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Sailing the Apostle Islands | True North Sailing Charters

Sailing adventures from Bayfield, Wisconsin in Apostle Islands National Lakeshore

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!

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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.

$85 per person 

$25 Children's Discount

(Private Boat Options Available) 

Bayfield Adventure Sailing Area

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 or Schooner Bay location depending on your selection..


We use our catamarans, Piper or Echo 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.  All Echo trips include two inflatable paddle boards available for you to use.

Apostle Island Excursion Map

$695 - $795 

Full Boat Reserved 

(Includes up to 6 guests)

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Full Day in the Islands

A Full Day Sailing Adventure in the Islands. Trips depart from Schooner Bay Marina just north of Bayfield. and depending on wind and weather conditions as well as your preference set sail for Stockton, Raspberry or Manitou Islands.  Visit the historic fishing camp, Stockton Island hiking trails, or the remote Raspberry Island Lighthouse.  


Typically we use our catamaran, Echo 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. All Echo trips include two inflatable paddle boards available for your use.


Full boat reserved

(Includes up to 6 guests) 

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Multi Day Apostle Islands Expedition

Sleep aboard and explore the Apostle Islands with the newest boat to our fleet named Echo, a Gemini Legacy 35 catamaran. Trips depart from Schooner Bay Marina just north of Bayfield. This adventure offers a prolonged scenic experience in a comfortable and stable multi-day vessel. Explore the Apostle Islands' rugged sandstone sea caves, unique lighthouses, and pristine remote beaches.


The trip includes opportunities for paddle-boarding, dinghy excursions, beach combing and islands trail hikes. Board Echo the night before at 7pm and sleep aboard in Schooner Bay Marina. The following morning the captain will join your group as you set sails into the islands where you stay one night at anchorage among the islands before returning the next day. 


Full boat reserved

(Includes up to 6 guests) 

Two Days and Two Nights


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.

Book Online


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.

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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.

Gift Cards

Sailing Gift Cards!l Deals

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.


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.

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


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9:00 a.m. - 5:00 p.m. Daily

Open Seasonally May - October

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