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Sailing adventures from Bayfield, Wisconsin in Apostle Islands National Lakeshore
Black Friday Gift Card Sale!
Looking for an unforgettable gift for friends or family? True North Sailing Charters has got you covered. Our gift cards are the perfect way to give the gift of adventure and relaxation. Our sailing trips are a unique way to experience the beauty of the Bayfield area. We offer a range of options for every type of sailor. Recipients can choose from a variety of trips, including day trips, sunset sails, and even overnight journeys.
True North Sailing Charters in Bayfield, Wisconsin is committed to providing guests with a unique and safe Apostle Islands sailing experience. Help hoist the sails or sit back and relax as we navigate the gorgeous waterways of Lake Superior and the Apostle Islands under sail. We look forward to helping create magical moments with you and sailing into the sunset!
Sailing Adventures
Sailing trips depart from our slip location in Bayfield, Wisconsin
or Schooner Bay Marina.
Bayfield Adventure Sail
A 2 hour, 15 minute sail out of Bayfield, Wisconsin aboard "Starling" a 33' Cheoy Lee Clipper. Set sail on Lake Superior and enjoy the sights of the North or West Channel, LaPointe, Madeline, Basswood and the surrounding islands.
Enjoy the original teak decks, two sitka spruce masts and the elegant lines that make for a classic maritime experience. Meet at our dock located in Bayfield.
Please select a time and date below that would work for your group and we will review and confirm with you as soon as possible.
$85 per person
$25 Children's Discount
(Private Boat Options Available)
Apostle Islands Excursion
A 5 Hour sailing experience in Apostle Islands National Lakeshore. Trip routes are dependent on wind and weather conditions that day as well as your preference but possibilities include visiting the sandstone shorelines, sand-spits and lighthouses in the surrounding area on Hermit, Oak, or Long Island. Half day trips depart from either our Bayfield location.
We use our catamaran, Piper on half day trips. The shallow draft allows us to access secluded beaches and explore remote island coastlines. The spacious shaded solon leads to the forward trampolines that are great for sun bathing and watching the water rush past beneath you.
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​Please select a time and date below that would work for your group and we will review and confirm with you as soon as possible.
$695
Full Boat Reserved
(Includes up to 6 guests)
Full Day in the Apostle Islands
A Full Day Sailing Adventure in the Islands. Trips depart from our Bayfield location. Depending on wind and weather conditions as well as your preference set sail for Oak, Raspberry or Manitou Islands. Visit the historic fishing camp, Oak Island hiking trails, or the remote Raspberry Island Lighthouse.
We use our catamaran, Piper on full day trips. The shallow draft allows us to access secluded beaches and explore remote island coastlines. The spacious and protected cockpit area insures a dry and comfortable sail in all conditions. The deck is a great spot as well for sun bathing and hanging out.
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​Please select a time and date below that would work for your group and we will review and confirm with you as soon as possible.
$1095
Full boat reserved
(Includes up to 6 guests)
Marathon, Florida
(Our Winter Location)
Afternoon Sailing Adventure
Paddleboard, Beach, and Dolphin Experience
Set sail on the stunning waters of Marathon and Key West, a sailing destination steeped in history.
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Step aboard Echo, a 35’ Gemini Catamaran sailboat designed for comfort and adventure. Whether you're a seasoned sailor or a first-time passenger, your experience will be unforgettable. Relax and take in the scenic beauty, or get hands-on at the helm with guidance from our knowledgeable Captain. Ideal for families or small groups, Echo comfortably accommodates up to six passengers for a personalized sailing experience.
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Enjoy a 3 hour cruise with optional seasonal activities like paddle boarding, beach stops, and swim breaks. Thanks to her unique shallow-water anchoring capability, Echo offers close-up access to pristine beaches and vibrant marine life. Below deck, you’ll find a cozy cabin with a galley and restroom for added comfort during your voyage.
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A private sailing excursion with Echo offers more than just breathtaking views; it’s your chance to encounter the Florida Keys vibrant wildlife. Wild dolphins frequently join us, playing alongside the boat and crossing our wake. While sightings aren’t guaranteed, these waters are alive with dolphins and other incredible creatures.​
$295
Full boat reserved
(Includes up to 6 guests)
Three Hours
If we are not able to go out due to weather or if you do not think it would be a good experience (due to rain, cold, etc.) you have the option to either reschedule or have a full refund.
WHAT PEOPLE ARE SAYING ABOUT TRUE NORTH SAILING
Our experience was amazing! Very relaxing! Captain Abe was very knowledgeable and even let us help him during our sailing tour. We would definitely recommend them to everyone!
It was a very pleasant time. Dusty was so helpful. The boat was in great shape. I could not have asked for anything more.
Our family of four enjoyed our sail outing tremendously. The skipper is kind and helpful, the lake and islands are beautiful, and sailing is too fun. Half of us helped crew the boat, and half of us just sat back and took it all in. Highly recommend.
A DIFFERENT KIND OF ADVENTURE
Step aboard one of our sailing yachts and feel the outside world melt away. Close your eyes. Feel the sun on your face. Breathe in the fresh Lake Superior air. Listen to the wind fill the sails and feel the waves slap against the hull.
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A sailing tour offers a unique and special experience you won’t find anywhere on land. See Bayfield, Wisconsin and the Apostle Islands National Lakeshore from a new perspective.
Frequently Asked Questions
CONTACT
SAY HELLO
OUR LOCATION
HOURS OF OPERATION
9:00 a.m. - 5:00 p.m. Daily
Open Seasonally May - October