The Lonely Island Tour
Considered one of the wildest cruising grounds in the world, the Canadian North Shore of Lake Superior offers a sailing experience unlike any other. Its waters are clean, cold, and crystal clear, and scattered along this rugged coastline are four remote and rarely visited islands: Passage Island, the Slate Islands, Michipicoten Island, and the most isolated of them all—Caribou Island, home to one of the last remaining herds of woodland caribou. Venturing into these waters is not without its challenges. The weather is notoriously unpredictable, assistance is far away in the event of trouble, and navigating through thousands of rocky reefs requires skill and focus. But for those prepared to rise to the occasion—with an experienced captain, a solid boat, and a courageous crew—this remote wilderness reveals a truly magical sailing experience. Join Captain Mark Gordon and First Mate Ned Corkran aboard Amicus II, a 40-foot steel expedition cutter, for an ambitious and challenging sail training expedition as they attempt to visit all four of these remarkable islands in a single unforgettable journey.
This expedition covers more than 400 nautical miles and includes the possibility of rough weather, long sailing days, and overnight passages. For that reason, it may not be the ideal choice for your first sailing experience. We recommend joining one of our other trips first—or coming with a strong sense of adventure and a willingness to embrace the challenges of life at sea. As a sail training expedition, participants will be actively involved in all aspects of the journey, including standing watch, navigation, sail handling, and daily responsibilities such as cooking and cleaning.
Dates and Cost
June 21 – July 2
Cost: $2,040 (This course is currently full)
To register, please contact the North House Folk School. You may also book this trip as a private charter—choose your own dates for $650 per day.
Participants will need a valid passport or enhanced driver’s license, as well as a Remote Border Crossing Permit (RBCP), which must be secured before the trip begins. The RBCP is simple to obtain, and we’ll provide step-by-step instructions to guide you through the process.
Stories from the Sea
Real adventures, real smiles — hear from those who made waves with us.
Steffanie GerkinTrustindex verifies that the original source of the review is Google. Had an amazing time on this stunning sailboat, will definitely be back to do this again! john hallTrustindex verifies that the original source of the review is Google. We had a fantastic time sailing with Captain Matt in Lake Michigan from the shore of Milwaukee, WI. Recommended! Sean RyanTrustindex verifies that the original source of the review is Google. Had a fantastic sunset cruise with Captain Matt. He was ready to go and we started on time and went a little bit long. Matt made sure we were safe, made the best of light wind and was engaging the entire time. I highly recommend! J Andrew GearyTrustindex verifies that the original source of the review is Google. Excellent! I booked a sunset sailing trip with my family for our Milwaukee vacation. The communication setting up the trip was clear and the captain was responsive. The directions on where to go and what to prepare for were clear and very useful. We had an amazing time on the sailing trip! It was a beautiful night and the crew was great. The captain and his crewmate treated us very well and were a lot of fun to chat with during the voyage. I would not hesitate to recommend or even book another trip with Sea Dog Sailing. Thank you for a wonderful experience! Rachel MacGregorTrustindex verifies that the original source of the review is Google. This was the BEST experience, I could not recommend it enough! I came to visit my sister in Milwaukee after she moved here and decided to try this because it sounded fun but it was by far our favorite thing from my entire visit (and I work in the travel industry so I am great at finding lots of fun things to do). Captain Bob was fantastic, so knowledgable about sailing and the lake and city, plus we got to try steering some which was really cool! Joseph FasiTrustindex verifies that the original source of the review is Google. Magical and fun. Captain Bob was the best host and made the day spectacular. I have lived in Milwaukee for many years and have never savored the view of the skyline as we did from 5 miles out in Lake Michigan on a beautiful sunny day. He answered my incessant questions with patience and knowledge. I look forward to another charter with Sea Dog Sailing. the one down side— Now I have what may be a burning desire for a sail boat of my own! Noah HunterTrustindex verifies that the original source of the review is Google. Capt. Robert and his crew were so welcoming as soon as you walk down to the boat. If you have never been sailing you absolutely have to book a trip with this crew. My wife and I have never been and they made an amazing trip for both of us, explaining what they were doing with lines and sails, telling us how things work with the lake and sailing, and overall making us feel as comfortable and safe as possible. The boat is a beautiful vessel, the only downside was we wished we could’ve stayed and sailed longer! So if you’re in Milwaukee and want to experience something fun and exciting with a expert captain and friendly crew, book a trip with sea dog sailing! Scott HartmanTrustindex verifies that the original source of the review is Google. Had a great time sailing with Captain Bob and his crew. 5 stars, would recommend!