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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.
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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
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)
Island Hopping Adventure in the Apostles
True North Water Taxi specializes in island adventures in the Apostle Islands. Departing from Bayfield, Wisconsin, we take you beyond the shoreline to explore multiple islands in a single four-hour trip, combining scenic boat travel with opportunities to step ashore for short hikes, picnics, and discovery.
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Our routes may include Long Island’s wild sandy shoreline, Hermit Island’s quiet trails, Basswood Island’s historic brownstone quarry, Oak Island’s secluded forests, Raspberry Island’s lighthouse and shoreline paths, or the expansive beaches of Stockton Island.
Each stop offers a new chance to experience the beauty, history, and character of the islands. Safe, reliable, and operated by local captains, True North Water Taxi is the most flexible and unforgettable way for adventurous families and couples to explore the Apostle Islands together. Your dog is welcome aboard as well.
$395
(includes 2 adults and one small child or dog)
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.
Area Adventures
True North guests receive special savings on local stays and adventures. Enjoy ten percent off kayaking day trips and water taxi hiking excursions, along with access to other unique nearby lodging listed below.
10% off Whitecap Kayak Day Trips
Whitecap Kayak leads guided day trips to some of the most stunning shorelines in the Apostle Islands, including the sea caves. Their guides make it easy for beginners and experienced paddlers to explore Lake Superior safely and enjoyably, and cabin guests receive a ten percent discount during their stay.
10% off Sailor Springs Glamping
Sailor Springs Glamping offers cozy canvas tents set in a quiet forest setting near Lake Superior, with one night minimums that make it easy for quick getaways. Each site is pet friendly and designed for comfort, giving guests a simple and relaxing way to enjoy the outdoors.
10% off North Channel Cabin Stays
North Channel Cabin is a quiet lakefront retreat on Madeline Island with wide views of Lake Superior and the Apostle Islands.
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It is a comfortable and private place for couples, families, or small groups to relax and enjoy the island.
10% off Marengo River Cabin
Marengo River Cabin is a quiet three bedroom retreat along the Marengo River in Mason, surrounded by public land with trails and plenty of space to relax. It offers peaceful river and valley views and an easy place for families or friends to unwind in nature.
10% off Apostle Island Hiking Trips
True North Water Taxi brings you straight to the best Apostle Islands hiking spots with fast access to remote beaches, lighthouses, and forest trails. Their captains make travel easy and personal, giving you a simple and memorable way to explore Lake Superior for the day.
10% off Penny Print Studio
Penny Print Studio is a local shop that creates custom apparel and keepsakes inspired by the Lake Superior region. They print the True North Sailing Starling shirts and Whitecap Kayak shirts that guests often take home to remember their time on the water, blending quality with a strong sense of place.
Frequently Asked Questions
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
