Itinerary for the perfect day spent exploring the Upper West Side and Upper East Side of Manhattan including the 91st Street Garden where You've Got Mail was filmed, The Dakota, Strawberry Fields, The Great Lawn, the MET Museum, a classic Jewish deli and a local wine bar.

Enjoy and don’t forget to share feedback, link at the bottom. Tell us what you liked and what didn’t!



91st Street Garden Riverside Park

Free | Public Park
Riverside Dr & W 91st St


Start the day with a morning walk through Riverside Park. Between 90th and 91st Street you’ll find the 91st Street garden. It’s well maintained and picturesque little spot.

More notably if you are fan of 1990s Nora Ephron romantic comedies set in New York City…..we’re talking You’ve Got Mail style, you’ll recognize it as the place where Shopgirl meets NY152 and discovers it is who she hoped it was all along. It’s a sappy moment but it makes you love falling in love and love New York City just as much. :)


Jacob's Pickles

$$ | Southern bar & eatery focused on fried chicken biscuit sandwiches, housemade pickles & beers.
509 Amsterdam Ave, New York, NY 10024
(212) 470-5566


After leaving the 91st Street Garden you’ll be just a 10 minute walk to brunch. Jacob’s Pickels is an Upper West Side hotspot so if you visit on the weekend give yourself some time and expect to wait a bit. The cuisine is American Southern so it’s pretty heavy food. Mostly fired and mostly with a gravy or sauce. Brunch items include; Hot Chicken Biscuit - Buttermilk Fried Chicken in Nashville Hot Sauce, Shrimp & Bacon Grits, and Buttermilk Fried Chicken Caesar Salad.


The Dakota

Historic, gabled apartment building home to many celebrities over the years, including John Lennon.
** Not a museum ** Active apartment building
1 W 72nd St, New York, NY 10023
(212) 362-1448


After brunch stroll through the streets of the Upper West Side. You can take Amsterdam, Columbus or even Central Park West south to the Dakota but be sure to wind in and out of a few cross streets in the W80s, and W70s on your way down and enjoy a little tree-lined peace and quiet (as much as you can get in Manhattan).

The Dakota is a good place to stop as it has played a major role in New York and Upper West Side history. The building was completed in the 1890’s and has been home to many famous celebrities over the years including; The Steinway family, of Steinway piano fame, Peter Tchaikovsky, actress Lauren Bacall and of course John Lennon. Just an infamous is the list of celebrities that have been rejected from the building, including; include Cher, Billy Joel, Madonna among many others.

Famously, on December 8, 1980, Lennon was assassinated by Mark David Chapman outside The Dakota.

Central Park - Strawberry Fields

Free Public Park | Brick-&-mortar branch of the online retailer, featuring stylish menswear & in-store fittings.
95 5th Ave, New York, NY 10003
(646) 869-4933


Strawberry Fields is directly across the street from The Dakota so you will be in great position to enter the park and enjoy a stroll. This area includes a memorial ‘Imagine’ mosaic for John Lennon and was named after The Beatles song “Strawberry Fields Forever”.

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Le Pain Quotidien

Central Park location of larger chain offering light food and coffee
Just north of the Sheep Meadow in Central Park.


If you are walking through Central Park and thinking to yourself I wish we had gotten something to eat or drink before we came in…don’t worry there is a Le Pain just north of the Sheep Meadow. It’s a good pit stop located right in the middle of the park.


Central Park - Bethesda Terrace & Fountain

Free Public Park | Bi-level, lakeside terrace with a large fountain & carvings representing the seasons & times of day.
72 Terrace Dr, New York, NY 10021
(212) 420-9020


Bethesda Fountain & Terrace are both beautiful spots to see in Central Park. The area is essentially at the core and center of Central Park. The original plans for the park include this sweeping Promenade that led to a grand terrace overlooking the Lake. The design and carvings you’ll find capture the period when the park was originally designed.

It’s also a hotspot for photographers, weddings, parties etc. so expect some crowds but nothing that overwhelms the area.


Central Park Reservoir & Great Lawn

Free | Public Park
Entrance on 5th Avenue near 90th Street


The Great Lawn and nearby the Central Park Reservoir are both must see spots in Central Park. Whether you've been a thousand times or never been to New York City before, the reservoir is always worth a visit. Beautiful views of the Central Park South skyline peak up behind the trees and if the weather is nice the water shimmers just right. Before or after a stroll around the reservoir you can relax on the Great Lawn, which is just a short walk. Bring a magazine or book and something cool to drink and spread out a blanket and enjoy the day!


The Metropolitan Museum of Art (MET)

One of the world's greatest collections of art, from ancient to contemporary
1000 5th Ave, New York, NY 10028 (near 82nd street)
(212) 535-7710

TIP: Pay what you want to get in


Casually referred to as "The MET", this fine arts and history museum attracts couples, friends, historians, writers, artists, musicians, and practically every other human identity. The MET is famous for its highly valuable, absurdly rare, original, and sought-after paintings, lithographs, sculpture, and artifacts.

This museum features world renowned European painters and sculptors. Within, you will find works by Pablo Picasso, Vincent Van Gogh, and Claude Monet. More into sculpture? That's great, because a large portion of the first and second floors features original Grecian and Roman sculpture. This museum is massive to the point of intimidation, but don't let too much beautiful art deter you from exploring the absolute beauty and originality within The MET. I'm sure you'll return.


Russ & Daughters at the Jewish Museum

$$ | Cafe for kosher Jewish comfort fare (including smoked fish & bagels) by a legendary purveyor.
1109 5th Ave, New York, NY 10128
(212) 475-4880 ext. 3

Sunday Open Until 5:45pm


After your stroll through the park, you’ll be in good position to stroll up Madison Avenue. From 60th - 80th it’s wall to wall top designers and boutiques. The shops get a bit more local in the E 90s. In addition to all of the major names you’ll see along the way; Vera Wang, Carolina Herrera, Milly, Monique Lhuillier, Lanvin, Prada, Cartier, Goyard…you get the idea.

If you’ve worked up an appetite on your walk there is a Russ & Daughters located inside the Jewish Museum on 92nd Street. Russ & Duaghters is a local chain offering Jewish delis classics like Knishes, Pastrami, Herring and Lox.

If you are looking for a top vegan spot Candle 79 is a great option on Lexington and 79th. Also E.A.T. is a neighborhood favorite offering an upscale Jewish deli vibe delivering amazing quality dishes in a classy but casual space. E.A.T. is one of Eli Zabar’s restaurants the long time Manhattan grocer behind Zabar’s on the Upper West Side.


$$ | This cozy, rustic spot with a patio & back garden draws lively crowds for small plates & wine.
1486 2nd Ave, New York, NY 10075
(212) 472-4552


If you are looking for a cozy romantic spot to grab a drink after dinner checkout Uva. It’s also a neighborhood favorite that always attracts a good crowd and offers dinner as well as a large wine list and a back patio. It can get crowded on summer weekends but worth a vist. If you are looking for a more casual spot you can grab a seat at Eli’s Night Shift on 79th and 3rd - a cafe for Zabar's specialties that turns into a bar for local beers & shandies after dark. Yup, Eli Zabar again.

see what else is planned . . .