About Superior Sailing
Superior Sailing is a small captained charter operation based on Pageant Road in Bayfield, Wisconsin, sailing the waters its owner calls the Caribbean of the North. Captain Peter runs every trip personally aboard the Bertha Stern, weaving decades of Lake Superior experience and local stories into each voyage through the Apostle Islands.
Trips are fully crewed, so guests need no sailing experience — simply step aboard and help trim sails as much or as little as they like. Itineraries are flexible charters shaped around what the day offers: island beaches, sandstone sea caves, historic lighthouses, and the old brownstone quarries that built cities across the Midwest. The sailing season follows the Lake Superior summer, roughly June through September, with small private groups keeping every outing personal.
What sets Superior Sailing apart is the single-captain, single-boat format. There is no rotating crew and no fleet schedule to serve — just a skipper who knows these islands intimately and tailors each charter to the wind, the weather, and the guests aboard. For travelers who want the Apostle Islands narrated by someone who has spent a lifetime on this water, it is a genuinely personal way to sail.
