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, shopping Madison and dinner at local Italian spot.

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 You’ve Got Mail and similar 1990s Nora Ephron romantic comedies set in New York City, 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 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 W 80s, and 70s and 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.



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 - Model Boat Pond

Free Public Park | Small pond with a place to rent model boats
E 72nd St, New York, NY 10021


This is another very pretty spot to stop in Central Park. Little ones (and some big ones) will enjoy renting and sailing the little model boats that can be floated on the pond. This area is usually covered with a great mix of sunshine and shade to please everyone in your party as well.


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!


Madison Avenue

$$$$ | High End Fashions


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, I’ve listed just a couple of landmark spots you have to stop. Partly for the clothing but partly for their landmark status in the city. If you are a history or interior design lover you will also find the visit very inspirational.

Ralph Lauren’s Men’s and Women’s Stores are both beautiful inside and out.


$$$ | Upscale rustic Italian | Cozy vibe
402 Lexington Ave, New York, NY 10128 (near 92nd street)
(212) 831-1402


Continuing to stroll up Madison is a great walk. When you’re ready for dinner head to Sfoglia on 92nd and Lexington. Make sure you have a reservation. This is a neighborhood staple and it usually fills up fast with regulars. It’s a small intimate restaurant with a cozy collection of wood tables and chandeliers.

The food is always a delight. While I always enjoying getting a few new dishes you must (I repeat MUST) also get the chicken. Usually chicken is one of those dishes I skip at a restaurant but this one is AMAZING! Enjoy a leisurely date night dinner here and cap your meal off with one of their homemade deserts and a couple of espressos (and by espresso I mean more wine ;).

see what else is planned . . .