New York City: see it all in 4 days!*

*Okay, okay, I think it's impossible to see all of New York even if you're there for a week or more. But this itinerary will help you cover A LOT in a short amount of time!

New York, New York - it's one of my favourite cities in the world and somewhere I always dreamed of living someday (I settled for the Canadian version instead... Toronto). There is something so captivating about this city that you can't help but fantasize about a life here. I've been to NYC many times over the years and wanted to put together a good 'first-timers' guide to hit some of the main sights (and some hidden gems!)

There is simply too much to do and see in NYC, and depending when you're there (summer vs winter) your activities might look a bit different, but this is a good starting point to begin your planning! Use this guide primarily to get a sense of the neighbourhoods and some top picks within them. You can rearrange the days and even clump different neighbourhoods together depending on your own trip and schedule.

Day 1: Financial District & Brooklyn

Morning – Battery Park & Statue of Liberty

• Subway all the way down to Battery Park for views of the Statue of Liberty.

  • If you want to get even closer, you can take a boat to Liberty Island to see Lady Liberty in person... or if you want a budget-friendly option, hop on the free Staten Island Ferry for great views from the water.

  • Optional: depending what time it is... stop in for a drink at The Dead Rabbit pub.

    
    

Midday – Financial District (FiDi) & World Trade Centre

• Walk up through Wall Street and the Financial District to see the Charging Bull (rub its balls for good luck).

• Grab a late breakfast/early lunch at Leo's Bagels.

• Head over to the One World Trade Centre to see the 9/11 Memorial & Museum (Ground Zero). Walk the outdoor memorial first, option to also visit the museum (recommend reserving tickets online in advance).

• Walk to the Oculus to check out the architecture and browse the shops if you're in the mood for a bit of shopping.

  
  

Afternoon – Brooklyn

• From Oculus, it's a 10 minute walk to the Brooklyn Bridge. Make your way across to Brooklyn for cool photo opps on the bridge!

  • Alternatively, the Brooklyn Bridge is a good spot to do early in the morning (fewer crowds) or at sunset/evening (for the city lights); some people like to walk from Brooklyn toward Manhattan to take in the skyline views - if this is something you'd prefer then just play around with the order of your schedule... ie start in Brooklyn and then head to FiDi.

• Explore DUMBO (Down Under the Manhattan Bridge Overpass): check out the flea market (if open), take the classic bridge photo, and grab a coffee at Devoción.

• Walk along Brooklyn Bridge Park, find a bench, and soak in the skyline.

  
  

Dinner

• Finish the day with a classic New York pizza at Grimaldi’s.

Late Night - Williamsburg

• If you're not too tired, head up to Williamsburg for a little bar crawl. Get to Bedford and stroll along popping into any spot that speaks to you. I suggest: Horses and Divorces (dive bar), Skinny Dennis (also divey, saloon vibes - get the frozen coffee!), Radegast Hall & Biergarten (German beer hall). If you need a late night bite and aren't pizza'd out... grab a slice from Joe's.

Day 2: Upper East Side, Central Park & Upper West Side, Midtown

Morning – Upper East Side (UES)

• Walk up or take the subway to the UES. Start with coffee at Ralph’s Coffee at the Ralph Lauren HQ—very cute and classic NYC.

• Meander the streets... lots of good (expensive) window shopping.

• Optional: Try the Met (Metropolitan Museum of Art) or the Guggenheim

  
  

Midday – Central Park

• Walk west into Central Park and get ready to... meander! Word of the day. Pick a path and follow for as long as you like. A few options for your time in the park:

  • Rent bikes to cover more ground than walking.

  • Bethesda Terrace & Fountain.

  • Belvedere Castle.

  • Picnic (pick up some drinks/snacks before heading in).

• Stroll through the park toward the Upper West Side.

Afternoon – Upper West Side (UWS)

• Find lunch at a local spot on the Upper West Side. Try Jacob's Pickles.

• More meandering!

• Optional (strongly recommend): Museum of Natural History.

Evening – Midtown

• Walk south back to Midtown/home base. Take a quick break if needed then head out to explore Midtown at night.

• Sights to see include:

  • Rockefeller Centre.

  • Radio City Music Hall.

  • Empire State Building (book in advance if you want to go up! however, my recommendation is actually to go up to the 'Top of the Rock' at the Rockefeller Centre because then you'll get to enjoy the view WITH the Empire State Building in it).

  • Grand Central Station - grab a bite at Oyster Bar if you can nab a spot

    
    

Day 3: Chelsea, High Line, Hudson Yards & Times Square

Morning – Hudson Yards & The High Line

• Walk over to Hudson Yards. Grab a coffee at Jack's Stir Brew.

• Option to go up to EDGE Observation Deck (if you didn't do one the day before - I don't think you need to do more than one observation deck).

• Walk south along the High Line (very cool pathway and greenspace elevated above street-level).

Afternoon – Chelsea & Times Square

• Exit down from the High Line and grab a drink and some olives at The High Line Hotel (very cute patio in the summer). Peruse the Chelsea Market after.

• If you're hungry you can grab brunch at Jack's Wife Freda (cute breakfast spot, sit down), or wait until you get to Times Square for Los Tacos No. 1 (casual standing room)

• Hop on the subway or walk north to Times Square for a broadway matinee! (make sure you buy ahead of time, or you can try lining up in the morning at TKTS but that will cut into your sightseeing).

Dinner

• Head down to Herald Square. Visit the historic Macy’s and have dinner at Keen’s Steakhouse (reservations recommended).

Late Night - Chelsea

• If you're up for a little nightcap (or two), there are soo many options, but a couple of options in the neighbourhood include:

  • Bathtub Gin - dark, vibey speakeasy

  • Trailer Park Lounge - kitschy, fun, good drink specials

  • Swingers NoMad - fun indoor mini golf bar

Day 4: Little Italy, Chinatown & Greenwich Village

Late Morning – Flatiron District & Lower Manhattan

• Long walking day (again). Subway down to the iconic Flatiron Building. Grab a coffee and light bite (save room for lunch).

• Walk south past The Strand bookstore (iconic!) and continue on through Union Square.

• Continue down Bowery until Houston, where you will probably see a line for Katz Deli. Join that line (and make sure you have cash!) Pastrami sandwich and pickle for early lunch.

Afternoon & Evening – Chinatown, Little Italy & The Village

• After lunch, get some more steps in as you stroll south through the Sara D Roosevelt Park (greenway) to Chinatown.

• Explore Mott, Mulberry, and Doyers Street for unique shops. Canal Street is also nearby and known for its knock offs.

• Head back up to neighbouring Little Italy. If you've worked up an appetite again, there are lots of options here! I suggest kicking off another pizza tour... starting with NYC's first pizzeria Lombardi's.

• As you head north, grab another slice at Prince Street Pizza and head toward Greenwich Village. Walk through the streets of NYU, stroll through Washington Square Park for good people watching, and check out iconic spots like Carrie Bradshaw's apartment and the Friends apartment (exterior) - you can find and save these locations on Google Maps.

• Grab a cocktail at Dante's before checking out a comedy show at The Comedy Cellar (pre-book!)

• After dinner... more pizza! Try John's of Bleecker Street. There are tons of cool bars for a nightcap as well.

Final thoughts

I hope this can serve as some inspiration for some of the neighbourhoods, restaurants, activities and sights you can cover in a few days in NYC. One glaring omissions from this list is a sporting event... specifically my picks would be a Yankees game (spring/summer) or a Rangers game (fall/winter), but you've also got PWHL, WNBA, NFL (x2), another MLB and NHL team... the options are endless.

If you want me to create a custom itinerary for your next trip, reach out to me!