In Search Of: A Summer Retreat

Back in the days when normal yuppies could afford it, my parents use to take us to Nantucket for a few weeks each summer. Thus, I learned the value of the laid-back summer vacation where the key goals were riding your bike, bobbing in the waves, whether to have chocolate or rainbow jimmies on your ice cream, and, once you hit teenagerdom, how to lighten your hair with lemon juice. Now that I'm old enough to have to pay for my own summer vacation, and I haven't turned out as a wildly successful hedge fund manager, or wife of one, Nantucket is increasingly out of reach. (I mean, entry level house price of $1 million - I think not). So, the quest is on to find a suitable replacement where, for the time being, we can go rent a cottage for a week or two and, some day in the future, buy a house and convince a few friends to do the same.

I'm definitely an ocean-over-mountains person and particularly partial to islands. The odds are good I will spend my remaining years on the East Coast, so that's the geographical boundary. And, due to the childhood referenced above, really we're talking New England. Although I'd entertain the possibility of crossing the Northern border. So, some options I've been pondering:

Cuttyhunk Island. So this is a small island off Cape Cod, part of the mostly-private (read: owned by the Forbes family) Elizabeth Islands. Reached by ferry from Rhode Island, but no flights, it is short on cars and definitely the quiet side of vacation islands (think one seasonal restaurant, one general store, etc.) Seems really appealing, although I can't seem to locate much of a rental or sale market, so it's hard to know what the price are like.

Block Island. Never been, but clearly larger and more accessible than Cuttyhunk. Certainly discovered, but doesn't seem to have suffered the private-jet-from-Teterboro problem that Nantucket has. Definitely pondering a weekend at this place to check it out.

Maine. I spent a wonderful teenage summer as a nanny in a place called Squirrel Island. No cars, one little general store, lots of paths over rocks and reachable on a little ferry from Boothbay Harbor. So quaint: square dancing on Saturday, an ice cream counter in summer, and the kids doing plays for the whole town. But I can't seem to find anyone renting a place there. I just know there are a bunch of islands in Maine like this, but can't seem to meet anyone with personal knowledge.

Canada. I know nothing about Canadian islands, but Prince Edward Island seems appealing. Would be a hike to get there, but maybe worth it for the peacefulness and price?