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New York is one of the greatest cities in the US for a long weekend city break. While New York is big enough to easily spend a week or more exploring 3 days gives you the a good amount of time to experience a mix of things and get a good feel for the city esepcially if it’s your first trip!
I love New York, and living in Boston, weekeend trips to New York are so easy & fun, so I’ve been lucky enough to take many trips there in the last few years! This is how I’d spend 3 days in New York City if I was a first time visitor.
Itinerary:
- Day 1: Central Park, Top of the Rock & Times Square
- Day 2: The High Line, West & Greenwich Village, Rooftop Hop OR a Broadway Show
- Day 3: 9/11 Memorial, Statue of Liberty, Brooklyn Bridge & DUMBO + Williamsburg
Other NYC Info:
Planning a getaway to NYC? See my full New York City travel guide here!
Disclaimer: This article contains some links where I earn commission through booking. There is no extra cost to you, and I only recommend things I’ve used and love or places I’ve stayed and enjoyed!
Day 1: Central Park, Top of the Rock & Times Square
Spend your first day in the city exploring some of the most iconic sites! Wear sneakers – this day will have lots of walking & exploring!
- Morning: Explore Central Park & Check out Darling Rooftop for the Best Views
- Afternoon:
Morning: Explore Central Park & Check out Darling Rooftop for the Best Views
Central Park
No trip to New York is complete without visiting the iconic Central Park. Central Park is absolutely massive and spans a huge portion of the center of Manhattan, while it’s nicest in summer, spring & fall, it’s still worth a visit in the winter. Snowy Central Park is stunning, albeit cold. Central Park is free to visit.
Highlights of Central Park:
- Bethesda Terrace
- Bow Bridge
- Strawberry FIelds
- Central Park Carousel
While you’re in this area you can also peak into the infamous Plaza Hotel that sits right on Central Park and is most famous (to me) for being where Kevin stays in Home Alone 2.
Darling Rooftop
After a morning exploring head over to the Darling Rooftop at the Park Lane hotel for lunch & the only rooftop views of Central Park. Make a reservation in advance for this one!
Afternoon: Explore 5th & 6th Ave, Rockefeller Center & Head to the Top of the Rock for Sunset
Exploring 5th & 6th Ave
From Central Park & Darling it’s a 12 minute walk to 30 Rock. Stroll down the 5th Ave, the infamous shopping street, see St. Patrrick’s Cathedral, & Radio City Music Hall. Some of the most famous stores in this area that you can pop into or window shop:
- Saks 5th Ave
- LEGO Store
- FAO Schwartz Toy Store
- American Girl Doll Store
Top of the Rock
Admiring the NYC skyline from above is one of my favorite things, and there are tons of paid options and rooftop bars. One of my favorite views is from the Top of the Rock at Rockefeller Center. Time this with sunset if you can it’s so unreal!
Tickets are $54 per person, and you can explore for as long as you want once you’re up there. There’s 360 views of the city – you can see the Empire State Building, Central Park & more.
Evening: Wander Times Square & Dinner
Spend you evening exploring the iconic Times Square, a short 10ish minute walk from 30 Rock. From Times Square I recommend heading towards Bryant Park there’s a bunch of great restaurants in this are It’s also a great area to stay – see my recommnedations below!)
Restaurants to Try:
- STK – upscale steakhouse & lounge
- La Pecora Bianca Bryant Park – Italian
- Parker & Quinn – American restaurant
- Joe’s Pizza on Broadway – some of the best slices in NYC (counter service)
Day 2: The High Line, West & Greenwich Village, Rooftop Hop OR a Broadway Show
Spend Day 2 exploring one of my favorite areas of Manhattan, the west side. Some of my favorite neighborhoods (and restaurants are in this area!)
Morning: Walk the High Line & Explore Little Island
Walking the High Line is one of my favoritre things to do in the city. The High Line is a park/walking trail built on a former elevated railway on Manhattan’s west side. It offer stunning views of Manhattan, Little Island Park, and features stunning garden and unique art displays. The west side of Manhattan is home to some of Manhattan’s most picturesque neighborhoods and this is a great way to explore them.
You can get off the High Line at different points to explore. Getting off to explore Little Island Park is one of my favorite parts!
Afternoon: Wander through the West Village & & Greenwich Village
Two of Manhattan’s most picturesque (and pricy) neighborhoods are the West Village & & Greenwich Village, these are right next to the High Line. I love wandering down the streets around here. Some of the highlights of the area (other than the insanely picturesque streets & cute shops and cafes)
- Washington Square Park
- NYU
This is also a great place to grab lunch there are SO many good restaurants in this area (predominantly Italian)
- Mama’s Too – pizza counter service
- Arthur & Sons – sit down Italian
- Carbone – sit down Italian
- L’Antica Pizzeria Da Michele NYC – sit down Italian
- Boucherie West Village – French sit down
Evening: Rooftop Hop or Catch a Broadway Show
One of my favorite things to do in NYC is visit rooftop bars. There are SO many, and this is something many cities are severely lacking. If rooftop bars aren’t your thing another great night activity is to see a Broadway or Off Broadway show. NYC has so many options and some of the best Broadway shows in the world!
My favorite Manhattan rooftops:
- Daintree
- Spyglass Rooftop Bar
- The Skylark Rooftop
To check out what shows are on Broadway follow this link.
Day 3: 9/11 Memorial, Statue of Liberty, Brooklyn Bridge & DUMBO + Williamsburg
Spend your last day in NYC exploring the highlights of lower Manhattan and then heading across the infamous Brooklyn Bridge to explore two of Brooklyn’s best neighborhoods, DUMBO and Williamsburg.
Morning: Visit the 9/11 Memorial & the Statue of Liberty
9/11 Memorial
To visit the 9/11 Museum you’ll need to reserve entry. The memorial outside is free to visit. Your ticket guarantees you entry and there is no time limit to how long you can spend at the museum and memoria. Tickets are $33 per person
Statue of Liberty
No trip to New York is complete without some views of the Statue of Liberty. From the 9/11 Memorial it’s about a 10-15 minute walk to Battery Park. You have a few options here depending on how much time you have, how close you want to get to Lady Lib, and how much you’re willing to spend for this itinerary i’d go with 1 or 2 in interest of time!
- View the Statue of Liberty from Battery Park (closest) or from the Brooklyn Bridge (possible, but you’re farther away) – both of these options are free
- Take a ferry to Liberty Island and explore the Statue of Liberty Museum. You’ll get up close views of the statue, and the option to explore the museum at your leisure. Tickets here – $69 per person. Roughly 2 hours (express option)
- Take a ferry to Liberty Island (same as above) but also to Ellis Island and enjoy sites such a s the Wall of Honour, and access to the Ellis Island National Museum of Immigration where you can explore for as long as you wish. Tickets here – $79 per person, roughly 4 hours (comprehensive tour option)
Afternoon: Walk the Brooklyn Bridge & Explore DUMBO
Brooklyn Bridge
Walking the Brooklyn Bridge is one of my favorite things to do in NYC. Walking across the Brooklyn Bridge gives some of the best views of the city, and it’s free! The bridge is about a mile long, how long it takes depends on how often you stop to take photos. You can walk from Manhattan to Brooklyn’s DUMBO neighborhood. From Battery Park it’s about a 20 minute walk to the beginning of the bridge.
Explore DUMBO
The Brookyln neighborhood on at the end of the Brrooklyn Bridge (DUMBO) is one of my favorite areas to explore. Check out the iconic streets with Brooklyn Bridge views and Brooklyn Bridge park. This neighborhood has tons of great coffee shops and restaurants and is a great palce to spend an afternoon exploring.
If you’re hungry for lunch grab some of the best pizza in NYC at Grimaldi’s
Evening: Explore Williamsburg & its Rooftops
From DUMBO head north to one of Brooklyn’s funnest neighborhoods, Williamsburg. Williamsburg is filled with vibe-y rooftops, cool thrift shops, & amazing food. It’s probably easiest to uber from DUMBO to Williamsburg, but you can also take the subway if you want, but it’s not exactly a direct route.
Spend the late afternoon/evening exploring Williamsburg. I highly recommend heading to a rooftop for sunset or dinner. There are plenty of great rooftops to explore in Williamsburg, but my top recommendations are:
- Bar Blondeau – The Wythe Hotel
- The Water Tower Bar – Arlo Hotel
- Westlight – The WIlliam Vale Hotel
Williamsburg has great food options for dinner. Some of my favorite spots are:
- L’Industrie – casual pizza
- Ace’s – Detroit style bar pizza
- Birria LES – amazing tacos
- Birria Landia – food truck
- Juliette – French restuarant
- Bamonte’s – sit down Italian
- The Commodore – casual chicken restaurant
Where to Stay in New York City
New York is massive and there are so many amazing neighborhoods and hotels to choose from. I”ve narrowed down my favorite hotels by neighborhood. I love staying in all of these areas, so it’s hard to choose a favorite. It really depends on what you’re trying to be closest to when you’re in the city! For a first trip, I’d recommend Manhattan (Midtown or West Side) but Williamsburg Brooklyn is also only one subway stop from Manhattan!
Midtown Manhattan – Bryant Park Hotel
Midtown is accessible to everything, it’s easy to get up or downtown or take the train across the river to Brooklyn. One of my favorite hotels in this area is the Bryant Park Hotel (this is also a great place to stay at Christmastime) Bryant Park is right near the 5th ave & 44th street.
The location is key for this hotel, the rooms were standard for NYC, a bit small, but modern and clean. The hotel also had a cool lounge/bar in the basement that was fun to grab a few drinks at after dinner.
West Village – The Standard High Line Hotel
The West Village is my favorite neighborhood of NYC. This whole area reminds me of a European city. It’s filled with stunning streets, a lot of greenery for a major metropolitan city, some of the best restaurants in New York & more. If I were to ever move to New York (and make way more money than I do now) I’d want to live in the West Village.
The Standard High Line Hotel is one of the nicest hotels in this area. I loved my stay here, and the High Line is one of my favorite things to do in New York City.
Downtown – The Marriott Downtown
The Marriott Downtown is closer to the financial District. This neighborhood tends to be a bit cheaper on weekends than other areas like Midtown, so this can be a good option for being in Manhattan, but saving a little money.
This hotel had great views, decent sized rooms, a restaurant/bar on site & was convenient to the subway.
Williamsburg – The Hoxton Hotel
Williamsburg is where I stay most often when I visit New York, particularly the Hoxton Hotel. I love this place. They have amazing skyline views, their rooftop is home to Laser Wolf, an Israeli restaurant with awesome skyline views, and their lobby coffee shop is one of my favorite places for remote work & people watching.
Williamsburg – Arlo Hotel
Right across the street from the Hoxton is my other favorite WIlliamsburg hotel, the Arlo. The Water Tower bar at the Arlo rooftop is one of my favorite bars in New York, and the roodtop pool is unreal. I love staying at this hotel. The location is so convenient for exploring WIlliamsburg and being one stop on the L from Manhattan.
Getting Around New York City
Subway
The subway is by far the most convenient way to get around New York. While it can seem a bit overwhelming it’s actually not that hard to navigate. Google Maps has gotten very good at giving detailed subway instructions when using the app.
Full subway map and routes can be found here.
Uber/Lyft
You can alwaya get an Uber or Lyft in NYC, but you should compare the time to taking the subway, with traffic and less direct routes, sometimes the subway is a lot faster.
