A visual walking guide to some of Manhattan’s most photogenic areas.

The weather is getting nicer and spring is the perfect season for wandering around the city! How many of these NY areas have you walked through?

Below I’ll show you some of my favorite spots!

The Seaport District

Enjoy the view of the water from Manhattan’s southern tip. The are is also home to restaurants, museums, shops and bars.

Photo credit/ Illustration by Deanna Kei

South Street Seaport: Watch the boats come and go. Explore the local galleries, shops, and dinning.

Big Gay Ice Cream: Stop for a treat at New York’s most colorful ice cream shop. Take a selfie on the rainbow popcicle bench. Stroll around the surrounding cobblestone streets.

Pier 17: Look down on the water from the open air roof top. There are special events and activities held here each season.

Pier 17: The perfect view of the Brooklyn bridge from the rooftop.

Stone Street: Grab a drink at one of NY’s historic bars.

Stone Street: Take a break on a bench and soak in the atmosphere on this lively street.

South Street Seaport: Stop for lunch with a view under the purple overpass.

Seaport Museum: Check out the inside of a ship!

Empire Outlets: Ride the ferry across the water to Staten Island for shopping at NYC’s newest outlet mall.

Empire Outlets: Enjoy the city skyline view from across the water. Then hop on the ferry for a free boat ride back to Manhattan.

2. Downtown

Shops, parks, cafes and restaurants intermingle with office buildings. Enjoy a leisurely walk up from the Seaport district.

The Oculus : Visit the beautiful new underground shopping mall and transit hub at the site of the WTC.

The Oculus : There are multiple levels to explore and some of the street level stores lead down into the Oculus as well.

The World Trade Center Memorial: Pause and listen to the sound of the rushing water as you honor and remember the victims of 911

The Oculus: Enjoy the view from outside. The uniquely shaped structure is unlike any of the surrounding buildings.

The Mural Project: Artists brightened up the space across from the Oculus.

The Mural Project: : Enjoy the colorful artwork that adorns the building north of the Oculus. Snap a photo or two!

3. The Flatiron district

The Flatiron district is home to many bridal shops, home goods shops, and furniture stores.

The Flatiron: One of New York’s most famously photogenic buildings.

Madison Square Park: Stop and enjoy the greenery with a view of the Flatiron.

The Flatiron district: Grab a seat or pass through on your way uptown.

4. Midtown South

Meander around east of Broadway to find little treasures hidden in plain sight.

Midtown South: Explore the city blocks

Church of the Transfiguration: Admire the beautiful outdoor court yard

Church of the Transfiguration: Take a short stroll through the garden area.

Church of the Transfiguration: Snap a photo at the stone archway

Church of the Transfiguration: One of New York’s historic churches.

K Town: Check out the shops and restaurants, and maybe even go for karaoke

5. Midtown

One of New York’s most popular areas. There are so many different things to do and see here if you don’t mind the crowds.

The New York Public Library: New York’s famous library is located behind Bryant Park, blocks away from Times Square

Rockefeller Center: The site of the Tree Lighting and ice skating rink in the winter, this area is a tourist destination all year long.

Rockefeller Center: The area is decorated differently each season.

Rockefeller Center: Do you recognize this as the same spot where the iconic angel decorations are set out at Christmas time? It looked like a totally different place while this installation was up. It's always worth a visit to see what the latest display is.

Rockefeller Center: In the warmer seasons the ice skating rink is transformed into an outdoor eating area.

St Patrick’s Cathedral: A beautiful church full of history, located next to Sak’s Fifth Ave. It’s open to the public for viewing.

St Patrick’s Cathedral: This architectural masterpiece sits on 5th avenue, just across from Rockefeller center.

East midtown: It’s fun to walk along the blocks of apartments to the east.

Sak’s Fifth Avenue: Manhattan’s iconic luxury department store. A must see for anyone who loves fashion.

Sak’s Fifth Avenue: Located across from Rockefeller center and next to St. Patrick’s Cathedral.

Sak’s Fifth Avenue: Shop all 10 floors of luxury brands and enjoy the gorgeous displays that fill the store.

East Midtown: Stroll the city blocks with a view of the water to the east.

East Midtown: Tired of walking? You’ve got options! Hop on a citibike!

Dag Hammarskjöld Plaza : A small but beautiful park across from the Japan Society building.

The Lipstick Building / Latham and Watkins: This office building is famous for its unique shape.

About this guide: These photos were taken during Spring of 2019 on my i phone. As a NY native I wanted to try and experience the city in a different and more intimate way. On days when I had errands to run I began collecting photos on my phone of some of the beautiful scenery that peppered my daily routes. I felt like a tourist and began noticing things I hadn’t seen before.

I enjoy taking photographs but I’m not a photographer; I’m an Illustrator. I wanted to find a way to share these photos on my Illustration Instagram and my solution was to add my illustrations into the scenes. I pulled from my favorites and included characters I felt fit into each photo. The illustrations above are from my older work and possess the loose, whimsical mood I wanted to express with this guide. I really enjoyed this project and I’m looking forward to adding a part two with fresh illustrations as I re-explore the post covid city!

Deanna Kei is a NY based Fashion and Beauty Illustrator. She works with brands to create unique and engaging content featuring their products and collections. To commission illustrations for your brand please write to deannakei@gmail.com . She also has a line of prints, totes, and phone cases.

The Seaport District

2. Downtown

3. The Flatiron district

4. Midtown South

5. Midtown

Subscribe to my VIP newsletter

As a member you’ll receive the latest fashion news, runway reports, fashion week coverage, style tips, promotions, printables, exclusive illustrations and more!