Superior Charters & Yacht Sales

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

Most Popular Midsize Sailboat

From $2736

Sleeps 10
4 Cabins

Chat Eau – 38’ Lagoon Catamaran

Book and learn more about the Chat Eau, our 38’ 2010 Lagoon catamaran that sleeps up to ten guests! Enjoy the comfort package with cockpit cushions, speakers, and more.

Book Now

Most Popular Large Sailboat

From $2159

Sleeps 10
4 Cabins

Sanctuary – 49’ Jeanneau Sailboat

Sanctuary – our 49’ 2008 Jeanneau sailboat – is waiting and ready to take you on a fun Lake Superior cruise! Revel in the harmony between performance, elegance, and comfort.

Book Now

Second Most Popular Midsize Sailboat

From $1056

Sleeps 8
3 Cabins

Clear Air – 37’ Jeanneau Sailboat

Book the Clear Air, our 37’ 2012 Jeanneau sailboat, for an unforgettable Apostle Islands boat rental. This model won Boat of the Year in 2012. Take her for a spin!

Book Now

From $798

Sleeps 6
2 Cabins

South Twin – 33′ Jeanneau Sailboat

Learn more about South Twin and book a fun Lake Superior cruise. Check out our 33′ 2014 Jeanneau sailboat, complete with standing headroom throughout and lots of storage.

Book Now

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

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 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!

Why Choose Superior Charters?

Family Owned & Operated

In-Depth Knowledge & Experience

Passionate About Our Business

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