Updated: Dec 14, 2021
All you need to know about exploring the iconic city like you live there 🍕🥨🍎
This itinerary is a 3 day guide to making the most of your time and hitting all the best spots! Feel free to linger longer if you have more days. Have a question? Feel free to ask, I am happy to help you enjoy every minute and save as much money as possible while doing it!
Day 1- Wear good walking shoes and start early!
The 60th Street and 5th Avenue Walk:
You've arrived. Let's gooooo - I recommend beginning this day at either the Metropolitan Museum of Art or the Natural History Museum. Both open at 10, are near Central Park, amazing, and could easily be a full day (depending on how much time you'll have in the area). Hit either museum in the morning, and then proceed with the walk down town around noon. This route is full of pit stops you can go inside and warm up along the way. There will be plenty of opportunities to eat when you get hungry.
Another Museum option is the Cloisters, in Fort Triton Park – the renaissance museum in a castle overlooking the Hudson. Although not as central, or as huge of an art selection, a real place that will make you feel like you have left NY for another time and place. If you have an extra day this is a GREAT place to wander and take photos. More on that later...
The Met Cloisters 10-5
99 Margaret Corbin Drive
NY NY 10040
If you go here don't miss the unicorn tapestries.
The Met Fifth Avenue 10 - 5:30
1000 Fifth Avenue
New York, NY 10028
If you go here – DO NOT miss the Egyptian section or the roof top view.
American Museum of Natural History
Central Park West at 79th Street New York, NY 10024-5192 Phone: 212-769-5100
If you go here – Do not miss the dinosaurs 4th floor.
See Day 3 for more on prices and discounts for Museums...
Once you start your walk down town you will get a real appreciation for NYC. This is definitely a city best seen on foot.
Next Stop: Go inside the Lincoln Plaza shopping mall – Upstairs on the second floor are the big holiday stars that change colors and light up – DO NOT MISS THIS
AKA the Shoppes at Columbus Circle – on floor 2 star exhibit ** BEAUTIFUL **
We are ready to cross over to 5th Ave for our hike!
*Begin your walk headed East along 60th Street, the border of Central Park, at Columbus Circle
*Walk from West to East along the bottom of Central Park to 5th Ave
*Eat hot dogs/ good street food (also good and cheap souvenirs in this area)
*Wander into Central Park and see some really awesome sites/ landscapes
*Do a little pit stop for Rock Climbing in Central Park
*Start walking down 5th Ave – admire windows, street lit snow flakes and take your time window shopping.
There are Decorations all around
Windows are always displayed well!
5th Avenue –
Even if you can't afford to shop at Cartier or Prada, you must stroll down NY's famous shopping row. Have your own little breakfast at Tiffany's or peek into shops along the way. There are also more accessible options like H&M and Sephora. Apple and Rolex are impressive pit stops also.
*Dress warm! Invest in those gloves that allow you to touch your phone screen so you don't have to freeze every time you want to take a picture!
*Walking from fifth avenue and 60 St. (Central Park) going South in direction, plan the following stops: Rockefeller Center, St. Patrick's Cathedral, The New York Public Library and stop in Bryant Park's Winter Wonderland. You have a few hours, and want to be by the Chrysler building by dusk to watch the sun setting. Check your sun set time and take time wandering.... *Walk over to The Plaza, act like you’re staying there, just stride into the Grand Lobby. Get a good look at the Palm Court Restaurant, and all the shops inside; then stroll out like you’re going somewhere, as the dressed up bellmen opens the big doors for you. OK...then you’re back on 5th Avenue, and Trump Tower is just across the street, with Tiffiany's beside it. First, go into Tiffany's and oooh and aaah at the Tiffany Diamond. Then hit the Trump Tower, under the scrutiny of lots of guards. Wander all around the atrium, go up the escalator, and enjoy the views. Next stops are Bergdorf Goodman and Sax. Farther down 5th Ave is St. Pat's Cathedral and Rockefeller Center to explore. That little stretch of 5th is a GREAT thing to do with kids who are old enough to appreciate it, and it's free. It’s also hard not to be impressed no matter how old or young you are. The lights and the cold, along with the city hustle and bustle are like no other place in the world.
St. Patrick’s Cathedral - stop for art and prayer
(Right across from Tree)
Address: 460 Madison Avenue, New York City, NY 10022
Phone Number: +1 212-753-2261
Go inside, warm up, see beautiful architecture. St. Pat’s is right across from Rockefeller Center and next door to Saks Fifth Ave. dept. store. The place is always full of tourists taking photos. Go inside and warm up! See Christmas displays and admire the beauty. People walk around inside looking at the many displays, and there is usually quite a crowd.
*If you're exploring the holiday windows, be sure to stop long enough outside Saks Fifth Avenue to enjoy the light show (it runs every 8 minutes or so).
Rockefeller Plaza – STOP FOR TREE
Walk around the square plaza. See the tree and angels from a variety of view points and find the best photo! NY never skimps on Christmas spirit, although the crowd may be difficult and the weather cold!
KEEP walking down 5th Ave until you reach the….
NY Public Library https://www.nypl.org
*When it opened, the NYPL was the largest marble building in the country, and home to over a million books – you will know it by the two large marble lions on either side of the steps.
Warm up and go up to the 4th floor for some REAL architectural beauty.
476 Fifth Avenue (42nd St and Fifth Ave)
New York, NY, 10018
SUN - 1 PM–5 PM
MON - 10 AM–6 PM
TUES, WED -10 AM–8 PM
THURS - SAT 10 AM–6 PM
Bryant Park – STOP to take in the majesty of the Chrysler Building rising up over the Public Library (bonus: watch at dusk as the tower begins to glow). Bryant Park is a 9.603-acre privately managed public park located in the New York City borough of Manhattan. It is located between Fifth and Sixth Avenues and between 40th and 42nd Streets in Midtown Manhattan.
There is a Winter Wonderland exhibit set up here and you can walk through and get candy, Hot Cocoa, see cool stuff AND ICE SKATE FOR FREE – if you have your own skates. If not you can rent them! Fun village and by now it should be getting dark. The Christmas lights begin to twinkle right on time.
Walk over to….
Grand Central Terminal
Address: 89 E 42nd St, New York, NY 10017
89 E 42nd St, New York, NY 10017
Grand Central Terminal is a commuter rapid transit railroad terminal at 42nd Street and Park Avenue in Midtown Manhattan and.... Great place for eating – if you want fast and cheap try the food court, also to warm up – or stop at the Oyster Bar if that more meets your needs. There is a whispering gallery outside of the Oyster Bar if you are into that sort of thing. Look up! The Zodiac ceiling, the Clock, you will feel like you’ve been there before because these are featured in so many places. From there, catch a train up to Broadway/ Times square if you don’t want to walk…. Or if its too cold! It would not be cool to say you went to NY and didn’t ride the subway. There are usually some street musicians down there playing, and maybe a hustler offering to give you a ticket for some cash…. Keep your eyes open and look like you know where you are going!
Broadway – Cool strip to walk and people see, if this is not your thing skip and walk through Times Square. DO NOT GO TO Central Park in Dark. Stay in busier areas.
If you want to see a show, and don't care what you see (and don't mind waiting in line), snag discounted, day-of tickets at the TKTS booth in Times Square. It opens each afternoon and offers tickets that haven't yet sold at 20-50% off. The TKTS app will tell you what's available each day. Arrive at the booth early, as the lines will get long. Head off of Times Square for better pre- and post-show food and drink. Restaurant Row (46th St. between Broadway and 9th Ave) has a lot of great options, as does Hell's Kitchen. You will experience shorter lines at the TKTS booths at South Street Seaport or the Brooklyn location.
Question: Can I really go to a Broadway show in casual clothing?
Answer: Yes, that's what most people are doing now.
If it fits your traffic pattern and you prefer to freshen up, feel free- If not do not miss the opportunity!
ALL of that was one well planned day – the 5th Avenue adventure! That is the Christmas time MUST!
If you followed this plan your route looks like this:
This shows beginning at the Museum of Natural History which makes the easiest traffic pattern)
Lower Manhattan Day!
The Spirit of NY down in the financial district will move you like nowhere else. This day is not as spread out as the first, there is a lot of action clumped into the Lower Manhattan area. Walking will be the fastest way to navigate the busy streets. Just take a taxi, Uber or train to the Statue of Liberty to begin.
Statue of Liberty/ Ellis Island/ Battery Park
National Museum of the Native American
The freedom tower and WTC memorial
South Street Sea Port
Statue of Liberty –
If you know you are coming and want to see this attraction, book your tickets in advance.
Tickets are $25.50/ person for a reserve or pedestal ticket, $28.50 for crown access, and sell out 6 weeks in advance typically. So check your options as soon as you know your travel dates. Late afternoon tours, after 2PM and 3PM, will not have enough time to stop at Ellis Island Immigration Museum.
Regardless of if you are going up into the statue or not, the ferry ride and Ellis Island are worth the trip. The views of the skyline, historical presence and monumental significance are awe inspiring. Dress for the weather, plan for some lines and a security check to enter.
National Museum of the Native American
10 AM–5 PM daily, Thursdays to 8 PM - except December 25
Admission is FREE!
There are tons of exhibits and history under one roof, with some cool hands on activities under one roof! Great place to spend a few hours.
Walk up Wall Street to the Bull
Ok so it’s just a sculpture right? Well not exactly, it’s a pretty famous little landmark that signifies fighting through the hard times. After a black Monday market crash in 1987, a Sicilian sculptor dropped it off there illegally in 1989 to thank America for the opportunities it afforded him. Since, its been photographed countless times, from both the front, and the back! Pick your angle.
Walk over to the Freedom Tower – WTC memorials
It is the tallest building in the US, the tallest building in the Western Hemisphere and the 7th largest in the world. Definitely worth a stop! But seriously, the draw here is the WTC memorial. Two large square imprints of the ground zero towers engraved with the names of all who were lost on that horrible day. The water falls and names could not be more thought provoking of the magnitude and reverence we feel. An excellent place to pause and reflect.
The Oculus in NYC is a newly opened artistic landmark within walking distance of the World Trade Center. The transit hub, serving the PATH, cost four billion dollars, making it the most expensive train stop in the world. With its modern design, it immediately became an attraction! The entrance can be accessed through 4 World Trade Center from Liberty Street. Nearest metro train (subway) stations are Cortland St., Fulton St. and Chambers Street. Come and eat, shop or commute! (Window shopping is also appropriate)
Surrounding the WTC and freedom tower is Liberty Park, home to The Sphere, the iconic sculpture salvaged from the World Trade Center site. Another statue, America's Response Monument, can also be found close by. You are already there, so the stroll is convenient.
Walk to Trinity Church
Trinity Church Wall Street 120 Broadway New York, NY 10271 212.602.0800
*Right now (2019) the church is closed for some renovations, but still an awesome pit stop.
Visit the place First President George Washington worshiped during the brief period that NYC was the capitol of the United Stated. Many graves mark the ground on both sides of the famous little church, and serves as the final resting place for Alexander Hamilton, his wife, and son. More recently, it served as a refuge to many on September 11th, 2001 and suffered no damage on that day in spite being so close to the tragic destruction. You many remember this church for the movie National Treasure.
Walk/ Uber or train to South Street Sea Port for dinner/ ice cream
This is where you’ll find a great view of the East River and Brooklyn Bridge, and if you are looking for cheap tickets for a Broadway show the place to stop! Not usually busy - TKTS South Street Seaport, near the Fulton street metro stops - (199 Water street, in the back) you can see what tickets are available for shows same day or next day matinee for a 40 – 50% discount. Cobblestone streets line upscale galleries, bars, cafes, and shops. If you come at 12:00 noon you can do tai chi with the Chinese, under the highway! Historical ships and a museum are also here to wander and explore. While this area is under construction since Hurricane Sandy did a lot of damage, it is still a great stop and enjoy the moment kind of place with lots of choices for eating!
If this fills your day, or you head off to Broadway, you can easily stop here. This is a perfect place to enjoy NY, however if it’s still early or you are not going to Broadway, try walking the Brooklyn Bridge (weather permitting). See details for this on Day 3....
If you followed this plan you're route looks like this....
Day 3 Central Park to Brooklyn Bridge -
There are a few more things you have not yet done in NYC, and you have to get up and get out to enjoy the day! Today may vary based on what you did Day 1 and 2, but this is going to be a fun adventure! You will need public Transportation as this day is more spaced out.
Central Park – (Midpark at 72nd st.) the Bethesda Fountain and Terrace and Belvedere Castle are close enough together to be worth a stop. Wander/ explore Central Park for fun!
Central Park Zoo –
830 5th Ave, New York City, NY 10065-7001
A small 6.5 acre Zoo in the middle of Central park, this is a great place to spend a few hours.
The main zoo area has 4 “zones”: Tropics (indoor multi-level rainforest); Temperate (up the hill to see red pandas, snow leopards, bears, etc.); Polar (indoor penguin exhibit); Central Garden (sea lions). The Tisch Children’s Zoo exhibit is out the gate and down the path from the Main Zoo section. Don’t miss a visit to the 4-D Theater too! A typical zoo visit is approximately 1.5-2 hours.
Adult (13 & over) $13.95 / Child (3-12) $8.95 / Child (2 & under) FREE / Senior (65+ $10.95
Ages 3 & up $7
The High Line – An elevated railway no longer in use now a public park – with gardens and beautiful scenic landscapes. Runs from Gansevoort St. to W. 34th between 10th and 12th Avenues. Spend a couple hours here, eat, relax, live! Take a bottle of wine up and watch the sun set here. There are many entrance points in the Chelsea District, you may want to enter at the most northern access point located at 34th Street. Walk, wander, enjoy the amazing views, have a picnic, and appreciate the small escape from the City below.
Roosevelt Tram –
The most modern aerial tramway in the world, running every 7-15 minutes from 59th Street and Second Avenue in Manhattan to Tramway Plaza on Roosevelt Island. For the price of a subway ticket ($2.75 each way) you can take the tram to Roosevelt Island and enjoy some amazing views from the East Side of Manhattan. A 10-minute ride giving unobstructed views of the bridges and Manhattan skyline. No cars drive on Roosevelt Island, it’s a nice place to walk or take the tram back and enjoy the view again.
Sunday through Thursday: 6 AM - 2 AM
Friday and Saturday: 6 AM - 3:30 AM
Remember on Day 1 I suggested beginning your day at a museum? Here is where we circle back. The MET cost’s: General admission is $25 for adults; $17 for seniors; $12 for students; and free for Members, Patrons, and children under 12. General admission tickets include exhibitions and are valid for three consecutive days at The MET Fifth Avenue, The MET Breuer, and The MET Cloisters. Meaning, if you went to the MET on Day 1, today you could go to the Cloisers, or the MET Breuer, FOR FREE or return for longer time to explore! There are all great choices. Or take advantage of the Suggested Admission: For New York State residents and New York, New Jersey and Connecticut students, the amount you pay is up to you. These tickets may be purchased at a Museum admissions desk with a valid ID.
The Natural History Museum:
A major tip is purchasing your ticket. If you come the day of, the amount given is “voluntary.” You can give as much or as little as you desire. The cavate is having to wait in line, which can be 25 – 30 minutes. Go early and save time and a few dollars. Paying on-line is much faster, and more expensive. Prices: Adult $23 / Child (2-12) $13 / Senior & Student $18.
Constructed in 1874 with Teddy Roosevelt as one of it’s founders, this place is impressive! Dinosaurs and Megalodon artifacts are a favorite! The dioramas of animals on display are well designed and make you think of all the differences in species and unique quality of each.
The Empire State Building:
Another not free favorite is the sky ride on the 2nd floor! A simulated roller coaster that takes you on a NYC adventure! Great but especially if you need an indoor activity and have the extra money to spend! 30-minute ride, narrated by Kevin Bacon, expect a line! Skip the money for paying for the observation deck and get this experience instead.
Ticket Info: Adults - $47; Children - $30; Seniors - $39
Hours: Mon.-Sun. 8am-10pm
Walk the Brooklyn Bridge – If you didn't do this on Day 2, and the weather is permitting - enjoy the skyline and take in the view from the monumental Bridge. Many people take this scenic walk (even when it’s freezing which I don’t recommend) but it is all about the weather and good shoes. While views are more dramatic at night when the city lights are on - it is warmer with the sun shining! So You decide which works best for you.
*This is where you will see amazing views - for free - Stop and take pictures, take in the scene and go at your own pace!
There is a pedestrian walkway above the traffic, so it is perfectly safe. The trek is just over a mile long, Under the bridge, Brooklyn Bridge Park waits, which great for walking, playing, or relaxing with a view. The surrounding neighborhood is also fun to wander = DUMBO (Down under the Manhattan Bridge overpass) which is like old NY, cobble stone, and iron posts, just the “home” feeling. You can walk this bridge in either direction, however the best views are going towards Manhattan. I recommend taking a subway to Brooklyn then crossing back over on foot. The A or C subway run in both directions and are easy to navigate. Get off at the High Street Brooklyn Bridge Stop and you are there!
EAT. Pizza. Bagels. Egg sandwiches. Even the macaroons are better here. Everything is delicious. Book stores and shops line the Brooklyn streets and it is a unique area to explore.
If you followed the main points of this itinerary (not including museums) your map would look like this: (However, the MET would easily fit this traffic pattern)
While ALL of this can be done in 3 busy days, it can also be spread out if you have more time!
Please leave questions and comments below, I look forward to hearing from you!
I have LOVED living in NY and now as a Florida resident, LOVE visiting. There is NO PLACE like it!
Prefer to See NY when it's not Christmas? Go here....
Need a trip to the South?
Visiting Florida at Christmas? Check out Saint Augustine, America's first city!
Or if you just need a good road trip to the Sunshine State, find trip ideas here....
Maybe I am partial to New York because growing up there gave me insight to so many people, cultures, lifestyles, extremes, and the lay of the land. I absolutely feel my best when I am home, Something about the energy of the city that just feels good in my veins! I hope that this guide inspires you to explore NY with confidence, enjoying every moment of your time.
Please share your experiences for the benefit of your traveling friends everywhere,