Sailing Charter Captain

Sailing Charter Captain

All Hands Sailing is looking for contractor/employee captains for the 2025 Summer Season (May-October). You must have at minimum a USCG Six-Pack Great Lakes license. We’re a small, four boat charter business located in Bayfield, Wisconsin, gateway to the beautiful Apostle Islands on Lake Superior. Our captains can do a wide variety of trips ranging from short 2.25hr sails to as long as 9 days on the water. We offer a lot of flexibility for our captains and work hard to make sure they feel supported, whether it’s adapting schedules or providing educational opportunities.

Payment:

We offer contract and employee positions. Employees start at $20/hr, with more possible depending on experience. Unlimited overtime & guaranteed work is available for employee captains. Contractor pay is as follows:

2.25 hr trip: $100

5.5 hr trip: $200

8 hr trip: $300

Overnight trip: $350/day

Both employees and contractors may set their own hours, and we release our full-summer work schedules in mid to late April. Work is not guaranteed for contractors.

Work Experience

Our ideal captains have a true passion for sailing and education, passing on the wonder and joy of the wind and water to each person that steps on the boat. While we prefer captains to come in with a base-level sailing knowledge, we can offer education and training to help bridge gaps.

• Must have a USCG Six-Pack Great Lakes or greater

• Some sailing skills or knowledge - we can offer education to some degree

• Background in education or guiding preferred but not required

• Excellent customer service skills

• Commitment to safety of vessel and passengers

Job Responsibilities

Boat Operation:

• Steer and operate vessels using equipment such as depth finders, radios, buoys, lights and lighthouses

• Dock and undock sailing vessels, sometimes navigating through tight spaces, such as marinas

• Alter navigation plans based on weather conditions to keep vessels and passengers safe

• Inspect boats and ships to ensure efficient and safe operation of vessels and equipment and their conformity to regulations

• Read gauges during engine operation to ensure safe levels of temperature, oil pressure, etc.

• Compute positions, set courses and determine speeds using charts, compasses, and knowledge of local conditions

• Anchor vessels for several hours or overnight, picking safe locations and monitoring boat throughout the duration of anchorage

• Manage sails throughout a variety of wind conditions, adjusting size and shape to keep the vessel safe and comfortable for passengers

Day Trips:

• Board passengers and give instructions on how to be safe and comfortable on boat

• Provide excellent customer service throughout the trip, working with clients to ensure their comfort/happiness

• Teach and educate passengers about sailing and operation of the boat, about the nature and history of the Apostle Islands and Lake Superior

• Visit islands and shorelines, anchoring the boat and allowing for dinghy access to caves/beaches, etc.

Overnight/Summer Camp Trips

• Board groups the night before departure and give tour/explanation of the vessel

• Set goals/itineraries with groups and work to achieve them

• Educate groups on how to sail the boats with the goal of being able to step back from active management of the boat

• Work with camp counselors to ensure students are getting daily needs met, like food/water

Job Types: Full-time, Part-time, Contract

Pay: $200.00 - $400.00 per day

Expected hours: 10 – 60 per week

Benefits:

• Employee discount
• Flexible schedule

Schedule:

• 12 hour shift
• 4 hour shift
• 8 hour shift
• Overtime

Ability to Commute:

• Bayfield, WI 54814 (Required)

Ability to Relocate:

• Bayfield, WI 54814: Relocate before starting work (Required)

Work Location: In person

Salary : $200 - $400