15 Best Things to Do in City Island, NY

City Island, NY
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A little island off the coast of the Bronx, City Island is a charming destination in New York City.

The 2.5-kilometer island has a population of just over 5,000 people, living in a seaside town with an old-school charm.

Rich with nautical history, City Island is an unknown destination that will surprise any visitor wanting to explore New York City.

Here are the best things to do in City Island, NY:

Discover Boating History at the City Island Nautical Museum

Exterior of City Island Nautical Museum
Wusel007, CC BY-SA 4.0, via Wikimedia Commons

Situated a few meters from the shore is the City Island Nautical Museum, which houses the history of the island's boating industry.

City Island became a hot spot for quality wooden boat construction in the 20th century.

The builders of the time gained the reputation of doing the best repairs on any marine vessel.

City Island was basically the yachting center of New York.

The museum houses the various tools and parts dating back to the 1800s, the heyday of the city's boating construction.

See the photographs detailing the beginnings and evolution of City Island from the Industrial Revolution to the present day.

Scale models of old school boats and yachts are also on display for visitors to appreciate their history and evolution.

The Nautical Room displays various memorabilia of boating in the city, including a partially completed boat that dates back to the 1930s.

Sailing enthusiasts must visit the City Island Nautical Museum.

Shop Vintage Finds at 239 Play

Kids at heart will love 239 Play, a specialty store specializing in vintage items.

Visitors would find an array of antiques and knick-knacks, from old 80s and 90s toys to old-school home displays.

Entering the store along 239 City Island Avenue feels like entering a friend’s house in the 80s, with all of the goods filling the space.

239 Play also houses small pocket events for the neighborhood on select evenings.

Admire the Architecture of the Samuel Pell House

The Samuel Pell House is a classic piece of architecture that reflects the island’s old-school charm.

Built in 1876, the three-story Second Empire style house was owned by Samuel Pell, a captain and fisherman who was a leading oysterman.

People living in the New York metropolitan area loved oysters.

His home reflected the Pell's success, with fifteen rooms, a parlor, music room, dining room and servant’s quarters.

The Pells resided in the home until 1907.

The house became a New York City landmark status in 2002.

The home has appeared in movies and TV, such as the 1969 film “Arsenic and Old Lace.”

Visitors can admire this unique piece of architecture that has been preserved through the years, giving people a taste of how people used to live on City Island.

See the Sights on Short, Sleepy Street

Walk along the kilometer and a half stretch of Short, Sleepy Street, the little east-west streets that branch off City Island Avenue.

Visitors will enjoy exploring the Victorian-style homes that line the streets, reflecting the island’s quiet and relaxing everyday life.

Along 21 Tier Street is the home featured in the 2001 Wes Anderson film, “The Royal Tenenbaums.”

It’s a low-key but enjoyable activity to do on City Island.

Try Seafood by the Waterfront at the City Island Lobster House

Exterior and signage of City Island Lobster House
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A restaurant with a gorgeous view of the Long Island Sound, the City Island Lobster House is a great place to enjoy some fresh island seafood.

Visitors can enjoy the house’s specialty, freshly steamed lobsters caught from the nearby waters.

Also, enjoy the variety of other fresh seafood such as crab legs, shrimp, salmon and mahi-mahi.

Don’t forget to order the fried sea scallops and calamari as appetizers.

Enjoy the fresh catch with their delicious cocktails, from Piña coladas and frozen margaritas to their own City Island Iced Tea mix.

Taste the island’s freshest at the City Island Lobster House!

Enjoy Fresh Seafood at the Original Crab Shanty

After a day out in the island sun, stop by the Original Crab Shanty to taste the island’s freshest catch.

Opened in 1977, the Original Crab Shanty serves both City Island tourists and locals some of the best crab and seafood in the city.

Try crowd favorites like the steamed king crab legs, Baltimore-style Mediterranean crabs, and hard-shell crabs.

The restaurant also offers other dishes, such as prime rib and filet mignon.

Enjoy their main dishes with pasta such as penne ala vodka and Sharon’s Pasta.

Come in hungry and come out happy after visiting the Original Crab Shanty.

Enjoy Outdoor Play Time at Ambrosini Field

Ambrosini Field is the perfect place for those looking for a place to run and do outdoor sports.

Ambrosini Field is the only public field and playground complex on the island.

Locals love to go there for some fun and sport outdoors.

Visitors can play some baseball on the premises.

It’s also an excellent place for a quick run and jog, with the wind coming in from the nearby shores.

Ambrosini Field is great for kids, too, with slides, flexible bridges and a large tic-tac-toe board for them to play with.

Ambrosini Field is a little patch of green heaven in this little seaside town!

Grab Fishing Gear at Jack’s Bait and Tackle

Locals Jack and Rose Rumpf established Jack's Bait and Tackle in 1945.

It's the go-to destination for fishing gear and fresh bait on City Island.

Visitors can stock up on their fishing gear and bait before they go to the shores to sink their hookers.

Visitors can also rent their boats for fishing at the shop.

They can also link up with boat charters during their visit.

Jack’s Bait and Tackle is an excellent destination to gear up for one of the island’s favorite pastimes.

It’s also a great place to know the locals and tips and tricks on landing the best catch.

Learn to Sail at the New York Sailing Center

Sailing on New York's water
Kamira / Shutterstock.com

The New York Sailing Center is a great place to get your toes wet and learn how to conquer the waves.

Located along Pilot Street, the New York Sailing Center offers classes for both beginners and intermediate boaters, from basic to bareboat and everything in between.

The New York Sailing Center also offers American Sailing Association Certified Courses, such as Coastal Navigation, Coastal Cruising and Radar Endorsement.

You can buy memorabilia of their water adventures at the store on the main center’s grounds.

It’s a great place to learn the ropes and get into sailing, only a few minutes away from mainland New York.

The Focal Point Gallery is a little local artist enclave in the island’s heart.

Artist and enthusiast Ronald Terner opened the gallery to showcase up-and-coming local artists and works.

Opened in the 1970s, the humble gallery showcases works of different mediums from artists from the Bronx and beyond.

The gallery’s exterior also exudes that old-school charm in line with the rest of the island.

It’s an excellent place for art lovers to come and see local art when they visit City Island.

Relax at the Promenade on Fordham Street

After a day of going around the island, the Promenade on Fordham Street is a great place to settle down and relax.

Take a stroll along the small trail near the shore, with the view of the water landscaping your walk.

It’s a great place to lay a mat down and have a picnic and chat with friends or sit alone and read a good book.

The promenade is a great photo spot; visitors can take snapshots with the beautiful water background to commemorate their visit to City Island.

Grab a Shoreside Snack at Tony’s Pier

No visit to City Island is complete without seafood, and Tony’s Pier provides a no-frills food experience.

Tony’s Pier serves simple and hearty seafood dishes that would fill up the hungriest stomachs.

Order some of their delicious dishes such as the fried flounder, broiled salmon and fried shrimp.

For groups, their seafood platters are perfect for sharing, a mix of steamed, broiled and fried seafood served with a side of French fries.

Enjoy the seafood and the gorgeous water view as you sit on their outside pier seats.

Feel like a local and drop by Tony’s Pier today!

Sail the Waters with the City Island Yacht Club

Established in the 1900s, the City Island Yacht Club has become a premier sailing destination for over a hundred years.

The City Island Yacht Club is an excellent place for young and old alike to get into sailing on the open waters.

The club offers recreational yacht cruises for members and visitors and hosts sailing races seasonally.

A club is an excellent place for kids to go camping and learn how to sail during the summer.

Junior races are also open for the kids.

After spending a day out sailing, visitors can come and dine at the Galley in the club, serving fresh seafood dishes.

Enjoy the chef’s specialties paired with the restaurant’s fine wine selection.

Other Things to Do Nearby

Spend the Day in the Sun at Orchard Beach

People walking around Orchard Beach
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Across the bridge into the Bronx is Orchard Beach, a little patch of sun and sand just a few minutes' drive from New York City.

Visitors can spend a day in the sun on the beach’s 115-acre shores.

The beach is a great place to go with family and friends.

Swingset on Orchard Beach's sand
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Visitors can set up mats, have picnics, or relax and get a nice tan.

Visitors can also bring their balls and play beach volleyball on the sand.

It’s also a great place to play and bring your furry friends with you.

Aerial view of Orchard Beach
Bebo2good1, CC BY-SA 4.0, via Wikimedia Commons

Hike the Trails at Pelham Bay Park

People walking along Pelham Bay Park
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Across City Island Avenue into the Bronx is Pelham Bay Park, an idyllic outdoor retreat just a few minutes outside of City Island.

It’s the largest park within the boundaries of New York City, with loads of outdoor activities for visitors and locals alike.

Visitors can hike the park’s trails, with a beautiful expanse of nature landscaping their stroll.

Boardwalk at Pelham Bay Park
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There are also two golf courses within the park’s expanse, perfect for lovers of the sport who want a relaxing atmosphere to play in.

Pelham Bay Park is also an excellent place for sports, with basketball courts, handball courts, football fields, and tennis courts.

Pelham Bay Park also makes for a great fishing destination with its ideal location next to the Long Island Sound.

Visitors will have a great time in Pelham Bay Park!

The waters of Pelham Bay Park
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Final Thoughts

City Island is a little unknown haven just a short drive outside New York City, offering a quiet retreat and a beautiful ocean landscape.

City Island is an excellent place for people to experience the old-school charm and a wonderful, hospitable community vibe.

City Island isn’t something you would think of when you think of New York, making the experience all the more exciting.

Book your trip to City Island today!