3 Top Tips for Enjoying Holiday Activities in New York City

Nov 29, 2016

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Many of us have some special destinations or events we enjoy traveling to with regularity, and one of those special times and places for us is New York City during the winter holidays. It helps that we have family in Connecticut who we usually get to see when we go to the NYC area, but even without that draw, seeing the real Santa at Macy’s on 34th Street, the outdoor ice skating rinks, the department store windows, the Rockefeller Tree, and more just makes NYC a favorite of ours and a destination we highly recommend to other families looking for similar holiday experiences.

Saks Fifth Avenue Windows

I’ve written about our holiday visits to New York City before, but I figure it can’t hurt to share this year’s version of our top three tips for visiting NYC during the holidays.

See Santa at Macy’s on 34th Street, but get an Express Pass

Santa is obviously a busy fella in November and December, so it is reasonable that he can’t spend his days in every single city around the world and instead sends some similarly dressed “helpers” to handle the mall visits in smaller cities. He has to choose to go where he can see the most kids at once, and that makes NYC a top destination for the real Santa, and consequently for us. Of course, he also appreciates the entire Santaland that Macy’s on 34th Street provides for him and that the reindeer can hang out in nearby Central Park while he visits kids at Macy’s.

Ready to enter Santaland!
Ready to enter Santaland!

Santaland at Macy’s on 34th Street is indeed a land filled with rainbows, candy cane forests, and Christmas decor galore. It is absolutely worth visiting, but the lines can be outrageously long at times. A way around the majority of the line is to get a free Santaland Express Pass online 48 hours before you want to visit Santa.

Entering Santaland via the Express Entrance
Entering Santaland via the Express Entrance

The tradeoff of the Santaland Express Pass is that you will miss I would guess 2/3 of the Santaland experience when using the Express Entrance, but if you are also missing a two hour line, that may be a good trade-off, especially with little kids or unenthused spouses. Personally, I think if the regular line is under an hour, the full Santaland experience is probably worth it, at least once. You can always reserve the Express Pass for your group and then cancel if the regular line isn’t too bad to get the full experience. The elves can give you a good line time estimate when you arrive.

Santaland experience


Unfortunately, there is no way to skip the line to order photos, so build that into your schedule if you want a printed or digital copy of your official Santa photos. They do let you take pictures with your own camera during your Santa visit, but it generally takes us at least 30 minutes after seeing Santa to go through the line to obtain the official Macy’s photos. Only one member of the group waits in that photo line and the others can retreat to a different part of Macy’s to shop or have a post-Santa snack.

...not everyone appreciated Santa this year
…not everyone appreciated Santa this year

After your Santa visit, I recommend grabbing a green juice at the juice bar that is directly next the the Santaland exit and then either head up a floor to the holiday decor shopping area (conveniently located next to the couch and furniture shopping area) or stay on the 8th floor and head to the Annie’s Pretzel area around the corner for a seat and a carb loaded snack.


Go Ice Skating, But Not at Rockefeller Center

I’m sure some will disagree with me on this, but I personally think that the best holiday ice skating venue in New York City is not under the tree at Rockefeller Center. To be honest, I’m not a fan of Rockefeller Center at all during the holidays as it is just overwhelmed with people to the point that it isn’t fun (to me). If you have never seen the tree there I guess it is worth braving the crowds once, but we have gotten to the point where I purposefully avoid that claustrophobic area during peak holiday times. This also applies to the ice rink there.

Instead we prefer outdoor ice skating at Bryant Park just next to the Public Library on Fifth Avenue. Admission is actually free if you happen to have your own skates, but otherwise it is $20 for the skate rental. They do take express reservations online if you want to pay extra to avoid a potential line there, but we took our chances and didn’t experience a wait the evening of Black Friday.

Walk right behind the NY Public Library to find Bryant Park

It is still going to be crowded, but the area in general is less claustrophobic than Rockefeller Center.

Bryant Park Ice Skating

As an added bonus, they bring in dozens and dozens of different food stall vendors to Bryant Park for the holidays, so it is easy for everyone to get a post-skate snack or entire meal at a reasonable price. My best tip for enjoying your outdoor meal is walk just outside of the main food stall area to find more tables if you want to actually sit down.

If you do have your heart set on ice skating in Rockefeller Center under the tree, but hate lines then consider splurging on a VIP ice skating session, but it is indeed a serious splurge. Or just go to Bryant Park….

Choose Your NYC Holiday Hotel Wisely

This is always true when you visit NYC, but I think it is even more important for a special holiday visit that you choose your hotel wisely. I don’t think there is a better points-friendly hotel in New York City for a holiday visit than the Andaz at Fifth Avenue. It is directly across from the Central Park Library and Bryant Park, and a very easy walk down to Macy’s on 34th Street.

View from the Andaz Fifth Avenue

It is also an easy walk up Fifth Avenue to Rockefeller Center (if you dare) and to some of the nearby department store windows on Fifth Avenue including Sak’s Fifth Avenue, Bergdorf, and more.


The cluster of Times Square kills a little of the holiday magic for me, but if you stay at the Andaz on Fifth you get a relatively calm oasis in the middle of the city.


Walking near the Andaz Fifth is an enjoyable experience

They also offer a complimentary evening wine happy hour from 6-8PM in case you need a little assistance getting into the holiday mood, as well as complimentary coffee in the mornings to get you going before you get out of the door.

Staying at the Andaz Fifth Avenue will run you 25,000 Hyatt points per night or 12,500 points + $150 per night on a points + cash rate. Paid rates here can be between $400 – $500 per night around the holidays, so points are a good plan. If you have top tier Hyatt elite status also know that they let you enjoy room service breakfast instead of having to go to the restaurant, which is a real treat…get the lemon poppyseed pancakes at least once!

I’m very thankful that miles and points make regular holiday visits to NYC a reality for us, as it truly is a special spot from late November through New Year’s, and even more special when you are a little strategic about where you stay and what you do. I’d love to hear your top tips for visiting NYC during the holidays!

Saks Fifth Avenue Lights Show

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