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An Insider’s Guide to City Island

Words by Sioban Massiah, Photos by Kelsey Sucena 07/13/2022

View from Pelham Cemetery.

Growing up in the Bronx, there was that special moment where the leaves would start to grow back on bare trees, you’d hear the faint sound of a Mister Softee ice cream truck in the distance and you would get a text or a call that would let you know summer was quickly approaching.

“Want to go to City Island?”

The first sign of any warmth—our very own groundhog shadow—generated a mass exodus to one of the Bronx’s most underrated treasures, City Island. A New England–esque town just a short bridge away from the bustle of the mainland, City Island holds a 1.5-mile strip full of restaurants where you can get amazing fresh seafood and locally popular drinks (if you’ve ever heard of a Henny Colada—a pina colada with Hennessy cognac in place of rum—know it got popular because of City Island). However, the quaint neighborhood is much more than seafood and drinks. Families reside off that main strip of restaurants. There’s a small-town charm that survived the massive destruction brought by Hurricane Sandy a decade ago and dates back generations.

View of the waterfront

Vibe on the Island

Once you drive over City Island Bridge (the only way on and off the island unless you have your own boat) you hit the main strip of City Island Avenue, lined with restaurants serving various cuisines but known largely for its seafood. If you are looking for popular chains like Starbucks and McDonald’s, you won’t find them. Locals, or “clamdiggers” as they like to call themselves, have fought ferociously against such development. The only franchise allowed on the island in more recent years is Dunkin’ Donuts—one assumes to make coffee more easily available to the large population of police officers, firemen and workers from nearby hospitals. There are relatively few apartments or condos—most everything (the new

41 Degrees North

is an exception) has been denied by the island’s commerce board to preserve its quaint, small-scale environment.

The Lobster House.

Great Eats

Once you arrive on City Island, most of the restaurants are to your right, but there is a hidden gem just to the left:

The Lobster House

, a favorite for my family dinners, with options for all of us picky eaters. Good drinks, amazing crab legs, oysters, lobster roll and delicious options for fish—you really can't miss. Plus, being off the main strip means less traffic and less noise, especially welcome on summer weekends when the island is at its busiest.

For the best king crab legs (and trust me I've done my research), go to

Sammy’s Fish Box

toward the end of the strip. It’s an island favorite, so make reservations or grab a to-go order for home or a picnic. Try the Piri Piri whole red snapper or Chilean sea bass, accompanied by a drink of choice, either the Dusse Colada or Gilly's Aperol Spritz. Both Sammy’s Fish Box and The Lobster House are family-friendly, with lots of indoor and outdoor seating.

Portofino.

If seafood is not your thing, don’t fret because this boat town caters to all food lovers. Two of my favorites are

Ohana Hibachi Steakhouse

and

Portofino

(where I still get seafood). Both are good for groups or those with kids but can easily be a cute date night spot. Ohana is a traditional hibachi-style restaurant though it also has an eight-course meal (the “Jap ‘A’ Rican”) that mixes Japanese and Puerto Rican dishes. Portofino, an authentic Italian spot, satisfies my oyster cravings, and I follow with either the lobster Allargiatta or the shrimp fra diavolo.

Seafood City

Believe it or not, my go-to City Island spot isn’t one of the finer dining restaurants. The place that holds my heart, that was my first stop when I moved back to NYC after a stint in California (despite it being a bit chilly in October and not peak time on the island), is halfway down City Island Avenue, with cafeteria-style seating and a view of the sun setting on the water.

Seafood City

is popular with the younger crowd. Affordable food options, strong drinks and music blasting from the outdoor speakers make this great for after work or a chill weekend hangout with friends. So many of my favorite summer memories include watching the sunset with a Bluetooth speaker and an order of fried shrimp and Hennessy Coladas, laughing on a bench until the restaurant kicked us out—and then staying in the parking lot until they had to kick us out of there too. A night there even led me on an adventure to an eerily accurate fortune teller.

Nautical Museum

Pelham Cemetery

More Than Food

The best way to enjoy City Island is to find a parking spot and spend a few hours walking along—and around—the 1.5-mile strip. One unexpected find that I stumbled on during a summer date was

Pelham Cemetery

, the only waterfront cemetery in NYC. Though maybe an unusual first-date spot, this tucked-away burial ground has ample benches to enjoy the serene water views and is a great place to clear your head and take a walk during the beautiful day (or night if you dare). A block from the cemetery is the

City Island Nautical Museum

(weekends only), good for history buffs. They offer extensive information about boats and artifacts collected from the island in the actual museum with their exhibits and library, as well as outside of the museum by conducting walking tours of City Island and offering webinars so you can experience the history from the comfort of your own home.

On the other side of the main road and bordering the water are the

City Island Wetlands

. Locals use the area to host clambakes, but you can people-watch and eat takeout. It’s a great place to casually sit and see the waterfront.

239 Play

Back on City Island Avenue, you’ll find

239 Play

. Formerly only selling online, this brick-and-mortar store for Dan’s Parents House is full of vintage toys, figurines, comics and posters. You're likely to walk out with something that reminds you of your childhood.

Jill's Cottage.

Thanks to the pandemic, I have become a bit of a plant mom. So I like to frequent

Jill’s Cottage

, about a 3-minute walk from 239 Play; this local plant shop will have you leaving with a new plant baby.

Though City Island may not be what you picture when you think of the Bronx, you can't forget to mention it as a Bronx staple. It’s a major part of summer memories for natives of the borough and beyond, and these local spots are part of the City Island experience. A few hours on a calm day at a preserved part of NYC history is a great addition to a NYC summer itinerary.

Sioban Massiah is a multimedia content creator, strategist and producer, writer, speaker and host. A native Bronxite, she has endless New York City stories to share.