The only path, if you are starting in Windigo, is to first get to Rock Harbor via Voyageur or seaplane.
After spending the night in Rock Harbor you can take the Voyageur or a water taxi. Normally the water taxi to Malone Bay is a bit expensive at $322 for one or two people but "only" $370 for a group of 6. I'm not sure if there might be a small chance of scheduling the water taxi for a later afternoon departure as the Voyageur arrives in Rock Harbor at 3pm CT.
Getting back to Windigo from MB would be via Voyageur on its way from Rock Harbor back to Minnesota.
Logistics- Rock Harbor to Windigo- How do you get back to Rock Harbor to catch boat
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