Just a three to four hour drive east of Toronto waits a mossy, rock-cliffed oasis of vintage cottages. Wealthy million and billionaires have famously spent their holidays in this naturally stunning slice of Ontario.

The Thousand Islands are a plethora of islands on Saint Lawrence River in the eastern part of Ontario. This summer we are traveling from Toronto to the Thousand Islands as a seasonal embrace of Canadian-made island hopping. Island hopping isn’t new to the area; back in the 19th and into the 20th centuries the 1000 Islands were used as secondary homesteads for the rich. Wealthy families from Canada and the United States bought properties and built mini palaces on the waterfront spots.

One island east of them all is called Singer Castle on Dark Island, home of an enormous estate that was built by the owners of the infamous Singer sewing machines. 

The beautiful cliffs in this Canadian island-region are perfect for jumping. Many of the Thousand Islands are landing spots for locals, who travel by Sea-Doo, boat, or swim to the land points to be used and reused as a summer afternoon picnic spot. Although some islands are privately owned (by the likes of Cindy Crawford, for example), many are occupied by Parks Canada who oversee the maintenance of the natural wellbeing of the granite islands. And unlike visiting the waterfront of Lake Ontario, cottage country or Toronto Islands, the spots in the 1000 Islands are still quietly occupied by a limited population of area persons.

Though the 1000 Islands may be a destination for celebrities and the über wealthy, there are still rentals available for us mere peasants to enjoy one of Ontario’s most unique travel destinations. The 1000 Islands is ideal for a day trip along the water, or spend an afternoon traveling from island to island in a kayak or canoe, or motorboat.

This AirBnb includes an island of your very own and a private boat ride to get there. This cabin sleeps 6 and goes for a mere $200 a night, making it ideal for any and all summer getaways. Travelling with a smaller party? This lakeside cottage is dying for a photoshoot aaaand is only $123 per night.

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