Planning an express trip to a city as big as New York can seem overwhelming, but it doesn’t have to be. Pick out a couple of must-see neighborhoods and pre-book one “main event” for each day you’re there… (I will help you with that!) Then, let the city guide you with its fast lane charm and sea of complex characters. There will never be a dull moment. If there is, you’ve done something wrong!
Where to stay: Sonder One Platt, Financial District
Sonder is an affordable boutique hotel with locations in major cities all around the globe. There are 7 just in New York City alone. Think of a design-centric Airbnb but with New Age traveler technology. Your room number and passcode are provided through the Sonder app where you can also make requests for housekeeping. There is at least one staff member on site 24/7; otherwise, check-in & check-out are completely contactless. The room features a full kitchen and building amenities include a gym, spacious lounge, and rooftop. They also offer luggage storage which is so key!
The Financial District, or Fidi, is a wonderful spot to explore as it is home to many top attractions including Wall Street, New York Stock Exchange, World Trade Center, Pier 17, Stone Street, and much more. It is also well-connected to the rest of Manhattan, just 30 minutes via Subway to Central Park or Rockefeller Center.
How to Get Around
During our stay in New York City, we used a combination of Subway, Uber, and of course, lots and lots of walking. I believe taking the Subway is a must if you want the full New York experience. It is definitely the most affordable option and it provides a glimpse into the life of locals, from glamorous to eccentric to downright bizarre. Of course, it’s always important to be aware of your surroundings and protect your possessions, but for the most part the Subway is safe and always well-populated. Uber rides range from $20 to $60, so we only took it when we absolutely had to.
We flew into Newark and took an Uber into the city. It was around $40 and took about 30 minutes. We arrived to Sonder well before check-in at 12 pm but they allowed us to store our luggage. From there, we wasted no time and jumped right into the activities below!
Lunch @ Stone Street: Mad Dog & Beans Mexican Cantina
Stone Street is one of the city’s oldest streets and was actually the first road to be paved in New Amsterdam, which later became New York. Cobblestone streets and Dutch colonial style buildings set the scene for a picturesque lunch spot. In winter they have heated bubbles perfect for outdoor, COVID-friendly seating. There were many options for dining, all with enticing menus, but we settled on Mad Dog & Beans Mexican Cantina. There I ordered sangria, street corn, and a papaya salad (actually served out of a papaya–woah!) ¡Delicioso!
Wall Street, Stock Exchange, World Trade Center
Given the express nature of this trip, we did little more than walk by these attractions, admiring them from the outside. Worth it, though! We actually weren’t able to make it to the World Trade Center (will save for a future visit), but it’s very doable because each of these attractions are within walking distance. On Wall Street you can snap a picture with the bull (some people were actually climbing on top of its head — don’t be that person).
This was a spot that we stumbled on after picking up post-lunch Americanos at Starbucks. We were out for a walk by the river, just a couple blocks off of Stone Street and wandered up the elevator to the rooftop where apparently, they put on concerts during the summer. There were ‘Cozy Winter Cabins,’ set up at the time, for the holidays, but we just drank our coffee on the terrace overlooking the Brooklyn Bridge. Simply gorgeous and definitely worth a visit if in the area!
5th Avenue – Rockefeller Center – Bryant Park
Tourist trap? Yes. Must-see? Also, yes. From a visitor perspective, these three destinations feel like quintessential New York City. 5th Avenue gives off major ‘Breakfast at Tiffany’s’ vibes while Rockefeller Center is where they film the Today show and also home to the famous Christmas tree. It is close to Times Square if you should want to visit that as well, (not my cup of tea). Though we had already seen these spots on our first visit to New York, we wanted to explore them again during the holidays. You can start near Central Park, walk the length of 5th Avenue (window shop ’til you drop!) and stop along the way at Rockefeller Center and Bryant Park.
Jazz Club: Flat Iron Room
From Bryant Park, we walked about 20 minutes south to the Flat Iron District, home of the namesake Flatiron Building as well as a top notch, snazzy jazz club – the Flat Iron Room. A little lazy on the names if you ask me, but the club speaks for itself. Entering through the secluded corridor you’ll be escorted to a dark room with intimate tables facing the stage where jazz musicians perform nightly. MAJOR speakeasy vibes Reserve in advance as the place was fully booked the night we went. The reservation gets you a two-hour slot at your table and from there, you can chill at the bar or the standing area if you so please.
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Uff da, if Day 1 wasn’t busy enough for you, get ready for Day 2! First stop, caffeine.
Coffee: Joe & The Juice
The city is littered with the chain café / juice bar fittingly named “Joe & The Juice.’ At times it felt like there was one on every block. The coffee is served in adorable pink and purple take-away cups that made me very happy indeed. I opted for a flat white and banana muffin which got my morning off the a sweet, lively start.
I certainly wouldn’t consider myself an art person…nor even a museum person. To be honest, I had only really heard of the MET because of the MET Gala. But, as an aspirant well-rounded traveler I thought it apt to pay a visit to the city’s most renowned museum located in the iconic Central Park. At $25 a ticket, I would say it is worth seeing. The best part? The Egyptian Temple of Dendur. That in itself makes the museum visit worthwhile!
Given that the MET is located in Central Park, the most obvious pre or post museum activity would be to tour around the sprawling greens of Upper Manhattan. The best way to see the park, in my opinion, is to rent a bike. You will feel you are part of the action but can still hop off for photo ops at the Gapstow Bridge and rock lookout.
The West Village
While not an obvious transition from Central Park, this neighborhood was a must-see for me given my affinity for all things Sex and the City. Yes, you may have heard that Carrie Bradshaw’s apartment in the series is located at 66 Perry Street, a classic New York City brownstone in the West Village. Fans can snap a picture in front of the stoop, but be careful not to walk on the stairs as the current owners do not love that their apartment is now a tourist attraction. (Hey, comes with the territory if you ask me!) While in the neighborhood you can stop at Magnolia Bakery for a sweet treat.
Dinner: Felice 56
In a city overflowing with Italian eateries, Felice leaves their mark as a classy, reputable chain with an authentic and delectable menu. We made a reservation for 7 pm and were treated to excellent service, fresh pasta, and a smooth, romantic ambience. I ordered Tonnarelli Cacio e Pepe, a pasta dish with some cheese that is fancier and much more mature than I will ever be.
While not for the faint of heart, LAVO provides a quintessential New York nightlife experience that will get you close and personal to some major DJs and apparently, the occasional celebrity. (If that’s your thing). It was absolutely packed and definitely not conducive to social distancing, but that’s the price you have to pay if clubbing is on your New York agenda. It was outrageously fun and worth whatever variant I may have picked up there. We purchased tickets in advance for New Years Eve through Joonbug (fast pass is recommended unless you want to wait in an hour-long line). Visit their upcoming events page to buy tickets for specific DJs.
Are you still kicking after that night out at LAVO? Good, because I’ve got a whole new line up excursions for your last day in New York City that you’re not going to want to sleep on!
It’s time to talk about a necessary evil. To fly back to the Cayman Islands, we needed an antigen test the day before travel. There are many pop-up sites on the streets in high traffic areas of the city, but those can take 48 to 72 hours to receive results. Not to mention, some are exceptionally sketchy in appearance and overall vibe. We went to Bloom Labs and paid $75 for an antigen test that we got back in 3 hours. PCR tests are also available, albeit more expensive. There was a line outside the site but it went very quickly. I recommend this lab to any traveler needing quick results as it is an efficient, and professional testing site.
From the testing center in Midtown, we went walking in search of a restaurant to satisfy our sudden Japanese craving and stumbled upon Mazu Szechuan Cuisine in the young, vibrant neighborhood of Murray Hill. While the restaurant wasn’t necessarily dripping in ambience, nor overly gourmet, it provided large portions and essentially got the job done. What was more impressive was the area, which as it turns out, is something of a nightlife hub for recent college grads. Definitely a cool place for young travelers to test out a new bar scene or grab a quick bite.
Shifting gears, it’s time to get to Brooklyn before the sun sets. One way you can do this is by walking, jogging, or biking over the emblematic Brooklyn Bridge, which is roughly a mile in length. Of course, you can also drive over it too, but what’s the fun in that? When we walked it on our first visit to New York City in the summer, it was packed with photo-happy tourists and savage cyclists showing no mercy to those in their path. Travel vloggers beware.
Whether you make it all the way across the bridge or go the route of Subway, once you’ve arrived in Brooklyn you must go to to the Pinterest-famous photo spot on the corner of Washington and Water Street. Old-fashioned red-brick buildings frame an iconic view of the steely-blue Manhattan Bridge. This photo-taking venue is located in the artsy neighborhood of Brooklyn named Dumbo. Your Instagram feed will thank you. From there, we walked to the waterfront and passed by Pebble Beach and Jane’s Carousel, stopping for a rest in the Time Out Market. Further walking adventures carried us all the way to 1 Hotel Brooklyn Bridge for the most expensive chai tea latte of my life in their coffee shop, Neighbors.
Brooklyn Nets Game
What do you do to reward your Instagram husband for taking countless pictures of you during your New York City trip? You agree to an NBA basketball game and will yourself to stay awake through all 4 quarters. Go Nets! Kevin Durant? Love that guy!
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Hi, I’m Kate! I’m a Wisconsin native who traded her snow boots for flip-flops in May of 2020 when I packed my whole life into two suitcases and moved to the Cayman Islands with my partner, Bryan. I created Island Diaries as a way to document my island adventures and share about the Cayman lifestyle. A Midwest girl at heart, I bring a fresh perspective to Caribbean life, serving as a guide for locals and tourists alike on all things Cayman Islands. Whether you are local to Cayman, planning to visit, or just curious about island life, I invite you to explore Island Diaries and let this site guide you on your next island adventure!
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