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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!
Sailing Adventures
Sailing trips depart from our slip location in Bayfield, Wisconsin
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 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.
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
Set sail from our Bayfield location for a full day of exploration and excitement in the Apostle Islands! Depending on wind, weather, and your group’s preferences, we’ll chart a course to Oak, Raspberry, or Manitou Islands. Discover hidden treasures like the historic fishing camp, Oak Island’s scenic hiking trails, or the remote beauty of the Raspberry Island Lighthouse.
Your adventure takes place aboard Piper, our spacious and versatile catamaran. With its shallow draft, Piper is perfect for getting up close to secluded beaches and untouched island coastlines. The wide deck is ideal for soaking up the sun, while the protected cockpit ensures a comfortable and dry ride in any conditions.
Whether you’re hiking remote trails, exploring historic sites, or simply relaxing on deck with the sound of the waves, this full-day sailing trip promises fun, adventure, and unforgettable memories.
Book your date and time now, and let’s make your sailing dream a reality! We’ll confirm your reservation as soon as possible.
$1095
Full boat reserved
(Includes up to 6 guests)
Bayfield - Madeline - Apostles
Water Taxi
Bayfield Water Taxi is your gateway to adventure on Lake Superior. We offer fast, friendly boat service from Bayfield, WI to Big Bay State Park, Madeline Island, and other stunning spots throughout the Apostle Islands. Whether you’re planning a family beach day, a scenic hike, or a backcountry camping trip, our private water taxi makes getting there part of the fun.
Our most popular route takes you straight to Big Bay State Park—no cars, no waiting, just a smooth ride across the water to one of the most beautiful beaches in the Midwest. We also offer custom drop-offs and pick-ups at campsites, cabins, and hidden shoreline gems. Safe, flexible, and run by experienced local captains, Bayfield Water Taxi is the easiest way to explore the islands with your crew.
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.
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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Can I reserve a private tour?Yes! Private tours are available for up to six guests. Enjoy a romantic escape, plan the perfect anniversary, or create a one-of-a-kind family adventure. For larger groups, check out our group sailing charters. Choose your destination, and go!
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What about bad weather?Lake Superior is known for beautiful weather. Still, there may be the rare case where the weather takes a turn on the day of your charter. If it were up to us, every sailing day would be amazing. On days when it isn’t, we do our best to wait out the weather to see if it clears. Our boats will sail in light rain and other “safe weather”. Ultimately, all departures are at the sole discretion of the Captain. In cases where poor weather risks safety and we absolutely must cancel a scheduled charter, voyages will be rescheduled.
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What should I wear?On Lake Superior, the wind can add a chill to the air. Be sure to check the weather forecast on the day of your sail, and consider bringing a light jacket just in case. Storage for personal gear is available in the cabin. Light-colored clothing with long sleeves can help reduce the effects of the sun. Guests may wish to bring sunscreen along for their trip. Correct footwear is important while sailing. Decks can become wet with sea spray; we recommend comfortable, fast-drying shoes with good traction. White or light-colored soles are preferable, as dark soles can leave marks on the yacht.
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Will I get seasick?Seasickness is a reaction to unfamiliar motion while aboard a vessel. While most of our guests do not experience seasickness, a small percentage of people may be prone to seasickness. In our experience, this often includes people susceptible to other forms of motion sickness. If you do get seasick, it’s OK! Alert a crew member and we can help you overcome it. To help reduce your chances of becoming seasick: Stay above deck and breathe fresh air Look to the horizon, instead of into a phone or book Avoid the restroom and cabin area Get plenty of shade and avoid direct sunlight Sail on a full stomach, and avoid foods that may upset you
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Can I reserve a private tour?Yes! Private tours are available for up to six guests. Enjoy a romantic escape, plan the perfect anniversary, or create a one-of-a-kind family adventure. For larger groups, check out our group sailing charters. Choose your destination, and go!
-
What about bad weather?Lake Superior is known for beautiful weather. Still, there may be the rare case where the weather takes a turn on the day of your charter. If it were up to us, every sailing day would be amazing. On days when it isn’t, we do our best to wait out the weather to see if it clears. Our boats will sail in light rain and other “safe weather”. Ultimately, all departures are at the sole discretion of the Captain. In cases where poor weather risks safety and we absolutely must cancel a scheduled charter, voyages will be rescheduled.
-
What should I wear?On Lake Superior, the wind can add a chill to the air. Be sure to check the weather forecast on the day of your sail, and consider bringing a light jacket just in case. Storage for personal gear is available in the cabin. Light-colored clothing with long sleeves can help reduce the effects of the sun. Guests may wish to bring sunscreen along for their trip. Correct footwear is important while sailing. Decks can become wet with sea spray; we recommend comfortable, fast-drying shoes with good traction. White or light-colored soles are preferable, as dark soles can leave marks on the yacht.
-
Will I get seasick?Seasickness is a reaction to unfamiliar motion while aboard a vessel. While most of our guests do not experience seasickness, a small percentage of people may be prone to seasickness. In our experience, this often includes people susceptible to other forms of motion sickness. If you do get seasick, it’s OK! Alert a crew member and we can help you overcome it. To help reduce your chances of becoming seasick: Stay above deck and breathe fresh air Look to the horizon, instead of into a phone or book Avoid the restroom and cabin area Get plenty of shade and avoid direct sunlight Sail on a full stomach, and avoid foods that may upset you
Gift Cards!
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.
CONTACT
SAY HELLO
OUR LOCATION
HOURS OF OPERATION
9:00 a.m. - 5:00 p.m. Daily
Open Seasonally May - October
