Arrival:

You’ve arrived in the Big Apple! Or, at least, La Guardia airport which is right across the main island. With such a quick trip, I would avoid booking something around La Guardia and just heading straight to a hotel that you booked in the city. There will be plenty of taxis & shuttles to take you into city – even at midnight. We had already booked a place around La Guardia (and it was not the best….) so we checked in after arriving around midnight and headed straight to bed. 

Day 1:

Our first day was filled with an hour long trek into the city (that’s why I say just head straight there). Luckily, we scored an amazing hotel right in Midtown overlooking Times Square. The hotel was a DoubleTree Suites by Hilton Hotel. We were pretty fortunate to find this deal on Expedia. Otherwise, it’s pricey to stay in Midtown. Besides the cost and the crazy amount of people, Midtown is a great location because it’s central to a lot of things and you can walk around at night with the bright city lights – just like all the movies 😉

NYC is a lot to drink in, so for the first day we just walked around Times Square. It’s kind of my favorite part of traveling – to walk around and observe the different environment, the different people and take note of what I want to do. 

For breakfast, we just stopped somewhere to get donuts. Then we walked around some more and even got some free ice cream that they were sampling on the block! There’s always something happening in this area.

For lunch, we walked to the famous “Halal Guys” cart on West 53rd st & 6th Ave. There are 3 Halal Guys carts on this block but the original one is on 53rd st. They sell gyros and chicken and it’s pretty damn good. Also, it’s cheap. Each platter was $8 – $10 AND I always had leftovers with the regular size platter. YUM. 

Alright, now to use the subway system for the first time! It may seem a little intimidating but it’s really one of the easiest ways to get around. Grab a map from your hotel for the subway lines – most hotels give it out for free or you can find it in the subway hubs. Find the closest stop to you and then the closest one to your destination. There will be letters or numbers over the stop – that’s the line you’ll be hopping on. 

We used the subway to get to the 9/11 memorial. It’s right around the new One World Trade Center, which is a really cool architectural sight to see. Buy your tickets in advance and you can to wait in a slightly shorter line. The 9/11 memorial will take you a couple of hours but it was worth it. We all remember what we were doing the moment those planes hit… but to see the tragedy up close and personal is really something else. It’s all very emotional; take part in every single part of it. (There are tissue boxes in every room of the Memorial.)

That night we had tickets to go to The Comedy Cellar – the famous comedy club of NYC! We arrived early to check in. The Comedy Cellar is 21+ only. But we had my 19 yr old brother with me….which is fine as long as you email the club in advance! Stop by Artichoke Basille’s Pizza on the same street for some delicious NY style pizza. 

Then end your night with a show at the Comedy Cellar – one of my favorite places of the trip. So much laughter. Plus there’s so much to do on this street if you still want to go out. After the show, we grabbed dessert at a little creperie on the same street.

Summary:

• Walk around Times Square
• Lunch at The Halal Guys
• Familiarize yourself with the subway 
• Pay your respects and visit the 9/11 Memorial
• Head to Greenwich village for The Comedy Cellar!
• Stop by a local pizzeria beforehand (Artichoke Basille’s Pizza is on the same street)
• Laugh the night away at the Comedy Cellar (they have food & drinks too)
• End the day with some dessert at Creperie NYC on the same street
• LYFT back to the hotel

*Phew, what a long first day! I promise the other ones will be shorter! 

Day 2:

Wake up and remember you’re in the beautiful, concrete jungle of New York! We were pretty beat from the first day so we slept in and just ate some leftover Halal guys. Then it was off to explore. We bought a RockPASS for a tour of Rockefeller Center and access to the Top of the Rock. The Rockefeller Center tour is NOT the NBC Studio tour but still really good! Our guide walked us all around Rockefeller Center and told us the history of each piece of architecture and art. I really loved hearing the stories of old New York and the Rockefeller’s legacy. Afterwards, we headed to the Top of the Rock which is probably the greatest view the city has to offer. One one side, you’ll see the sprawling Central Park and on the other, you’ll see the Empire State Building. That means your selfies will have Empire State in the back. 😉

Then we were hankering for some ramen – so we headed to the highest reviewed ramen shop in NYC – Ippudo in East Village. It’s a very popular and hip place that makes everything from scratch….mmmmmm delicious.

Our Day 2 fell on a Friday so we headed over to the MoMA for free admission (from 4-8). The MoMA can definitely take up a big chunk of your day; we snuck in right before closing time so we only spent an hour or so before getting kicked out. Modern art is pretty interesting….

We grabbed a quick dinner at The Shake Shack – the famous East Coast burger stop – before heading to our night show…… Drunk Shakespeare! The Shake Shack was good….I would recommend ordering the portobello mushroom burger and a shake. (Though I have to say, I would still vote In N Out as the better regular burger.)

I highly, highly recommend Drunk Shakespeare. It’s an off-broadway show filled with ridiculousness and Shakespeare! What more could you want. What more could make you feel like you’re in the performance capital of the world?! It’s in a little old building with a sketchy elevator but they welcome you with a shot of something magical first. As if to say, you made it through the hard part. You’ll laugh and laugh and cry of laughter, you’ll sing along as they attempt to include dance battles into Macbeth or whatever play they’re performing for the night. You’re part of the show as you yell along and watch the main actor get absolutely hammered. It’s a blast!! Make sure you buy your tickets in advance so you don’t miss out!

Summary:

• Buy a RockPASS for Rockefeller Center Tour & access to the Top of the Rock
• Take a tour and learn the history of Rockefeller Center and the impact of the Rockefeller family on NYC
• Snap selfies at the Top of the Rock and take in the gorgeous view of the city
• Stop for food – enjoy Ippudo in East Village for some tasty, tasty ramen
• Discover modern art at the MoMA (free from 4-8pm on Fridays)
• Eat dinner at popular burger stop, The Shake Shack
• Laugh your ass off, marvel at the words of Shakespeare and enjoy an intimate performance at Drunk Shakespeare, the drunk off-broadway show

Day 3:

We started our day by heading to the Chelsea Market! There are a ton of cute, local shops and businesses to discover in this  renovated underground hall. Chelsea Market also houses many foodie stops soooo come hungry. We stopped at Takumi which served Japanese-Mexican fusion….nom nom nom so good. Then there were ice cream places and desserts perfect for right after. I was stuffed. All the more reason to go shopping and walk it off as we browsed the little shops in the Market. 

Right around the Chelsea Market is the High Line – an old railroad track that’s been transformed into a beautiful park. We spent a few hours just walking up the park, looking at the fantastic view of the bay and relaxing on the grass. Stop by to get a beer at one of the beer gardens along the High Line. 

For dinner we decided to do a pizza crawl! We headed to the West Village. We hit up Joe’s Pizza (a very NYC style place – only cheese or pepperoni!) and then Bleecker Street Pizza. I really liked Bleecker Street Pizza because of their tasty toppings. We were stuffed after 2 slices at each so our crawl turned into just a few stops. 🙁 West Village has a lot to offer too so we walked around a bit and then stopped by a little dessert shop for macarons.

Just around the corner from these pizza places are pubs and bars. We headed to the Fat Cat so we could play some pool. Fat Cat was a lot of fun! It was crowded and filled with more than just pool tables. You could play shuffle board, ping pong, chess, checkers, etc. There was a cover that night but it was only $3. The best part was that there was an excellent jazz ensemble playing. We forgot about pool and ended up just sipping on drinks and listening to talented musicians jam out. 

The night’s still young! We bought tickets to the Upright Citizen’s Brigade to watch sketch comedy and improv at the place that Amy Poehler (my faveee) founded! So at 10pm we hopped on the Subway to Chelsea. We went to the midnight show called Backyard Brawl where two sketch groups battle out for votes. It was such a good time! And it was only $5! What! What a deal! They serve beer and wine too!

Summary:

• Chelsea Market (try Takumi for Japanese-Mexican fusion)
• Walk down the High Line and enjoy the sunshine, art and architecture around you
• Attempt a pizza crawl for a taste of NYC’s pizza – try West Village for slices at Joe’s Pizza and Bleecker St. Pizza
• Mosey around West Village, indulge in dessert at local fro-yo shops or bakeries
• Watch and listen to talented musicians jam out at Fat Cat where you can drink and play games or just sit back and relax
• Vote for the funniest sketch team at UCB’s Backyard Brawl midnight show

Day 4:

Start the day off with Chinese food! We ate at Xi’an Famous Foods which is delicious, authentic Chinese food. It’s a small little shop with first come, first served seating but they make their food fast and people were eating and leaving just as fast. We got beef noodles which were sooooo good and pretty cheap. Most items were under $10. Afterwards, we decided we would attend a matinee Broadway show! So we got tickets to Hamilton….just kidding. We went to the TKTS booth in Times Square to buy tickets for Rotten Tomatoes or Aladdin. Score – Rotten Tomatoes had just 2 tickets left to be seated right behind the orchestra. The TKTS booth sells discounted tickets so it was a pretty good deal….we were pretty close to the stage. I would highly recommend Rotten Tomatoes….it’s a hilarious musical about musicals and going against Shakespeare himself. Its definitely a unique show on Broadway with an extremely talented cast.

One of the great things about the East Coast is that all the states are so close to each other. We have family in New Jersey that invited us for dinner so off we went. Then, it was only a 30 min bus ride from the city to NJ. I loved all the East Coast scenery – big, unique trees, lots of green, green land and the colonial style houses were fantastic to see. 

After dinner, we went to a local, “dive” coffee shop called Inkwell for liquid desserts. The coffee shop is rooted in punk rock history. Then it was off to bed.

If we didn’t go to New Jersey, I probably would’ve headed to  Queens or Brooklyn to explore!

Summary:

• Brunch at Xi’an Famous Foods – authentic, Chinese food
• Watch a Broadway show by taking advantage of Sunday matinee and the TKTS booth prices; go watch Rotten Tomatoes for a comedic musical with a unique storyline!
• Go to NJ if you have family there! Hah
• If not, head to another borough like Queens or Brooklyn to explore!

Day 5:

The last day was filled with touristy things and re-visiting some favorites.

We got up early to visit Lady Liberty. Buy your tickets in advanced, online. If you want to go to the Lady’s crown, buy your tickets wayyyyy in advanced because they sell out months and months before. Bring a jacket with you so you’re not chilly on the ferry ride over. You’ll still have to wait in a big line when you get on Liberty Island but they give you a walkman so you can listen to the history of the Statue. We had some time before hopping on the boat so we walked around Liberty State Park (which is only on the New Jersey side and where the boats take off). It was great to see the NYC skyline across the bay. 

Once we got on the boat and arrived on Liberty Island, we picked up our headsets for a self-guided tour on the island. The tour ends with the Statue of Liberty. She’s an impressive lady and it was thrilling to imagine the millions of immigrants being welcomed by her torch. 

You can take some time to see Ellis Island if you want, we just passed by it on the boat.

We were starving so we ate at the island….which is not ideal but what can you do when you’re hungry!

Then we drove back into the city. We parked somewhere and then walked around. Our first stop was Carnegie Hall which was really impressive. They do free tours early in the day. Then we snuck into the Metropolitan Opera…I say snuck in because I’m pretty sure there was an event going on since everyone was dressed up and taking photos in front of posters. Those under 25 get a discount on Met tickets – noted for future trips.

We passed by the Lincoln Center and then headed to Central Park. Central Park was so alive with people and energy! I loved it. You could definitely spend days and days at the park but we had dinner reservations! (I’ll be back for you Central Park.)

Our dinner reservations were at a NYC favorite/tradition – Carmine’s. Carmine’s is family-style Italian food. Fair warning: their portions are out of control….you really need to bring a family there. The food was good, the martinis were tasty and the atmosphere was lovely. 

We couldn’t leave New York without one more show, so we headed back to UCB after dinner to watch stand-up. It was a good way to laugh off all those calories from the Italian comfort food.

After UCB, we drunkily ate our leftovers and got ready for our flight home the next day!

Summary:

• Liberty State Park (if you’re in New Jersey)
• Statue of Liberty
• Walk around and check out Carnegie Hall, the Metropolitan Opera and Lincoln Center
• Spend a few hours exploring Central Park
• Come hungry (and with a group) for dinner at Carmine’s, a traditional, family style Italian restaurant
• Laugh off your food coma by watching stand-up comedians take the stage at the underground UCB
• If you wanted to skip the Statue of Liberty, I would seriously consider spending half your day at Central Park! There are gardens, the lake and restaurants for you to discover! 

5 days is just a taste of the city has to offer…so make plans to come back and stay for a little longer! I know that’s what I’ll be doing!