- Most Popular Midsize Sailboat
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
Book the Clear Air, our 37’ 2012 Jeanneau sailboat, for an unforgettable Apostle Islands boat rental. Take her for a spin!
Sailing Vacations
Charters for Both the Novice & Experienced Sailor
The perfect choice for novice or inexperienced sailors!
When you book a captained charter, you are booking both a sailboat and hiring a licensed captain to take the wheel and navigate so you can relax during your vacation.
Great for those with confident sailing abilities!
Bareboat charters are a fun and exciting sailing experience for those who have prior sailing experience and can confidently sail and manage a sailboat on their own during their charter.
Choose the Perfect Sailboat for Your Vacation
No Charters found.
- Sleeps 10 Passenger Capacity Sleeps 10
- 4 Cabins Cabins 4 Cabins
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.
- Sleeps 10 Passenger Capacity Sleeps 10
- 4 Cabins Cabins 4 Cabins
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.
- Sleeps 7 Passenger Capacity Sleeps 7
- 1 1/4 Cabins Cabins 1 1/4 Cabins
Enjoy the perfect Lake Superior boat rental with Harmony, our 31′ Pearson sailboat. Sail in comfort with a new bimini and mainsail.
- Sleeps 6 Passenger Capacity Sleeps 6
- 1 1/4 Cabins Cabins 1 1/4 Cabins
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!
- Sleeps 6 Passenger Capacity Sleeps 6
- 2 Cabins Cabins 2 Cabins
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.
- Sleeps 6 Passenger Capacity Sleeps 6
- 2 Cabins Cabins 2 Cabins
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.
- Sleeps 6 Passenger Capacity Sleeps 6
- 2 Cabins Cabins 2 Cabins
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.
- Sleeps 6 Passenger Capacity Sleeps 6
- 2 Cabins Cabins 2 Cabins
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.
- Most Popular Small Boat
- Sleeps 6 Passenger Capacity Sleeps 6
- 2 Cabins Cabins 2 Cabins
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.
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
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.
- Second Most Popular Small Boat
- Sleeps 6 Passenger Capacity Sleeps 6
- 2 Cabins Cabins 2 Cabins
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.
- Sleeps 5 Passenger Capacity Sleeps 5
- 2 Cabins Cabins 2 Cabins
Take some time off and book a Lake Superior charter aboard [email protected], our 35′ 2004 Catalina sailboat! Experience the perfect combination of luxury and performance.
- Sleeps 9 Passenger Capacity Sleeps 9
- 3 Cabins Cabins 3 Cabins
Learn more about Seren Wen, 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.
- Sleeps 7 Passenger Capacity Sleeps 7
- 2 Cabins Cabins 2 Cabins
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…
- Second Most Popular Midsize Boat
- Sleeps 9 Passenger Capacity Sleeps 9
- 3 Cabins Cabins 3 Cabins
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.
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
Rivulet, our 38’ 2016 Jeanneau sailboat, is the perfect size for an enjoyable Bayfield sailboat charter. Have fun sailing the Apostle Islands aboard Rivulet!
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
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…
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
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!
- Sleeps 9 Passenger Capacity Sleeps 9
- 3 Cabins Cabins 3 Cabins
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!
- Most popular catamaran
- Sleeps 8 Passenger Capacity Sleeps 8
- 4 Cabins Cabins 4 Cabins
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…
- Second Most Popular Large Sailboat
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
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.
- Most Popular Large Sailboat
- Sleeps 10 Passenger Capacity Sleeps 10
- 4 Cabins Cabins 4 Cabins
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.
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
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.
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
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.
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
Our 44’ 2014 Jeanneau, La Bonne Vie, is ready to take you and your family on an unforgettable Apostle Islands cruise. Climb aboard this sweet boat and sail away in style.
- Sleeps 8 Passenger Capacity Sleeps 8
- 3 Cabins Cabins 3 Cabins
Set sail on the spacious Windigo 50′ Jeanneau Sailboat. Sailing vacations start at 2 days in length. Book online today for this great sailboat adventure!