Lake Superior Sailing Vacations & Charters

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.

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.

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!

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

Come see why our 2004 Catalina 310 sailboat has earned the title of most popular small sailboat! This sweet little boat is a great fit for a small family or couple for some time away on the Big Lake.

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

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 aft 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 Sterling, our brand new, limited edition 34′ 2023 Jeanneau sailboat! She sleeps six and comes with an easily accessible swim platform, functional galley, quality woodwork and more.

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 a bimini and dodger.  The swim platform, with cockpit shower and swim ladder are easy to access with the walkthrough transom.

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 the Clear Air, our 37’ 2012 Jeanneau sailboat, for an unforgettable Apostle Islands boat rental. Take her for a spin!

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

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 recent upgrades to electronics and personal touches by the owners. 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 classic sailing vessel has everything you need to have a great vacation!

Added to our fleet in 2019, Liberty is a modern and comfortable take on a catamaran. Learn more about it and start planning your next sailing trip aboard Liberty!

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.

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.

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.

Set sail on the spacious Windigo 50′ Jeanneau Sailboat. Sailing vacations start at 3 days in length. Book online today for this great sailboat adventure!

Sapphire is a 1999 34′ Jeanneau sailboat featuring two cabins, one head and can sleep up to six people. This boat has been well cared for and thoughtfully equipped. Sapphire offers a spacious deck and advanced sailing technology, ideal for your Apostle Islands cruise!

This brand-new Lagoon 42′ Catamaran arrived in Bayfield in the spring of 2022, and she is beyond beautiful! The perfect setting for those very experienced catamaran sailors and for laid-back captained trips.

Book Windeavor, this brand new Jeanneau for your next family vacay! This newly styled Sun Odyssey 410 has walk-around decks and a spacious interior.