NYC:  Wanders Below Midtown

In our first NYC post, we shared the story—why we came, what we loved, and how we somehow survived three months of nonstop motion. But the real heart of our time in New York was in the wandering. No agenda, no appointments, just laced-up sneakers and curiosity leading the way. Below we share a few perfect days.

Hotel Chelsea and the Trailer Park Lounge

Wander #1: Chelsea to Meatpacking

Grab a coffee at Variety on 7th & 25th—a low-key gem with excellent cappuccinos (oat, extra hot) and shockingly un-New York prices.  Walk west down 23rd St, past the newly revitalized Hotel Chelsea— once home to Janis Joplin, Arthur Miller, Sid & Nancy, and an entire generation of dysfunction.  Across the street, peek into the Trailer Park Lounge for kitschy, trashy, tinsel-covered dive bar vibes. We loved this spot.

The Eighth Ave Fever Dream

Cross Eighth Avenue at your own risk. It’s a chaotic scene of grime and bad decisions, complete with mystery puddles and a constant cloud of weed.

Once, we saw a jogger get full-sprint chased by a guy, yelling bloody murder. Can you imagine being out for your casual morning run when some deranged stranger decides you are the villain from his dream and he must give chase?  That jogger clocked his best pace of the year.

The Garbage Fail

Detour down to 22nd Street, our block.  It’s leafy and lovely, lined with gorgeous townhouses, and… heaps of trash. In plastic bags (how is this still the system?). The rats own this block after midnight.  We lived it.  We know.

The Street Sweeping Fail

You may also wonder at the residents sitting in their cars, mid-morning, laptops open, working away. This is the legendary NYC street-sweeping shuffle.

Twice a week, New Yorkers will sit for exactly 1.5 hours to avoid getting a ticket—because if you’re in the car, it’s technically “attended.” George Costanza said it best: “A garage, I can’t even pull in there. It’s like going to a prostitute. Why should I pay, when if I apply myself, maybe I can get it for free?”

Of course, many don’t bother with the tricky maneuvering when the sweeper arrives—pulling out, waiting, then squeezing back in without losing the spot to a lurking vulture. The result? Streets that maybe got kind of clean. Maybe.

Honestly? Forget street sweeping. Let’s invest in sidewalk pressure washing. At this point, the gum on 6th Avenue might be old enough to vote.

High Line, giant pidgeon, Standard Biergarten

Back to our Wander

Hop on the High Line at 23rd Street—the epic elevated park that kicked off this whole urban renewal thing. Head north to Hudson Yards (meh, unless the giant pigeon is still roosting), and then U-Turn and walk south toward the Whitney. Enjoy the wild gardens, public art, and all the glassy new buildings trying very hard to be interesting.

Pop into the Whitney—it’s compact, thoughtful, and captivating. Afterward, wander the cobblestone streets of the Meatpacking District, where meat is still technically packed. Stop for a pint at the Biergarten at the Standard Hotel, where people once posed nude in the windows (so 2009).

Little Island

Cross the West Side Highway

Stroll over to Little Island—a charming park perched on tulip-shaped stilts. It’s nice inside, but honestly, the best part is how cool it looks from the street.

A little farther north, duck into Pier 57 for a drink or snack to take up to the rooftop for panoramic views, including that dramatic angle over Little Island’s tulip-stems.

Wrap it up by exploring the art galleries tucked beneath the High Line between 19th and 22nd, or graze through Chelsea Market.  We recommend Very Fresh Noodles and Los Tacos #1.

For great eats anywhere along the route, check out our ranked lists of restaurants.

scenes from a scenic bike ride

Wander #2: Cycle the West Side 

Riding a bike in NYC feels like something our 1990s selves would’ve called a death wish—but plot twist: it’s actually one of the best ways to get around. Dedicated bike lanes abound. Citi Bikes are everywhere.  It’s Sean’s preferred commute—even in the dead of winter and even without gloves—because it’s fast and cheap.  And he’s too busy to buy gloves.

For an easy intro, hop on a Citi Bike and cruise the Hudson River Greenway (West Side Bike Path): start at any point and head north to the 96th Street tennis courts.  Then U-Turn and head south. Along the way, you’ll pass riverside parks, dog runs, piers packed with sunbathers in the summer, soccer players, and many pedestrians you’ll need to carefully dodge.

Wave at the kayakers by Pier 96, cruise past the Intrepid (yes, that’s an aircraft carrier just sitting there and yes, it’s a good tour if you’re interested), and continue past the glittering mess that is Hudson Yards. Soak in the view of Little Island and coast through Battery Park, where the Statue of Liberty peeks out at you like, “You made it.”

End at the Seaport—grab a drink, sit by the water, and wonder how the hell you are getting home.

riding the subway

Subway Shenanigans

To some, it’s terrifying. To us, it’s freedom. Walk 40 blocks, hit a wall? Subway. Sudden downpour? Subway. That plant you bought turns out to weigh 50 lbs? Subway.

A staple Instagram feed, Subway Creatures, captures the best (and worst) of underground NYC, and we, too, saw our fair share of spectacles.

• The good: a couple guys clutching oversized bottles of corner-store wine and fistfuls of bodega roses, en route to a date.   
• The bad: the guy in a stained tracksuit screaming “You ever really look at a pigeon?!” to the whole car, while everyone stares intently at their shoelaces.  
• The ugly: the time Doug hopped on a train, only to realize—too late—that human excrement was very much in play. He and a stranger locked eyes, silently asking, ‘Is that…?’ before sharing a look of horror and a synchronized dash to the opposite end of the carriage.  Bonded for life by the outrage and the laughter.

And yet. We love the subway.

the pretty West Village

Wander #3: The West Village

Start where 9th Avenue melts into Greenwich Street—that dreamy, movie-set version of NYC, lined with classic brownstones, tucked-away cafés, and leafy trees spilling over wrought-iron fences. This stretch is the West Village postcard.

Just east, Hudson Street offers cozy wine bars, tiny-perfect boutiques, and restaurants that make effortless cool look… effortless. Stop at The End of History for mid-century glass pieces priced like museum artifacts. Or grab a slice at L’Industrie Pizzeria on Christopher Street—but know your order before you reach the counter, or face the wrath of the line.

New Yorkers Get a Bad Rap

Yes, they are direct, Yes they expect efficiency. Yes, they can be surly.  But here’s the thing: New Yorkers might secretly be the most helpful humans on Earth.

Struggling with a stroller? Someone will wordlessly grab the other end and carry it down the stairs with you. Call out a group of kids for knocking over a trash can? Instantly backed by a chorus of “yeah!” from every direction.  Emerge from the subway looking lost?  Someone might simply point and say “East.”

That’s classic New York.

Back to the Wander

Stroll east on Bleecker for cheese havens (hi, Murray’s), vintage finds, and designer shops. Detour through Grove Street—one of NYC’s oldest—and maybe snap a pic at the Friends apartment (we see you).

Roam.  No matter how turned around you get, you’re only ever two minutes from somewhere adorable.

For a drink, try White Horse Tavern—beloved by literary ghosts, including Dylan Thomas, who reportedly drank his last whiskey here before his death. Or, have a cozy meal at Justine’s on Hudson.

people watching in Soho, Little Italy, La Esquina, Back Room

Wander #4: Soho to LES

Soho is where cobblestone charm meets $900 sneakers. Start on West Broadway, meander through cast-iron buildings, and pop into McNally Jackson, one of the city’s best indie bookstores.

Detour to Tribeca for coffee at Blue Bottle (yes, from Oakland; yes, owned by Nestle; yes, still the best in NYC). Window-shop along Prince and Spring Streets, then pause at Jack’s Wife Freda for a sidewalk table and world-class people watching.

Keep drifting east and breeze down Mulberry Street through Little Italy—a little touristy, a little chaotic, a little fun.  Where the sidewalk cafés spill into the street. Gelso & Grand is a lively pick for pasta and people-watching. Then wander down Elizabeth Street, a quiet block with nice shops.

Keep moving east into the Lower East Side, especially around Orchard Street, where the vibe gets funkier and more fashion-forward. You’ll find everything from edgy streetwear to minimalist chic. Check out spots like Assembly, Komune, and Kallmeyer. It’s like Soho’s cooler, slightly disheveled cousin who wears interesting pants and doesn’t care what you think.

Need food?

Brunch at Clinton St. Baking Company. For dinner, try Cervo’s—seafood at a lively bar—or La Esquina for tacos and a side of speakeasy attitude. Want a true speakeasy? The Back Room delivers on ambiance, and your cocktail comes in a teacup. More recs here.

the iconic Flatiron, La Cabra coffee, Apollo bagels, Jackson holding court at Soothr, Union Square market, McSorleys and Pete’s Tavern

Wander #5: Flatiron, Gramercy, and the East Village

The neighborhood lines blur a bit here—especially since real estate agents have renamed half of Manhattan, giving every third block its own invented name.

Start at Eataly, the sprawling Italian food wonderland that somehow convinces you it’s totally reasonable to buy a truffle for $350. Exit and take in the fabulous Flatiron building, that iconic skinny pizza slice of architecture, and then head southeast down Broadway.

Cross over to ABC Carpet & Home, a kaleidoscope of design: maximalist, whimsical, and full of beautiful things for your home if budget is not an issue.

Gramercy and Union Square

Head to Gramercy Park, one of Manhattan’s most serene little pockets. The park itself is famously private, accessible only to those with a key, but the streets around it are fair game, and they’re lovely.

Grab brunch at Friend of a Farmer, a charmingly rustic spot with homey vibes. Or go full NYC institution and book a table at Gramercy Tavern.

Continue south and dive into the chaos of Union Square—at its best (or most unhinged) during the December holiday market, where you can elbow your way to artisanal ornaments and hot cider. Year-round we come here for the Greenmarket, held several times a week, where local farmers bring a bit of country calm to the city crush.

East Village

End your wander in the East Village, which once had a reputation for being a bit sketchy after dark but is now teeming with fresh-faced 20-somethings and great places to eat. We mostly come here to hang with our kids, but we’d make the trip just for the cardamom bun and cappuccinos at La Cabra, or the sesame bagel—dark toasted, with tomato, olive oil, and salt—at Apollo Bagels.

The area’s packed with cool shops, dive bars, and some very good food. 9th Street between 1st and 2nd is full of small boutiques and vintage finds, and 3rd Avenue below 14th has a couple great thrift stores worth a dig.

For dinner, Nowon, Penny, and Soothr are all excellent picks. For drinks, go old-school at McSorley’s (New York City’s oldest continuously operated saloon). Light or dark ale, served two at a time. That’s it. That’s the whole menu. Or try Pete’s Tavern, NYC’s oldest continuously operating restaurant and bar. See the distinction there? Go to Pete’s in December for peak festivity.

Washington Square Park and the Comedy Cellar

Wander #6 : Greenwich Village After Dark

Greenwich Village is best explored after dark, when the streets glow and jazz leaks out of basement bars.

Stroll through Washington Square Park, NYU’s Quad, and check out the performers, the games of chess, the general buzz.

Then scoot over to the Comedy Cellar – the ultimate bang for your buck. For $20, you might see a future star—or someone who already has a Netflix special, just dropping in to test new material in a tiny basement room. It’s cramped, no-frills, and pretty magical.

For a bite near here, we liked DOMODOMO sushi.  Or check out our other recs here.

And those are just our Downtown Wanders. Click here for Uptown and Elsewhere Wanders—because there’s just so much to see.