Superior Charters & Yacht Sales

Book a Sailing Cruise on Lake Superior near the Apostle Islands!

Apostle Islands Captained & Bareboat Charters

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At Superior Charters, we offer both captained and bareboat charters for your sailing vacation on Lake Superior. These options give both the novice and experienced sailor a tailored vacation to fit their abilities, skills and needs. Learn more about captained and bareboat charters, visit our FAQs page.

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Sailing School Courses • Yacht Management • Yacht Sales • Brokerage Boats

A Sailing Charter Fleet That Stands Alone

Join the thousands of skippers and crew that come back year after year. Discover chartering in the Apostle Islands with Superior Charters.

Superior Charters offers the largest selection of sailboats for charter available at one harbor in the United States. We are located in Bayfield, Wisconsin. Family owned and operated since 1979, Superior Charters has built a reputation of providing impeccably maintained yachts and superior service so you can have the best possible experience while booking your charter, taking a sailing course, or letting us manage your yachts and sales.

Situated among the 22 islands of the Apostle Islands National Lakeshore, Superior Charters & Yacht Sales offers a unique sailboat cruising experience on Lake Superior by offering more than 50 sailboats to choose from to make your charter exactly how you imagined. Whether you are new to sailing or an experienced cruiser, the crew and staff at Superior Charters will help you create an enjoyable and carefree sailing and boating experience!

So, what are you waiting for? Reserve your next charter and sail into a dream getaway on the water!

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Small sailboat cruising through Lake Superior
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Why Choose Superior Charters?

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Family Owned & Operated

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In-Depth Knowledge & Experience

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Passionate About Our Business

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High Level of Customer Service

Our Guests Have Excellent Experiences on our Charters!

Multiple Trips With Superior Charters

We have had the opportunity to charter several times with Superior Charters. The service, fleet and staff have always been first rate. We had a great trip with no issues. Would highly recommend for Apostle Island cruising!

– Mike B., TripAdvisor
Professional & Personable

This was a trip with my two sons to celebrate my 70th birthday. Because we had not chartered in a while, we needed a two - four-hour checkout ride. Captain Mike Simon was our instructor. He was great and recognized what we knew and what we needed to refresh.

– Timothy H., TripAdvisor
Sailing with the Kids - Family Fun!

Awesome! First time with Superior Charters and sailing any of the Great Lakes. Staff and Owners were easy to work with and have a top-flight fleet. Boat was pristine and experience was Incredible. Highly recommend to any family.

– Mark W., TripAdvisor
Fantastic Service!

Cindy and the whole staff are amazing! I called to set a first time sailing experience for my wife's birthday. Cindy was very helpful in selecting a great boat for us and a captain to take us out for the day.

– Steve E., TripAdvisor
Excellent experiences for over 18 years

I have been going up to Bayfield and using Superior Charters for over 18 years. The people are great - real people that care about your trip, your safety and providing a learning environment. Highly recommend them.

– CJ R., TripAdvisor
Sailing was amazing!

We went back for our second year and had Dave as our half day refresher Captain. He is amazing and so full of great knowledge. After our half day refresher course we set off on our own and had an amazing trip! We saw the amazing caves on Devils Island and boated through them in our dingy! We had great times with wind, great times without wind, amazing meals, and a great time swimming in the cool water. The night skies, with the full moon were breathtaking! Superior Charters helped us select the perfect vessel, made sure our slippers and crew knew what we were doing and then let’s us free to embark on our own adventure!

– Rebecca B., TripAdvisor
Great weekend

If you ever get to see Lake Superior from the water you are a lucky person. My third trip with my family was again a success sunshine, wind and stars aplenty. Superior Charters provides excellent service and information with a smile. The checkout Captains will add to your local knowledge every time. The front desk is full of information. We arrived the night before our checkout and our boat ws immaculate as advertised. So take advantage of this jewel of a charter company in a beautiful corner of the world

– Tom V., TripAdvisor
Great Cruising Area

We just finished our eighth annual trip with a boat from Superior Charters and we highly recommend them and the Apostles Islands National Lakeshore area. Superior Charters has a good selection of boats and will work with you to identify the best choice for you. They will be ready to check you in and get you on your way.

– Jim M., TripAdvisor