Even a simple stroll around town isn't boring
Since City Island is known for it’s insanely beautiful Victorian architecture, you’d be remiss not to wander around the quiet, picturesque streets and take it all in. Streets and avenues like King, William, Belden, Horton, and Minnieford are ideal for architectural eye candy that's sure to inspire (and also depress you greatly, once you return to your apartment). Make sure you check out the Schofield House (65 Schofield St) -- built in 1840, it's the oldest home on the island and a recent NYC landmark. Another gem is the Samuel Pell house, located at 586 City Island Ave (Pell was a captain and descendant of the Pell family that once owned the land. Talk about legit.)
There are lots of great local merchants
Stroll down City Island Ave, the town’s main street, to visit some of the local shops and art galleries unique to the island. Starving Artist Cafe is a gallery and coffee shop rolled into one, selling cool art books and handmade jewelry. If it’s antiques you’re looking for, Early Ruth Art & Antiques has enough bric-a-brac to fill that large country home you don’t have. Jewelry lovers can head to Calico Juno Designs which specializes in gemstone and wire designs.
Local theater prices beat Broadway every time
Since you’re not getting into Hamilton any time soon, enjoy a play by the City Island Theater Group. They’ve put on everything from Evita to The Glass Menagerie to Steel Magnolias. Tickets are normally $20, the theater is small, and best of all you’ll feel like you’re catching a small town play right in NYC.