Life With Landing / Tales of a Digital Nomad

Tales of a Digital Nomad: How We Spent Four Months Living in New York City 

By Madison Liston Gomes | Feb 3, 2023
Living as digital nomads in New York City, Landing members Madison and Ivan pose on the Brooklyn Bridge

It feels so strange to admit that I had never visited the most touristy city in my own country. I’ve always wanted to check out New York City, but there are too many incredible things happening there all the time. How do you pick? Do you go in the summer for the gorgeous weather? Fall for the Thanksgiving Day Parade? Winter for the Rockefeller Center Christmas Tree? 

However, living the digital nomad life with Landing meant we didn’t have to choose! Here’s how my husband Ivan and I spent four months in New York City celebrating several holidays, discovering incredible bars and restaurants, and taking advantage of the never-ending stream of things to do in the Big Apple: 

Celebrating holidays in New York City

Halloween in NYC

Only in New York City can you get FOMO on a regular basis from having to choose between two incredible events happening at the same time. There were so many free Halloween events to choose from that we struggled to narrow it down to even two!

The first was the Tompkins Square Halloween Dog Festival. It is the world’s largest costumed dog event, so how could we resist? Dogs and their humans walked across a stage and modeled their costumes, an announcer described what they were wearing, and judges judged. 

However, the event was so popular and crowded that we actually never saw any of this happening! We found a spot near the stage’s exit and watched the pups as they trotted off to celebrate their brief modeling career. The costumes were outrageously cute and creative, making this one of the most wonderful and wholesome events we’ve ever been to in our lives. I highly recommend it for anyone spending the fall in NYC. 

For the second event, we were the entertainment! We joined the Greenwich Village Halloween Parade, the largest Halloween parade in the world. We read that all you have to do is show up wearing a costume at the starting point to join the parade, but what we didn’t realize is that you are then packed into a dense crowd and have to wait over an hour to be released into the streets for the actual parade. The good news is the density of the crowd kept us warm on a chilly Halloween night. 

When we were finally released into the official parade, we saw people pressed up against their apartment windows, standing on their roofs, and filling the sidewalks to see. It was a cool look at life in NYC, and interacting with fellow paraders and spectators give this big city a small-town feel. 

Halloween wasn’t even on my list of things I wanted to experience in New York before we came here, but I’m so glad we did—it was a Halloween I will never forget!

Thanksgiving in NYC

The Macy’s Thanksgiving Day Parade is no doubt a bucket-list experience. It has been on the TV at my family’s house every Thanksgiving morning for my entire life, and getting to experience it in person was very cool.

For Thanksgiving dinner, we ordered a classic spread from Butterfield Market. They had all of the traditional foods in small servings, the price was affordable, and the food was delicious. 

Insider tip: The night before the parade, the balloon floats are inflated in the street and placed in nets, so you can walk around and get an up-close view of them. 

Christmas in NYC

There is a good reason why so many Christmas movies take place in New York City—the festivities here are on an entirely new level! The Christmas season in NYC is absolutely iconic, from seeing the Rockettes Christmas Spectacular at Radio City Music Hall to shopping at the city’s countless Christmas markets. 

Sampling all the amazing food in New York City

New York City has some of the most famous food in the world! We ate more pizza and bagels than we ever have in our life, drank at some of the best bars in the world, and feasted on the cuisines of all seven continents. 

The New York classics 

When you live in New York City, you have to try enough of the top pizza and bagel spots to form your opinion on which is the best of the best. They’re all worth visiting (and several are super historic), but for us, the best pizza goes to the Hot Boi pizza at Scarr’s, and the best bagel goes to the everything bagel at Leo’s. Another New York classic we absolutely loved were the hotdogs from Billy’s Hot Dog Cart right by Central Park. 

The best bars in the world

Double Chicken Please is recognized as the sixth best bar in the world, and the drinks cost no more than those at a typical NYC bar. Reservations are definitely the way to go, but you can get lucky and snag a spot. We realized we were in the area after dinner one night and decided to check it out. After waiting for just half an hour, we were brought into the swanky back room. 

The vibe here is casual, allowing the focus to be on the creativity going on behind the bar. All of the drinks are inspired by foods, such as Cold Pizza, Beet Salad, and Key Lime Pie. They were completely delicious and unlike anything we had ever tried before. 

Our other favorite bar tops our list for a very different reason. Nubeluz is a new bar on the 50th floor of the Ritz Carlton NoMad. The drinks are good (especially the Salt Air Margarita), but what is leaps above here is the view of the city. It’s a great way to get the observation deck experience, but instead of paying to stand somewhere and take pictures, your money is going toward tasty drinks. 

Tasting international cuisine 

New York City truly has everything you could ever imagine for food—and if it makes it in this city, then it’s the best of the best.

We tried Sri Lankan food for the first time at Lakruwana in Staten Island and ate so much of it that we could barely stay awake for the ferry ride home. We found our new favorite Indian restaurant ever at Angel in Jackson Heights. We had the best boba at Xing Fu Tang in Flushing and may not be able to settle for boba elsewhere ever again. We also ate Senegalese food for the first time at Pikine in Harlem, and it was so amazing Ivan cried (although that may be because he took a huge bite out of a scotch bonnet pepper). 

We even made it a goal to find food or drink from all seven continents (including Antarctica!), and made this video about it:

Exploring the many events in NYC

Living in New York, you eventually get full from all this delicious food and have to find ways to spend your time that don’t involve eating. Fortunately, NYC has you covered, with an overwhelming abundance of things to do

Broadway lotteries

Almost every Broadway show has a lottery you can enter for the chance to buy great tickets at a fraction of the standard price. If you are in NYC for a quick vacation, you can’t risk not winning and missing the show, but if you’re living there long-term as a digital nomad, this is your time to thrive!

We won the Broadway lottery for “Harry Potter and the Cursed Child,” “The Book of Mormon,” and “Funny Girl” (starring Lea Michele!). Together, the tickets for all three of these shows ended up costing us less than a regularly priced ticket to one show. It was magical!

Live audience

Tickets for “Saturday Night Live,” “The Tonight Show,” “The Late Show,” and so many more shows are totally free online! Ivan is a fan of Stephen Colbert, so I surprised him with tickets to “The Late Show” and he absolutely loved it. This is definitely a fun way to experience one of the industries that makes NYC such a special city. 

Always something

I’m not exaggerating when I say there is always something going on in this city—and, surprisingly, these things are often free. If you follow local Instagram accounts (or just walk the streets), you’ll see what I mean. We went to a free Diwali event at Times Square where Jay Sean was performing. I got pulled into a parade through Chinatown when walking out of a massage. And, the Wall Street tree-lighting ceremony was right outside our Landing (and featured the Aflac Duck!). 

New York City is a truly wonderful, random, and culture-rich place to be, and I could not be more appreciative of our time here. It was absolutely legendary getting to experience the seasons, holidays, free events, and so much more that we never would have been able to make happen on a quick trip. 

Winter has officially arrived in New York City, so thanks to our digital nomad lifestyle, we’re off to live somewhere much sunnier. But I’m already looking forward to our next time in New York City. It truly captured my heart. 

Madison Liston Gomes

Madison is a YouTuber, foodie, and full time traveler with her husband Ivan. She strives to follow the maddest adventures on her heart while connecting people and opening minds through her YouTube channel. You can join her “madventures” on YouTube under the channel name madventure.