Sailing Vacations

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 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.

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.

Enjoy the perfect Lake Superior boat rental with Harmony, our 31′ Pearson sailboat. Sail in comfort with a new bimini and state-of-the-art mainsail.

Learn more about Boca, our 32′ 1981 C&C sailboat, equipped with everything you need to have an enjoyable Apostle Islands cruise. Boca is a well kept and updated classic!

Book and learn more about Pearl, our 32′ 2001 Beneteau sailboat. Great for Port Superior charters, Pearl is easy to handle and very versatile for all types of charters.

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.

Learn more about the specs, details, and accommodations on Breeze, our 33′ 2010 Jeanneau sailboat! Take her for a spin when you book an Apostle Islands boat rental.

Take a ride on our 33′ 2014 Jeanneau sailboat, North Twin, for some fun sailing in the Apostle Islands. Easy handling and safety make for an excellent charter experience.

Come aboard our 33′ 2013 Jeanneau sailboat, Pavati, which sleeps six comfortably in two cabins. Enjoy use of a large galley, roomy forward cabin, and other amenities.

Bella, our 34′ 2015 Jeanneau sailboat, is at the ready for your next family vacation on Lake Superior! Bella’s pure lines and inviting cockpit are sure to thrill sailors of all backgrounds.

Experience true happiness aboard Bliss, our 34′ 2014 Jeanneau sailboat! She sleeps six and comes with an easily accessible swim platform, functional galley, quality woodwork, and more.

Book and learn more about Knot-n-Call, our 34′ 1984 Pearson sailboat. Sail this beauty when you book a Port Superior charter!

Take some time off and book a Port Superior charter aboard [email protected], our 35′ 2004 Catalina sailboat! Experience the perfect combination of luxury and performance.

The Avalon is perfect for a small group of guests to enjoy cruising the waters on a classic Bayfield sailboat charter! Equipped with new sails, rigging, and more, she’s ready for adventure.

Learn more about Grins, our 36’ 2008 Jeanneau sailboat. Come aboard and enjoy all that this beautiful area has to offer on a real blue-water boat with unequaled technical fittings.

Mackinau is new to the Superior Charters fleet for 2019.  Grab your friends and family and come aboard this classically styled Hunter.  Enjoy the great outdoors with a large cockpit that is fully covered with…

Learn more about Twilight, a 36’ 2008 Jeanneau sailboat that sleeps nine. Lounge in the spacious cockpit and soak up the sun. Book a trip aboard this beautiful boat and explore the area.

Book and learn more about the Fly Away, our 37’ 2004 Beneteau sailboat! This beauty is a great option that can fit the whole family with its impressive interior space.

Rivulet, our 38’ 2016 Jeanneau sailboat, is the perfect size for an enjoyable Bayfield sailboat charter. Have fun sailing the Apostle Islands aboard Rivulet!

This 2004 39′ Beneteau sailboat has three cabins and sleeps up to eight guests. Enjoy well thought-out details and roomy cabins. Go for a sail on Oasis when you book a charter online.

It’s all about summer sailing aboard Summerland, our 39’ 2004 Beneteau sailboat. This modern vessel has everything you need to have a great sailing vacation!

Feel Sweet Freedom aboard our 39’ 2010 Jeanneau sailboat. Perfect for large groups, this sailboat is sleek, fast, and graceful; a modern classic. Reserve this beauty online!

Book a Bayfield, WI vacation aboard Giddyup, our 2011 40’ Jeanneau sailboat! This modern vessel sleeps eight guests and was built for speed with performance rigging and other features.

The Lagoon is a brand new 40′ boat, added to our fleet in 2019. It is a modern and comfortable take on a catamaran. Learn more about it and start planning your next sailing trip!

Book and learn more about True North, our 40’ 2014 Jeanneau sailboat. Clean lines and safe deck layout make for a carefree sailing experience that everyone can enjoy.

Soak up the sun – and some much-needed peace and quiet – aboard Quiet Star, our 41’ 2014 Jeanneau sailboat, complete with two private staterooms and full canvas.

Set sail on our 2014 43′ sailboat that is big enough to accommodate a large group of friends and family with its spacious interior and exterior! Book online now.

Enjoy the classic styling and roomy accommodations aboard this 1987 Beneteau Oceanus 43′ Sequel is a recent addition to the Superior Charters fleet, and is definitely worth a look.  Book this boat for your Superior getaway today!

Book the sailing vessel Guidance for your next family vacation! This brand new 44’ 2019 Jeanneau sailboat is an excellent choice for a Lake Superior cruise.

Our 44’ 2009 Jeanneau, La Bateau, is ready to take you and your family on an unforgettable Apostle Islands cruise. Enjoy easy access to the sugar-scooped stern and other amenities.