About Time Out Sailing
Time Out Sailing is Duluth's only private sailboat charter, operating out of Lakehead Boat Basin on Park Point — just across the Aerial Lift Bridge from Canal Park. Founded in 2016 by Captain Jake, the company runs USCG-certified captained charters on Lake Superior and through the Duluth–Superior harbour, the world's most inland freshwater port.
All trips are private, so your group has the boat to yourselves. Options include half-day and full-day sails, sunset cruises, overnight adventures, and custom outings for proposals, birthdays, and corporate team-building. Routes typically pass under the iconic Aerial Lift Bridge, cruise past ore boats and grain elevators in the harbour, and head out onto the open waters of Lake Superior where you can feel the sheer scale of the largest Great Lake.
Time Out Sailing stands out for the intimacy and flexibility of a private charter versus the larger excursion boats. With a small group aboard, guests can take the helm, trim the sails, or simply relax while the captain handles everything. The experience is hands-on or hands-off — your call. It's one of the most memorable ways to see Duluth from the water.
