Ideal NYC Itinerary- from a Native New Yorker!

I’m always getting asked about non-traditionally touristy things to do in NYC, and what are my top must-see sights for a weekend in NYC, so I’m combining the two in a post. Right off the bat, you’re going to be walking a lot-so here is a link to some of my favorite cute and comfy shoes for walking. I tried to throw in at least one activity per day that is specifically for kids. Aside from the bars, most of this stuff can be done with kids! As a Native New Yorker, it’s always my goal to show you the parts of the city that make it so special to those of us who live here, the real New York. I wouldn’t dream of sending you to Times Square, but even I like to get a little touristy now and then! This post outlines all the non-touristy must sees and the CLASSY touristy things I would want to do if I only had three days in NYC.

*anything in bold is a link, just click!


Before we get started, I realize we need to talk transportation. As I mentioned above, you’re going to be walking a lot! For the longer distances, take the bus or subway. NYC has a great public transit system, you can get anywhere for $2.75 so I urge you to use it! Uber and Lyft are so absurdly expensive these days, if you must take a car, take a yellow taxi! I assure you though that the subway is not hard, I’ve been taking it alone since I was 10 so I promise you can too. GoogleMaps is great for helping you to navigate around and will tell you what train/bus to take.

Day One: Uptown & Skyline Cruise

You’ll be spending the majority of the day on the Upper West, Upper East sides and Central Park, then ending it downtown after going on a cruise all around Manhattan.


  • For breakfast, there is no better way to welcome say welcome to New York than a bagel. Head over to the Upper West Side. You can take the B, C, 1, 2 or 3 trains to get there. My two favorite bagel spots: Absolute Bagel (possibly the best in all of NYC) or H&H Bagels. I have a slight preference for Absolute because I can’t eat dairy, and they have extensive tofutti (dairy free cream cheese) options, in every flavor. H&H has some too, but not as many options!

  • Take your bagel to go and eat it in Central Park, weather permitting, just walk a few blocks east and you’ll hit the park. Central Park separates the West side from the East side from 59th Street to 110th street.
  • If you went to Absolute Bagel, you’re very close to the Cathedral of St. John the Divine and may want to hit that up first. It’s one of the largest churches in the world, looks straight out of Paris and has the most beautiful gardens (and peacocks!) on its grounds.
  • Then take two or so hours to walk around Central Park. It’s easy to get lost in the park, so just try to remember that you’re ultimately heading east, but getting lost is fun and fine! Some of my favorite spots in the park: The Reservoir (walk around the northern end for the best views of the city, The Conservatory Garden, The Boat Pond, The Bethesda Fountain and Cherry Hill. If you don’t want to just sit/walk around, rent a boat from Loeb Boathouse, even eat lunch there too!

*If you have kids, there are so many playgrounds and things for them to do in Central Park! Some of my favorite memories from childhood are from the Central Park Carousel (covid permitting), see a puppet show at The Swedish Cottage Marionette Theatre (covid permitting), take them to see the Balto statue or the Alice in Wonderland Statue, of course, The Central Park Zoo and playgrounds: Ancient playground (next to the Met), 72nd Street playground, Billy Johnson playground (next to the zoo) and Adventure Playground. Also, the Museum of Natural History and The Children’s Museum of Manhattan (both Upper West Side) are right next to Central Park and are great options.


  • After relaxing (or not) in the park, walk east to leave. Head to the Met, or any museum on Museum Mile. Check out my Museum Blog Post for more info on these! If you go to the Met, don’t skip the roof! You can grab a drink or snack up there (covid permitting) and get some seriously amazing city views.


  • The evening activity is a touristy one, but its so much fun! Check out this link to book a sightseeing cruise at sunset (must book in advance)I. It is the best way to see the city skyline in all its glory, plus you sail right next to the Statue of Liberty too. You’ll board a charming 1920’s inspired yacht, be seated at private table, waited on by an amazing staff, have drinks and snacks on board and can wander onto the deck for pictures at any time. If you’re not into the city skyline at sunset, they have a variety of options, including a brunch, jazz music, champagne & cheese, nighttime city lights, as well as sail boat cruises. I would say this one is an absolute must!

Day Two: Downtown


  • Don’t worry, if you didn’t make it out for a drink in the West Village last night, you’re going there today. I recommend making a reservation in advance if its on the weekend and grabbing brunch. Some of my favorite brunch spots downtown are 12 Chairs (middle eastern food, soooooo good), Hudson Clearwater (has a really cute backyard), Bluestone Lane and Banter NYC.


  • After brunch, stroll around. What’s great about the area you’ll be in is it’s so compact; there are so many neighborhoods very close to each other: the West Village, Greenwich village, Soho, NoLita, etc. You can easily spend the morning just roaming around and going in and out of shops.
  • Once you’ve had your fix, head over to The Highline. The Highline is a new-ish addition to the city- an elevated park that runs from Gaansevort St (below 14th) to 34th street along 10th avenue in Chelsea. Its very well maintained, situated on an old railway and has wonderful views of the city and Hudson River. One of my favorite activities with friends is to come up here during the evening with a bottle of wine (shh). The highline is right next to Artichoke Basille’s Pizza, and you absolutely must grab a slice either on your way up or down.

*If you have kids, you can take them to The Children’s Museum of the Arts (covid permitting), it’s located near Soho.

  • If you’re into NYC history (or history in general) a fun and informative activity may be to go to head over to the Lower East Side and visit the Tenement Museum. I talk more about it in my museum blog post, but you can tour preserved apartments from the 1800’s or take a walking tour of the neighborhood. The Lower East side is a fascinating neighborhood with a rich history, so I definitely suggest checking it out!

Tenement Museum


  • Two choices here: classy night out, or classic NYC grunge.
  • Classy: there are so many rooftop bars on the LES, all with great views of the city, linking a list to some of them here. As you probably know, NYC can be insanely pricey so if you’re not feeling $20 for a cocktail tonight, I gotcha.

  • Grungy: walk up a ways to the East Village. This may not be everyone’s cup of tea, but something my friends and I have done for years is get dinner at the BYOB Indian restaurants. There’s a row of them around 6th street on 1st avenue, linking one of them here. They are loud, so filled with Christmas lights that you can barely stand up and the guys on the street will hassle you to come in by offering free naan. It’s cheap, a lot of fun, a unique only-in-New-York experience and is BYOB as I mentioned, so don’t forget a bottle!

Day Three: Brooklyn

NYC has 5 boroughs, so I didn’t want you to only see Manhattan. Brooklyn lays across the East River, and is HUGE in comparison to Manhattan, so don’t expect to cover as much ground, I’m just telling you about a few fun places. Look up what time sunset is, you’re going to want to time your day so you’re doing the last activity at sunset!


  • Subway over to Williamsburg. This is an area that has changed drastically just since I was in high school (we used to go to parties in abandoned warehouses, now those exact buildings house $4,000/month one bedroom apartments). Williamsburg is where you’ll find a young, vibrant crowd and there is no shortage of fun activities.
  • Have brunch at Sunday in Brooklyn, 12 Chairs, Rabbithole, Juliette, Aurora or Meadowsweet.
  • If you’re into thrifting like I am, you’ll want to check out the manyyyyy thrift shops of Williamsburg, here’s a list of them. You can walk around, see the sights and pop into stores.


  • Grab a beer at Brooklyn Brewery or take some to go and sip them in Domino Park.The park is right on the water and has amazing views of the city, it’s also a great place to take kids because of the sprinklers and playground.


  • Next, you’re going to head towards Brooklyn Bridge Park, it’s about a 40 minute walk, so you might want to take a very scenic ferry ride (ferry rides cost $2.75, the same as the bus/subway.
  • However you get there, the goal is to end up at Grimaldi’s Pizza for dinner (if you haven’t had your pizza fix yet). This is some of the best pizza in the city. Unfortunately, Grimaldi’s doesn’t take reservations, instead you have to wait in line for a table; its worth it though, promise!
  • If you’ve had enough pizza, here are some other options for dinner.

*Jane’s Carousel is right on the water and great for kids (or anyone!)

  • As I mentioned before, it’s important to know what time sunset is today. If you didn’t time it correctly though, absolutely no worries! The last activity is walking across the Brooklyn Bridge and it’s wonderful at any time of day or night. If you don’t make it to the bridge in time for sunset, it looks just as good from Brooklyn Bridge Park! Walking across the bridge toward Manhattan is the absolute best because it looks like you’re walking straight into that skyline, and there is no better way I can think of to end an NYC trip.


If you have more than 3 days or want to sub some activities with others, here are some suggestions:

As always, PLEASE let me know if you plan to, or do follow this itinerary in the comments and give me ALL the feedback; it will make my day! I hope you find this guide helpful and that you have a wonderful time!

Don’t forget to follow me on Instagram for more NYC sights & tips!


  1. Tess wrote:

    I live in New York, and want to follow this itinerary one long weekend! Brilliant suggestions.
    One q – are the gardens of St John the Divine open to the public?

    Posted 7.8.21
    • admin wrote:

      Thanks Tess! Exactly, everything is tourist OR new yorker friendly. Yes they are! During covid they closed them during the week, but on weekends they are definitely open. It is SUCH a hidden gem

      Posted 7.8.21
  2. Maricarmen wrote:

    This is a very interesting and complete guide. Thanks for the Indian restaurants suggestions. I suggest you to check the app Citymapper, more useful and complete than Google Maps.

    Posted 7.11.21

Comments are closed.