Rachel Josar is completely, unabashedly optimistic about New York City. She’s lived here for some 17 years and has been located in Ridgewood for the last five. There, she’s started a local, New York-themed, concierge business called “They Had Fun.” There, she pitches herself as a curator for digging up new and interesting things to do in the city.

Before doing this, Josar spent a decade working for a family of wealthy financial executives uptown, where she would plan everything for them, from intimate date nights to Saturdays on the town. Soon enough, she developed a rolodex of restaurants and other rainy day recommendations which she decided to take out the door into her own businesses. Like many an ideas of the era, the concept started out as a podcast; “They Had Fun” booked the likes of local street fashion photographer Johnny Cirillo and Sammy Buttons, a street musician.

Two years ago, Josar decided to try to expand the concept into a full-service concierge business involving selling personalized itineraries that come complete with routes and details already mapped out thorough Google Maps.

“Originally I catered to tourists,” said Josar,”Or ‘visitors,’ as we like to call them.”

Josar working out of a cafe in Bushwick (left), where she plots detailed maps of place in the city for people to go (right). She also produces a show where she profiles some of her favorite local spots in the city, like the Windjammer in Ridgewood.

“When I think of a ‘visitor’ I think of someone who doesn’t live here but likes to travel,” said Josar, “They’ve been to other big cities so they know how to call an Uber from the airport, and they aren’t asking where to stay in Times Square because they already booked their favorite hotel in Chelsea,” she says about this ideal customer. That difference is key to Josar’s style of curating places for them to go; her itineraries are designed to engage the paying customer with a certain idea about New York culture. 

She sells these to them for a flat fee, ordinarily around $150, for a single curated guide. For an extra $50, she will also handle reservations. For $50, Josar also sells somewhat cheaper “itinerary consultations” that involve less work.  

According to Josar, people visiting the city are overwhelmed by endless options. The internet is saturated with recommendations from Yelp, TikTok influencers and r/AskNYC Reddit threads. This is where Josar comes in. A typical $150 day lasts about eight hours, with four to five stops and comes with travel tips. Through a questionnaire, customers will tell her things like their favorite modes of transportation, their overall budget and some of their favorite cuisines. Like a search engine opperating out of a human-sized internet, Josar will then plug those details into her own reservoir of places to go. 

In addition to tourists, Josar says she also picks up businesses from couples wanting date night itineraries and other locals wanting to rediscover the neighborhood of their hometown. She has sent couples on citi-biking brewery tours, and planned birthdays for Jersey residents looking for a night in the city.

Aside from reservations, she says she intentionally tries not to mark any times on the itinerary.

“Think of it as a jumping off point,” Josar says, telling me that she thinks this idea captures the magic of the city that lets you get lost in it, time and time again, from the unfamiliar roads to the  unfamiliar curbside art stalls, to the bar that always happens to be playing your favorite song. 

On her podcast, Josar stresses the importance of her “Just Say Yes” mindset. On a recent episode, she interviewed Kurt Maitland, a writer who calls himself “one of the best-known faces in New York City’s whiskey circuit.” On the program, Maitland regales her about a time he gotten locked out of an apartment and decided to, instead, spend the day killing time in lots of other places, instead.

Ridgewood’s Sundown cocktail bar is among the kinds of small, local businesses that Josar suggests hitting up in the neighborhood.

To give an idea of the kinds of places she looks for, Josar wrote us a list of recommendations for a perfect Sunday in her own backyard of Ridgewood; bookmark it for a warmer day. 

First, start with lunch at Mt. Everest Deli, a family run bodega along Myrtle Avenue that she says is home to some of the best Indian food in the neighborhood, as well as a variety of international snacks and spices. Her suggestion: get the steamed veggie Momos, enjoy the spicy sauces and sit across the street in the plaza in front of the Ridgewood Veterans Memorial or the nearby Clemens Triangle. 

After savoring the momos, she recommends walking down Myrtle to Parrot Coffee, a local grocery store where you’ll find an olive bar, jarred spicy pickled peppers, feta, nuts by the pound and all the Mediterranean snacks you didn’t know you craved.

Then, she recommends walking further along to the newly opened Topos Too, the second bookstore run by the people behind the first Topos, also in Ridgewood. This one focuses on new books and Josar recommends losing yourself in the hipster bookstore’s many varied selections, and also ordering some coffee, wine, beer or some snacks in the back.

To top things off, Josar suggests either hitting up Sundown, a small, intimate minimalist cocktail bar that also boasts olives, cheese and a recently-opened basement club that books indie bands and hosts karaoke nights called “Sundownstairs.” If you’re feeling hungry, Josar also vouches for Decades Pizza, one of the neighborhood’s many new pizzerias, where if you make its happy hour (weekdays, 5-7pm) you can catch a slice for $4 and a martini that comes with some arancinis for $18. 

Photos taken by taken by Molly Healy for Bushwick Daily.

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