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Lake Superior Sailing Trips

Choose My Sailing Adventure


Book any Dreamcatcher Sailing trip for our 2020 season by January 31, 2020, and we will send you a FREE Howl Gift Card valued at 10% of your trip cost!

Book that sailing trip by January 20, 2020, and that FREE Howl Gift Card will be valued at 20% of your trip cost!

Welcome to Dreamcatcher!

Looking for a great group adventure in Lake Superior? Try sailing! We offer special family rates on each of our boat tours to ensure the trip includes only the people you invite along.

Take a few boats at once — up to 18 people can sail from Bayfield. You can anchor or raft up together out in the Apostle Islands and swim, picnic, and explore. It’s perfect for reunions, anniversary or birthday celebrations, or to simply be together. These trips are extremely popular! Book yours today.

For information on our area, lodging, dining, and more, visit the Bayfield Chamber website!

Bayfield's Premier Sailing Company

Anniversary cruise

"We signed up for the couples trip, (so 2 other couples) but ended up being the only couple on the boat. Bronte was an excellent captain and host. He truly loves what he does and that makes it that more enjoyable. We went the week before Applefest and they worked around the weather and we got a perfect day in between the rain days."

– Randy · TripAdvisor
Private cruise!

"A group of four of us took advantage of the special they were offering for a 2 1/4 hr private sail boat cruise. It was a beautiful afternoon and our Captain Abe was wonderful! He was very kind and informative and made us feel totally comfortable! There was seating on the back of the boat as well as a restroom and places to put our things. A wonderfully relaxing trip! Can’t wait to do it again!"

– Wanderingwinelover · TripAdvisor
Come sail away, Come sail away, come sail away with Abe & Dreamcatcher Sailing

"What a relaxing and peaceful way to spend a couple of late afternoon hours. Abe, our captain, made us feel welcome and comfortable right from the start. The wind wasn’t real cooperative but he went out of his way to give us as much sailing experience as he could. Despite the intermittent winds, We enjoyed the cruise and Abe’s commentary on the area and its history. We highly recommend Dreamcatcher Sailing."

– Mike G. · TripAdvisor
Peaceful Sailing out of Bayfield WI

"We were in Bayfield in September and used Deamcatcher Sailing for a peaceful sail out of the dock. I would recommend this company for this type of adventure, reservations can be made on line, the captain was friendly and competent and he did his level best to keep us going even in the light breezes of the afternoon. We were offered the wheel if we wanted. What a great time for some serenity (light winds) and on other days (stronger winds) for high adventure. Great opportunity for families to experience sailing."

– Trying2Retire · TripAdvisor