The best weekend in New York City

Day 1: Welcome to New York! Arrive via plane or train, and check into your hotel. 

The first stop is Edge, the highest viewing platform in the Western Hemisphere.  Make a reservation on the website in advance. 

The check in process feels like a Disney World ride, so give yourself time to walk through all the ticket lines to get to the top.

It’s $10 extra to go at sunset, which was my original plan, but I chose a 4pm reservation to try and avoid crowds.  Be warned, it’s very windy, so the sun helps keep you warm on the observation deck.  There are pricey snacks and champagne, but we opted to enjoy the view and head to happy hour at a speakeasy.

Raines Law Room has major 1920s prohibition vibes.  Get a reservation in the parlor so you can enjoy the dim lighting, antique furniture and Gatsby-era ambiance.  This place is good for happy hour drinks, but there are limited food options.  We got an assortment of cheese, spiced nuts and charcuterie.  

Dinner is on a rooftop in Eataly. On the way you’ll get a cool view of the Flatiron building (currently under construction as of April 2021). Look for signs for Serra by Birrera and take the elevator up. This Italian restaurant is updated seasonally. Make your reservation in advance on OpenTable.

Walk off your delicious dinner with a stroll to Times Square at night.

Day 2: Get up early to catch the sunrise on the Brooklyn Bridge.

We ubered in the morning to Park Row & Centre Street (right by City Hall Park), but you can also take the subway and get off at Brooklyn Bridge - City Hall Subway Station or Chambers Street.

Be sure to stay in the right lane as the left one is reserved for bikers. The walk is a little over a mile. Don’t forget to turn around and admire the impressive New York City skyline.

Once you arrive in Dumbo, get breakfast at Butler’s - the egg sandwich was tasty. They charge $3 for a glass of water, so bring your own! 

We stopped at the cross section of Washington and Water street for a cool instagram spot with two red brick buildings framing the Manhattan bridge. If you get here before 8am the street isn’t too busy with cars or other people on a photo hunt for the same spot.

In Dumbo, Almondine is a french bakery where you can grab a pastry for your walk back. I enjoyed the french macaroons and chocolate croissant.

Back in Manhattan, get some sweet treats at Milk’s Flagship store. The cookies and cake are out of this world.

For some green space and exercise, walk to the High Line Park by Hudson Yards. It’s a new park built into an old elevated rail line. The High Line opened in 2009 as a hybrid public space where art and nature mix. I love looking at the plants and architecture along the path.

There are entrances at 30th street, 34rd street or Ganesvoort Street. Check the website http://www.thehighline.org in advance for hours information, and you may need a (free) timed reservation on the weekends.

Get off at the 23rd street exit and head to LOULOU Nyc for an early happy hour. There is a 4-5 menu with light snacks and drink specials.

I highly recommend the Mexican Stiletto which comes in a glass bird. LOULOU has a party vibe, florals and plenty of outdoor seating.

The mushroom flatbread, shishito peppers and truffle fries were delicious after so much walking.

Also pictured here: the Chelsea, a raspberry vodka drink with foam on top. Make a reservation in advance with the restaurant directly or on their website: https://www.loulounyc.com/

Next stop: a rooftop happy hour. The A.R.T. Nomad is one of my favorite views.

It’s on a hotel’s rooftop, but is open for reservations from non-guests.

You can look up at the Empire State Building, or straight down through a glass viewing platform. The view from the roof is fantastic, but they’ll make you order food with your drinks so don’t plan on spending more than 90 minutes here.

Dinner is at Rosemary’s, an Italian restaurant in Greenwich Village with a romantic countryside vibe. You can make a reservation 2 weeks in advance through their website or Resy. There are indoor and outdoor seating options.

Day 3: Wake up and order your bagels in advance at Brooklyn Bagel.  Now, head out to get coffee at Seven Grams Caffe which is on the way. 

Walk on 28th street between Broadway and 7th to experience the flower district.  Enjoy your bagels at the restaurant, or take them to the High Line if it’s open (usually after 10 on the weekends).  

If you want a sweet treat on the way back (or a brunch alternative), Maman has beautiful pastries and a floral interior.

Take the subway uptown to Central Park and walk to the Bethesda Terrance and fountain.  Give yourself time to listen to the street musicians, purchase a print or painting, and enjoy the green space that is almost 900 acres in the middle of New York City.  If you have time, get lunch at Tavern on the Green, or rent paddle boats.  There is also a castle, Belvedere, in the park.

Check out is usually at noon, but you can leave your bag with the front desk and come back to get it before you have to leave New York City.

Other ideas if you have time...

If it is rainy, head to a museum like The Met, the Moma, or the Whitney.

No trip to the Big Apple is complete without pizza.  Grab a slice at Zazzys or Grimaldis.  The OG is in Brooklyn, but it’s just as tasty in Manhattan.

Go to Grand Central Station and marvel at the iconic teal ceiling.  Get a drink at Campbells, which used to be a bank.

Tour the Empire State Building and get a view from the 82nd floor.  For $20 extra you can see Manhattan from the 102nd floor, the newest observation deck.

Take the Staten Island Ferry (its free!) to see lower Manhattan from the water.  People use this to commute, I’ve done it with friends as a free activity that involves a boat and a unique vantage point.

Stay: We stayed in the Hyatt Herald Square at 30 W 31st Street.  The hotel has a boutique feel and the front desk staff was extremely friendly.

If you get a city view you can wake up to see the Empire State building each morning.  There is a rooftop where you can bring your own drinks and snacks. 

I’d definitely stay here again, and chose it for the proximity to Penn Station (walkable with your luggage!), Times Square, Chelsea and lower Manhattan.  As a bonus, we passed by the Flatiron District a lot, which is my favorite mix of city and park and has a lot of space to hang out.