12 Ways To Go Beyond Your Guidebook In NYC [Video]

The tagline of Jessie on a Journey is “taking you beyond the guidebook,” and that’s what I aim to do in every post I publish. It’s not that I don’t see the value in guidebooks, but my typical travel style includes getting lost in new neighborhoods and discovering the lesser-known. As a native New Yorker and a licensed tour guide, I know how to get off the beaten path. While this list is in no way exhaustive, I wanted to provide some unique things to do in NYC.

Tip: Want to explore NYC with a guide? Book a private custom photo safari and get high resolution photos of your group to keep!

1. Get Drunk On Sugar At Prohibition Bakery

Mini cupcakes and booze intermingle perfectly at Prohibition Bakery in the Lower East Side. The cozy establishment is the brainchild of a classically-trained chef (Brooke Siem) and a mixologist (Leslie Feinberg), who collaborated to create treats that truly taste like the cocktails they reflect, whether it be a brandied cherry-topped “Old Fashioned” or a gin-laced “Bee’s Knees.” My personal favorite isn’t exactly a cocktail, but the sweet and salty “Beer & Pretzel.” Guests on the East Village Cocktail Tour I lead agree!

2. Drink Absinthe Like Al Capone At William Barnacle

NYC is full of modern-day speakeasies paying homage to Prohibition (though the high quality of the drinks speaks to a time before dirty bathtub gin). That being said, it’s not always easy to find a bar that was actually open in the 20s. Enter William Barnacle Tavern, once a club called Scheib’s Place when it was illegally operated during Prohibition. The speakeasy was owned by Bavarian gangster Frank Hoffman, who smuggled in alcohol through dynamite lined tunnels. You can explore these tunnels and more in the attached Museum of the American Gangster, though it’s also worth popping into the tavern for some absinthe. Sit at the very bar gangsters like Al Capone and Lucky Luciano drank at — it’s original — and savor bohemian-style absinthe through Manhattan’s only absinthe drip. The absinthe is poured over a sugar cube, which is then lit on fire to caramelize it. As the sugar sits on an absinthe spoon, ice water drips onto it from a spout to dissolve it into a glass of absinthe below. This softens the drink. By the way, absinthe is made from fennel, anise (a licorice-tasting digestif) and wormwood, a mild muscle relaxer that is not hallucinogenic. If you see any green fairies it’s because you’re susceptible to the placebo effect.

3. Drink In History At The Noble Experiment

The USA undoubtedly loves its whiskey; but did you know that by the 1720s there were 16 rum distilleries in New York? Rum is the first spirit that stuck with New Yorkers, though Prohibition didn’t help with keeping the tradition alive. Luckily in 2012 New York passed the Farm Distillery Act, making it easier for distillers sourcing local ingredients to get licenses. Since then a number of distilleries have popped up, including the Noble Experiment in East Williamsburg making Owney’s Rum. They use 100% domestic ingredients and all-natural non-GMO molasses to craft their tasty spirit, and a rum tour with tasting is $10. Their tasting room also has free bar snacks and board games to enhance the social experience.

4. Cook In An Immigrant Home Through The League Of Kitchens

This is hands down the coolest thing I’ve ever done in New York. Through Visit.org and League of Kitchens I booked an experience sharing culture and cooking in the home of Damira, a woman who moved to Brooklyn from Uzbekistan in 2013. We made delicious barak (dumplings), eggplant salad, cucumber salad, beef and vegetable stew…not to mention Damira had a full spread already laid out upon arrival. You’ll be so immersed in culture you’ll forget you haven’t left NYC! 

5. Learn The Art Of Mustard Pairing

Who knew mustard sommeliers were a thing? At Maille in the Upper West Side you can savor over 50 unique mustards infused with ingredients like chardonnay, beetroot, candied ginger, and a complex mixture of apricots, curry spices and wine, to name a few. You can sample from the tasting bar, get pairing advice from the onsite mustard sommelier and partake in make-your-own mustard classes for some DIY fun!

6. Pair Perfume With Wine

Some of you may know I’m a certified sommelier. One of the most important rules we learned was perfume is not welcome in the tasting room, as its scent can overpower the wine’s characteristics. Kelly & Jones turns this notion upside down with a Notes of Wine Fragrance Collection meant to be paired with vino. Buy the perfume online to do an at-home tasting or head to Jill Lindsey. This cute boutique sells the perfumes and has a wine bar!

For the full list of quirky things to do in NYC, check out the video below.

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