True North Sailing Charters

top of page Skip to Main Content   .png) # Sailing adventures from Bayfield, Wisconsin in Apostle Islands National Lakeshore True North Sailing Charters in Bayfield, Wisconsin is committed to providing guests with a unique and safe Apostle Islands sailing experience. 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 look forward to helping create magical moments with you and sailing into the sunset!     ## Sailing Adventures Sailing trips depart from our slip location in Bayfield, Wisconsin  ## Bayfield Adventure Sail A 2 hour, 15 minute sail out of Bayfield, Wisconsin aboard "Starling" a 33' Cheoy Lee Clipper.  Set sail on Lake Superior and enjoy the sights of the North or West Channel, 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.  Meet at our dock located in Bayfield. Please select a time and date below that would work for your group and we will review and confirm with you as soon as possible. $98 per person $20 Children's Discount ​ (Private Boat Option Available - $460)  [Book Now](https://x2-checkout.xola.app/flows/mvp?button=5fee0a7ce3577363845c0719&theme=light&xwm=eyJvcmlnaW4iOiJodHRwczovL3d3dy50cnVlbm9ydGhzYWlsaW5nY2hhcnRlcnMuY29tIiwiY2hhbm5lbCI6IkQ5dFlva2VUV0tiaU1GRzMifQ%7E%7E)  ## Apostle Islands Excursion 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.  Half day trips depart from our Bayfield location. We use our catamaran, Piper on half day trips. The shallow draft allows us to access secluded beaches and explore remote island coastlines. The spacious shaded solon leads to the forward trampolines that are great for sun bathing and watching the water rush past beneath you. ​ ​Please select a time and date below that would work for your group and we will review and confirm with you as soon as possible.  $795 Full Boat Reserved (Includes up to 6 guests) [Book Now](https://x2-checkout.xola.app/flows/mvp?button=5fee0efb073cb94a3f299216&theme=light&xwm=eyJvcmlnaW4iOiJodHRwczovL3d3dy50cnVlbm9ydGhzYWlsaW5nY2hhcnRlcnMuY29tIiwiY2hhbm5lbCI6IkQ5dFlva2VUV0tiaU1GRzMifQ%7E%7E)  ## Full Day in the Apostle Islands Set sail from our Bayfield location for a full day of exploration and excitement in the Apostle Islands! Depending on wind, weather, and your group’s preferences, we’ll chart a course to Oak, Raspberry, or Manitou Islands. Discover hidden treasures like the historic fishing camp, Oak Island’s scenic hiking trails, or the remote beauty of the Raspberry Island Lighthouse. Your adventure takes place aboard Piper, our spacious and versatile catamaran. With its shallow draft, Piper is perfect for getting up close to secluded beaches and untouched island coastlines. The wide deck is ideal for soaking up the sun, while the protected cockpit ensures a comfortable and dry ride in any conditions. Whether you’re hiking remote trails, exploring historic sites, or simply relaxing on deck with the sound of the waves, this full-day sailing trip promises fun, adventure, and unforgettable memories. Book your date and time now, and let’s make your sailing dream a reality! We’ll confirm your reservation as soon as possible. $1295 Full boat reserved (Includes up to 6 guests) [Book Now](https://x2-checkout.xola.app/flows/mvp?button=5fee11343e9ca809843183ea&theme=light&xwm=eyJvcmlnaW4iOiJodHRwczovL3d3dy50cnVlbm9ydGhzYWlsaW5nY2hhcnRlcnMuY29tIiwiY2hhbm5lbCI6IkQ5dFlva2VUV0tiaU1GRzMifQ%7E%7E) [](https://www.truenorthsailingcharters.com/watertaxi) ## Island Hopping Adventure in the Apostles True North Water Taxi specializes in island adventures in the Apostle Islands. Departing from Bayfield, Wisconsin, we take you beyond the shoreline to explore multiple islands in a single four-hour trip, combining scenic boat travel with opportunities to step ashore for short hikes, picnics, and discovery. ​ Our routes may include Long Island’s wild sandy shoreline, Hermit Island’s quiet trails, Basswood Island’s historic brownstone quarry, Oak Island’s secluded forests, Raspberry Island’s lighthouse and shoreline paths, or the expansive beaches of Stockton Island. Each stop offers a new chance to experience the beauty, history, and character of the islands.  Safe, reliable, and operated by local captains,  True North Water Taxi is the most flexible and unforgettable way for adventurous families and couples to explore the Apostle Islands together. Your dog is welcome aboard as well. $395 (includes 2 adults and one small child or dog) [More Information](https://www.truenorthsailingcharters.com/watertaxi) If we are not able to go out due to weather or if you do not think it would be a good experience (due to rain, cold, etc.) you have the option to either reschedule or have a full refund. Book Online ## WHAT PEOPLE ARE SAYING ABOUT TRUE NORTH SAILING  Our experience was amazing! Very relaxing! Captain Abe was very knowledgeable and even let us help him during our sailing tour. We would definitely recommend them to everyone!  It was a very pleasant time. Dusty was so helpful. The boat was in great shape. I could not have asked for anything more.  Our family of four enjoyed our sail outing tremendously. The skipper is kind and helpful, the lake and islands are beautiful, and sailing is too fun. Half of us helped crew the boat, and half of us just sat back and took it all in. Highly