I love to travel, and I loathe feeling like a tourist. This aversion to on-the-beaten-path exploration prompts me to ask a lot of questions at dinner parties. My favorite line of inquiry for well-traveled friends and random strangers alike re: globe-trotting has long been Where’s the first place you go when you get off the plane? I want to know what’s more urgent than checking my bags at the hotel. Where is the do-not-pass-go, do-not-collect-$200 spot one must directly venture to upon arrival? Everyone has a #firststop in a city that they frequent.
Exploring the world through the hyper-local lens of vetted musts is, IMHO, the only way to travel. In our new series, I’ll be sharing those places with you. It’s going to be a melting pot of long-standing institutions and stumbled-upon dives. To kick things off, we’re taking a page from my personal black book. Every trip I take to New York City starts in an alley. In that alley is the best cocktail north of the Mason-Dixon line.
I was in my early 20s the first time I went to New York. My father had lived there in the ’70s after growing up in Texas, and his choice to willfully trade the open range for the Big Apple seemed an act of defiance. He showed me around his version of New York City, covering haunts and stomping grounds, diners overturned into kitschy gift shops, and seedy neighborhoods since fully gentrified to the tune of multiple frozen yogurt chains. It is one of the best travel memories of my life.
Directly after our trip together, he suffered a brain injury. I started traveling on my own to New York and San Francisco, cities he’d lived in when he was my age. The ritual felt like tracing over the faded lines of a map. Making my own way through his neighborhoods on the East Coast, I spent most my time on the Lower East Side. My friends in town lived in Brooklyn or Alphabet City, so I crashed on a lot of couches and bought everyone dinner at places they otherwise couldn’t afford as a thank-you (you know, “gestures of gratitude”—the original Venmo).
One night, a colleague cobbled together a group dinner at a restaurant in an alley between Bowery and Chrystie. To this day, I don’t recall if the gathering was business or personal. (I was working for a film studio, so the line between work and play was often razor thin.) I showed up to dinner at Freeman’s Restaurant knowing only one person peripherally. I left with four people whom I now count among my favorites in the world, and I blame the best cocktail in Manhattan: the Freeman’s cocktail. Also to blame (in no particular order) is décor that manages to juxtapose a haunted mansion with an eccentric uncle’s taxidermy collection (without veering into camp), a killer seasonal menu, and a back alley entrance that feels clandestine and magical year-round.
Pictured above is the entrance to Freeman’s (aka Freeman’s Alley). One truly can’t go wrong making this your premier destination upon landing in Manhattan. A permanent fixture on the otherwise rotating menu, the Freeman’s cocktail is made with rye whiskey and pomegranate molasses; it’s as though the best old fashioned you ever had got a swift kick in the pants of Southern hospitality. On a school night, ETA from JFK to this drink clocks in at roughly 50 minutes. The restaurant also serves an impeccable brunch, if you’re so inclined.
If you find yourself taking our advice and using Freeman’s as your next NYC #firststop, here’s what other gems await a stone’s throw from the establishment.
The lobby of The Bowery Hotel is the touchstone in NYC where business time meets quittin’ time. The Lower East Side institution is storied and wildly adaptable. One can execute a business deal as easily as a birthday party here, such is the magic of the Bowery. If Fred Flintstone had lived in Manhattan, he would have punched that time card, slid down the tail of that brontosaur, and landed squarely in the lobby for revelry sans commute. This is the cool kids’ table. The rooms have teddy bears. Stay here.
Don’t miss this vintage boutique jewel box. A most trusted fashion maven introduced me to Edith Machinist years back, and my first purchase was a 1990s sweater that vaguely resembled Fruity Pebbles. The selection is imaginative and fairly priced. Living in L.A., I struggle with the dilemma of cultivating an actual wardrobe built for “weather.” Vintage is ideal since it enables me to invest in winter pieces sporadically every few years. As you may have guessed, Fruity Pebbles sweaters are not the base of the West Coast fashion pyramid, but the style does have legs.
The city that never sleeps calls for the most bespoke of legal addictive stimulants. If you’re like me and you take your cafés like Larry David (begrudgingly cool and aggressively unaffected), Café Grumpy is for you. The local coffee chain serves up delicious house-roasted brews. Order the Heartbreaker Blend espresso. It is aptly named.
Catch some music at Piano’s while you’re in the neighborhood. The bookings are consistently great, and the venue strikes an idyllic chord between intimate and lively, a quality the LES has in spades. I especially love it in the winter months. Ducking into a show to escape the frozen snow tundra of the city is the best excuse for a late night out.
I first came to Schiller’s via a writer friend/NY native who had relocated to L.A. The pitch to end an evening here was so impassioned that it bordered on yelling. Despite a few incendiary write-ups accusing Schiller’s of “jumping the shark” of hipsterdom, it still ranks among my favorite restaurants for an after-hours meal or hangover-nursing breakfast. I’ve also had full-blown business lunches here. It’s entirely charming and conveniently located on the corner of Rivington Street, which serves as a bastion of hope when talking tourists through a meeting point step by step at rush hour.
This concludes our 24-hour tour. For the seasoned jet-setter, I’m also running down my top five carry-on must-haves below.
- ShhhSilk Single Silk Pillowcase ($79)
- Raden A22 Carry ($295)
- Tom Ford White Patchouli ($115)
- “Ladies” by Matt Maust Sticker ($5)
- Killspencer Zippered Pouch ($129)
1. These naturally hypoallergenic silk pillowcases have an invisible zipper, making them too easy for hotel travel. Your skin and hair will thank you.
2. My technology-enhanced, lightweight A22 in matte black charges all my devices on the go. It handily beats finding an outlet in a terminal. When I realized I could also fit three pair of boots comfortably in the side with the battery pack (the smaller side), I hugged it. I’m not even a hugger.
3. I make a point of not wearing fragrance on flights out of consideration for the other passengers, but a spritz of Tom Ford upon arrival is my figurative “first stop.” A favored perfume is an emotional rescue after a journey.
4. I require all travel belongings to be black on black. This compulsion makes my luggage impossible to differentiate from the masses, so that’s a great excuse for cool stickers. I have this Matt Maust one on the back of my carry-on. It’s very popular in the security line at JFK.
5. All my relevant travel documents, headphones, and devices get stashed in my Killspencer leather pouch to streamline for takeoff. It folds into my larger purse upon landing and doubles as a clutch for events. The pebbled leather is like butter.
Have a first stop we should know about? Tell us in the comments below.