Having driven an hour North to sail Lake Champlain for years, I can relate to what you're saying. We did that at the younger end - with two babies in fact (and a dog) - for several years. We loved sailing there and have very fond memories. But destinations and anchorages are somewhat limited on the Lake(and I recall some hellacious thunder storms way back then - from what i've seen in Maine in electrical storms this seasons, 2016 Lake Champlain's storms would be terrifying!!). Our sailing was usually up the lake from Charlotte, and back down a day or two later. We used out spinnaker a lot! In fact I often remember sailing under spinnaker up to Valcour Island, in the moonlight, as my family slept below. Wonderful days on the lake. And the swimming!
Then we traded that hour drive for an 8 hour drive - to various ports in Maine - for 4 or 5 years.
And we did a year from the lake to the Bahamas, and another shorter Bahamas trip a few years later with our very young children.
I'd likely feel the same as you do if I was still sailing on the lake. I think we're extremely lucky in this area that the coastal terrain is so varied with snug anchorages virtually everywhere. I've tried to envision myself as a daysailer, and I struggle with the idea, at least with our present boat. Then imagining a small lighter daysailer down the bay, and the weather kicks up, and I've got to get home. That's one downside to this area; it's not a lake and you need enough boat to get you home.