Planning the perfect weekend in New York City can be difficult if you’re not familiar with Manhattan for numerous reasons. First, you have to know where to stay (NOT in Times Square FYI) and from there it’s really best to map out everything you want to see and do so you don’t waste any time because things are likely much farther apart than you think.
It’s always best to explore with someone who lives there or is very familiar with the city, but usually, that’s not possible so I am here to help guide you!
We recently took our friends from California into NYC for a night and covered a ton of the city and sights in less than 48 hours. I’ll share the details from that trip below and include an additional bonus family trip at the bottom for those of you planning trips with children.
B O O K I N G Y O U R S T A Y
The common misconception is that you need to stay in Times Square - this is FALSE. Stay as far away from Times Square as possible and book your stay in Chelsea or basically anywhere south of 30th St. and west of 5th Ave. You'll be much happier when you're not battling through tourist crowds 24/7.
I T I N E R A R Y
The following itinerary is based on our 2-night stay in Manhattan. I'll include our transit details and additional recommendations as we go through the weekend, but keep in mind this is just to help guide you when you're planning your weekend.
D A Y O N E
1. Arriving in Manhattan
We chose to take the New Jersey Transit and arrived in Manhattan at Penn Station (34th St.). The fastest way to get to your hotel will be via train* unless you get into the city during rush hour when everyone is going to or from work. We booked our stay at the Four Seasons Chelsea on 25th St. and 7th Ave., which means the best trains to take are either the C/E or the 1 - we took the C train out of Penn Station and got out at 23rd St., then walked to our hotel.
- A/C/E trains run down 8th Ave., however, the A train is express so it doesn't stop at each station like the C/E, but additionally, the E train stops at the World Trade Center so to make it simple, just take the C train if you're going downtown
- 1/2 trains run down 7th Ave.
*when I say train I am referring to the subway, I realized this can be confusing
2. Happy Hour at the Barcade: we were seeing Phantom of the Opera at 8pm and didn't have much time in between checking into our hotel and exploring before the show started so we posted up in the Barcade on 24th Street for apps and drinks.
3. Dinner at Legasea (7th Ave. & 36th St.)
Always book reservations for meals. Otherwise, YOU WILL BE STUCK WAITING for at least 30 minutes, unless you get lucky. I booked all of our meals with OpenTable to ensure we could get in and didn't waste any time waiting around when we could be exploring.
4. Phantom of the Opera @ The Majestic (8th Ave. & 44th St.)
We walked from the restaurant to the show, which allowed us to walk our friends through Times Square at night since they had never seen it before. I will admit that Times Square is cool the first time you see it, but you want to see it at night when everything is all lit up.
5. Back at Barcade for a nightcap
We walked from the Majestic at 44th St. back to our hotel at 25th St., allowing us to see the city at night, walking past The Empire State Building and other sights our friends wanted to see before ending the evening back at the bar near our hotel.
In less than 12 hours, following the above itinerary, we covered 3 neighborhoods: Chelsea, Midtown and Times Square. We took our friends through Chelsea, showed them a cool NYC bar where you can drink local beers and play arcade games, had a beautiful seafood dinner in Midtown and saw Broadway.
D A Y T W O
1. Brunch @ The Smith
Again, BOOK YOUR MEALS, especially if you want to have brunch on the weekend. The great things about using OpenTable is that the app makes it super easy to move your reservations if you wake up late or get behind in traffic.
We walked from the hotel on 25th St. to The Smith on 11th St. & 3rd Ave., which was about a 30-minute walk, but allowed us to walk our friends down 5th Ave., past the Flatiron building and then through Union Square to see the Greenmarket.
Takeaway: when you plan your meals, plan to walk to each spot instead of taking the train or a cab so that you can cover more sights and make better use of your time.
2. Strand Bookstore: 18 Miles of Books
Our friend Adriana loves books as do we, so I thought it would be cool to pit stop into Strand after brunch since it's right around the corner. Strand is always crowded, but if you head up the top floor, it's much quieter and you see their rare book collection!
3. Central Park (5th Ave. & 59th St.)
We took a cab to Central Park from brunch because, 1. Central Park is FAR and 2. I knew the Lyft driver would drive us down Park Avenue and around Grand Central, which I thought would be cool for our friends to see! Always try to plan sightseeing around everything you do when possible.
I purposely had us go to 5th Ave. & 59th St. so we could see The Plaza and the crazy Apple Store. Then we proceeded towards Bethesda Fountain, seeing more sights and going by way of The Mall and Literary Walk, which is beautiful in the spring, summer, and fall!
4. Leaving Manhattan
In an effort to finish the quick trip like real New Yorkers, I wanted everyone to ride the train one last time so we proceeded to take the C train back to 23th St. from Central Park to grab our luggage because we needed to catch the NJ Transit train out of Penn Station at 4pm.
We grabbed our bags and then took the train back to Penn Station, which from 23rd St. is only one stop, making the fastest way possible.
*Pro Tip: hotels will hold your luggage after you check out so that you can continue to sight-see without having to lug your bags around
S U M M A R Y
In less than 48 hours, we covered sights from 11th St. & 72th St. between 8th Ave. & 3rd Ave. and saw the following:
- Chelsea (Chelsea Market, Barcade)
- Midtown (dinner @ Legasea)
- Broadway Show @ The Majestic
- Times Square at night
- Herald Square @ 34th St. (Macy's, more shops)
- Empire State Building
- 5th Avenue Shopping
- Flatiron Building
- Madison Square Park (home to the original Shake Shack)
- Union Square (Union Square Park, The Greenmarket)
- NYC Brunch
- Strand Bookstore
- The Plaza
- Central Park (Literary Walk, Strawberry Fields, Bethesda Fountain)
Amongst all that we covered, here are a few additional things I wanted us to see that we weren't able to fit into our trip, but I highly recommend:
- The Highline (Chelsea)
- The Whitney (Chelsea)
- Washington Square Park (West Village)
- World Trade Center (Tribeca)
- Rockefeller Park (Tribeca)
- Irish Hunger Memorial (Tribeca)
- Battery Park
- The Standard Biergarten (Chelsea)
- Please Don't Tell (East Village Bar)
- Rockefeller Center (Midtown)
- St. Patrick's Cathedral (Midtown)
For those of you traveling to NYC with children, you can find a full itinerary here that I put together for some friends who were staying in Brooklyn near Park Slope a few years ago.
This trip is based on where they were staying and includes their personal travel time, so keep that in mind and make adjustments to your own trip as needed. All of these ideas are family friendly for children 8 years and older, which is based on the ages of the children from the family that used this trip itinerary.
I hope everyone enjoyed these brief tips and can use this as inspiration if you're planning a trip to New York City! Please, leave comments and questions below in the comments or send me an email.