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Superior Charters & Yacht Sales

Yes! We're booking for the 2021 season!

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

Apostle Islands Captained & Bareboat Charters


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.

Check Out Our Guests' Favorite Sailboats

Don’t see the boat you’re looking for?

Take A Sailing Course With Us!

Looking for Something Else?

View our additional sailing services

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 30 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!

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!

Superior Charters made it so easy

We had such a great time in the Apostles! Superior Charters made it so easy. Being able to board the night before allowed us to maximize our time on the water. Check out was a breeze, the communication from the office was great, and the boat was clean and well stocked. I highly recommend planning your next adventure with Superior Charters.

– beccac175, TripAdvisor
Another "Best of the Best"

We have chartered with Superior Charters for the last three years and have known Cindy Alpha and Cindy Bravo for a long time. Superior Charters is a first class organization with first class people running it. If you want to enjoy sailing, learn to sail or just take a sailboat ride, Superior Charters is the way to go. First class all the way.

– Timothy H., TripAdvisor
Excellent Place to Charter a Bareboat. Top Notch.

Had a wonderful experience with Superior Charters...Clean, modern yacht; easy check-in and check-out; nice people. I will definitely charter here again - probably next month!

– justinmF4442YP, TripAdvisor
Top Notch

Our experience with Superior was top notch. Everything was perfect, from initial phone discussions to figure out what would be best for us (novices), to the friendly staff, to the clean boat, to the simple check in and check out process.

– andrewdV2256LD, TripAdvisor
Apostle Islands Bareboat Charter Sail

Just finished my fifth charter with Superior a little over a week ago. This is a well run, professional charter company. The boats have always been in good shape. Friendly. Reliable. Superior's check-out captains are reliable and ready to answer any of your questions.

– jdittmer2018, TripAdvisor
No Brainer

Our boat was in excellent condition. The staff was professional. Booking the boat and trip was easy and their communication was excellent. They have an unusually large fleet of boats to choose from and they are all fairly new. Giving you the option to clean the boat yourself to save money is nice. If you are looking to charter a nice boat this place is a no brainer.

– 70Justin, TripAdvisor
Perfect Wedding!

We chartered two sailboats from Superior Charters for our Wedding Reception!!! Our friends and family got to experience going out into the islands on sailboats, something me and my new husband love doing. Everyone at Superior Charters was AMAZING in helping our dream wedding come true. Thanks to their dedicated maintenance and cleaning staff the boats are perfect, and if something isn't right, they always go out of their way to fix any issues. They helped us figure out so many of the detailed logistics and also worked with us on timing and schedule to make for a wonderful experience for our guests. Our wedding day was absolutely perfect! THANKS SUPERIOR CHARTERS :)

– sailor-architect, TripAdvisor
We can't wait to go back!

We did a 3 night charter sail with Captain Christine. It was everything I hoped it to be and more! We had never been sailing so were not sure what to expect. Christine was patient with our lack of knowledge and let us be involved as much or as little as we wanted with the sailing experience. We had all types of weather and made the best of them all. The ability to pull up to an island and row up to the dock and hike was perfect along with jumping off the back of the boat into the water for a swim!!! It's the perfect social distancing trip. I can't say enough about it - we will definitely be back.

– megmyra1, TripAdvisor