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New York City Itinerary for Repeat Visitors

January 20, 2020
Brooklyn Bridge New York City

3 Full Days in New York City For People Who Have Already Visited Before

Whenever I hear the name “New York City” I instantly think of at least 3 different song lyrics simultaneously…center of the universe, I wanna wake up in a city that never sleeps (duh), concrete jungle where dreams are made of…quite a variety of musical genres now that I think about it.  And it’s very fitting that this happens because I come to New York to see and hear Broadway.  There have been times when I have seen 4 shows in 48 hours, that’s how intense I am about it.  And, this time was no different.  I went to New York City to see Hamilton, although I did spend much more time exploring the city than I have in prior trips in the hopes of creating an itinerary for repeat visitors to New York.  Because as much as I don’t feel as though I truly have been to New York unless I see the Statue of Liberty from a distance at some point during the trip, I really only care to visit Ellis Island, the Empire State Building, and the Statue of Liberty once every 10/15 years.  So here goes, a New York City itinerary for people who have been to New York City before by a tourist, for tourists.  


Library Hotel New York City          Library Hotel New York City


When I was looking for a nice place to stay in New York, I did my usual TripAdvisor search, which includes me putting in the dates I will be in the locale and then sorting by ranking and viewing the price point.  It was very clear that the Library Hotel Collection was the ideal place to stay in New York City as their hotels held the 2nd, 3rd, 6th, and 9th best spots in the city.  I reached out to them and was lucky enough to have them host me at two of their locations: the Library Hotel and the Hotel Giraffe.  Thematically, the Library Hotel was top notch with each room filled with loads of books related to a particular subject; I stayed in the African Heritage room.  The Library Hotel also has a stunning rooftop area which was amazing as we had it to ourselves during New York’s second snowfall of the year.  We stayed two nights at the Hotel Giraffe and I really fell in love with the place because I loved coming back to its relaxed vibe after a long day out in NYC.  Also, our hotel room had its own balcony!  Now that is a rarity in New York.  And, of course the highlight of both hotels was that there was a delicious complimentary breakfast and complimentary Happy Hour daily.  Actually, there is food and drinks out 24/7 should you want a late night snack after a long night out in the city.  The service was impeccable and the locations perfection; it would be impossible to have a complaint at either property.  


Hotel Giraffe New York City     Hotel Giraffe New York City



Foot, Subway, Uber, and Taxi…in that order. Some people are all about walking everywhere by foot, and ideally, yes that is the best option.  But, all of that walking definitely adds up for me and blisters inevitably start to form no matter how comfortable my walking shoes are, which is why I recommend the subway for longer distances with the disclaimer that it is difficult for tourists to follow!  Between Uptown/Downtown, Express and Local, and the actual lines themselves, you should only take the subway if you are confident in knowing how to get somewhere.  Uber is the next best option, although pricey, it is cheaper than a taxi.  The only downside is having to walk to certain street corners to meet your driver because let me tell you from experience, as a tourist that can be tricky if you don’t have any clue where you are.  Take a taxi if it is a) freezing b) unbearably humid c) you are totally lost or d) simply don’t have the time to wait for someone to come to you and pick you up.


Brooklyn Bridge New York City     Eggloo Chinatown New York City


Day 1: 

First order of business, getting a bagel obviously.  Once that is out of the way…I now totally get why walking the Brooklyn Bridge is one of the top things to do in New York City. This may seem counter-intuitive, but start the trip off taking the subway from Manhattan to Brooklyn to walk the Brooklyn Bridge.  Hear me out…your feet will not feel like they are going to fall off from walking all over the city and the view of Manhattan will really give you that “I’m in New York City” feeling.  I think it is a must to walk from the Brooklyn side into Manhattan.  It is less crowded and you get to see the Manhattan skyline straight in front of you instead of having to awkwardly turn around and look behind you every minute.  And trust me, the views are beyond spectacular.  The Pedestrian entrance is right next to Cadman Park in Brooklyn, so if you are riding the subway in from Manhattan, look to get off at either Clark Street Station or High Street Station.  Once you’ve walked across the bridge and walked up an appetite, head just .6 miles or so further to either Chinatown or Little Italy (both are right next to each other) depending on what you are in the mood for.  I went for some hot dumplings at Nom Wah Tea Parlor and then this crazy ice cream dessert at Eggloo even though it was freezing cold.  The commitment was worth it. 

Right nearby is one of the best museums in NYC and the next stop on your agenda.  The Tenement Museum on the Lower East Side is interactive, relevant, and really paints a picture of what the conditions and life was like for immigrants moving to the United States.  On your first go around in New York, you probably went to Ellis Island, so now you will have some context on this next trip you take to the Big Apple.  I also love that they have all sorts of tours highlighting immigrants from all different countries, so you can choose a tour based on where your family came from.  I went on the Hard Times tour and it was fantastic.  I would suggest buying tickets in advance.  We were able to purchase tickets the same day but I just went in January and on a snowy Tuesday which is definitely a quiet time to visit.  After the tour, grab an appetizer pickle at The Pickle Guys before getting your deli on at either Katz’s Deli a touristy, overpriced restaurant with the best pastrami (don’t make the mistake of getting turkey like I did) or the trendier alternative, Russ & Daughters Cafe.  If you’d like to explore the New York City nightlife, the Lower East Side is where you gotta go.  TimeOut, Thrillist, Yelp all have the top spots like Arlene’s Grocery, Beauty & Essex, Copper & Oak, etc. If you aren’t into the nightlife scene, check out One World or Top of the Rock for a view above of the city.  


Chelsea Market New York City     High Line New York City


Day 2:

Starting Day 2 off on a bit of a somber tone, but also a necessity for those who have yet to visit since the memorial was opened.  We all remember where we were the day it happened, and we all want to pay our respects at the 9/11 memorial and museum.  The memorial itself will get you completely choked up, but it has been recommended to me that the museum, while emotionally taxing, is powerful and very important to see as well.  Once you have recovered emotionally, head up towards the trendy Meatpacking District for some window shopping.  After roaming the streets for a while, walk a couple of blocks up to Chelsea Market.  Ideally, you go to the market on a weekday because then you can actually enjoy the walk through as opposed to dodging people right and left.  Grab some lunch and a tea or coffee to-go before you walk up the old New York Central Railroad track, now an aerial greenway and park.  The High Line is always one of the highlights of my New York trip in both summer and winter as it’s just a great way to view parts of New York City.  Also, the High Line goes on for quite awhile so don’t feel like you have to walk the entire way! 

Freshen up back at your accommodation (free wine and cheese at the Hotel Giraffe is what I’m talking about) before your next stop, which is my favorite part of the trip…going to a Broadway show!!!!  You want to make sure you give yourself enough time before the show to get there and get situated, so I made sure to allot enough time on this day to do so.  Of course, if you can get tickets to Hamilton, fantastic, but if not there are some amazing shows out there to be seen.  My favorites that are currently playing are Phantom of the Opera and Wicked.  And my all-time favorite musical is Ragtime, which I have yet to see so Broadway…please bring that back!  But tangent… After the show, you will be in Times Square which is not a New Yorker’s favorite place but as a tourist, I have to admit I definitely enjoy seeing it all lit up at night.  End your night with some New York pizza and if you aren’t too sugar-ed out, some cheesecake from Junior’s Deli.  Or, you could head to the trendy Soho district for a falafel at Taim.  And, if you are a trooper and want to hit the town, props to you!  Maybe a rooftop bar if you’re feeling fancy (or the weather is just really nice)?!     


Eataly New York City     Central Park New York City


Day 3:

We are heading to midtown and uptown today and starting off the day getting a photo op at the Flatiron building because it’s pretty nuts to see a building that shape and size.  Conveniently enough, Eataly is across the street, and it’s the perfect place to grab brunch/lunch.  Eataly is a huge open market with a variety of Italian restaurants.  We chose to go to the rooftop restaurant because it was currently Italian Alps themed and there was raclette and rose so…enough said.  After lunch, take the subway Uptown from 23rd street to 68 St-Hunter College to visit the Frick Museum, the mansion of Henry Frick, a wealthy New Yorker whose hobby of collecting artwork developed into one of the pre-eminent small art museums in the United States after his death.  For those of you who, like me, don’t have a strong background in art or art history, I recommend going on the 15-minute docent led introductory tour that the Frick has daily at 1:00 PM and 2:00 PM.  Actually, I recommend everyone go on the tour.  Call ahead to confirm daily hours!  Tickets are $22 for adults and $12 for students. 

Afterward, walk outside and Central Park is right across the street.  Walk along Terrace Drive which cuts straight through the park and leads you directly to the Boathouse where I highly recommend taking a paddleboat ride through the park on a nice, sunny day.  Spend some time people watching and exploring the park before heading to Levain Bakery for the world’s best cookie.  There will most likely be a line and it will be totally worth it to wait in said line.  I got the chocolate chip walnut cookie and the double chocolate peanut butter cookie.  Most. Delicious. Thing. Of. Life. It will probably be late in the day by the time you get through all of these activities, so tonight I planned some events that don’t have as early of a start time.  This way, you’ll be able to go back to your hotel and change and then head to Greenwich Village for some dinner/jazz/comedy, whatever strikes your fancy!  While NYU doesn’t have a college campus, it definitely does have a college town and that town is Greenwich Village.  You totally feel that vibe here and it’s really a lot of fun.  We went into a random dive bar with happy hour drink prices because in New York, you always want to look for those HH deals and then went to an adorable place called La Laterna for dinner with a stunning patio area.  The Comedy Cellar is the known entity in Greenwich Village for a popular comedy show and the Blue Note is one of New York City’s most famous jazz clubs and both venues have multiple shows per night.  It’s a great note (see what I did there?! ha) to end your NYC trip on!    

Where are your must-see spots in New York City?  Let me know below!


Looking for more info for your New York City trip?  Check out some of my other NYC posts! 

Winter Packing List: What to Wear in New York City

Hamilton on Broadway: What to Know Before You Go



Are you on Pinterest? Pin these New York tips for later!


Thank you to the Library Hotel Collection for hosting me.  All opinions are my own.  This post contains affiliate links which means I receive a small commission if you make a purchase using this link. Thank you for the support.


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  1. Annie on January 11, 2019 at 6:07 pm

    Coming from a New Yorker’s perspective I have to say that I enjoyed reading your recommendations. Good luck.

    • on January 11, 2019 at 6:59 pm

      Thank you so much! Do you have any additional recommendations? I would love some in the comments from a New Yorker’s perspective!

  2. Abigail on January 11, 2019 at 6:08 pm

    Reading your post made me SO INCREDIBLY excited for my upcoming trip to NYC! 🙂 You are obviously the expert and you listed most of my favorite things I’ve done/seen/eaten in NYC for 2nd/3rd/10th timers that aren’t the usual suspects (ellis island, empire state building etc. etc). I couldn’t agree more… Tenement Museum, Russ & Daughters, The Pickle Guys, The Highline, Katz’, Chelsea Market…Winners! 9/11 memorial and museum are both intense and powerful and emotionally draining. Everything you said. But so important to see. And I can relate very much to a highlight always being a show. We aren’t going to “Hamilton” sadly – so jealous you got to see it in NYC – but we do have tix to “Dear Evan Hansen” which I’m looking forward to. Ok so one of my other fave things to do is grab a picnic from Zabar’s and enjoying it in Central Park weather permitting. 🙂 And I’m adding Brooklyn Bridge, Comedy Cellar, Frick, and Eggloo to our to do list for our upcoming trip!!! Thank you for this fun to read and useful post! And your hotel accommodations look amazing!! xoxox

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