My band members and I were recently invited to perform in Canada for a special show on a huge family estate just across the border from Syracuse, New York. Such requests for our music at private venues are, happily, not particularly unusual. In most cases, the client has been to Cayman or the Bahamas and heard us perform and they simply want to evoke the good times they had when they were visiting the Caribbean.

This time, we flew 1,600 miles to an area known as the Thousand Islands of Canada, which in reality constitutes an archipelago of 1,864 islands that span the U.S.-Canada border in the St. Lawrence River.

The islands range in size from more than 40 square miles to smaller islands occupied by a single residence, or often uninhabited outcroppings of rocks that are home only to nomadic birds.


For three days we made our home in Gananoque, Ontario, a small town with a year-round population of just over 5,000. The main thoroughfare known as King Street is dotted with pubs, ice cream parlors and restaurants, and after sundown, minstrels can be heard around every corner and down every alleyway as they strum guitars and sing into the wee hours for tip jar compensation.

The drive from Syracuse, New York, to Gananoque (just a little over an hour) was a breathtaking adventure as we passed farms teeming with life. The farmers take full advantage of the area’s short summer harvest season.

Miles of whitewashed fences lined the winding roads and dissected the rolling green hills where magnificent horses grazed near weatherbeaten old barns and rocket-shaped grain silos.

The hay rolls that dotted the valleys looked like giant sugar cookies waiting to be consumed by dairy cows and goats.

Though all this country and wide-open greenery was a completely different sight for we who had made our home in the tropics, it was nothing compared to the islands – all 1,864 of them. We stopped counting at 84!

The water that surrounds these islands is unpolluted and clear; so clear in some areas that a rocky bottom can be observed in 80 feet. It is enticing – you want to dive into the translucent freshness. However, it is also very cold, particularly for someone who is used to the water temperatures 1,600 miles to the south.

For a reasonable price, you can rent a cottage and boat on one of the islands.
For a reasonable price, you can rent a cottage and boat on one of the islands.

Heart Island

Heart Island is one of the more interesting places to visit here. In 1900, George Boldt, general manager of the Waldorf Astoria Hotel in New York City and manager of the Bellevue-Stratford Hotel in Philadelphia, launched a campaign to build a huge six-story, 120-room masonry structure, one of the largest private homes in the United States, as a present to his wife, Louise.

The construction of Boldt Castle ceased abruptly in early 1904 after Louise unexpectedly passed away from a heart condition. George Boldt was so devastated that he never returned to Heart Island, leaving the structure as a monument of his love for his wife.

For 73 years, the castle was exposed to the harsh winter weather and occasional vandals. Today, it’s one of the most popular tourist attractions in the area.

Dark Island

Dark Island, near the U.S.-Canada border, is the home of Singer Castle, which was built by Frederick Gilbert Bourne, president of the Singer Manufacturing Company – producer of the Singer Sewing Machine. In 1965, the castle sold for approximately US$35,000. In 2005, it was listed at US$22 million.

Michael Jackson, who always had an obsession with chateaus and “Thriller” zombies, tried to buy the castle at one time, but he was turned down by the owners.

Playhouse in Gananoque
Playhouse in Gananoque

Deer Island

Then there are the shadowy rumors about Deer Island, a 40-acre island owned and managed by the secret Skull and Bones Society. It is where the “Bonesmen” get the opportunity to get together and rekindle old friendships.

One member describes it this way: “To call the island ‘rustic’ would be to glorify it. It’s a dump, but it’s beautiful.”

Finally, there’s the debatable connection with Thousand Island salad dressing … I’ll save that story for another date.

Interesting fact: You can rent your very own private island for around $500 per day, and a boat rental will cost you around $175 a day; that was in Canadian currency – rather a cheap price for the ultimate in seclusion and privacy.

There is one major drawback: you only have about three to four months a year to enjoy it all. After that, you’ll need a snowmobile to go grocery shopping and a hole in the ice if you want to catch a fish.

No, thank you. It’s back to my coconut trees and white sands for the rest of the year.