Updated: May 2023

New York City (NYC) is truly a MAGICAL place

Anyone who thinks otherwise is kidding themselves, hasn’t found the right area to suit their liking, orrr is KIDDING themselves. Hahahaha. I MIGHT be partially biased because I was born and raised in the state of New York, so NYC will always hold a special place in my heart.

I made this guide because tourists often miss out on things when they travel simply because they are unaware that these places exist. The suggestions in this walking tour are easy to follow and because everything is located in Midtown Manhattan so you can easily walk from one place to the next. If you have mobility issues I would skip the Empire State Building and start on 5th Ave so the walking is minimal. The best part about this outdoor NYC walking tour is that it’s completely FREE!

If you have extra money, don’t feel like it or are unable to walk, or want to go inside all of the locations you can upgrade this tour. With The New York Sightseeing Pass (NYSSP), you can easily enhance your experience in New York City. With the pass, you don’t have to worry about navigating the subway since the pass includes the Hop-On Hop-Off Big Bus, paying entrance fees for 150+ attractions, and you are eligible for discounts at various locations and stores.

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When Should You Visit

If you have never been to NYC, in my opinion, Christmas time is the best time to go. *Sings*  “It’s The Most Wonderful Time Of The Year!” There is just something sensational about visiting during Christmas time. Everyone is in a jolly mood, the city is filled with beautiful lights, and there are more free things to do than normal. Even if you aren’t visiting during the holiday season all of the places on this tour are still worth the visit in the off-season.

What To Do

Empire State Building

You really shouldn’t visit NYC without visiting the Empire State Building. This historic building is a symbol not just for New York, but honestly for the entire United States. It is known as the Most Famous Building In The World and was just voted the Number 1 Attraction in the United States in 2022 by TripAdvisor. The ESB has no shortage of things to do inside its walls and is included with the NYSSP.

• Observation Decks on the 86th & 102nd Floors
• Over 10 different Exhibits
• Shopping
• Restaurants

The last time I was in NYC I visited the NEW Starbucks Reserve at the ESB and it’s absolutely a vibe for date night, sneaky links, and brunch with the girls. It’s hard to believe that this 3 story hideaway is a Starbucks! Hurry and make reservations for the restaurant or one of the experiences.

After exiting the Empire State Building you are going to walk up 5th Avenue.

5th Avenue

If you actually walked from the Empire State Building there are many sights along the way like the New York Public Library, Bryant Park, and St. Patrick’s Cathedral. A big part of the holiday season involves shopping. Many flagship stores call 5th Ave home. Fifth Avenue stores are on the pricier side but don’t fret, window shopping is just as great around this time of year as well. The storefronts are usually really special for Christmas. If you don’t go to any of the stores you need to stop by Saks 5th Avenue at night. Saks 5th Ave has a beautiful light show that is projected on the outside of the building, every 10 minutes, starting at 17:00 (5 PM) and ending at 23:00 (11 PM).

Rockefeller Center

If you turn around from Saks’ light show you will be at Rockefeller Center. Rockefeller Plaza is probably one of the most recognizable locations in NYC due to the enormous Christmas Tree on display during the holiday season. There are so many things to do at this location it could probably warrant a post of its own.

• The Christmas Tree At Rockefeller Center (On Display Starting 11 November 2023)
• Ice Skating (Opens 4 November 2023)
• Go To A Live Taping at NBC Studios – Tickets are usually free
  • Saturday Night Live (SNL)
  • The Tonight Show Starring Jimmy Fallon
  • Late Night with Seth Meyers
  • many other shows
• Top Of The Rock Observation Deck (included with the NYSSP)
• View The Large Golden Statue, Prometheus
• Channel Gardens (Christmas Angels)
• Shopping

Radio City Music Hall

Radio City is actually one of the many buildings included in the Rockefeller Center Complex, even though most people would not think of them as related. When I was younger my father’s company gave us tickets to see The Christmas Spectacular at Radio City Music Hall every year. It became somewhat of a tradition, to watch this show with the iconic Rockettes. Once my family moved to Florida we didn’t go to the plays anymore, but I always had fond memories of them. Christmas of 2015, I thought it would be a cool idea to get my whole family together and see it one last time.

Even as an adult these ladies were still entertaining. Maybe even more so as I fully understood the dynamic of what was really going on. Like, wait that’s the same Rockettes in every scene? Do you mean to tell me it’s the same ladies for every outfit change? And just knowing that 36 women can go from scene to scene seamlessly just adds more magic to the show. While the show has changed a bit (they put in some 3D elements), some parts still haven’t changed. To be completely honest these tickets are pretty expensive if you buy them directly from Radio City. BUTTTT if you are savvy like me you could at least look for discounted tickets. I was lucky enough to find them on Groupon for a great steal! Get Radio City Music Hall Stage Door Tour included with the NYSSP.

Giant Christmas Ornaments

Along 6th Avenue, you can find Giant Christmas Ornaments also known as Gigantic Holiday Cheer. The most popular of the set is the gigantic red ornaments. They can be found across the street from Radio City Music Hall at 1251 Sixth Avenue. If you walk along Sixth Avenue you can see quite a few beautiful oversized decorations.

My family has been taking pictures in this exact spot for years.

Times Square

Times Square is a good place to visit regardless of the time of year. With all the tall buildings and flashy lights, it’s a wonder how people could look away. It really is captivating, especially for someone who has never been there. In 2013, I went to Times Square to see the ball drop. This was on my Bucketlist and I was so happy I got to complete it. The energy you could feel from that place was electric.

Even though it was like 9 degrees Fahrenheit that day, people stood in the cold from around noon just to see the ball drop at midnight. We got lucky while we were out there and ran into a cousin who happened to be working that night. He was nice enough to escort us close enough that we had a perfect view.  While I would suggest you get there early if you want to actually get a good spot to see the ball drop make sure you are dressed properly and pee before you leave the house or wear a diaper. Even if it is not cold when you leave the house wear layers. Another alternative to standing in the cold is to get a hotel that overlooks Time Square and view the show from the warmth of your room. It will be expensive but not impossible to book if you plan ahead and have plenty of money to spend.

You can find a map of all the places you need to go here

Want to save money while traveling in NYC?

Get the NY Sightseeing Pass. It will save you money on many of the attractions listed and give you ideas for places you would have never visited. It is “The only Pass that includes the Empire State Building, Top of The Rock, Edge, One World Observatory, and a $70 discount on the NY Helicopter Tour.”

What are things you have enjoyed in midtown NYC during the holidays?

Leave your comments down below.

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