
.png)

.png)
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)
Florida Keys Winter Adventure
(Our Winter Location)
Escape to the turquoise waters of the Florida Keys on a captained week-long sailing adventure aboard a sleek and comfortable catamaran. Available during the winter months, this unforgettable journey blends relaxation, exploration, and adventure as we navigate the stunning coastline and hidden gems of the Keys.
​
Spend your days sailing through crystal-clear waters, spotting dolphins, snorkeling vibrant reefs, and discovering secluded beaches. Whether you prefer lounging on deck, swimming in tropical coves, or exploring pristine shorelines, each day brings new opportunities to experience the beauty of the Gulf.
​
Our flexible itineraries are tailored to your interests, ensuring a truly personalized experience. Contact us to discuss available dates, pricing, and trip details—we’ll help plan the perfect sailing getaway for you.
Reach out today and let the Keys inspire your next adventure!
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

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