You can get a downloadable map of this itinerary here.
***Allison grew up in Birmingham, Alabama. After graduation, she moved to New York to pursue her dream of working for Condé Nast. She loves spending her free time exploring the different boroughs of New York, but also enjoys taking any opportunity to travel back home to cheer on the Crimson Tide.
I’ve called New York home for three years, which means I have seven more until I’m considered a true New Yorker. But what I lack in time, I subsidize with depth of experience; I’m undeniably in love with this city and have spent the past few years absorbing it wholly. That being said, my itinerary is shaped to accommodate the run-in-the-mill visitor who might want to hit the tourist spots but also explore local pockets. This weekend could be tailored to personal interests – art, music, shopping, Instagram (really), food, sightseeing – but I tried to hit a bit of each note to give a well-rounded experience.
Also, talk to any denizen, and they’ll give you a completely different run of show— but isn’t that the beauty of New York, after all? While we’re all collected on top of each other, each person’s posture to and narrative with the city is different. This is my idea of a quintessential New York weekend, but you are free to make it what you will.
BEST TIME TO TRAVEL: In my humble opinion, there’s never an inopportune time to scoot over to the Big Apple, and timing is all subjective to the traveler. New York in the fall is— well, New York in the fall, and absolutely everything Nora Ephron cracked it up to be: crisp, golden hued, and delightfully quaint. Albeit tourist-ridden, the holidays are undeniably festive and action packed. And then there’s the intoxicating and utterly magical springtime and early days of summer. New Yorkers have emerged from their wintry slumbers and are billowing out to the streets, parks, and sidewalk cafes, lingering and indulging in the long-elusive warmth before the heat and stench of July arrives.
My recommendation? You can’t go wrong with May-June for warm weather, or October-December for a cozy, festive getaway.
WHERE TO STAY: As a downtown dweller, I’d recommend staying below 14th Street in an Airbnb in East or West Village, Soho, the Lower East Side, or TriBeCa. Looking for turndown service? I’d point you toward The Bowery Hotel,Walker Hotel, Gramercy Park Hotel, or Freehand. Yes, the later two aren’t downtown – I don’t discriminate – but they’re centrally located and beautiful.
friday.
Begin in the West Village for your evening programming, and enjoy the stroll from whatever direction you travel from. It will be buzzing with activity and in all its early evening glory. Soak it in!
First matters first, put your name in at either Via Carota, Fedora, or Joseph Leonard. The later two offer reservations, but for walk-ins, be fully prepared for an 1-2 hour wait at either spot (alright, 2-3 hours at Via Carota). But that’s why you’re in the West Village, and there’s a bar worth your time and dollars on every corner. I love Highlands for a whiskey, Wilfie & Nell’scozy ambience (but it gets crowded), Fairfax’s modern simplicity, and Bell, Book & Candle for their soup-of-the-day martini and generous happy hour.
You’ll have time for a drink or two before your table is ready, and trust me — any restaurant above is worth the wait. All three are best enjoyed by splitting as many items as possible. My favorites? The olives, carrots and any pasta at Via Carota; pear cider (ask for it), steak tartare toast, miso eggplant, and roasted chicken at Fedora, and truly anything at Joseph Leonard.
After dinner, walk over to Arthur’s Tavern for live jazz, or Marie Crisis Cafe for an old-school piano bar. FYI, both might have a small line, but are well worth the experience.
Just want a drink without the fuss? Try the Waverly Inn for an old New-York sentiment, or The Rusty Knotfor a dive-bar atmosphere.
saturday.
To wane the effects of your West Village crawl, start your Saturday at Daily Provisions, Danny Meyer’s outpost known for their breakfast sandwiches and buttery, sugary cruellers. Go early and be courageous; it gets packed on Saturdays, but the food and coffee can’t be beat.
Begin your day of sightseeing at Grand Central – one of my favorite spots in the city – then move toward Bryant Park and up Fifth Avenue. It might be packed with tourists (especially at Christmastime), but I love looking at the department store windows or strolling through the park anytime of year. Also, if you’re feeling brave and desire to check off Rockefeller Center, Times Square, and Radio City, consider this your chance.
Grab lunch downstairs at the Plaza Food Hall. This is a hidden gem and my go-to whenever I need a bite by the park. There is several vendors to accommodate multiple palates, and most are New York local. Take it to-go through Central Park, and stop in Sheep’s Meadow (weather permitting) for an al fresco picnic. On any warm day, the open green space is filled with New Yorkers basking in the sunshine — picnicking, playing games, and even throwing birthday parties. After you’ve had your Vitamin D fix, continue heading west until you’re back in the land of concrete and veer down 74th street for a chocolate chip walnut cookie at Levain (my FAVORITE).
Then, hop on the subway down to the Meatpacking District, and check out the Whitney. Admittedly, I’m not the museum authority (I’m more of an outside, moving-around kind of girl), but I do love the Whitney’s always fresh American art and digestible exhibit size. If you hit your art quota, there’s plenty of places to grab an afternoon drink nearby, or you can linger on the Highline, which starts at the Whitney.
Rest up for a bit, then grab drinks in the East Village (my hood!). I’d point you to The Wren, or start further west and try Dante. Tonight is a fun, upbeat dinner at Dirty French, Vic’s, or Little Prince in Soho. After dinner, go dance in the Lower East Side! There’s a bar on every corner and fit for every mood; you can’t go wrong. And I’m not one to judge if you end the night at Katz or grabbing a slice on a corner.
sunday.
If you followed last night’s suggestions, you need a bagel. The internet will give you a run down of a dozen places that proclaim their authority in the space, but in my experience, it’s pretty hard to mess up eggs, cheese, and some sort of breakfast meat sandwiched between New York-style bagels. Dodge lines and people submitting their sandwich to Food in the Air, and just pop in your local bodega and ask for a BEC on a roll and coffee with half & half, hold sugar and bag (yes, you can get your coffee in a to go bag). Must you want a determined destination, I do love Murray’s Bagels and Tompkins Square Bagels, and they know how to manage a line. If you’re feeling brave, you can also work in a walk/jog along the West Side Highway before or after your bagel excursion. The view and fresh(ish) air is worth the early morning physical excerption.
Work your way downtown through Little Italy, then Chinatown. For me, these are pass throughs, and I wouldn’t recommend stopping for a meal in Little Italy or buying a knock-off; that’s where the tourist trap line is drawn. Continue on to Lower Manhattan, ending up at World Trade Center to visit the 9/11 Museum, cruise through the Oculus, and catch a view of the Statue of Liberty. You can even walk over to the Stock Exchange and Wall Street, if that’s your thing.
Move slightly northeast, and cross the Brooklyn Bridge into Dumbo. It will likely be filled with tourists and influencers taking pictures, but it’s an experience and one of my favorite views of the city. You’ll land across the East River on the Brooklyn Heights Promenade. You can stroll along the water or wander through Dumbo or Brooklyn Heights for a bit.
For dinner, enjoy Italian with a view at Cecconi’s, or venture through the brownstones of Brooklyn Heights toward Jack The Horse Tavern or Lucali(go early – you will have to wait). Is the weather perfect, and you’re in the mood for something more casual? Walk north along toward Williamsburg for Tacoina. Finally, round out your night – and weekend – with a scoop from Ample Hills in Brooklyn Heights or Van Leeuwen in Williamsburg, arguably two of the best ice creams in the city— a topic in which I am an expert.