Tiny City Island has such quaint, anachronistic charm, it's a wonder it's within NYC limits. Take a daycation here by hopping the 6 train to Pelham Bay Park (the last stop on the line) and transferring to the BX29 bus, which takes you directly into town.
Stop one: Sugar and Spice (536 City Island Ave, 718-885-9229, sugarandspiceonline.com), a cozy caf that serves pastries for the kids and coffee for you. Next up: fishing. At Jack's Bait and Tackle (551 City Island Ave, 718-885-2042, jacksbaitandtackle.com; $60 for 12 hr rental on weekends), families can rent a four-person fishing boat. Rods are available for purchase.
After you've caught (or at least pursued) some flounder and bass, make your way to P.S. 175's nautical-themed playground (200 City Island Ave). (Bring a small cooler to keep your catch fresh.) Tykes can steer a fake ship and splash around in an anchor-shaped sprinkler while younger visitors lay claim to the baby swings.
Grab a picnic bench overlooking the water at Johnny's Famous Reef Restaurant (2 City Island Ave, 718-885-2086). Clam chowder and fried calamari make great lunch picks.
Stroll down City Island Avenue, the neighborhood's main drag, and hit Kaleidoscope Gallery (280 City Island Ave, 718-885-3090); it sells Melissa & Doug toys, jewelry, art supplies and a big collection of kaleidoscopes (and kits to make your own). A few doors down is local fave Lickety Split Ice Cream Parlor (295 City Island Ave, 718-885-9195). Treat Junior to a cone, then let him play with the eatery's Hula Hoops and sidewalk chalk.
Learn a bit of the area's history at the free City Island Historical Society and Nautical Museum (190 Fordham St; 718-885-0008, cityislandmuseum.org. Sat and Sun 1--5pm), which is housed in a 19th-century building that was a school until 1976. Check out the display of wooden boats and the original school desks. The community room is another kid favorite—you'll find an old typewriter and sewing machine and a topographic map of the area.
Stick around for fresh lobster and king crab legs at Sammy's Fish Box (41 City Island Ave, 718-885-0920, sammysfishbox.com). Kids under ten eat free from the children's menu—they should love the fish and chips.
Take an after-dinner walk down one of the many residential, bungalow-lined side streets, where you can watch the sun set over the water.