There is no more fabulous gift than a surprise. A secret you have been holding close, waiting with bated breath for the perfect moment for the big reveal. That is what I did to celebrate my second anniversary with my boyfriend Kerwin. Those who know me know there is no more extraordinary love language for me than planning a trip. Researching the best hotels for the location and price, finding ideal airline tickets, and building out a full itinerary are the most prolific ways I show my affection.
This year, I nailed it. On a warm and rainy day in Chicago, sitting at a table at Beatnix, I hand Kerwin a white envelope. He looks at me, confused. When I told him I had a gift for him, he was expecting something wrapped in ribbon. He slowly opened the envelope with a bewildered look on his face until he unfolded the piece of paper confirming two flights to New York City. I pulled off the biggest surprise.
Weekend trip to New York City
Coming from a family of immigrants, Kerwin has always wanted to visit New York City. It was where his Mom first went when she came here from the Philippines nearly 30 years ago. New York City meant something to him, so I surprised him with a long weekend trip to New York City for our two-year anniversary.
Thursday- Check-in at Hotel
Thursday afternoon, I frantically finish up my work by 4 pm so we can rush to the airport for a 5 pm flight. It’s a short two-hour flight from Chicago to New York City. Once we arrive, we take a cab into the city to our hotel.
Checking into the Downtown Millennium Hotel, I realized the location could not be more perfect. My research paid off. Our hotel is in the heart of the Financial District, across from the World Trade Center, near the Brooklyn Bridge. I spot pizza place on our drive, which seemed the best way to kick off a trip to New York City.
Buzzed from the arrival in a new city, we walk a few blocks from our hotel to Joe’s Pizza. It’s our first slice of New York Pizza. The most significant difference between New York and Chicago-style pizza has nothing to do with the taste. When you order a deep-dish pizza in Chicago, it takes at least 45 minutes to prepare. Grabbing a New York slice, you can be out the door eating your pizza in less than a five minutes.
Friday
Unlike New York, Kerwin and I allowed ourselves the luxury of a few more hours of sleep than usual. He had a morning work call, and I had a couple more hours of shut-eye calling my name. The weather forecast shifted from when I checked it at the beginning of the week. It was going to be a sunny day after all. We get ready and head out to figure out how to navigate the Subway for the first time. Where we stayed in the Financial District was about a 15-minute Subway ride to Central Park.
Walking outside of our hotel, straight ahead is the 911 Memorial, and a block further is the Subway Station we get on. I bought a one-way ticket, and Kerwin did the same. “Hurry, hurry!” he yells as another subway train pulls into the station. I grab my ticket, scan it, and run on the train before the doors close. That’s when I turn to Kerwin and ask, “Which train are we on? Are you sure we are going the right way”? His answer surprised me and made me laugh. He replied, “Don’t they all go in the same direction”?
We were on the wrong train.
It didn’t take long to hop off and onto another train heading toward Central Park, but it made us both laugh. In Chicago, the Metra only goes in two directions if you take it: into the city and out of the town. You will likely get on the right train because it only goes one way. The Subway in New York City is more complicated, but with the help of Google Maps, we figured it out in no time.
Liberty Bagels
New York has a magical feel to the city that is hard to describe. Every movie about it was right. The whole morning, we said, ” I can’t believe we are in New York City.” New York City holds significance, especially for immigrant families like the one Kerwin grew up in. I cannot even begin to describe how amazing it feels to take a weekend trip to New York City, a mini adventure amid our daily schedules.
We walk by the Plaza where the famous Home Alone 2 was filmed. The first Home Alone was filmed in Chicago, and that is a claim to fame that we Chicagoans hold onto.
Arriving at Liberty Bagels, I am stunned by the number of cream cheese options, from dill pickle to strawberry. They had all the sweet and savory flavors you can imagine. I pick a bacon, egg, and cheese bagel and Kerwin a strawberry cream cheese, both on an everything bagel. Grabbing our bagels, we find a seat across the street to eat in the shade before heading into the park.
It was already starting to get hot. My hair, which I spent half of the morning curling, was already in a ponytail. The humidity had done a number on the curls.
Central Park
Central Park is huge. 840 acres, huge, to be exact. We walk through the park and try to think of all the movies we know that have been shot here. Of course, we stopped by the infamous Bethesda tunnel where Chuck and Blair from Gossip Girl were married. As we look at the water beyond the tunnel, I see a few people paddling boats. That looks exactly like what we want to do today.
Boat Ride at Central Park
The Boat House, a famous restaurant for being featured in Sex & the City, is also, in fact, a place where you can rent boats. Kerwin and I could rent a row boat for the hour at the Row Boat Rental. I had yet to learn how far back you could row before making this purchase, signing the waiver, and getting into the boat. The lake in Central Park is a lot larger than I had anticipated, and the best part is that there were turtles you can spot along the way.
The sun beat down on us, but we weren’t paying attention to the heat. Nothing screams summer more than being in a boat, and the views of the city in the background were unbeatable. When our hour was up, we decided to get out of the heat and head to the Metropolitan Museum of Art to see the legendary art exhibits and cool off.
Metropolitan Museum
A friend recommended we visit the Egyptian exhibit, and I am so glad they did. The Metropolitan Museum is one of the largest museums in the country. There are numerous exhibits and it’s easy to get lost. We decide to focus first only on the Egyptian exhibit because there is no way we are going to see everything the museum has to offer.
The museum has beautifully decorated mummy coffins and even a giant temple in one of the rooms. The exhibits are detailed and it’s easy to get lost in all of the information. Kerwin takes an interest in the weaponry, and the sword displays. As someone fascinated with Egyptian history, I was most intrigued by mummies. After a few hours, we decided to call it a day because our feet ached.
Dinner near Hotel
After a long day in the sun and walking around the Met, Kerwin and I take the train back to our hotel. As soon as we step into the hotel, it starts to pour rain. I watch it from our hotel for about an hour while we prepare for dinner. Finding a nice restaurant within our price range in this area was difficult. Still, we finally found Trinity Place, an American restaurant in what used to be a bank, which was very fitting for the Financial District. The food was delicious, but the best part was splitting a slice of New York Cheesecake and then calling it a night.
Saturday
Coffee at Ole & Steen
The following day, first on my list is to get coffee. We drank a lot of water the night before and stopped by Target to get a Powerade. Now that I was hydrated, I could drink my coffee. New York City summers are so hot, from the crowds to the hot asphalt, drinking lots of water is important. This morning felt slightly cooler, so we lucked out of the heat.
Ole & Steen has a chic and elegant feel to it, a place I would have loved to bring my laptop and stay a while. But today, we get our oatmilk vanilla lattes to go and walk towards the battery.
Staten Island Ferry
I had heard that the Staten Island Ferry has some of the best views of Chicago. The ferry runs every hour at The Battery, and it takes about 30 minutes to get to the other side. Although scammers often try to convince you to purchase tickets, the Staten Island Ferry is completely free to the public. Boarding the boat, we find a good seat to enjoy the views. Shortly after the boat starts, I walk to the back of the ship to get better city views.
On the ferry, some tourists like us want a closer look at the Statue of Liberty; for others, this is their commute to work. I glance over to get a closer view of her, The Statue of Liberty in all of her glory. She is smaller in person than on TV, but her height doesn’t take away her magnitute. Kerwin whispers over the crashing waves, “I want to take my parents on this if we get a chance to return”. There isn’t much on Staten Island so we turn right around and get on the boat coming back. After all, I only came for the views.
Union Square Farmer’s Market
Up next on our to-do list is to find a farmer’s market. Aside from being on a boat, farmer’s markets are the epitome of summer. This farmer’s market is good, except for the fact that there was no ready-to-eat food. I was hopeful there would be something we could grab for lunch, but being a traditional farmers market, they sold bread, butter, fresh fruits and vegetables, and all the things you would need to cook with. Our hunger would have to hold off for a little while. I stroll through the market and purchase a few jewelry pieces from a local artisan.
Washington Square
We needed to check out Washington Square and the iconic arc to go to New York City. The streets on Washington Square are attractive. Some are peddlers selling art, others are sunbathing on the grass, and in a far corner, we see a young couple making out on a park bench as if no one else is around. New York is like that: a diverse crowd, which is why I love it. Our stomachs start to grumble and I know it’s time to find lunch since my farmer’s market place didn’t work out.
Lunch in Little Italy
It is on our way, so we’ll stop by. It’s been years since I have been to Little Italy or Chinatown. I was on a trip with FBLA in middle school the last time that I went. All I remember is that I tried an eclair in Little Italy for the first time, but it could be a great spot for lunch. I should have anticipated our touristy Little Italy has become. Employees of the restaurant stand out in the street and try to convince you to try their pasta.
We had to walk a couple blocks down the street to find a quieter restaurant who wasn’t using typically touristy sales tactics to convince us to dine with then. Kerwin and I split a pizza and drank all the water in sight while contemplating if we should buy a fake designer bag.
Chinatown
Chinatown is known for street vendors who secretly sell fake designer bags, and we almost fell for it. A guy took us to a purse shop and opened a door leading to a secret bag room filled with purses that all looked real. I eyed the Dior Saddlebag. It’s a purse I could not afford if it were real, and the quality of the fake was nice, but I couldn’t bring myself to buy something I knew was fake. Ultimately, I left empty-handed but excited for the next surprise I had for Kerwin.
Sunset at the Empire State Building
The goal is to see the sunset over the Empire State Building. I bought Kerwin and I tickets as another part of the anniversary suprise. Except for one big mistake the plan was perfect. I timed the sunset incorrectly. It said that sunset started at 8 pm, so I purchased tickets for 6:45, and by 7 pm, we were out on the sky deck. The experience is ideal for photos, but we waited for the sun to come down. In total we wait 3 hours for the sun to go down entirely. The views were incredible, but the wait and the crowds made us both dying to leave as soon as the sky turned black.
Times Square
After the long 3-hour wait to see the sun go down, I foolishly plan to visit Times Square at night. It’s true that Times Square is the worst place to visit in New York City, but you have to see it when you visit for the first time. The jumbo screens and bright lights are magnetic and it is breathtaking, but the crowds are also overwhelming. After the long day, we quickly walked through Times Square before looking for somewhere to eat dinner. But being near the Theatre District, of course it had to be a dinner and show. Or diner and a show.
Stardust Diner
The last time I went to the Stardust Diner was on my 18th birthday, nearly 10 years ago. The diner is a restaurant where the waiters and waitresses are aspiring Broadway stars. In between taking orders, they perform songs and dances for the audience. The talent rather than the food is why you go to Stardust Diner. All the tips you provide at the end of the meal go toward the employees getting acting and dancing classes to meet their goals. It’s past 10pm by the time they do the finale and it’s time for us to head back. After all we have an early morning tomorrow and I want to get enough sleep.
Sunday (final day on our weekend trip to New York City)
Brooklyn Bridge
The last day on our weekend trip to New York City starts early. I have no idea how I convinced Kerwin, but the plan is to wake up and see the Brooklyn Bridge at 5:30am. It’s past 5:30 by the time we wake up, but we head out and walk the 10-minute walk to the Brooklyn Bridge at around 6:00am.
Aside from a few runners crossing the bridge on their daily route, there are no crowds and no people. Kerwin and I take a few photos, enjoying the few crowds. After all we wanted a few photos for our anniversary. When Kerwin suddenly says, “That’s Casey Niestat”. No way no way. The Brooklyn Bridge is one of our favorite YouTubers’ running spots. I spot him and Kerwin says “hi” he kindly waves, and that small gesture made our day.
Walking along the bridge and we discuss how much fun we have had on our weekend trip to New York City. We both have a newfound love for New York. Kerwin even suggested a fall trip. Maybe one day we will move to New York City, but for now, the goal is to make Chicago our home and New York a fun destination.
The bridge is longer than you would thinking. It’s almost a mile long. We walk all the way across and head over to Dumbo Street for a few photos at the iconic spot with the Manhatten Bridge.
After snapping a few pictures and asking another couple to take a few of us together, we get a cup of coffee at Joe’s Coffee to warm up before walking back to start packing up our bags to go home. The trip went by so fast. Truthfully, I was not ready to pack up my bags to go home, but we have had the best time so far and still have the rest of today to enjoy.
Brooklyn Flea Market
The hotel held our luggage as we headed back to Brooklyn to explore the Brooklyn Flea Market near Dumbo. This flea market is an antique and vintage lover’s dream, but Kerwin, that’s not Kerwin and I’s vibe, so we didn’t find anything. At this point, our feet are starting to feel exhausted from the days of walking, and the next stop takes us a lot longer.
Pier 16
It takes us four stops to rest our tired feet from the Brooklyn Bridge to Pier 16. By the time we reach the pier, we find a seat with views of the Brooklyn Bridge and reminisce about our weekend. Eventually, it’s time to head back to the hotel and get ready to go back to the airport, but not before one last slice of pizza.
Joe’s Pizza
It really wouldn’t be a weekend trip to New York city without another slice of pizza. Joe’s Pizza was one of our favorite food spots on this New York trip, so we had to grab one more on our way out of town. Kerwin and I got pepperoni slices, which tastes even better the second time. Although it’s early we decide to grab our bags and head to the airport, and I am so glad we did because the journey took longer than we thought.
Back at the airport
Since it’s in the middle of the day and we have already navigated the subway successfully we decide to take the subway and the bus to the airport instead of an Uber. An Uber from the Financial District to LGA airport can easily be over $100. After spending as much as we did over the weekend, I was happy to save a few bucks by taking the subway, but the trip took over two hours.
First, we took the subway to the Roosevelt Bus station, which took about an hour. The bus ride was about 15 minutes, but that wasn’t the only bus. We got on another bus at the airport to take us to our terminal. There was so much traffic that the bus to our terminal added another 45 minutes onto our trip, even though we were at the airport. I was so glad we got there early. After sitting for nearly two hours my feet were happy to rest, but sad our weekend trip to New York City is coming to an end.
This trip was everything I could have hoped for out of a perfect weekend trip to New York City with my Love.
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