UPDATED 4/4/21
Want to go to New York City for an extended weekend to see the top sights? Here’s how to see the best of New York City in 4 days solo over 50 so you can enjoy New York without breaking the bank.
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Tips for New York City
I want you to have the BEST time in New York City. It’s an amazing city with so much to do and see. It can also move quite quickly, so if you’re not used to this, you may feel out of your element or overwhelmed. Therefore, I would be remiss not to provide you my little travel and safety tips to ensure you have the best experience in New York City:
- The best time to visit New York City is off season. October and April are lovely. The weather is pleasant, prices are much less than summer prices, and you’ll avoid crowds of tourists.
- Wear good walking shoes. You’re going to cover a lot of ground in this 4 day New York City itinerary.
- Do not over exert yourself. Stop as often as you need and stay hydrated, especially if you go in the summer. It can be damn hot and humid. I think I’ve lost 5 pounds in one New York City summer day.
- Don’t be afraid to take public transportation. The subway and bus systems are easy to navigate, quick, and inexpensive.
- Engage with New Yorkers. Despite what you may have heard, many are friendly and have helpful tips about their city they are proud to share.
- If you find yourself in an area or situation that makes you feel uncomfortable, leave.
- Always keep your belongings on you. Avoid keeping lots of things in your pockets.
- Bring a good day bag big enough to fit your essentials, any emergency items and camera, but not too big or overloaded while you’re pounding the pavement. You want to keep your belongings secure and easily accessible at all times. I always travel with my Victorinox Altmont monosling bag for these exact reasons.
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Arriving in New York City
Since there are multiple ways to get to New York City, I would avoid driving into New York City, if you can help it. Traffic and parking will absorb a lot of your time and money.
JFK and La Guardia Airports
Arriving to the “city that never sleeps”, be safe and allow at least 2 hours to commute from either airport to Manhattan. Three hours might be best if you’re arriving during rush hour, which I recommend you try to avoid, just to make sure you’re not stressing yourself out.
If you’re flying into JFK, the subway and most airport shuttles are your cheapest option to getting into Manhattan, but they will take longer. If you have the funds, the easiest and quickest way is to catch a taxi, which runs on a flat rate. Here are some helpful JFK to Manhattan transportation tips.
If you’re flying into La Guardia, again, the taxi is the quickest transportation, but rates are metered and also depend on where in New York you’re staying, so it could be pricey . Look for the taxi stand line outside airport pick up area. The line does move quickly.
You could consider the Go Airlink shuttle service as well. The latest, however, is the Via app launched in 2019, which offers a share riding service for a flat rate.
You can check for the latest taxi rates. No matter which ground transportation type, don’t forget to tip your driver.
Grand Central Terminal
I love the train, so if you’re fortunate enough to take this transportation, you’re going to head straight into the Grand Central Terminal, in the heart of Manhattan. Lucky you. If not, don’t worry – popping into this historic building is part of this New York City 4 day itinerary.
Port Authority
Arrange to arrive by bus to the Midtown Port Authority location. Like Grand Central, it’s a convenient location, unless you’re staying further south. Then you might want to arrive at the World Trade Center location.
Getting Around New York City
Walking is the standard in New York City. New Yorkers do a lot of walking. They also take public transportation, which is what I recommend as a solo traveler.
You can get a MetroCard for buses and subway services at any one of the subway vending machines or from an attendant (attendant’s take cash only). MetroCards require a minimum purchase amount up initially. After that, you have options. You can get a Pay-Per-Ride card, a SingleRide card, or an Unlimited Card that allows unlimited amount of rides within a certain timeframe.
If you want to ‘fix it and forget it’, like I do sometimes, you could just opt for the 7-day Unlimited Card and you’re covered on this entire 4 day itinerary, with Staten Island being the only exception.
Don’t forget to hang on to your MetroCard so you don’t have to buy a new one when you got back to New York City.
The subway can cover a lot of city blocks quickly, but the bus can also cover ground above ground providing for more viewing of the city if this is your first time to New York City.
Of course, there are taxis galore in the city, which could be pricey. More budget friendly on solo travel in New York City would be the above methods of transportation or even the Hop On-Hop Off bus, which can be part of your New York City Flex Pass.
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Where to Stay in New York City
Honestly, this depends on what you want to do and see. Different areas of Manhattan will have different prices. If you know in advance what you’ll be doing, then obviously stay close to those sights and activities. Why waste your precious New York City time getting from point A to point B?
That said, you’ll be all over Manhattan in this itinerary, so I recommend staying in a Midtown sustainable-rated hotel to be centrally located. Of these, the Residence Inn by Marriott or the Courtyard by Marriott are some good suggested stays.
Since I tend to be anxious to get out and about, I pick an accommodation that offers breakfast, or at least a coffee and nibble before I venture out. I like to save my meal expenses for lunch and dinner. For 4 days in New York City solo over 50, you may feel the same.
New York Sightseeing Flex Pass
There are many benefits to purchasing the New York City Flex Pass. By knowing what you want to do in advance, you can look up the price of entry and compare to the Flex Pass pricing, and possible required reservations, on over 100 attractions.
The Flex Pass’s “skip the line” options can also be a huge time saving value. You can also cancel it up to 24 hours in advance, if need be.
You can buy your pass online and download it to your smartphone. If you can’t download it, there are four Midtown locations where you can pick up your pass. Bring your confirmation with you.
The Flex Pass covers many of the top attractions on this New York City 4 day itinerary, like the Top of the Rock Observation Deck, Radio City Music Hall Tour, and the Museum of Modern Art (MOMA), for example. It does not cover The Frick, also on this 4 day itinerary.
I used the Flex Pass on this itinerary so it’s a great option but certainly not required.
New York City 4 Day Itinerary
Now you’ve got the lay of the New York City land, let’s get you out there seeing top New York City sights.
Day 1 – Welcome to The Big Apple
Staten Island Ferry
First, relaxing by way of ferry. The Staten Island Ferry, that is. Use your MetroCard and catch the subway to the Whitehall Terminal where you’ll hop on the ferry to Staten Island.
The ferry is FREE and takes about 25 minutes one way across the New York Harbor. You’ll get to kick back with fresh are while you take in the scenic views of lower Manhattan, the Statue of Liberty, Ellis Island and Governors Island. You’ll see why it’s been called, “One of the world’s greatest (and shortest) water voyages.”
Alternatively, you could take the 1 hour cruise around the Statue of Liberty and Ellis Island or the 30-minute fast cruise if you want to save some time.
Times Square
Feeling a little refreshed? Perfect. Hop the subway back to Midtown for some Times Square exploring and shopping (if that’s your thing).
Warning: This is a crazy tourist area, but it’s worth at least a bit of time to see the hub of New York City’s commercial, tourist and entertainment district all rolled into one for yourself. Keep your belongings close to you and no valuables in your pockets.
Broadway
Now’s probably a good time to head back to the hotel and refresh yourself for a classic New York City pastime: dinner and a show.
I know, I know… Broadway tickets can be pricey to downright expensive. I recommend purchasing as far in advance as possible and trying to score some show ticket deals. But this is New York City. How else can you best kick off your first night?
Conveniently located, you’ll be walking distance from your hotel to the Broadway district where shows and restaurants are plentiful. I hope you made your dinner reservations.
I’m no dining critic, so I’ll leave your restaurant exploration to you. Kodama Sushi and Sangria 46 were very nice choices for good food, service and reasonable prices; however, they were closed due to COVID-19, unfortunately. Of course, there are numerous other New York City eats in Midtown to choose from.
The more time you have to dine and absorb the sounds and smells, the better, but make sure to get to your Broadway show at least 10 minutes prior to curtain. If you’re late, you could end up waiting in the lobby until the next break. That would be a huge bummer.
After showtime, venture out for a night cap or just do a face dive into your hotel pillow.
Day 2 – Brooklyn and Then Some
I hope you had a great night’s sleep because this day you’ll be getting up early and working your feet.
Brooklyn
MetroCard in hand, the York Street station in Brooklyn is a convenient 22 minute subway ride from the Bryant Park station. Walk another 2 minutes and you’ll find the Brooklyn Flea on Pearl Street in the DUMBO (Down Under the Manhattan Bridge Overpass) neighborhood.
Open Sundays April through October, you’ll be able to explore the outdoor stalls full of antiques, eclectic clothing, food, collectables, and more. Grab a bite if you missed breakfast.
If you’re not there on a Sunday, then explore the cobblestone streets of DUMBO full of trendy cafes, boutiques and such.
Make your way to the water and hang out at Brooklyn Bridge Park, take in the Manhattan skyline scenery, and ride Jane’s Carousel. St. Ann’s Warehouse has a gallery and regular performances. DUMBO has many things to hold your attention in one morning.
Hang in DUMBO for 2 or 3 hours, then grab some grub to-go for your next adventure.
Walk the Brooklyn Bridge
Within minutes, you’ll be at the entrance to the Brooklyn Bridge Pedestrian walkway (watch for any construction) to walk back to Manhattan. Talk about more skyline views. This is why we start the day in Brooklyn.
Just over one mile in length, the Brooklyn Bridge is a leisurely stroll that could take you anywhere from 30 to 60 minutes, depending on how many snaps you take.
A couple of blocks past the base of the bridge is the Brooklyn Bridge City Hall Station where you can catch the Green 4 or 5 line north. This subway ride gives your feetsies a little break.
Get off at the 68th Street station and walk a few blocks west towards Central Park.
The Frick
The setting and art collection here are simply divine. I have been to this museum more than once.
Set inside Henry Clay Frick’s former 5th Avenue residence, The Frick Collection holds quintessential pieces I even studied in art school. It’s more of an intimate setting than a larger museum. It’s also a shorter visit time than most museums in New York City.
My favorite piece in the Frick Collection? The “St. Francis in Ecstasy” by Bellini. The colors mesmerize me. I can look at it forever.
However, if you have not been to New York City and wish to go to The Metropolitan Museum of Art, The Guggenheim Museum, or other, I completely don’t blame you. These are fabulous places to see, and I will offer that on a separate New York City itinerary. I have been to New York more than once, so of all of the art museums, I include The Frick as the go-to art stop for a four day visit.
Central Park
No matter what time of year, by now you should still have plenty of daylight to walk across 5th Avenue and relish Central Park with all of its beauty, iconic features and music.
From The Frick, walk eight blocks north and enter the park at 70th Street. There are maps of the park at the entrance or you can download one to your smartphone. You can arrange for a guided tour if you wish. This is the last attraction on your day’s itinerary.
Walking by yourself, zig zag along the east side of the park. I recommend meandering south past the Alice and Wonderland statue, a favorite for kids.
Southeast of the statue is the Conservatory Water holding model bloats floating and racing about. East is the Hans Christian Andersen statue.
Grab a drink and an appetizer at the iconic Loeb Boathouse outdoor bar (check for hours). It could be very busy but you can put your name on the waiting list. You may even see someone famous. I sat next to Mark Ruffalo and his folks last time.
If you want, rent a row boat.
From there, keep walking southwest towards the Bethesda Fountain, a great place for resting your feet while you people watch and listen to the outdoor musicians.
From the fountain, head south towards The Mall and Literary Walk. Check out what the local vendors are selling.
Keep walking south past the Naumburg Shell – there may be an outdoor performance – to the Balto Statue.
If time permits, you’ll walking past the Central Park Zoo. Although I’m not big on zoos, it is small enough for a quick diversion, but closes at 5pm on weekdays, 5:30pm on weekends and holidays. It is also available on the Flex Pass.
Past the Gapstow Bridge is the East Drive exit where you’ll walk out to 59th Street and the The Plaza Hotel. Pop into their second floor Rose Club to keep your New York City celebration going with a glass of bubbly. It’s a great excuse to rest your feet. Again.
Head back to your hotel to change before dinner or just stay out as-is. You’ve had a long day so it’s your call. If you have beautiful weather, I do recommend trying dining on a roof-top bar and catch the sun going down over the city.
Day 3 – More Free Sightseeing
Bryant Park
Take your morning coffee outside today in the memorable Bryant Park. Enjoy watching New York City go by.
Historic New York Buildings
When you’re ready to motivate, start a little walking tour of some of New York City’s iconic buildings and history.
Since you’re there, drop into the New York City Public Library (Stephen A. Schwarzman Building). It’s free and beautiful to see. They also offer free, docent-led library tours at 11am and 2pm Monday through Saturday. Tickets are first-come, first-serve. Tours last an hour.
Two blocks east is awe-inspiring Grand Central Terminal, one of the most popular filming locations in New York City – more than 50 films and TV shows have been filmed in this historic building since its opening in 1913 (after 10 years of construction). Look up at the ceiling. Amazing.
One more block east is the famous, Art Deco style Chrysler Building. You can enter the lobby only, but it’s so worth it to see the red marble and artistry of the period.
Start making your way to 1260 Sixth Avenue for your pre-arranged tour of Radio City Music Hall, another historic New York City building.
Grab a slice of classic, New York zahhh to-go on the way. Don’t forget to stop by the LOVE statue on 55th and 6th.
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Radio City Music Hall
If you can catch the Radio City Music Hall Stage Door Tour by 1:30 or 2pm, you’re doing great. Tours start every 30 minutes and last 75 minutes long.
Walk on the stage and through the hallways that hosted numerous, legendary performers who have played at Radio City since its opening in 1932. It’s amazing how much there is to learn about this entertainment institution that almost folded for good.
Rockefeller Center / Top of the Rock
Just a five minute walk away is famous, Rockefeller Center. Walk the plaza and fountains outside first and then enjoy the black marbled hallways before you head up to your ‘skip the line’ entry to the Top of the Rock Observation Deck.
The deck is open 365 days a year and offers 360 degree views of the city. It closes at 12:30am if you want to view the city lights. You can take as much time as you want, but I suggest allowing just an hour should you want to do more than I provide this particular day.
St. Patrick’s Cathedral
Exit Rockefeller Center towards 5th Avenue, and St. Patrick’s Cathedral is right across the street. It’s free to the public 7am to 8:30pm, but please observe the cathedral’s service schedules.
This marks the end of your third day in New York City. You may have time to catch another attraction, or just relax at your hotel a while before venturing out for your last night of dinner and drinks on the town.
Try one of the New York essentials for dining. If you have the energy, check out one of the many jazz clubs afterwards for libations and live music.
Day 4 – High on Art
I recommend an evening departure so you can still have time for a few more New York City musts on your last day.
Sleep in a bit. Arrange your transportation. Then leave your bags at the hotel when you check out so you can enjoy the day before your flight leaves.
The High Line
Catch the subway blue line south to 14th Street and 8th Ave and walk west to the High Line northern entrance.
The High Line is an elevated linear park and greenway that used to be part of the New York Central Railroad. You can walk its almost 1.5 mile path towards Washington Street if you have the time, stopping to enjoy the art work and murals along the way.
Chelsea Market
Stop midway through the High Line at the Chelsea Market Passage and pop into Chelsea Market to grab a bite. There are great food vendors and shopping. It’s also a cool place to duck out of the sun on a hot day.
MoMA
For your final New York City attraction in this fun-filled, New York City 4 Day itinerary, I give you the Museum of Modern Art (MoMA). There are a variety of exhibitions and must-view art pieces only the MOMA holds.
Sit outside and enjoy a bit of tranquility before your travels start again. If you didn’t get to eat along the High Line, the MOMA also offers a café for travel bound sustenance.
More Top Sights in New York City
I hope you enjoyed your 4 days in New York City 4 stay solo over 50.
Of course, you can’t see all of New York City in four days. If you’re fortunate enough to have more time in New York City, check out the following top sights and attractions.
- Empire State Building
- American Natural History Museum
- Washington Square Park
- Statue of Liberty / Liberty Island
- The Whitney Museum
- Prospect Park
- Carnegie Hall
- The Cloisters
- The Roosevelt Island Tramway
- 9/11 Memorial and Museum
- One World Trade Center
- Battery Park
- Brooklyn Botanic Garden
- Intrepid Sea, Air & Space Museum
- Bronx Zoo
- Lincoln Center for Performing Arts
- Madison Square Garden
- New York Botanical Garden
- United Nations Headquarters
- Apollo Theater
- Tour NBC Studios
- Circle Line Sightseeing Cruises
- Belvedere Castle
- New York Aquarium
- New York Yankees game
- AND MORE
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Let Me Hear From You
I would love to hear if this solo New York City 4 day itinerary was helpful to you. Post me your thoughts or questions in the Comments section below. Thank you!
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