Happy holidays everyone! I’ve said this before, but the holiday season is one of my favorite times in the city. Not only does everything look—at the risk of sounding cheesy—magically beautiful, but over the years I’ve developed so many city traditions that make being in New York feel—again, at the risk of sounding cheesy—even more special than it already does every other time of the year.
Of course, there is no shortage of opportunities to indulge in food and drink this time of year either. SantaCon is probably the most well-known drinking event of the season, but I personally prefer something a little more low-key and sophisticated. For those of you who fall into that same bucket, I’m here today to offer an alternative bar crawl that is just as festive but won’t leave you holding anyone’s hair back at the end of the night. In fact, inspired by one of my favorite holiday songs—The 12 Days of Christmas—it’s designed to take place over 12 nights instead of one. The perfect way to savor the holiday season if you ask me.
Below you’ll find your holiday road map. Enjoy the adventure and the holiday season!
First Day of Christmas: A partridge in a pear tree. Nothing screams Christmas more than a pear-flavored cocktail, and it’s important to start the crawl off on an extra Christmas-y note. You can find a great one called “Pear Me Up” at Baita, the Italian Alps pop-up restaurant in Eataly. Made with bourbon, mezcal, pear puree, nutmeg, and brown sugar simple syrup lemon juice (who knew that was an ingredient), it will get you feeling all warm inside. Just the way you’re supposed to feel when you settle in at the lodge after a long day of skiing.
Baita is located on the top floor of Eataly, 200 Fifth Avenue in the Flatiron District.
Second Day of Christmas: Two turtle doves. When I hear the word “dove,” it makes me think of chocolate. And on a bar crawl chocolate means chocolate martinis. While there are a number of places in the city known for their chocolate flavored drinks, Max Brenner is the one I recommend for the holidays. It just has that cozy holiday feel. It’s also right near the Union Square holiday market—my favorite in the city—so you can do some shopping afterward and kill two holiday birds (doves?) with one stone.
Max Brenner is located at 841 Broadway.
Third Day of Christmas: Three French hens. Champagne is the ultimate French drink, and the Plaza is the ultimate holiday hotel. So head straight to the Plaza’s champagne bar on Day 3.Yes, it’s an indulgence, but if Kevin McCallister could indulge at the Plaza in Home Alone 2 then so can you.
The Plaza is located at 768 Fifth Avenue, with the Champagne Bar next to the lobby.
Fourth Day of Christmas: Four calling birds. Is there any bird in New York more well-known than the NBC peacock? I hope not, because that’s the inspiration upon which I’m drawing here. Bar Sixty-Five at the Rainbow Room in Rockefeller Center is known for its views, and at 65 floors up you may actually be able to call back to the birds as they sing to you.
Bar Sixty-Five is located at 30 Rockefeller Plaza.
Fifth Day of Christmas: Five golden rings. To celebrate the fifth night of Christmas you should head to a bar on Gold Street, and Felice is one of the best in the Financial District. Order a glass of eco-friendly Italian wine, and if you’re feeling hungry go for the Crostone Ricotta. Because every holiday outing should include something with figs and honey.
Felice is on 15 Gold Street in the Financial District.
Sixth Day of Christmas: Six geese a laying. You have to go with eggnog here, obviously. It’s a holiday classic, and you should drink it in a bar that is also a classic, so head to Pete’s Tavern in Gramercy Park. It’s been open since 1864, and their eggnog has been getting praise for almost that long. Also, their holiday decorations are apparently off the hook. Bring your camera to this one.
Pete’s Tavern is located at 129 East 18th Street in Gramercy Park.
Seventh Day of Christmas: Seven swans a swimming. This is a little bit of a stretch, but swans swim in water, and ports are on the water, and port wine happens to be my favorite cold weather drink so I really wanted to find a way to feature it in this bar crawl. A lot of restaurants and bars with big wine lists serve port, but Pierre Loti has a bigger selection than most other wine bars I know. It’s also very cozy, a requirement for drinking this delicious dessert wine. Go for a glass of the vintage. It’s always the best.
Pierre Loti is at 53 Irving Place in Union Square.
Eighth Day of Christmas: Eight maids a milking. You may remember Cafe Lalo from that scene in You’ve Got Mail, where Meg Ryan is waiting to meet Tom Hanks for the first time and he stands her up because he realizes she is his arch rival. It also happens to serve a delectable selection of spiked milkshakes, coffees, and hot cocoa drinks. Get something with Bailey’s Irish Cream—it’s what Kathleen Kelly would do.
Cafe Lalo is located at 201 West 83rd Street on the Upper West Side.
Ninth Day of Christmas: Nine ladies dancing. This year I discovered that there is a burlesque version of The Nutcracker showing in New York. It sounds fabulous, and will definitely feature at least nine ladies dancing. And the icing on the cake? You can pre-order a bottle of champagne or wine—or a holiday cocktail—so that it’s waiting for you at your seat when you arrive.
Nutcracker Rouge is running at 383 Troutman Theatre Space (383 Troutman Street) through January 14, 2018. Tickets can be purchased on the website.
Tenth Day of Christmas: Ten lords a leaping. The King Cole Bar at the St. Regis Hotel is fit for royalty (proper attire is required), which makes it perfect for the tenth day of Christmas. It also makes it another splurge on the list, but again, it’s the holidays, so if you can afford to splurge then it’s probably okay to do so. One note on this place—it’s apparently where the Bloody Mary was invented. With that said, you may want to go earlier in the day, or break rules and have breakfast drinks for dinner.
King Cole Bar is at 2 East 55th Street (at Fifth Avenue).
Eleventh Day of Christmas: Eleven pipers piping. Nowhere in the city will you be more likely to hear bagpipes than at Highlands NYC, so head here on Night 11. And order a whisky, obviously.
Highlands NYC is located at 150 West 10th Street in the West Village.
Twelfth Day of Christmas: Twelve drummers drumming. It’s only appropriate to end on a note that brings us full circle, and City Winery is the perfect place to do that, for two reasons. Let’s get the obvious one out of the way first—the theme of Day 12 is music, and you can hear some fantastic music at City Winery. And, during this time of year, that music includes holiday music, which brings us back to the theme of this crawl, a holiday song. The second reason though is that it’s a winery, and while I’ve veered pretty heavily into cocktail territory in this post, this column is at its heart a wine column. So, it’s fitting that we end our holiday journey here. City Winery has many delicious wines to offer, but I recommend that you try one of their own. And ideally, try it in the context of one of the many holiday shows they are offering this season. Who knows, you may even hear the very song that inspired this post.
City Winery is located at 155 Varick Street in Tribeca/Soho. Tickets to all holiday shows can be found on their website.
By: Reagan Daly