Originally Posted by
thepointsguy
I also enjoy Fire Island (there are multiple sections, including family oriented), but it may be a bit much with an 11 month old with trains/shuttles/boats. As for other nice areas in NYC metro:
1) Greenport, NY on the North Fork. Beautiful, nice wineries. You can stay at the retro Greenporter hotel and get great cuisine in town. You can also take a car ferry from Orient Point to New London, Connecticut and drive back down to NYC after tooling around Connecticut/ West Chester. Do lunch in Old Greenwich, CT which is charming or go to Foxwoods or Mohean Sun casinos.
2) Monatauk, further out on Long Island is also a beauitful Long Island beach town, with lots to do.
3) NY Finger Lakes region
http://www.fingerlakes.org/ for wineries/relaxation/museums/shopping
4) If you wife likes to shop, Woodbury Commons is a famous premium outlets (Dior, Gucci, Prada, etc)
http://www.premiumoutlets.com/outlets/outlet.asp?id=7
5) Boston is only a 3-4 hour drive (if you go off-peak)
Enjoy your trip!
Surprised you didn't also mention Shelter Island. It's a 5 minute ferry ride from Greenport harbor. There are two child friendly hotels on the island.
I would avoid taking the ferry to New London, Connecticut and driving back to the city. The stretch of I-95 thru Connecticut is about as much fun to drive as the M25 at rush hour. Some of the roads on Long Island aren't much better but at least you have options. You can also take a train from Manhattan to Greenport if you don't want to drive.