Hi, Linda!
Dealing with children's various fears throughout the years can be taxing on Mom -- especially when you're talking about something that should be a happy occasion like a family vacation. I think you're wise to plan a Disney cruise especially since this one sails from a port driving distance from your home. You can show your son the world without worrying about planes.
The benefit you have is that if you book your cruise now, the
8-night Bahamas Cruise on the Disney Magic won't sail out of New York City until May. That should give you enough time to "test the waters" by taking a large boat or ferry ride a few times to see how he does. Plus, when my youngest child was that little, he argued with his siblings about our ship even being a ship at all -- he said it was a hotel that went to islands!
I suggest going to the
Planning Center on DisneyCruise.com -- take a look at the online brochure and order the FREE planning DVD. Watch the video podcasts and peruse the site. Once you've booked your vacation, schedule a character call, and maybe you can send him a special surprise in the mail from
DisneyStore.com to announce his amazing vacation.
I hope this helps, and please let me know if you have more questions. You know where to find me! Have a wonderful day and a magical vacation.
Bon voyage,
Andi