True North Sailing Charters, owned and operated by Abe and his brother Josh, is committed to providing guests with a unique and safe Apostle Islands sailing experience. We offer sailing adventures departing from our commercial slip in Bayfield, WI. Guests can choose to help hoist the sails or sit back and relax as we navigate the gorgeous waterways of Lake Superior and the Apostle Islands under sail. We recommend booking your trip early as our boats fill up quickly! You may also have the opportunity to meet our two other friendly captains, Captain West and Captain Dusty, during your adventure. We look forward to helping create magical moments with you and sailing into the sunset!
Bayfield Adventure Sail
Apostle Islands Excursion
Full Day in the Islands
A 2 hour, sail out of Bayfield, Wisconsin aboard “Starling” a 33′ Cheoy Lee Clipper. Set sail on Lake Superior and enjoy the sights of LaPointe, Madeline, Basswood and the surrounding islands. Enjoy the original teak decks, two sitka spruce masts and the elegant lines that make for a classic maritime experience.
A 5 Hour sailing experience in Apostle Islands National Lakeshore. Trip routes are dependent on wind and weather conditions that day as well as your preference but possibilities include visiting the sandstone shorelines, sand-spits and lighthouses in the surrounding area on Hermit, Oak, or Long Island.
A Full Day Sailing Adventure in the Islands. Launch from Bayfield, Wisconsin and depending on wind and weather conditions as well as your preference set sail for Stockton, Raspberry or Manitou Islands. Visit the historic fishing camp, Stockton Island hiking trails, or the remote Raspberry Island Lighthouse.
“Not all those who wander are lost” – J.R.R. Tolkien