There’s no better office than the deck of a sailboat.

As a captain with Dreamcatcher Sailing, you will independently operate 36 foot keelboats, providing education, entertainment, and excellent experiences to visitors of the Apostle Islands of Lake Superior. You can focus on shorter trips with adults, introducing people to the endless joys of sailing in one of the most beautiful cruising grounds anywhere, or on multi-day excursions with a variety of summer camp youths.

Our season runs from mid-May to mid-October, and we can offer full-time or part-time employment with very flexible scheduling.

Employee captains make around $18-20 an hour depending on experience. Plenty of overtime opportunities available. Contract captains can make $300-400 a day. This is a tipped job, and so actual income can be much higher.

Tagged as: Instruction and Guiding, Teaching/Education, Water Skills


OUPV Great Lakes or better, OR required days on water (365 days of sea service time)

Required Skills:

Strong sailing skills

Excellent interpersonal skills

Preferred Skills:

Experience working with teaching or environmental education a plus
Some sailboat maintenance/mechanic knowledge

About Dreamcatcher Sailing

Dreamcatcher Sailing provides sailing adventures on the world's largest freshwater lake, navigating through the Apostle Islands and other parts of Western Lake Superior. Trips range from short, two hour excursions to full day or overnight trips, some as long as 9 days. We work with a wide range of clientele from adults to groups of kids from regional summer camps. We offer competitive rates and comprehensive training for our different boats, along with any brush-up skills required for safe sailing. Our season ranges from May - October.

Application Instructions

Please send questions or applications to [email protected] Please send resume and/or experience log when applying.