  I’m also told that people want to cram in as much as possible, so buckle on your walking shoes because I’m going to wear you out.

Note: I actually wrote this as an email to a friend and converted it to a post, so you can take comfort with the knowledge that these are authentic, genuine recommendations and not click-bait.

Do note that this itinerary is best suited for two adults.  You may say to yourself, but FivePax is a family travel website, why cover a solo trip to NYC?  Listen, visiting New Your City with your kids sounds like a great idea, and it is, and we have that covered, but New York is expensive, the kids may not enjoy (or participate in) the culinary cultural immersion, and I’m not sure they appreciate the fact that bars are open until 4 am as much as mom and dad.   

General tips

For a first time weekend in New York City itinerary, there are a few things to get settled right away.  First of all, there is no space. None. I’m talking about personal space, luggage space, parking spaces, and outer space.  No, really, the city lights are too bright here so you can’t see the stars, but I digress. With that in mind, here are a few general tips to keep in mind for 48 hours in New York City:

Depart from NYC at night and pack everything you need in a backpack.  

I know it is tempting to stay one extra night and fly out in the morning, but why blow money on another expensive dinner and breakfast and another night in a hotel.  Just go home. Sleep on the plane. Pack only one backpack. On your last day bring your bag with you. There’s no need to return to your hotel after you wake up.  

This cannot be stressed enough: Wear comfortable walking shoes  

Nobody cares what you look like here.  I walked past a homeless person peeing on the sidewalk today and I was only aware of her existence because she grunted at me and drew attention to herself.  This is your first time in New York City itinerary and you are here for 48 hours. You want to see everything. You are going to walk about 15 miles. Don’t do that in your fancy shoes, they will get dirty. 

Also, don’t wear Uggs… I do notice Uggs and assume either you are my Appalachian brethren or you are a European who’s jeans are cutting off circulation in your testicles and you listen to David Hasselhof, not that there’s anything wrong with that.  Other than that, New Yorkers won’t notice, so just be comfortable.

For the love of God, don’t buy the hop-on hop-off bus thing.  It’s dumb.

Let’s get the touristy don’ts out of the way right now.  

  • Do not do the hop-on hop-off bus tour.  You will be disappointed. Also if I’m at happy hour and you ride by, I might hoot at you.
  • Do not go to Ellens Stardust Diner – c’mon man.  If that’s your bag, go to Disney.
  • Do not go to the Museum of Sex.  It sounds edgy. You’ll be disappointed.
  • Do not have high expectations of Little Italy.  A strip of Mulberry Street is all that is left. The rest has been engulfed by Chinatown, which, I might add, is a decent cultural immersion. 
  • Do not get Junior’s Cheesecake.  Sigh.  
  • Do not, and I repeat, DO NOT eat a hot dog from a street vendor.  We refer to their cooking method as “armpit water.”
  • If you are looking up Madame Tussauds and Ripley’s Believe it or Not, I can’t help you.  You’re on the wrong blog.

Do bring some cash for tipping and drinks.

There are a hand full of restaurants and bodegas that are cash only.  In fact, some of the better bagel shops and bars operate this way. You will also want to take care of the service industry because if you take care of them, they will take care of you.

Bring snacks

I mentioned this is a budget-friendly first time in New York City itinerary, right?  Yeah, do not get caught hangry. There’s so much good food here that you do not want to walk into a place in haste without researching it first.  Pack a few cliff bars because you never know when you’ll get the munchies.

Know the restaurant sanitation score signage

On the window of every restaurant in NYC is a letter grade indicating how well the establishment scored on a health inspection.  If you’re researching restaurants ahead of time New York City has a nice website that allows you to research in advance.  My general rule of thumb is anything that is an A is obviously fine.  Depending on cuisine, things like bagels are OK as a B, but I question something like Chinese that’s a B.  Grade C is out of the question. Grade Pending means the restaurant got either a B or a C and is contesting the grade, so I typically avoid those as well. 

48 hours in New York City Itinerary

Ok time to get on with the actual itinerary.

Where to stay

As a New Yorker, I avoid Times Square like the plague, or coronavirus (too soon?), but when you are on limited time, it is the best location for a 48-hour tour.  Times Square hotels cater to tourists so hotel deals are common in the area. The location is also excellent proximity wise to the Port Authority bus terminal, which is above the Penn Station subway station.  Trains and busses from the airports will drop off here. Times Square is also walking distance to things like Rockafeller Center, Grand Central Terminal, and the NY Public Library main branch so when you weigh all options, I would not overcomplicate your planning.  Just use booking.com and find the cheapest place in the area that gets decent reviews. You’re not coming for the hotel anyway.

Booking.com

How to get to Manhattan from the airport

I cover in-depth options on how to get to Times Square from JFK, but my recommendation is to take public transportation.  The AirTrain to the subway is cheap and easy.

From LGA, I recommend taking a cab. The cost will be $40.00 + tip.  Public transportation is possible, but it involves a bus and a transfer to the train.  I ride the public buses here, but I generally try to avoid long commutes on the bus just because traffic can be so erratic here.

From EWR, I recommend the NJ Transit train system.  The NJ Transit will drop you off right at Penn Station and the cost will be about $15.25 per person.  Traffic via any other mode of transportation is totally unpredictable. A taxi will cost you your firstborn child. 

What to do

Let’s assume your first time weekend in New York City itinerary has you arriving at JFK at 8:00 am. Realistically, this means you will get to your hotel at 11 am.  It is always safe to assume you will have some sort of delay getting to your gate to deboard the plane and there will also be some sort of traffic delay. If everything runs smoothly and you end up with bonus time, great, but let’s plan for reality.

The first thing you should do is fuel up with an early lunch.  For this, I recommend either Dos Toros if your hotel is south of Penn Station, or Shake Shack if your hotel is north of Penn Station.  Both options are quick, decent food, originated in NYC and are reasonably priced relative to other traps in the area.

Once you fill up, now is a good time to check into the hotel, catch your bearings, and get ready for a big day.

Walking Tour

It should be about noon at this point.  Hopefully, the weather is nice and you heeded my advice and have good walking shoes.  The first thing you will do is walk the neighborhood, in this order:

  1. Times Square
  2. Rockefeller Center
  3. St Pat’s Cathedral
  4. NY Public Library
  5. Grand Central Terminal
Beware of the mascots in Times Square
Times Square is not my favorite place, but you have to go on your first trip to NYC

If you want to do Top of the Rock, you can do that now.  Expect stunning views of the city from the top, but it takes a bit of time, is a bit expensive, and will probably be super crowded.  If you do not go to the top, this is technically a 25-minute walk if you just go from point A to point E, but I would budget a few hours to allow for actually going into the church or the library and to take pictures.  

If you do the Top of the Rock here, cut something out below.  Note that if you are coming on a popular weekend like Memorial Day weekend in the summer, I would advise buying Top of the Rock tickets in advance.

Grand Central Terminal
Grand Central Terminal

Grand Central Terminal to Central Park

You should arrive at Grand Central Terminal by about 2:30.  From here, walk (20 minutes) or subway (10 minutes) to Central Park.  If you are a Trump supporter, walk and take a picture of yourself in front of Trump Tower on the way.  I’ll leave my political commentary for somewhere else. After that, I would basically walk into the park from the 5th Ave side to the zoo and then out the other side near Columbus Circle.  Buy yourself some roasted nuts while you’re in there for $3.00.

The Vessel

At around 4:00, take the C train from Columbus Circle to the 34th Street Station and walk over to the Vessel.  Once you get the obligatory Instagram shot, find the Highline and walk it. In the summer, I would be a little nervous about this being insanely packed, but it’s a nice walk either way.  

The Vessel NYC
The Vessel

Authentic New York Pizza

The ideal scenario would be walking the Highline to Chelsea Market.  You can either have affordable food at the market or head to John’s of Bleecker for some of the best pizza you’ll have in your life.

Greenwich Village

Now that your stomach has a base of food, it’s time to start poisoning yourself.  Your first stop is going to be Blind Tiger around the corner from John’s.  Blind Tiger is a legit craft beer bar and at this point, you should still be early enough in the evening that it won’t be too crowded.  

I like Blind Tiger because I had a cool moment there a few years ago. One summer, a couple of friends came to visit to see My Morning Jacket at a music festival called Gov Ball.  The festival was a little overwhelming so we left and went to Blind Tiger. Apparently the band felt the same way and ended up at the exact same bar. We chatted the band over IPA’s.  It was a pretty cool highlight for my dudes.

Comedy Cellar

From Blind Tiger, head over to Washington Square Park, which can be pretty romantic, especially after a few drinks. You can see freedom tower through the arch in one direction and the Empire State Building in the other.  If it’s good weather, a guy will be playing the piano in the park.

After you take a breath, head to the 8:45 pm Comedy Cellar show that you booked in advance.  Be sure to choose the main location on Macdougal street.  I would try to get there at least 15 minutes early so you get a decent seat near the front.  I usually prefer the midnight show, but for this itinerary, I picked 8:45 to help minimize walking time and crisscrossing around the city.

Special note: Next to Comedy Cellar is a club called Cafe Wha.  Cafe Wha is where Bob Dylan, Jimi Hendrix, and Bruce Springsteen all got their start.  In the alley next to Cafe Wha on the 2nd floor is where two of my kids went to daycare. One day while my son was at daycare, the provider heard a bit of a commotion, and out her window was Aerosmith making a ruckus.  So that’s where my kids hung out before they turned 2. 

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Above the clouds

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View from Washington Square Park looking south

East Village

After the show, you have a few options depending on how late you want to stay up.  You can pick and choose from the menu below. Note that the below East Village bars close at either 2 am or midnight so if you choose to go full throttle and do everything, go here first.

For me, my next stop would be Please Don’t Tell.  PDT is a touristy speakeasy, but it’s cool.  To enter, you go into a phone booth inside a hot dog restaurant.  Once there, dial something on the phone. Someone will then open the secret door to let you in.  

After a cocktail at PDT head to Mcsorely’s, which will probably be super crowded.  Beers are served 4 at a time, but they are rather small.  It’s the oldest bar in America and it’s one of my favorite happy hour spots.  

I typically go to Mcsorleys at like 8 pm on a Wednesday when it’s locals though so I caution against crowds on a weekend during say fleet week.  Either way, I always walk out with a story. One time I went and when I went to the bathroom, two guys were snorting coke by the urinals.  The one guy bumped the other and they were having a serious discussion about whether or not they should scoop the dust off the bottom. I quickly left, but have told the story 100 times.

Rooftop Bars

If you have any fuel left, take a subway or an Uber to a rooftop bar near your hotel.  Options near midtown include The Fleur Room, The Lookup, or Magic Hour.. or just google it, as they are all cool, just make sure they’re open till 4 am.

First time weekend in New York City day 2

I can’t believe you made it to day 2.  Your legs are going to be toast. You will be hungover.  The best thing you can do right now is grab a New York bagel.  Ess-a-Bagels, Russ & Daughters, Murray’s, or Brooklyn Bagels are all solid.  I have a thing for bagels and after years of daily research, my favorite is actually Olde Brooklyn Bagel Shoppe in Brooklyn, but you don’t have time for that.  The others listed above are all good.  

I usually order first by asking if the bagel is hot or not. If hot, never toast it.  If it’s not hot, I’ll ask for lightly toasted. Cream cheese is usually the topping of choice, but a lot of New Yorkers also like to add some lox.  You can also get pretty much any style breakfast sandwich you want as a bagel.

9/11 Memorial

For your next sobering moment, the 9/11 memorial answers the call.  The museum is very well done and very moving. A word of advice is the lobby is not the museum.  We once spent a solid hour and a half in the lobby thinking it was the museum, only to realize when we thought we were leaving that we were just entering the actual museum.  Don’t be like us.

World Trade Center

While I enjoy both the Top of the Rock and the top of One World Observatory, for this itinerary, I would recommend doing OWO over Top of the Rock.  The views from each are really good either way. This is another situation where I would buy tickets in advance so you can skip the line.

Lunch

There are a lot of food options in Brookfield Place right across from WTC, but one of my favorite restaurants in the area is El Vez.  It is not exactly budget-friendly, but nothing in this area really is. The World Trade Center is close to an area called Tribeca, which is a very expensive place to live, even by New York standards.  Couple that with being in a touristy area and you will be hard pressed to find something not overpriced.

If the weather is nice and you have not had Dos Toros yet, there is a Dos Toros in Brookfield place as the most affordable option. I would grab a burrito and go and eat it on the lawn at Rockefeller Park.  

Staten Island Ferry

After lunch, head down to the Staten Island Ferry Terminal for a free ride around downtown Manhattan.   Yes, I said free. This is a budget-friendly first time weekend in New York City itinerary!  Note: the ferry does not drop you off on the island with the statue, but you will get close enough for some amazing photos, and the price is right.

South Street Seaport

If you do not have a flight to catch, the next place I would go is the South Street Seaport.  It is an easy walk from the Staten Island Ferry terminal along the East River Bikeway. There you will find good shopping and food and when you’ve had your fill, you can meander on over to the Brooklyn Bridge.  If you have the energy, walk up to one of the towers for more photo opportunities.

Bon Voyage!

If you leave thoroughly exhausted, I feel like I have done my job.  I hope you have a most excellent time in the city that never sleeps and I hope that my first time weekend in New York City itinerary gave you some good ideas. Please return after your trip and let me know in the comments about how things went!  We love hearing about the experience.