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Join The True North Crew!

Position Overview:

We are seeking a USCG licensed Captain (6-pack or greater) to join our team and lead our sailing charters. As a Captain at True North Sailing Charters, you will be responsible for ensuring the safety and enjoyment of our guests while navigating the stunning waters of Lake Superior. You will play a key role in delivering exceptional customer experiences, promoting a positive and friendly family atmosphere, and upholding our commitment to safety and professionalism. 

We highly prioritize fostering a positive, humble, and can-do attitude within our team at True North Sailing Charters. As owners, we strive to exemplify and reciprocate this mindset among our captains and guests, aiming to cultivate a work environment that reflects the natural beauty of the sailing destinations we explore. A significant portion of our tourists—approximately 70%—hail from the Minnesota Twin Cities area, comprising a delightful and amiable mix of families, friends, and couples. Spanning 720 square miles, the Apostle Islands Park offers a vast canvas for exploration. Sailing in any direction reveals captivating shorelines, pristine beaches, enchanting sea caves, historic lighthouses, and more. 

In your role as the captain, you will not only navigate the waters but also serve as a knowledgeable guide to the area. Guests often have questions about sailing, the islands, and the majestic Lake Superior, and your role will involve providing informative and engaging responses, enhancing their overall experience. As the leader of our sailing adventures, your positive demeanor and willingness to share your expertise will contribute to the creation of lasting memories for our guests amidst the unparalleled natural wonders of the Apostle Islands.


  • Safe Navigation: Safely operate and navigate the sailing vessel, ensuring compliance with all maritime regulations and guidelines.

  • Customer Experience: Provide an exceptional and memorable experience for our guests by offering insightful commentary, answering questions, and creating a welcoming atmosphere on board.

  • Vessel Maintenance: Oversee the maintenance and cleanliness of the sailing vessel, conducting regular inspections and communicating needed repairs as needed.

  • Safety Protocols: Implement and enforce safety protocols and procedures to ensure the well-being of passengers and crew members.

  • Team Collaboration: Work closely with crew members to ensure smooth operations, effective communication, and a positive working environment.

  • Emergency Response: Demonstrate proficiency in handling emergency situations, including knowledge of first aid and lifesaving techniques.



  • US Coast Guard License: Must hold a valid US Coast Guard Captain's license.

  • Experience: Proven experience as a Captain, preferably with a background in sailing charters or a similar maritime setting.

  • Communication Skills: Excellent verbal communication skills with the ability to engage and interact with guests in a friendly and informative manner.

  • Safety Conscious: Strong commitment to safety and a thorough understanding of maritime safety procedures. Make good weather for the safety of the vessel and crew. Be a defensive sailor knowing that we are not racing we providing happy mini adventures and returning the boat and guests back to the dock safely is the top priority. 

  • Customer-Focused: A customer-centric mindset with a passion for delivering exceptional service.

  • Team Player: Ability to work collaboratively with a diverse team and contribute to a positive and inclusive work environment.

  • Local Knowledge: Familiarity with the waters around Bayfield, Wisconsin, and knowledge of the Apostle Islands is a plus.


Captain Pay Structure - True North Sailing Charters

At True North Sailing Charters, we believe in recognizing the expertise and dedication of our Captains by offering competitive compensation based on the type and duration of sailing trips. Our pay structure reflects the diverse experiences we provide to our customers and the commitment required from our Captains.

1. Bayfield Adventure Sail (1-4 trips per day)

  • Trip Duration: 2 hours, 15 minutes

  • Boat: "Starling" - 33' Cheoy Lee Clipper

  • Captain Pay: $80


2. Apostle Islands Excursion (1-2 trips per day)

  • Trip Duration: Half day (5 hours)

  • Boat: Piper - 26ft catamaran (typically used for half-day trips)

  • Captain Pay: $125


3. Full Day in the Islands 

  • Trip Duration: Full day (8 hrs)

  • Boat: Echo - 35 ft Gemini Legacy catamaran

  • Departure: Schooner Bay Marina, north of Bayfield

  • Captain Pay: $200


4. Multi-Day Apostle Islands Expedition

  • Trip Duration: Multiple days (Sleep aboard, private captains cabin)

  • Boat: Echo - 35 ft Gemini Legacy catamaran

  • Departure: Schooner Bay Marina, north of Bayfield

  • Captain Pay: $500 for our two day trip 


Additional Details:

  • Captains will have the opportunity to rotate between different boats and trips, ensuring a varied and engaging experience throughout the season.

  • Cleaning and securing the boat after each trip is a responsibility of the Captains.

  • Pay rates are structured to reflect the time commitment and complexity of each sailing experience.

  • Trips may involve various routes and destinations within the Bayfield and Apostle Islands region.

  • Tipping is common for our trips, we state in our pre arrival emails that “Tipping is always appreciated, never expected” 


Note: Pay rates are subject to review and adjustment based on performance, experience, and other relevant factors. True North Sailing Charters is committed to providing fair compensation for the valuable contributions of our Captains.

How to Apply:

If you are a licensed Captain with a passion for sailing and providing outstanding customer experiences, we invite you to apply. Please submit your resume, cover letter, and any relevant certifications to


True North Sailing Charters is an equal opportunity employer. We encourage candidates from all backgrounds and experiences to apply.

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