New York City has always been widely considered to be the cutting edge of culture. A bustling beacon for all things art, fashion, and food, the City That Never Sleeps can certainly feel overwhelming for a short visit. Take it from a well versed Big Apple adventurer, three days is plenty to pack in all the necessary stops and really get to see all that this sprawling metropolis has to offer.
This guide will give you the perfect balance between must-see tourist attractions and hidden gems that the locals love. My best advice for novice New Yorkers is to stick to Manhattan for your first three-day foray. There’s plenty to see and do in this part of the city and the subway makes hopping from borough to borough a breeze.
Remember if you’re walking around Manhattan — though you won’t want to cover too many blocks by foot — that NYC is set up as a grid! This makes it easy to navigate the streets because you can just follow the numbers.
Also, it’s best to split up your itinerary in New York City geographically. There’s no point in wasting time going from uptown to downtown in one day. While NYC is known for being expensive, it can actually be easy to enjoy on a budget as there are plenty of free activities and cheap eats. Above all, be smart and stay safe, follow city etiquette (like not walking too slowly or stopping on the sidewalk to photograph something), dress comfortably, and you’re sure to have an amazing time in this so-called center of the world in any season!
Let’s start with the top shall we? Upper Manhattan is considered to be anything between 59th and 110th street. It’s split into two sections: the Upper East Side and the Upper West Side. Their respective reputations state that one is fancy and full of the NYC elite and the other has a slightly funkier feel. While there may be some truth to this, there’s plenty of worthwhile spaces to explore in both.
NYC is known for having some of the best museums in the world. In Upper Manhattan I always make sure to check out the Metropolitan Museum of Art, or the MET. This part of the city is also home to the renowned art institution, The Guggenheim. If deciding between the two, it may come down to your artistic preferences, more classic or more modern, though note that The Guggenheim does have a heftier price tag.
If art is not your thing, opt for the American Museum of Natural History to scope out dinosaur bones and space rocks. Afterwards take a stroll around one of the most iconic urban green spaces in the world, Central Park! Try to spot Strawberry Fields, The Mall, The Lake, The Carousel, and more while wandering these lush and peaceful grounds.
Regardless of which side of Upper Manhattan you’re on, it’s a good part of town to hit up one of NYC’s most famous and craveable chains, Shake Shack. If you’d like to grab a drink — definitely a traditional pastime in the city — this is also great area to find a cute wine bar or fancy cocktail spot. I would recommend The Dead Poet, Bob’s Your Uncle, or Prohibition on the Upper West Side. Saying that, any cozy neighborhood joint should do the trick and there's some great bars on the Upper East Side too.
Midtown, the aptly named middle part of Manhattan, consists of anything below 59th and above 14th Street. The most important thing to know about this part of NYC, is to avoid Times Square at all costs! Most locals refuse to go here unless it's absolutely necessary. That being said, you get a pass if you’re in the mood to catch a Broadway show. If you want to save some money hit up a TKTS Booth and go to a matinee at a discounted price.
Midtown is home to some of the more touristy attractions you may want to see, including the Empire State Building and Rockefeller Center. If marveling at tall skyscrapers is your thing, go for it, they’re impressive facades to be sure. If you’re only interested in the views, there are better ways to enjoy the spectacle of the NYC skyline.
Chelsea is another adorable area to spend some time in. Pro tip, all the galleries here are free! Wander between 18th and 28th street on the west side and pop in and out of cool art installations before heading up at the Highline to enjoy beautiful views. Just below is the iconic Chelsea Market which is ideal for shopping and chowing down in the area as you’ll find a wide selection of some of NYC’s best restaurants all in one spot.
The Meatpacking District is also considered a hip neighborhood here. It’s home to one of the best modern art museums, the Whitney, which is always worth a trip. I also love indulging in the time honored tradition of a rooftop sunset here and grabbing a drink at Le Bain. The Hudson River Park feels like a hidden NYC gem. At the designated Piers, like 45 and 57, you’ll find recreational activities, bars on boats, and grassy knolls with breathtaking views to relax and bask in the glow of discovering a less touristy spot.
Lower Manhattan, which is basically anything below 14th Street, is likely the youngest and hippest part of the city. There’s always something cool happening here, like live music shows and pop up shops. It’s home to Chinatown and Little Italy, both of which you’re going to want to wander around and enjoy a meal in. Don’t worry about deciding on a dining destination in advance in these areas, you can't really go wrong here.
The Financial District is where you can hop on a ferry ride and go right past NYC’s most legendary landmark, the Statue of Liberty. You can also head to Soho to browse or to buy as it’s NYC’s ultimate shopping destination. They've got independent boutiques, big brand name stores, and everything in between.
In the LES, popular with college kids and older longtime locals, you can partake in a Big Apple right of passage by enjoying the cheapest meal possible, a slice of dollar pizza. Otherwise, treat yourself to a well crafted feast at famous trendy hotspots like Russ and Daughters, Freemans, Katz’s Delicatessen, or Dimes.
For drinks, I love to hit up either a jazz bar or a dive bar around Bowery. Smalls, Home Sweet Home, and the 169 Bar will never go out of NYC style. For a fancier feel, this neighborhood also has its fair share of speakeasies such as Nitecap, Beauty and Essex, or Attaboy.
If you happen to have more time in NYC I would recommend venturing out into a few other boroughs! New York City is made up of so much more than just Manhattan. There are tons of sites to explore in Brooklyn, Queens, and the Bronx. Plus it’ll give you a relaxing break from the hustle and bustle of city center streets, which let’s face it can become exhausting.
Some of my all time favorite spots happen to be in BK in particular. An abbreviated list would include shopping until you drop in Williamsburg, going on a seaside ride at Coney Island, catching a live music show in Bushwick, enjoying a lovely stroll (and people watching) at Prospect Park, and chowing down at all the trendiest eateries in Greenpoint.
Last Updated 26 July 2022