My initial visit to New York City happened unexpectedly, sparked by a misunderstanding with my father that led me to believe my deceased mother had a strong desire to see the city before she passed away.
Years later, I learned that my mom had actually dreamed of visiting Paris. Nevertheless, my time in New York was fantastic, and I eventually decided to relocate here a couple of years later.
During that first trip, I checked off all the typical tourist activities that I mistakenly thought my mother had wanted to experience: ascending tall skyscrapers, admiring impressive architecture, and socializing in bars nestled beneath towering buildings.
While those experiences were enjoyable, I soon discovered there’s so much more to explore in this city—especially if you appreciate diverse cuisine, navigating the subway and ferry systems, and hunting for discounted luxury items.
Day 1: Boating and brownstones
The Staten Island ferry is widely known and admired for good reason—it’s free to ride the large orange boats between Manhattan’s southern tip and Staten Island. This route offers spectacular views of the Statue of Liberty and Lower Manhattan.
For fellow boat enthusiasts, I also suggest trying out the NYC ferry. With a flat fare of $4, it travels along the East River, passing under bridges and offering glimpses of waterfront buildings.
If you’re starting from Manhattan, particularly around East 34th Street, hop on the southbound ferry heading towards Dumbo in Brooklyn. Dumbo, short for “down under the Manhattan Bridge overpass,” is famous for its iconic views of both the Manhattan and Brooklyn Bridges—a favorite spot for Instagram-worthy photos. While many visitors might just snap pictures and leave, I recommend exploring further in Brooklyn, New York City’s most populous and arguably trendiest borough, depending on who you ask.
Make sure to visit Jane’s Carousel, a beautifully restored 1922 ride nestled between the bridges, and then take a stroll south through Brooklyn Bridge Park. Along the way, you’ll pass several piers—once bustling docks now transformed into serene picnic and recreational areas with stunning views of Manhattan. It’s a perfect setting for a romantic proposal, as my younger brother did last year. If proposing isn’t on your agenda but you enjoy activities like soccer, basketball, or roller-skating, you’re in luck.
Once you reach Pier 6, where you’ll find the inviting (albeit pricey) rooftop pizza restaurant Fornino, continue your journey by walking up Atlantic Avenue for some shopping and a coffee break at Goose Barnacle. This independent clothing store also houses a hidden bar in the back. Owner Dave Alperin, a fourth-generation Brooklynite, is friendly and incredibly knowledgeable about the area. He can provide insider tips ranging from where to find the best sandwich (try Mamma Roma at Lillo Cucina Italiana) to the location of a semi-secret basement speakeasy nearby called Le Boudoir.
From there, I would recommend taking a bus or cab to Fort Greene, a picturesque neighborhood known for its charming townhouses that resemble those often seen in Brooklyn-themed movies. Once there, consider dining at Olea. If you arrive before 6:30 PM, take advantage of their excellent happy hour deals.
Day 2: Rude T-shirts and not-quite Rolexes
In Manhattan’s Soho neighborhood, you’ll find a plethora of upscale shops perfect for those with a penchant for luxury goods or window-shopping. Start your stroll east along Prince Street from West Broadway, where you can admire the charming architecture that sets this area apart from the city’s usual skyline of towering modern buildings. Make sure to visit Fanelli Cafe, a local institution established in 1847, for a coffee or a bite to eat. Afterward, continue your journey south along Broadway towards Chinatown.
Chinatown offers a variety of excellent dim sum spots, such as Golden Unicorn, known for its grand dining hall on the second floor of a marble-like building. After enjoying dim sum, take a leisurely walk along Canal Street, exploring side streets where you can find inexpensive souvenirs like snow globes, small statues, and quirky T-shirts (some of which can be quite cheeky).
In addition to souvenirs, Chinatown is renowned for its counterfeit watches and handbags. If you’re not inclined to spend $30,000 on a watch but have around $100 to spare, you can find decent imitation watches that look quite convincing. For those seeking authentic timepieces, the food markets along Canal Street also offer genuine options that function properly—a subtle defiance against high-end brands. And if you’re in the market for “designer” bags, you’ll find plenty of options here as well.
If you’re still hungry, make sure to check out Great NY Noodletown—it lives up to its name, especially with their delicious roast pig on rice.
Afterward, continue south and make a stop at Whiskey Tavern, which I can confidently say is the friendliest bar I’ve ever visited (and I’ve been to quite a few). They go the extra mile with personalized welcome signs placed on your table or behind the bar, adding a nice touch to the experience. But the real charm lies in chatting with the locals and regulars. Being close to City Hall, it’s also a favorite spot for newlyweds celebrating with shots of whiskey and chicken wings.
If you’re up for more fun and enjoy singing or shouting, head over to Up Stairs, a karaoke bar discreetly tucked away behind an unassuming doorway on Canal Street. Drinks are affordable, and the place buzzes with enthusiastic revelers—it’s a lively spot for a memorable night out.
Day 3: Seaside shenanigans
If you’re like me and appreciate once-glamorous seaside attractions now steeped in nostalgic charm, hop on the F train to Coney Island. Many overlook New York City’s waterfront, but Coney Island offers plenty to explore despite not being the ideal spot for swimming (try Fort Tilden or Jacob Riis Park for that).
Start your visit by catching a Brooklyn Cyclones game at Maimonides Park. As a feeder team to the New York Mets, tickets are typically inexpensive and readily available. You’ll also enjoy a scenic view of the Atlantic Ocean. For a fun souvenir, grab a beer served in a foot-long plastic baseball bat. Sometimes, they even let fans “run the bases” after the game—an enjoyable experience, especially after indulging in a few of those baseball bat beers.
After the thrill of watching a Brooklyn Cyclones game, head east towards the Cyclone, one of the oldest and, by all accounts, most rickety roller coasters in the United States. This wooden ride, described as “pretty extreme” by Coaster Critic, will celebrate its 100th birthday in 2027, and it certainly shows its age. Proceed with caution!
Once you’ve experienced the adrenaline of the Cyclone, unwind with a drink at Ruby’s, the oldest bar on the boardwalk. Admire the black-and-white photographs capturing Coney Island in its 1930s heyday, and if you’re feeling adventurous, indulge in a cardboard box full of clams.
During late June to September, every Friday night, you can enjoy a spectacular fireworks show on the beach, which draws a large crowd. For a unique experience, pair the display with borscht and a drink (coffee or vodka) at Tatiana’s, a Russian restaurant and nightclub just a short stroll along the boardwalk from the Cyclone.
A quick side note: Coney Island isn’t just a summer destination. I once visited a day after it snowed, and it was a wonderfully unique experience.
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