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Your Ultimate 2020 Guide to the Holiday Season in NYC

Ahh… take a deep inhale of that NYC air. And nope; the smell isn’t absolutely disgusting around this time of year. It’s the holidays in Manhattan, and this means that instead of senile zoo scents or polluted winds, it’s chestnuts and cheer that fill the streets this year. Although 2020 has thrown some challenging hurdles at us since about March, one thing has not changed, and it’s this: there is simply nothing like New York City for the holidays. Welcome to the ULTIMATE - and very personally researched - guide to sightseeing, eating, and (of course) shopping in the most festive city this year.

**See bottom for a note on TIPPING during the holidays!


There’s nothing like Fifth Ave…

And no, it is not overrated. Strolling through Fifth Ave and gazing at the holiday display spectaculars is a feeling of nostalgia that cannot be replicated - not to mention, the outside of designer stores like Cartier and Chanel on both Fifth and Madison are always so cool. Even Central Park is right next door, waiting for the unsuspecting New Yorker to take advantage of its greenery. I would suggest a late afternoon to dark (which is around 4:30 these days; how crazy) stroll with a loved one or friend through Fifth, ending the night in awe with the Saks Fifth Avenue Light Show 2020. A few weeks ago when my delighted mother and I stood in front of Rockefeller Center (best viewing, for sure), we were dazzled by its royal appearance and the kind man selling sparkling balloons from behind the gate. The charming display happens every night about every ten minutes- truly a must see. Don’t forget to wear your walking shoes and bring a stacked wallet!

Ice Skating at Bryant Park

Is the Rockefeller rink way too crowded to be ice skating during a pandemic? Does giving money to the Wollman (owned by Trump) really grind your gears? Never fear: ice skating at Bryant Park is the perfect alternative, and by far my favorite location to fall flat on my face on a cold, hard rink. Truly paradise. No seriously- Bryant Park is the only free-admission ice skating in New York City, and is open from 8:00am-11:00/11:30pm on most days. While ice skating is the primary reason you should attend, I’ll be completely spending my month’s salary at the Holiday Shops. Bryant’s open-air, miniature kiosk-filled shopping formation is so adorable, and can be completed with a trip to the Lodge Deck for some festive cocktails. Come on. Letting dad and the kids slip around on the ice while topping off your holiday shopping with a spiked hot chocolate? What could be better than that?

LuminoCity Festival

I know. Let’s make the venture away from Manhattan and hop on over to Randall’s Island to experience this gem- picture Alice in Wonderland, but trippy. And a lightshow. I always recommend LuminoCity to friends, and every time I get the same response: “But isn’t that a little kids thing?” Um, NO. It’s literally an outdoor sculpture museum. First of all, it makes for the absolute best photos (the glowing mushrooms are always my fave), and contains food vendors and the cutest little gift shop. Tickets are around $30 general admission with the usual discounts (seniors, students, kids) and seriously, it is so worth it. Of course, masks are required to be worn throughout the duration of your stay. Seriously- the people who watch your Snapchat/Instagram stories are about to be so jealous.

Lotte New York Palace

Hello, Gossip Girl. Remember when Serena was sipping a cocktail at a bar in the first season and we were all like, “How the hell does a 16 year-old get served without ID in Manhattan?” And, oh I don’t know… that place where Chuck Bass lived? Yeah. That was the Lotte New York Palace Hotel, a luxury resort experience that puts even places like the 1 Hotel or NOMO SOHO to shame. Located in Midtown Manhattan, the Lotte is one of the city’s most iconic, glamorous landmarks. Do I hear photo op? Be sure to complement the area’s surroundings with nude, earthy tones in your fit, perhaps finished with a pop-of-color handbag to match the extraordinary tree colors. You seriously can’t go wrong with snapping pics during the day or night; most of the photo-grabbers are bound to be at the Rockefeller.


The Greens - The Rooftop at Pier 17

This destination is sure to be on any dining-related guide I release literally ever because it’s so freaking cool. Although most New Yorkers understandably get the heebie jeebies when hearing “enclosed dining space” like the Greens advertises for, it’s honestly as safe as the most congested city in the country can get. The prospective diner is required to reserve their own private dining cabin, and can get their drink served in a Yeti cup (I find this touching in an odd, hilarious sort of way). Because this location is as groovy as it is, I would absolutely suggest making a reservation as far in advance as you possibly can (which is about a week, unfortunately). But when you do get in- the boozy coffee? Exceptional. The fondue? So cheesy. And the vibes? Remarkably perfect.

Lillie’s Victorian Establishment

As the little Who girl in The Grinch once lamented, “Where are you, Christmas? Why can’t I find you?” If you’re feeling a little down and dreary this holiday season (which we definitely don’t blame you for), I know exactly where you can find your spirit: all you have to do is step foot in Lillie’s Victorian. Shake the snow off your parka and take a seat, because this establishment is one of the most festive, decoration-filled, yummy restaurants I could possibly recommend to treat yourself with this season. For dinner delectables (you can also do brunch here, if you prefer), I adore the pork belly bao bun small plate to sit with my every-time entree of steak au poivre. The wine list is superb. (Yes, that deserved its own sentence.) If you want to be wholeheartedly delighted with holiday decor, greenery, and any single type of festive decoration you can think of, I could not suggest Lillie’s more. They take “deck the halls” to a new level.

Oscar Wilde

The Irish playwright? Nah. The restaurant that appears as if it houses Kris Kringle himself due to the extraordinary decorations and holiday options? Yeah, baby. Not only does Oscar Wilde house New York City’s longest bar at 118.5 feet on a normal day, but they also offer a private dining experience by the fireplace that any couple would give up their Christmas list for. The menu and cocktail list are lengthy and delicious; whenever I find myself nestled at Oscar Wilde on a girls’ night out, I without fail select the Cemetery Gates, a drink that is served on fire (never fear- after its flames subside, the cinnamon stick is left with the most delicious charred flavor to add to the cocktail). The service never disappoints, and the experience is simply a treat overall. Although it’s fairly easy to make a reservation at Oscar Wilde (I’ve never personally had trouble with it myself, even on the weekends), I give the establishment a 5 Star Rating and will recommend it ‘til the reindeer come home.


Hudson Yards Mall

“But SARAH! A mall on your list of festive shopping experiences? Seems a little basic, don’t you think?” Well, my dear critic, I mirrored your exact sentiments before actually taking the trek there, myself. The Hudson Yards Mall, tucked right next to the beehive-structure Vessel and tourist-attraction High Line, does appear to be just that: a mall. However, once inside (if you couldn’t already tell from gazing into the crystal, see-through walls of the establishment), it is truly an experience even The Polar Express couldn’t compete with. Gleaming pine trees line the building, a sparkling hot air balloon rests in the air just inside its doors, photo ops like the tie-dye piano covers the mall’s upper floors, and gold twinkly-lights wrap around each and every escalator and railing. Not to mention: SALES, SALES, SALES. If getting way too excited about the holiday gift selection at Cartier and 20% off at Sephora makes me a little Grinch-y, I accept that. But regardless, if you’d rather wrap up your holiday shopping with a nice little bow this week, or simply gaze in awe at the gorgeous decorations, the Hudson Yards Mall is here for you this season.

Holiday Lane at Macy’s Herald Square

There is no way I could have left out one of the most darling, New Yorker-friendly destinations in all of Manhattan. If you’re looking for somewhere to bring the kids this year that doesn’t involve putting on ice skates, mosey on over to Midtown and stroll around Macy’s 9th floor extravaganza. Although Santa Clause will not be coming to town this season due to COVID-19 regulations, Holiday Lane at Macy’s Herald Square is still absolutely fabulous. My personal favorite Lane decoration are the trees, supplied in plenty and decorated with the most aesthetically-pleasing ornaments and streamers. Need to mail your letter to Santa last-minute? Holiday Lane has a shiny, red mailbox to send away your wishes, complete with larger-than-life star decorations and ornaments lining the walls in every room. It’s truly a can’t-miss for all ages.

Greg’s Trees

I am convinced that the only reason New York City doesn’t smell like garbage during the holidays as it would at any other point during the year is in huge part due to the Christmas tree stations parked everywhere from the Lower East Side to Greenpoint, Brooklyn. Greg’s Trees, in particular, is fantastic for the sole reason that I’m 100% convinced Greg is Santa Claus. Seriously, look up his picture. Just kidding; there are so many justifications for shopping at Greg’s Trees this season (rather than getting on Kris Kringle’s good side). Kiddie cutouts are plentiful, Claus visits are spontaneous (check Greg Trees social media for exact times of visits), and holiday baubles are ready to dazzle you with spirit. Greg offers both regular and “jumbo” selections of seriously affordable holiday trees (this is Manhattan; we’ll take what we can get), but what I love most about these stations is the wholesome family feel that’s complemented with the ever-spectacular customer service. No Grinches at Greg’s Trees! Happy tree hunting.


I get it. Tipping during the holidays (especially during COVID) can seem extraordinarily daunting and/or stressful. But, never fear! There are tons of resources at your disposal to help you figure out who to tip, when to tip, and how much. While tipping is not ever required, I highly encourage you to do so - especially in these troubling times - whether it’s your regular doorman who you’ve always favored, the waiter who brought you and your hubby a free glass of champagne at the end of the meal, or your housekeeper who never fails to make the apartment sparkle. We live in a world where money is scarce and any kind gesture is appreciated; do what you can, and don’t stress! Happy holidays, dear reader.

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