If you don't mind driving, you can get 20-30 days of iceboating per year if you live in new england. I have been averaging 26 days per year for the last 4 years.
I often drive 2-5 hours to get to the ice though. Anything within 300 miles is fair game for a weekend if the ice is good.
All you need to do is get good roofracks and snowtires and go for it.

Sail Fast
Eric Anderson

If you want a portable 2 seater, the Gambit is the thing to get. Another alternative is a DN with a sidecar for ocasionaly taking passangers.