A Long Weekend in Chelsea, NYC

Check in to a hotel with a story. You can’t go wrong with the infamous Chelsea Hotel, where Patti Smith lived with Robert Mapplethorpe, and Arthur Miller wrote After the Fall. It’s the setting for countless film scenes and the namesake of songs by Leonard Cohen, Nico and Graham Nash.

You might also stay at The Standard Hotel, which certainly sees its share of current celebrities. Jaws will drop at the view from its floor-to-ceiling windows straddling The High Line. If you look up at The Standard from the High Line, well… your jaw may also drop as you discover what locals think it's famous for.

If that’s a bit much, stay at the High Line Hotel, where the modern rooms are converted dormitories of Episcopalian priests. (Tip: don’t miss their bar, an homage to a famous 70’s psychic.)

After dropping off your bags, take a walk east along 23rd St to where the Flatiron district meets Chelsea. Stop at Eataly on 23rd and 5th for coffee and a pastry (north-east corner), or some lunch (Pizza-type focaccia is south-west, near the checkout.) If there are any foodies expecting souvenirs from your trip to NYC, this is where to pick them up. Eataly is a gourmet grocery store with open-seating restaurants and bars sprinkled throughout.

Exit on the east side. When you look to your right, you’ll see the triangular Flatiron building, just below the intersection of 5th Avenue and Broadway. The building points at Madison Square Park, which is only three blocks long. Take a walk through and check out whatever public art is on display. Grab a shake at the original Shake Shack, or gaze up at the clock on the side of The Metropolitan Life Tower. If it’s 5 pm, run inside and grab a seat at the bar of Eleven Madison Park. It’s extremely hard to get a reservation for their 6 or 9-course vegan tasting menu (it has 3 Michelin stars, so if you’re balking at the veganism part, get over it and just accept it — it’s ah-mazing!) Hot tip: if you get there right as the doors open, you might snag a seat at the bar, where you can order a la carte with a cocktail.

What should you do that night? Check out Gotham Comedy Club, only a few doors east of the Chelsea Hotel. It’s definitely worth investigating their lineup as names like John Oliver, Jim Gaffigan, Questlove, Judy Gold, Gilbert Gottfried and many other known comics are said to appear. Rumor has it that Jerry Seinfeld once stopped by unannounced to try out some new material! (Bringing the kids? They have an all-ages show on a Sunday afternoon almost monthly.) It’s a two-drink minimum, even at the kid’s show, but they do have a food menu from Jake’s next door.

Head out to the High Line. Once an abandoned elevated train track, it is now a lovely mile-and-almost-a-half pedestrian walkway. Entrances can be found between 9th and 10th avenues every two or three blocks in Chelsea. Interested in American art, go south to reach the Whitney Museum at Gansevoort St. in the Meatpacking District. (If you are there during the Biennial — do not miss it!) Go north to head out of Chelsea and into Hudson Yards. In either direction, you’ll find public art and sculptures among the carefully landscaped, yet seemingly wild gardens. Some nights, you’ll even find dancing or live music under the 14th St passage.

Fashionable high-end shops and restaurants permeate the Meatpacking District’s cobblestone streets, while Hudson Yards is a new development with a high-end shopping mall and José Andrés’ Spanish version of Eataly, Little Spain (try the smoked foods at Leña).

Enjoy a long lunch and then head to the galleries! While galleries are popping up on the Lower East Side and in Chinatown, early adopters left Soho in the early 90’s and found their homes between 10th Avenue and the West Side Highway, from 19th St to 25th St. If something catches your eye, just open the door, walk in and check out the art. There is no fee to do this. You can also take a guided tour (for which there is a fee) where you will learn about the most talked-about pieces of the moment, or just drop by on your own. Be sure to visit the galleries that are not on the ground floor, too! (Check out: the Gagosian, Dia Chelsea, Pace and the David Zwirner galleries — though any of the galleries might have something amazing!)

For this evening’s entertainment — try Sid Gold’s Request Room. This is not a typical karaoke bar — you sing with live piano accompaniment! If you are lucky, Joe McGinty of Loser’s Lounge and the Psychedelic Furs will be on the keys that night. (Be warned that they do see more than their fair share of really excellent vocalists.) Too shy for singing? Check out a speakeasy - Patent Pending and La Noxe are two crowd favorites.

Is it the weekend? Early risers and collectors will love Chelsea Flea, which takes over a parking lot on 25th Street at 8 am — but only on Saturday and Sunday.

You could also take a walk over to Little Island, the overwater park on stilts whose pathways resemble a children’s board game. In summer, they have a full calendar of events happening each day, all day, from Drag Bingo and Poetry Readings to Hip-Hop Dance Performances.

Then cross back into Chelsea and visit Chelsea Market. The building is home to a local news station, NY1, loads of yummy restaurants and many great shops (while there, be sure to check out Artist & Fleas for amazing gifts for every occasion). Chelsea Market, too, has an events calendar full of music, yoga and kids activities. Halloween in NYC is a great time of year — the place comes alive with stilt walkers, live creepy clowns and kids from every neighborhood trick-or-treating!

Where to eat

Breakfast

La Bergamote - 177 Ninth Ave at 20th St. They might make the best almond croissants on the planet. Or choose another pastry (or eggs, or quiche, or croque monsieur — you get the idea) at this French-owned patisserie.

Empire Diner - 210 Tenth Ave at 22nd St. This old-school, art-deco diner looks like it belongs in a movie, not in this neighborhood. Be sure to look up and check out the installment of Eduardo Kobra’s rainbow series featuring Warhol, Kahlo, Haring and Basquiat above it.

Lunch

If you haven’t gotten your fill from Eataly, Little Spain (they cook everything over embers at Leña) or Chelsea Market, try Chop-Shop (245 10th Ave, between 24th and 25th) for the perfect cucumber salad. For something more formal, Cookshop’s open kitchen never disappoints. It's a go-to place for brunch.

Dinner

Almost every place mentioned above will accommodate you for dinner — but be sure to reserve as to avoid disappointment. If that’s not enough, try:

Tia Pol (205 Tenth Ave) - Come here for happy hour and grab some fried chickpeas with a glass of sangria. Their gin and tonic is so clove-y and yummy.

Cosme (35 East 21st St.) - Okay, technically, it’s half a block outside of Chelsea, but this is just amazing Mexican food. Like the rest of the city, you’ll leave asking why they don’t have a star.

El Quijote (226 West 23rd St, under the Chelsea Hotel) - Because you want to sit at Andy’s regular table, or have dinner where Jimi Hendrix had one of his last meals in NYC.

Lastly, spend some time at the McKittrick Hotel. Preferably late at night, but Gallow Green is also a wonderful place for day drinking — just saying. Get tickets well in advance if you’d like to see a show.

Kids in Chelsea

Playgrounds: Northeast corner of Madison Square Park, Seal Park on 10th Ave at 22nd St, Chelsea Green on 20th between 6th and 7th, and there is a water playground on 11th and 23rd in summer.

Other Fun Stuff: Harry Potter Store on 5th Ave at 22nd St.. The ice-skating rink in front of the Standard Hotel in winter. The Museum of Illusions on 8th Ave and 14th St.. MoMath museum on 26th, across the north side of Madison Square Park (super interactive and really cool, perfect for a rainy day). Gotham Comedy Club has a semi-monthly all-ages show on a Sunday afternoon.