A New York Itinerary: 2 Days in the City

Yessss, this is the city baby! New York City has an electric feel unlike any other. I go between feeling overwhelmed with sensations to feeling like a bad-ass model on a catwalk. New York has that pull over people.

When you first visit and only have a New York itinerary, 2 days’ worth of exploring, what do you do?! It’s tough to narrow it all down, but as a veteran visitor, I’m more than happy to help. Let’s dive into the highlights and plan a great trip to NYC for you.

2-day New York City Itinerary

Day One

• Land at JFK or Penn Station, drop off luggage at StayPineapple
• Try a walking or bus tour for an overview
• Visit the Guggenheim, MoMA or 9/11 Museum
• Peruse 5th Avenue and check out Radio City Music Hall a block over
• Dinner at Chez Josephine
• Return to StayPineapple

Day Two

• Visit Times Square early for less crowds
• Walk to Chelsea for lunch and a sweet treat at Milk Bar
• Catch a Broadway matinee (or an evening show) or take the Ferry to the Statue of Liberty
• Dinner at Empanada Mama
• Return to StayPineapple

Tips for Visiting New York City for the First Time

You can skip over this if you’re a pro, but I have a few things that will hopefully help if you haven’t done an NYC itinerary before.

Get all the passes and tickets you can ahead of time. Lines are already a thing, so plan what you can. Look into shortcuts like CityPASS for discounts on the staples (Empire State Building, the Met, the museums, and more).

NYC cabs seem fun, but ride shares are much easier to hail and use. Have a few apps downloaded and ready when you land. Lyft work great in the city.

This might seem obvious, but check the weather. If it’s going to be a blustery day, that 20-block walk will be much less appealing. If you’re trying to see a bit of everything, map out a route ahead of time, or plan on a city walking tour (or bus) to get a lay of the land first thing when you arrive.

Pick the Perfect Homebase for Your NYC Itinerary

When planning trips, you always want to make sure your hotel is perfect. It’s really easy to spend the majority of your budget on accommodations in NYC. Even if you’re looking to splurge, it can be too much. I found a healthy medium at StayPineapple, a quirky, comfortable, design-forward spot that I’ve come to love (I’ve also stayed at their Boston property, which I cover in my Girls Weekend in Boston guide).

Not to mention, they’re pet-friendly too!

I love a little character, especially when I have to travel for business and all I see is the inside of a conference center. What an oasis of fun to return to my plush bed, massive yellow robe and bold decor at StayPineapple. For New York, rooms have plenty of space and from my window the noises below were perfectly muted to a hum. I love the tropical toiletries and little sweet treat left bedside when I checked in too. It’s worth taking in all the small details, like the pineaplple floor mosaics.

StayPineapple is great for visitors who want to see all the biggest sights, and it’s also a smart choice if you’re in town for business (like I often am) and need easy access to the Jacob K. Javits Convention Center. The walk from the Javits to StayPineapple was under 20 minutes, so if you’re in for a conference or trade show, you can knock out your work days and still be perfectly placed to enjoy the city at night.

If StayPineapple is booked, Yotel is another solid option in the same Midtown West area. The rooms are compact (very Manhattan) but cleverly designed, with a smartbed that doubles as a workspace and a rooftop bar that’s a nice perk. Also walkable to the Javits.

A few things to do right near the hotel

Because of the Midtown West and Hell’s Kitchen location, you’ve got a lot within walking distance:

• Hudson Yards and the Vessel are a short walk west, with the Edge observation deck if you want skyline views (book ahead).
• The High Line entrance is nearby too, and walking the elevated park down toward Chelsea is one of the best free things to do in the city.
• Hell’s Kitchen’s Ninth Avenue is packed with excellent, budget-friendly international food, perfect for a low-key dinner after a long day.
• The Theater District and Times Square are an easy walk east, so you’re well placed for a Broadway show.

A perfect low-key day in NYC

On my most recent trip, I was in the city for a travel conference and stayed an extra day just to relax, unwind, and do a few things that are cliche and wonderful. No judgment. When you’ve been to New York a thousand times, it’s freeing to show up with zero expectations and just enjoy the city at your own pace.

Here’s how that day went, in case you want to steal it. I grabbed a Blue Bottle latte to keep me warm on a brutally cold walk (it was 17 degrees), then snagged a rainbow bagel at Liberty Bagels because sometimes you just want the fun touristy thing. I’ll be honest about one miss: I ordered a chicken salad bagel for lunch and somehow ended up with a chicken parm panini instead. Still good. Not what I ordered, but still good.

Then I opened my laptop for a bit (the reality of the working traveler), got ready, and headed to a Broadway show. I saw Harry Potter and the Cursed Child, and Tom Felton was playing a grown-up Draco Malfoy during the run I caught, which was a genuine treat for anyone who grew up with those books and films. Beforehand I made it to a little blogger and creator meetup at a nearby bar to catch up with old and new faces.

Because it was so cold, I skipped a proper dinner out, did a quick spin around Times Square, grabbed a slice to go from one of the thousand pizza spots, and brought it back to my cozy StayPineapple room on the 24th floor. Some of the best travel days are the ones where you build in time to just exist in a place. If you’ve been to New York before, give yourself permission to have an afternoon like this.

Food: Take advantage of worldwide cuisine

I know it’s hyped but hear me out. It’s tough to try it all during a New York itinerary, 2 days worth especially is impossible. My best advice is to simply peruse a few favorites, savor them, and bookmark the rest for next time.

As I was staying near Hell’s Kitchen on this trip, the Chelsea neighborhood is only a 25-30 minute walk. This is perfect in almost any weather to earn back all those vacation calories you’re about to dive into.

For a lazy early afternoon, head to Milk Bar to grab a latte and a treat. Milk Bar was the dream of pastry chef Christina Tosi, who first opened a shop inside a Momofuku restaurant. On offer is everything sweet, from soft serve covered in fruity pebbles to decadent confetti-style birthday cakes. Locations move around the city over time, so check the current Milk Bar locations before you go. Recent spots have included a flagship near Nomad (1196 Broadway) and an outpost in the West Village.

If you want a sit-down lunch in the area, Momofuku’s restaurants are worth a look too, though the group has opened and closed various locations over the years, so check the current Momofuku list for what’s open when you visit.

The next night you’re in town you can do something totally different. If you’d like something casual, I’m a huge fan of Empanada Mama in Hell’s Kitchen and make a point to visit every time I’m in the city. The menu is extensive with a ton of Latin favorites. Don’t miss the guava and mozzarella empanada for dessert.

And don’t skimp on the touristy-but-fun stuff: a rainbow bagel at Liberty Bagels is the kind of over-the-top New York treat worth doing once, and a slice of dollar-ish pizza grabbed on the walk home is a rite of passage.

Sightseeing Near Times Square on your NYC Itinerary

If feeling stuffed, take the walk back downtown or hop on the subway to do a bit more sightseeing. This would be a good time to walk down 5th Avenue if heading out on a weekday in the off-season (like a warm winter day). Otherwise, you can choose one of the major museums, like the Guggenheim, MoMA or 9/11 Museum. After the sun goes down you could visit the observation deck at the Empire State Building, but definitely plan this in advance. People come from all over the world to do it. Otherwise, catch a Broadway (or off-Broadway) show. This also could be saved for a matinee after lunch on your second day.

It’s all about what you like and how much, or little, you’d like to see. An NYC itinerary in two days is tough, but can be a great way to get a taste for one of the greatest cities in the world. Especially if it’s your second or third time there!

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