Hidden Gems of New York: City Island

Perhaps the best well-kept secret in the five boroughs, City Island is a bewitching, seafaring town. With a quick drive across the island’s only bridge, you instantly forget that you’re still within one of New York’s five boroughs, and not hours away in New England. Culture and charm inhabit this quaint seaside escape, teeming with tree-lined streets, welcoming residents and fresh fish restaurants—all existing within a perpetual summertime mindset.

This untouched Bronx enclave with a small-town feel is a mere 40-minute drive from midtown. If you prefer mass transit, a jump on the 6 train to the end of the line, and a transfer to the 29 bus means you’ve arrived in this historical fishing village.

Whether you want clam chowder or a sailing lesson, here are all the reasons to call this gem of a town home.


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Head to The Black Whale for fresh fish, a killer meatloaf, and “unique potions” like a Whale-a-Cino or Banana Honey Shake. For warmer months, the back patio provides a respite from the bustle of City Island Avenue with occasional live entertainment.

City Island Diner, positioned on a camera-ready street, is an unparalleled small-town dining experience. The delicious breakfast is unfussy and the coffee refills abundant, as featured in an episode of Jerry Seinfeld’s Comedians in Cars Getting Coffee. The diner is a local favorite, and its cash-only policy highlights its time-honored charm while proving that old New York isn’t lost.

If you’re looking for something more upscale but not lacking in flavor, head to Bistro SK. This lovely French bistro offers hearty cuisine while owning the title of being the only French restaurant in the borough. Touting itself as the “Best Brunch in the Bronx”, which includes bottomless Mimosas and Bloody Marys, this spot is an ideal stop after a morning of sailing on the Long Island Sound.



Photo via The Standard Edition

Located where Tier Street meets the sea, cinephiles can see the Victorian home featured in both The Royal Tenenbaums and Long Day’s Journey Into Night, featuring Katherine Hepburn in her Oscar-nominated performance.

A new artists’ colony has revitalized the town, encouraging artists who would normally flock to Brooklyn to live and sell their pieces through new work space. Galleries offer visitors a chance to experience beautiful works from little-known artists perhaps on the verge of stardom, including Starving Artist, Mary Colby and Focal Point.

Step inside the history of the island at Dan’s Parents’ House, a delightful antique shop set in a structure built in the 1800s. The owners, insistent on keeping the building’s authenticity, restored the entire exterior with wood to keep in line with City Island’s old-school allure. This vintage store offers an array of quirky memorabilia including baseball cards, postcards, Star Wars figurines and polaroid cameras.


Morris Yacht and Beach Club

Morris Yacht and Beach Club is the premiere yacht and social club on City Island, with various levels of membership and events including trivia nights and a legendary Super Bowl party. The boat culture of the island prospers among these clubs, and Harlem Yacht Club provides sailing lessons of all levels. Members enjoy a myriad of events including a Cardboard Boat Race and jazz nights, where the club transforms its ballroom into an intimate club featuring award-winning jazz artists.

Riptide III Fishing and Cruises offers both day and night fishing excursions, and a genial crew ensures a warm welcome for visitors of all fishing levels. For those looking to unwind with a view, Riptide’s sunset cruises have a full kitchen, live DJ (who takes requests) and dancing along the East River as dusk falls

Those who thrive on adventure can take a trip to the deep with Captain Mike’s Diving Services. Offering scuba instruction and certification, visitors are in good hands with shop owner Michael Carew, a veteran of the NYPD scuba team. For warm summer days, visitors of all ages can also rent a paddle board and head out and explore the island from a whole new perspective.


City Island boasts stunning buildings and picturesque streets, where old Victorian architecture meets modern design.

For those wanting to explore seaside living with luxury amenities, 41 Degrees North, which is coming soon, offers a contemporary boutique condominium. Overlooking Long Island Sound, the stylish and open-plan design offers an array of enticing amenities, including private balconies, top-of-the-line appliances, a rooftop pool and a boat slip with docking for guests.

The island’s touch of New England makes these residences a charming getaway from the city, and an ideal place to come home to.

If you want to visit these delights regularly in your own backyard, Douglas Elliman can help you find your next home.

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