87. Best Guided Outdoor Experience

It’s a different view when you’re out on Lake Superior. Once you push off from the rocky shore and sail out across the lake’s frigid waters, there’s a sense of calm that’s coupled with the possibilities of adventure. Sail Superior, helmed by owner/captain Gregory Heroux, has been sharing this feeling since the crew ran their first tour in 2001. Since then, thousands of people have experienced the magic of a guided sailboat tour around Gichigami, seeing the nearby islands and attractions in a new way. After expanding the Sail Superior fleet to four boats with a full complement of sea-worthy staff, the company now offers a variety of guided adventures either via sailboat or Zodiac to local attractions like the Welcome Islands, Porphyry Island, and Otter Cove. If you want more time on the water, Sail Superior also does overnight and multi-day trips using their monohull and catamaran boats to travel far out of sight of the city. Finally, if you want to learn the ropes, Sail Superior is accredited to teach a variety of courses to meet ISPA (International Sail and Power Academy) standards. Looking ahead to 2026, Captain Heroux is planning his first trip of the season out to the bird observatory at Thunder Cape. “It’s the perfect way to start the season and why I love being out on Lake Superior,” he says. If this is the year to have a sailing adventure of your own, Sail Superior can promise you a place on deck!

By Justin Allec