The ultimate Manhattan weekend: a three-day guide to its must-see highlights

It’s been a decade since I settled in New York City, and I still find its brilliance captivating. I wouldn’t label myself a true local – having grown up in a quiet cul-de-sac and taken a school bus (not the subway) – but Manhattan has become my home over the years, with various neighborhoods along the way. The rent? Astronomical. The opportunities? Priceless. 

Jay-Z and Alicia Keys were spot on when they described NYC as a “concrete jungle where dreams are made.” People flock here to discover themselves; the options are limitless, and it’s up to you to navigate the beautiful chaos. The city comprises five boroughs, each possessing its unique charm – Manhattan, Brooklyn, Queens, Bronx, and Staten Island – but my focus will be on Manhattan, because if you're after the Big Apple’s highlights, this is where your journey begins.

• Best time to visit: Manhattan never sleeps, so come whenever suits your budget. However, I prefer to arrive during the day for safety, particularly if using public transport.

• Transportation from the airport: You have several options ranging from $ to $$$. Here’s a comprehensive guide on getting to and from NYC’s three primary airports: JFK, LGA, and EWR.

• Getting around the city: Walking or taking the subway is best. While rideshare services are available, be cautious; surge pricing can skyrocket during peak times, late nights, or inclement weather. Often, taking the train is faster than driving due to heavy traffic.

• Accommodation recommendations: For a quintessential NYC experience, try The Plaza – yes, from Eloise at The Plaza. (Also featured in Sex and the City and Home Alone 2!) For a trendy yet budget-friendly stay, consider The Dominick or Arlo in SoHo or Midtown.

• What to bring: Your comfiest shoes. You’ll be logging plenty of steps.

Friday

Morning: Start your day with a coffee and a quintessential New York bagel topped with bacon, egg, and cheese at Best Bagel Coffee, or opt for cream cheese and lox (smoked salmon) at Russ & Daughters. Then, venture to Times Square, the dazzling Disney World of NYC, which locals tend to avoid. It’s a must-see at least once, so arrive early to dodge the crowds. If a Broadway show is on your must-do list, make sure to swing by the TKTS booth for last-minute discounted tickets.

How to spend the day: Instead of heading up the Empire State Building, make your way east to Summit One Vanderbilt, a modern skyscraper offering breathtaking views of the city along with immersive art displays. It connects directly to Grand Central Terminal, which is also worth a visit – don’t forget to gaze up at the stunning ceilings! The terminal features a food court with plenty of lunch options.

If you have some extra time, hop on the 4 or 5 express subway to the Upper East Side and explore The Metropolitan Museum of Art. You could easily spend an entire day there, but even a couple of hours of wandering is well worth it.

Dinner: If you enjoy sake and Japanese small plates, be sure to book a table at Sakagura – a hidden gem tucked away below an unremarkable midtown office building that’s easy to overlook. For an upscale dining experience, indulge in the French-inspired seafood at the Michelin-starred Le Pavillon.

After dark: Downtown is the place to be for nightlife. Explore the East Village bar scene, starting on St. Mark's Place, or enjoy cocktails at a chic rooftop bar in the Lower East Side. Whichever route you take, your night will likely conclude with a $1.50 slice of pizza. (While some spots still offer 99-cent slices, many have raised their prices due to inflation.)

Saturday

Morning: Brunch is your best companion. Skip Jack's Wife Freda – the lines have become unbearable since its TikTok fame – and head to Two Hands, an Australian café serving hearty yet healthy meals. (Don’t miss the gigantic banana bread to share!) Their TriBeCa location is less crowded and is just across from two artistic landmarks: 56 Leonard Street, known as the “Jenga Building” (a skyscraper of stacked condos), and Anish Kapoor’s new shiny sculpture, which is essentially NYC’s version of his Cloud Gate (“the bean”) in Chicago.

How to spend the day: Head to the West Side Highway, which runs along Manhattan’s western edge and offers more space than The High Line. Take a stroll or bike ride down its path toward One World Trade Center, shining brightly ahead. If you’ve had your fill of panoramic views, you can skip One World Observatory, but be sure to visit the 9/11 Memorial and Museum. It’s a deeply moving experience, so pack some tissues.

Next, visit The Oculus, an architectural wonder both inside and out, and grab lunch at Gansevoort Liberty Market, where you’ll find a range of options from tacos to sushi. Continue south to Wall Street to see the New York Stock Exchange and the iconic Charging Bull statue. (Be prepared to wait for a photo op!)

Dinner: If the weather is pleasant, enjoy a pint and classic bar snacks on Stone Street, where the bars spill out onto the cobblestone roads. For a more formal dining experience, consider historic Fraunces Tavern or Dead Rabbit. Complete your downtown exploration at The Battery, a park at Manhattan's southern tip where you can catch a glimpse of the Statue of Liberty from a distance (and for free!) as the sun sets. Don’t miss the beautiful SeaGlass Carousel, which delights both kids and adults.

After dark: If you explored the east side on Friday, venture out in West or Greenwich Village on Saturday. This area boasts a variety of gay and lesbian bars, especially around Stonewall Inn, where the 1969 riot ignited the LGBTIQ+ rights movement. You'll find a blend of casual pubs, upscale lounges, jazz clubs, and speakeasies. Katana Kitten is a popular choice for cocktails – be sure to make a reservation – or head to Cellar Dog for live music along with shuffleboard, ping-pong, and billiards.

Sunday

Morning: Kick off your day with coffee and a cronut (a delightful fusion of croissant and doughnut) at Dominique Ansel Bakery, then prepare to shop until you drop in SoHo. One of the perks of living in Manhattan? Most brands, including direct-to-consumer ones, have either pop-up or permanent locations here. If there's something you've been eyeing online, you might just find it in person. If you’re just browsing, stick to the side streets off Broadway for a more relaxed experience.

How to spend the day: Once you've had your fill of shopping, hop on the subway and head uptown to Central Park for a leisurely stroll or bike ride. Extra points if you bring along snacks for a picnic, but you can also grab a hot dog from vendors like Nathan’s Famous. There’s plenty to do in NYC’s most renowned green space, but if you can only see one attraction, make it the Bethesda Terrace with its beautiful fountain. For a more active option, rent a rowboat and enjoy some time on the lake. 

Dinner: If you wrap up your Central Park explorations on the west side, hop on the subway down to Hudson Yards to check out the Vessel. While you can no longer climb it, it’s still worth a stroll through the plaza on your way to Little Island, a floating park that debuted in 2021. Before you go, swing by Chelsea Market to grab tacos from Los Mariscos or Los Tacos No.1, then enjoy them on the lawn while watching the sunset over lower Manhattan on your last night.

You may not have seen it all, but you'll have experienced enough to know just how soon you want to return for the rest.