thanks for the extra comment and picture. The plan is to do coast sailing just like your family did. It's my wife and I. We spent this year all over Narraganset Bay. We haven't been in open ocean but other O'Day 28 owners have told me they have done it to Block Island, Martha's Vineyard , etc. You're the first that's indicated they've gone that far. Next summer we head for open water.
Thanks for indulging me re: the pic.
At the time, our boat was almost new and loaded with the latest gear for such a trip. And while my dad opted to go "outside" most of the way North, he chose the inside route on the way South--down LI Sound, outside (and overnight) just from NY to Cape May, then inside up the Delaware and into the Chesapeake. I would go the inside route if in the same boat today, but certainly wouldn't hesitate to hit Block Island, etc., in the right conditions. Good luck in your cruising!