Pointe au Baril
The lay of the land: Pointe au Baril-ites see themselves as frontier cottagers—brave city dwellers who, every Friday afternoon, make the three-hour trek to “the Station,” a small port of multi­million-dollar marinas whence they set out to their island retreats to “get away from it all.”
Who goes: The same people POBers just spent the week with in the city: descendants of Toronto’s old money class, including Gail Regan and family (of Cara foods empire), Roger Martin (of Martin, er, Rotman School of Management) and the Westons (of, well, you know).
Typical weekend: Playing tennis, drinking gin and tonics, and partaking of the frenzied socializing centred around the century-old Ojibway Club.

Sans Souci
The lay of the land: Legend has it that Samuel de Champlain, who explored Georgian Bay in the 1600s, gave this exclusive island community its name. Today the translation (“no worries”) seems an apt description of its well- to-do cottagers’ carefree lifestyle.
Who goes: Fred and Nicky Eaton, former GG Adrienne Clarkson and former Leaf Pete Conacher.
Typical weekend: Many clearly can’t leave their administrative skills at the office. The community association, based on Frying Pan Island—the area’s main hub, home to the beloved Henry’s Fish Restaurant and Champlain’s Anchorage—has more board members than the Royal Bank.

Beaumaris
The lay of the land: You can’t afford one now, but it’s only a matter of time before the historic old estates of Millionaire’s Row come up for grabs. Not in their present, sprawling verandaed, turreted, 10-bedroom form, but as the condo-resorts that will inevitably be built in their place.
Who goes: Mega-mansion-owning Rosedalers whose cottages are even bigger than their city houses.
Typical weekend: Originally the summer retreats of captains of industry (Labatt, Eaton, Bronfman), the cottages are a throwback to the cushy days of yore, complete with hired help, formal dinners and cocktail cruises. Unfortunately for the owners, the mega-cottages now draw a constant stream of tour boats. Ah well, if the tourists become too bothersome, one can always hide out in the turret.

Sturgeon Point
The lay of the land: Of all the cottage communities in southern Ontario, the most exclusive has to be Sturgeon Point, located on a wooded peninsula overlooking Sturgeon Lake in the Kawarthas.
Who goes: Descendants of the original cottagers—properties in this tight-knit community are usually passed down from generation to generation.
Typical weekend: Though SP has a sailing club, a public beach and an annual regatta (complete with requisite spoon and egg race), this is less “cottaging” in the rustic, communing-with- nature sense than it is a collective yearning for simpler times.