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NYC Itinerary: 3 Days in New York City (My First Visit!)

by Caitlin J

So here’s a little recap of our NYC Itinerary: 3 days in the Big Apple. It was a short time, but this article is not, so let’s get into it! Hopefully, you can use this blog post to help you plan your trip to New York City, whether it’s for three days or longer. Overall, I was surprised by how much ground we covered in such a short time (less than 72 hours!). 

Keep reading to learn how we did and what we got to do with 72 hours in NYC. Plus, learn the details behind Jason and I’s engagement.

NYC Itinerary for Three Days

NYC Day 1: Morning

Driving from Northern Virginia to New York City

So NYC Day 1 started early. But not like super early… Since we had driven from Austin to Virginia, we were only five-ish hours from New York City. We could’ve left earlier, but I’m not that type of gal. We ended up hitting the road right before 8 AM.

It was going to be a straight shot, through Washington DC and Baltimore, then around Philly (sadly, not nearly close enough to stop in for a quick cheesesteak) before finally arriving in New Jersey. Once we were north of Baltimore, I blurted out with zero hesitation, “this is the furthest north I’ve ever been!” 

Yes, it’s a big deal.

Anyway, things felt different once we crossed the state and were in New Jersey. The Appalachian mountains faded out, and there were tons of power plants. And weird interstate rest areas…

Travel Tip: There are 23 rest stops along the New Jersey Turnpike and Garden State Parkway. Many of them were SO crowded, very outdated but had several fast food spots and gas. It was interesting, to say the least! Oh and all rest stops are named after deceased individuals with some sort of connection to the Garden State. Read more about the rest areas here.

Where to Park Your Car Outside of NYC

Only because this is the type of traveler that I am, I was Googling on the way up to New York City how to drive to get to NYC without driving into the city to plan where we would park our car. 

Also, if you arrived here from a similar search, HELLO!! :)

We ended up settling on Journal Square station in New Jersey ($14 for 24 hours). And besides the initial frustration from our inability to find the parking garage, it was perfect. If you need more help with parking in New Jersey to ride into NYC, I found this guide to be very helpful.

We parked our cars (see above for notes on how much we paid) and walked across the street to the Journal Square PATH station. From there, it was a quick 15-minute and $2.75 subway ride from New Jersey to the Upper East Side.

All in all, I highly recommend parking outside of NYC and riding a subway in. Getting to Manhattan is expensive (hello bridge tolls) and will eat up too much time if you’re only going to be in NYC for three days.

NYC Day 1: Afternoon

Welcome to New York! Arriving to the Upper East Side

So we arrived fairly quickly after boarding the subway in New Jersey. We were luckily just a few blocks from the stop and our hotel. One of the biggest parts of planning this short trip to NYC was making sure I nailed down the hotel and the neighborhood we stayed in. 

hotels in new york

We ended up choosing the Moxy NYC East Village, click below to check out their rooms!

Here’s what I took into consideration for where to stay in NYC:

  • I wanted a hotel that was an experience in itself. If we were going to be staying in NYC for a short time, a hotel packed with amenities and personality is definitely a top priority.
  • However, we didn’t want to pay too much for a hotel since it was essentially going to be just a place we slept and showered for a few nights in New York City.
  • We went during the holidays so we knew we’d have to pay more than usual and the clock was ticking to book a hotel in NYC. Every day that passed the average rates went up a little bit more…
  • Location is KEY when booking a hotel during a short trip (whether it’s NYC or a staycation in your hometown). Location can make or break your success at having a fulfilling short trip.

Alright, now time to talk about checking into the hotel. Most hotels will let you drop your bags if you arrive early. But always call to see if early check-in is available. It will be so helpful if you’re short on time. No one wants to lug around bags until check-in.

So we checked into our room at the Moxy East Village hotel. One thing we noticed when looking for a place to stay in NYC was how teeny-tiny the rooms were! So don’t be alarmed yourself when you see the prices in comparison to the room sizes. Real estate ain’t cheap on this island!

romantic things to do in nyc
The Ready Rooftop Bar in New York City

Beforehand, I made a reservation for the rooftop bar, The Ready Rooftop Bar, In retrospect, I probably didn’t need to make a reservation for this early in the day (2 PM) but it made me feel better knowing we had something fun to do while we waited to check-in and a place to gain our bearings before we set out to on the city.

We had a hotel in the East Village which was one of the New York City neighborhoods that appealed to us most. Honestly, it might be different for you, but if you’re short on time, prioritize where you’re staying.

About New York City’s East Village:

“The East Village is known for its happening nightlife and being the birthplace of American Punk Rock. Old-school bars, music venues, and performance spaces share the streets with posh cocktail lounges and hip restaurants. Daytime sees a more laid-back crowd browsing boutiques, vintage shops and tattoo parlors, and dining at casual cafes.” (Source: WIKI)

Don’t Skip: McSorely’s Old Ale House

So one of the first places we visited was McSorely’s Old Ale House. It is the oldest Irish pub in NYC. The floors are covered in sawdust, and it will be packed, with both locals and visitors. 

One of the most notable things about this bar is they serve two house beers: light and dark. These beers are actually contracted brewed by Sixpoints Brewing which contract brew many “house” beers you might see around the city.

After getting our fill of McSorely’s, we did some walking around. Walking around the Big Apple with no destination in mind is an adventure in itself!

I mean, NYC is one of those things where you don’t need an official “New York City” Itinerary. Just show up, it’ll be great, you’ll find fun, incredible things to do on every corner.

But please don’t let that stop you from planning out a schedule of some sort. Again, if you are short on time, it will help you to be focused and know what you want to do most.

NYC Day 1: Evening

Oh buddy, our first night in New York City was an epic one. We did Times Square, dinner, and Broadway! And a whole bunch of tipsy walking around, popping in and out of bars and bodegas.

I think this evening was the moment I fell in love with NYC. It’s so romantic at night. And I don’t care what the people who live there (or have been there a dozen times) say about Times Square…

YOU MUST GO.

romantic things to do in nyc
Times Square gets a lot of hate, but to us, it was spectacular! A must visit either before or after your broadway show!

You’ll feel so tiny in the most magical way. And I truly think the best time to go to Times Square is at night. Not like I have anything to compare it to. But being in that area where everything and one is lit up by the bright billboards is such a site. 

Yes, Times Square will be busy and packed, but don’t forget you’re in New York City. A city where 1,600,000 people live on an island 22.8 square miles big.

If you’re going to a Broadway show, I highly recommend stopping for a fancy dinner somewhere near your theater. (Check out this list for helpful places!)

You will most likely need to make a reservation. Not like a far in advance reservation, unless you’re a Michelin-only type of restaurant person.

Either way, I’m almost certain this type of evening is where the “dinner and a show” date night came from. I am certain that if I lived in NYC, I would be doing this every weekend. It was the most spectacular night.

Speaking of spectacular, we saw Moulin Rouge! at Al Hirschfeld Theatre. This is my all-time favorite movie. Always has been, and always will be. I must have seen this movie a bajillion times. So it felt surreal to be able to see a rather new broadway show featuring the storyline. 

romantic things to do in new york city

We aren’t normally splurgers, but we did splurge for this as it felt ‘almost’ once in a lifetime. We wanted to get great seats as we heard the seats during this show will have an impact on your experience.

Either way, make sure you do your research before regarding Broadway, this is probably my most important tip. I’m not much of a planner in advance, but this is the thing you need to do. Especially so if you want to go to a hot or new show. 

BTW, we had a wonderful dinner a block or two away at Becco. It was an all-you-can-eat pasta dinner at a reasonable price. 

With Jason and I both dressed up super fancy, we felt very high class at this place. I’ll say it one more time, but our dinner and a show was the highlight of our NYC itinerary.

After the show, we visited a bodega, cause you know, NYC bucket list. We continued to walk around and slowly make our way back to the East Village. 

We ended up stopping at some bar (my apologies for forgetting the name!) which was beautifully decorated for Christmas. It was random but romantic in only a way that a random bar in NYC covered in Christmas Lights could be. 

I’ll say it again and probably a few more times, but everywhere you go in NYC, there is something amazing to do or eat or see or drink right around the corner. Or maybe we were just the typical lovestruck first-timers.

Somehow we finally made it back to our hotel, which was a good thing because we had another big day ahead on our 3 Day NYC Itinerary.

NYC Day 2: Morning

Alright, let’s move on our second day in our NYC 3 Day Itinerary… I’ll be moving a bit quicker through this as we covered A LOT of ground on our second day.

One of the biggest highlights of this day was getting to explore Rockefeller Plaza and window shopping all of the pretty holiday windows along 5th Avenue, among the top designer stores in the world.

Here’s an important part you’re probably wanting to know about…

Where is the best place to see the NYC skyline?

My answer… Top of the Rock baby!

First off, it’s one of the views where you can get perfect shots of the Empire State Building. (On the other hand, you can climb the to the top of the Empire State Building but you won’t be seeing it, which like IDK seeing the Empire State Building is a *thing*)

Secondly, the price was *just right* for us. Some of the other options were quite pricey, but at $35-ish this was very reasonable.

Thirdly, I do suggest buying a ticket a few days ahead of time to make the most of your time. I felt it was best for us if we made the reservation as early as possible to make sure we got our booties out of bed. Lololol.

Even though we made reservations we still had to wait in line for about 45 minutes, I don’t know if this is because we went during Christmas time or if it’s the norm. But it was all good once we got in and got to head up.

At this point, I’m not going to describe anything else about the trip up because I don’t want to spoil anything. But now it is magical and do know that there are about 3 more floors you can climb up to once you get out to the first platform. 

In my opinion, as someone TERRIFIED of heights, I felt very dizzy at times, but like in a very exciting way. Just make sure to look down when climbing upstairs to avoid that weird feeling that you’re going to be blown off the top of the world. 

So somehow, once we came down from the top, we were trying to get back to the plaza, where the iconic Ice Skating rink is, but got lost underneath 30 Rock. There are dozens and dozens of tunnels down there. And I’m sure this will not happen to you but just know if it does, you will find your way out… just like we did haha

It’s those types of unplanned moments that can really take a trip from just another highly-scheduled thing to something magical. But again, I don’t know, maybe it’s just an NYC thing!

While we didn’t go ice skating on the plaza, strolling around it was plenty of adventure for us. I do think if you want to do this, you’ll want to look into making reservations ahead of time! (Again as someone who never does this while trip planning, I just want to give yall the heads up!)

You can read more about ice skating in my other NYC blog post here.

NYC Day 2: Afternoon

Oh did I ever mention that on our second day in New York City, we got engaged!?!? Well, we did! Let’s talk about the hours leading up to this point because it happened in one of the most romantic spots in NYC.

After exploring Rockefeller Plaza, we decided to make our way down 5th Avenue towards Central Park. One of the things I was most excited to do in New York City during Christmas was to ooh and ahh at all the decorated windows. 

All of these designer boutiques were quite the sight for someone like me. We didn’t stop in any of the stores except for the Gucci store. I was hoping I’d be able to convince Jason to let me buy a Gucci belt. Maybe if he saw one in person, he’d know why I wanted one so bad… but no dice.

We definitely worked up an appetite with all that window shopping, so we decided to pop in somewhere for some ~authentic~ NYC pizza. We choose Little Italy Pizza because it was the closest to us with the best (and most) reviews. Also, we saw a lot of day laborers taking their lunch break in there, which IMO is always a good sign of delicious food!

New York-style pizza is definitely my favorite type. The one we had was so greasy and thin. It was heaven. I could eat that pizza every single day of my life and not get tired of it.

After getting our fill of New York-style pizza we continued on towards Central Park. It was at this point that it started to flurry. Yay, snow! It did not last for long though, thankfully. These Texans are not the biggest fans of the cold.

Getting Engaged at Central Park

romantic things to do in nyc-6

Finally, we made it to the iconic Central Park. I could tell that the engagement ring was burning a hole in Jason’s pocket. He knew that I always found Central Park to be romantic (thanks to shows like Sex and the City and of course Gossip Girl), specifically Bethesda Terrace. 

So we slowly meandered through the park. We debated on getting a horse carriage ride but were mildly disappointed by how short most of the rides were.

Central Park is such an exciting place to be. You’re surrounded by all of the most expensive properties in the US (Hello, Billionaire’s Row!!).

Before getting to Bethesda Terrace, we walked through the tunnel next to the terrace where a group of folks were playing classical music with string instruments. Talk about setting the mood!

Finally, once we were at Bethesda Terrace, Jason got down on one knee and asked me to marry him. After seven years of dating, five years of living together, and four months of designing an engagement ring… the moment was finally here!

Of course, I said, “Yes, yes, yes!”. 

He placed our gorgeous ring on my finger, got up from his knees and we started French kissing in front of everyone. JK, on the French kissing part haha.

romantic things to do in nyc
Jason and I got engaged in Central Park when we visited during Christmas 2021!

To be honest, I was expecting more people to be excited and cheer for us, but I’m sure this is something that happens several times a day here. I did notice one woman get us excited for us.

This was our moment though. We didn’t need a photographer, I didn’t need him to pull out a piece of paper with a speech declaring his love for me, a prearranged picnic for us, and I didn’t need a flash mob singing our favorite song (though I did mention that it would be super funny if he pulled that off). We had each other and no one else around us mattered in that moment, which will always be special to us. And that’s all I wanted.

After the proposal, we walked a bit further to The Loeb Boathouse to get a proper glass of bubbly to celebrate. It was my first time having real champagne but the occasion 100% called for it. 

While we were there I texted our closest family and friends to tell them the news. It wasn’t exactly the surprise of a lifetime but each and every one of them was ecstatic that it happened. 

Travel Tip: If you want to go to The Loeb Boathouse to eat, I highly recommend making a reservation well in advance. The place was PACKED. We just came for some drinks so we were easily able to find a spot at the bar (which does not offer food service).

As we walked our way out of Central Park, we had to stop for some chili cheese dogs from one of the carts. Slowly, I was crossing more and more items off my “NYC Bucket List”.

NYC Day 2: Evening

Once we left our hotel in the morning, we did not come back until it was time to sleep. We were in NYC for 3 days and we needed to make use of every second. In a place like NYC, it isn’t hard. Something exciting is going to be around every corner.

So after Central Park, we decided to go to some of the other NYC attractions that were high on the list: Vessel, Hudson Yards, and the High Line. 

The Vessel was quite a stunning sight. Sadly, walking up it is closed as there have been a handful of suicides there recently. (As of publishing, it is still closed.) 

At first, I thought it was because of Covid (we went to NYC during one of the last big spikes in cases), but my followers on Instagram quickly let me know that that wasn’t the case.

After looking it up, it was heartbreaking to hear about the people that took their life there. Before they closed it (you can still go up to it, and in the base to look up, just can’t walk up the stairs.) They even tried to start a buddy system and had put up mental health signs. But those didn’t seem to be enough.

Idk, maybe they can install some higher barriers? But what do I know…

Let’s pivot though and get back to some of the other things we got to do during our 3 day trip to New York City!

After exploring the Vessel as much as we were allowed, I had to go to the bathroom, which was the perfect excuse to check out the Hudson Yards mall. It was beautifully decorated for Christmas time (or maybe it looks that magical all the time). Either way, it was the *definition* of bougie.

After checking those two spots out, we headed to the High Line to walk to Torch and Crown Brewing for our dinner reservations. (Even if a place isn’t super busy I like to make reservations when given the chance to do so ahead of time.)

The sun was setting and it was getting quite chilly as we walked The High Line so we decided to head down to street level to warm up with a cocktail. We ended up stopping at Hawthorn Bar which fit the bill. It was random, but the cocktails were good and the bartender was fun. It didn’t feel like a touristy place as you could tell there were a few regulars there

After one cocktail, we headed back on our route to Torch and Crown Brewing. When we got there the place was quite empty, which whatever. But overall, I was not impressed with this spot. It is one of the few craft breweries in Manhattan and maybe I had too high of hopes.

We ordered some beers and some wings, and I was very upset to hear that they didn’t have ANY ranch for my wings. Like what, no ranch in the whole building? GTFO. And no, blue cheese is not the same!

So we ate up our food and finished our beers to head out to another bar, specifically a speakeasy. 

NYC is known for having a good bit of speakeasies/hidden bars, but I think we definitely found the best one.

The Back Room was a spot that Jason found and we were both blown away! For so many different reasons too. We had to navigate down underground and through some very sus alleyways, but there were signs that told us we were headed in the right direction… 

The Back Room is one of only two speakeasies in New York City that operated during Prohibition and is still in existence today During our time there, we sat at the bar and got to see the bartender mix up drinks in teacups and coffee mugs. 

Yes, no fancy glassware here, and for good reason.

Why do they serve drinks in teacups at The Back Room? Well, that’s the way people used to secretly drink during prohibition! Because nothing suspicious about drinking out of a teacup late in the evening, right officer?

NYC Day 3: Morning

Sadly, it’s now day 3 of our NYC trip. Since day 2 was so busy we decided to lay around in bed a little bit and check out of our hotel in the mid-morning. Luckily we were able to keep our bags secured at our hotel while we did the last bit of our exploring.

We had a few things left to see, one being Washington Square Park. So as we made our way over there we stopped for coffee and macaroons at a bakery that I cannot remember the name of. Which is ok, it wasn’t a great bakery, just one that we found.

We got to Washington Square Park to try to take some selfies when this super kind woman (with the cutest dog ever) asked if we would want her to take our picture. We said yes of course and got this beautiful shot below:

Washington Square Park was fun, we passed through New York University ‘campus’ on our way there. And once we were at the plaza it was such a happening spot. There were skateboarders, TikTokers, and couples enjoying pastries.

After Washington Square Park we started to work up a bigger appetite and decided to go somewhere beautiful for brunch. We landed at the Crosby Street Hotel.

Now, this is like a $1,000 a night hotel, something we could never afford. But we could afford a brunch and a few cocktails. So we did just that. The waiter here was so kind and helpful as we sat at the bar and debated what cocktails to order. (The cocktail menu was so impressive!) 

The lobby of the hotel was stunning, and we did some peeking around to check it out. In front of the hotel, they had an actual Botero statue who is one of my favorite artists. I did a report on him in one of my college Spanish classes (he is Colombian) and I fell in love with his work from there. All of his stuff, paintings, and statues, feature the funniest, chubbiest characters. I’m sure there’s some art-school-level explanation around his art. But I’m not an art student, and I like what I like.

NYC Day 3: Afternoon

On our last day, I had plans to meet up with one of my beer Instagram friends, Mandy.  (check out her Instagram and blog!) I adore this chick!! She lives in NYC and is such an expert when it comes to tasting beer, wine, coffee, and cider. In fact, she actually has a book coming out in 2023 called “How to Taste!

She suggested we should definitely check out the Market Line Food Hall. More specifically, The Grand Delancy, which is a beer bar. And by god, this was such a stunning bar. I mean see for yourself below!

Within the Market Line Food Hall are a dozen or so vendors, eateries, and other local sellers. We ended up getting some amazing pickles from Pickle Guys. He was so kind and let us taste all he had to offer! 

After exploring the food hall a bit, we went to the Grand Delancy for some brews and food. The cool part about the Grand Delancy is you can order food from other vendors and have it ‘delivered’ to the beer bar. We ordered smash burgers from Mighties which were *chef’s kiss*. Some of the places were closed on the day we went, including a pizza joint that I got tons of recommendations for.

Once Mandy showed up, we ordered some more rounds and discussed all about our NYC trip with her. I kinda loved it since this was at the end of the trip and she was happy to answer any of our, “umm what’s up with that?” questions.

She also gave us some fab recs on getting to Brooklyn and where to enjoy some great craft beer. I absolutely love meeting up with my IG friends whenever I go traveling so this was another highlight of the trip. Ok, everything was a highlight of the trip,  but it’s New York City!

As our time was winding down in NYC, we decided to make it to Brooklyn for some craft beer…

NYC Day 3: Evening

Most of the craft beer in New York City is actually in Brooklyn or other surrounding boroughs. We were kinda pressed on time. Don’t forget our car was still in New Jersey…

We had two choices: rush through three breweries or enjoy our time at one. So we did the latter.

We ended up choosing Grimm Artisanal Ales, which was a perfect choice in my humble opinion. Their beer list was so long and featured a solid selection of all types of beers: lagers, IPAs, sours, farmhouse. The beer list was SO LONG.

We had to sit outside during our visit, and though it was cold there were plenty of heaters as well as a temporary outdoor tasting room. (Which don’t even get me started on those in NYC).

We didn’t want to spend too much driving in the dark, so after a few half pours of beer, it was time to make the journey back to New Jersey to pick up our car and return home to Virginia.

Travel Advice for Planning a Short Trip to New York City

Overall, we had such a great time in NYC! To be honest, I was not expecting to fall in love with New York City as I did. I mean everyone loves NYC but I also always heard it was dirty and expensive (it was both of those) and would chew up and spit you out. Don’t forget I grew up in Virginia and everyone I knew that wanted to be famous moved to NYC.

This city took my heart away. It was my first visit, but I know for sure it won’t be our last. Especially since this place will always be special to us as it is where we got engaged. You can also tell how much I loved it by how long this damn post turned out to be… Sorry about that…

So that’s all folks! If you’ve stuck around this long, thank you so much for reading our NYC itinerary for 3 days. I hope this helps you plan your trip to New York City. And before you leave, here are a few other places that we wanted to visit but didn’t have time to

  • Attaboy (speakeasy)
  • Beer Culture (beer bar) 
  • Chelsea Market (indoor marketplace)
  • Death and Co. (upscale cocktails)
  • Katana Kitten (Japanese)
  • Otto’s Shrunken Head (tiki bar)
  • Please Don’t Tell (speakeasy)
  • SERRA (Italian)
  • The Empire Rooftop (rooftop bar)
  • The Metropolitan Museum of Art (museum)
  • Veselka (Ukrainian)
  • More Brooklyn Breweries such as TØRST, Other Half Brewing Company, Interbro Spirits and ALES, Finback Brewery, and Kings County Brewers Collective and Threes Brewing.

Thankfully there’s always next time! Which hopefully will be in the fall as I hear the colors are gorgeous up there that time of year…

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