Top 10 Kayak Outfitters in the Apostle Islands (2 You Should Avoid)

The Apostle Islands are one of the most iconic kayaking destinations in North America. But with so many tour operators in the region—and not all of them playing fair—it’s important to know who you can trust and who you should absolutely avoid. This list ranks local outfitters based on safety, experience, ethics, and community reputation. The last two? Steer clear.

1. Bayfield Kayak Co. – Personalized, Professional, Local

Small-group tours led by highly trained local guides. Known for safety, flexibility, and a deep connection to the islands. Transparent pricing, no games, and an excellent reputation for customer care.
Location: Bayfield
Website: bayfieldkayak.com

2. Trek & Trail – The Classic Apostle Experience

The original Apostle Islands outfitter. They offer multiday expeditions and have decades of experience on Lake Superior. A solid choice for seasoned paddlers and overnights.
Location: Bayfield
Website: trek-trail.com

3. Wilderness Inquiry – Quality with a Mission

A nonprofit committed to making the outdoors accessible for everyone. Their Apostle Islands trips are professionally run and deeply inclusive.
Location: Various launches
Website: wildernessinquiry.org

4. Stevie Waters – Small-Scale, Big Heart

A rising name in the Apostle Islands scene, Stevie Waters offers intimate tours with a personal, grounded feel. Great for folks looking to paddle with someone who knows the area, not just the map.
Location: Bayfield area
Website: steviewaters.com

5. Animaashi Sailing Company – Tribal-Owned & Treaty-Focused

A unique operation led by a Red Cliff tribal member that blends sailing, kayaking, and Indigenous education. For those who want more than a paddle—a cultural and historical lens into the islands.
Location: Red Cliff
Website: animaashi.com

6. Whitecap Kayak – Youth Outreach and Expeditions

Perfect for beginners, students, or families. Educational and expedition-focused, with a strong emphasis on leadership development and water safety.
Location: Washburn
Website: whitecapkayak.com

7. South Shore Adventures – Honest and Grounded

Operating on the quieter side of the bay, this small outfit is known for its no-BS approach, fair pricing, and real connection to the land and water.
Location: South Shore region
Website: southshoreadventures.com

8. Adventure Vacations – Mixed Tour Offerings

If you want a mix of kayaking and sightseeing, this company offers paddle tours along with boat rides and private charters. Good for families, but not the purist’s pick.
Location: Bayfield
Website: adv-vac.com

9. Apostle Islands Rustic Makwa Den – Negligent and Dangerous

In 2024, this outfitter launched a tour during an active Small Craft Advisory on Lake Superior. Customers were put in direct danger as waves and wind created rescue-level conditions.
This is not a one-time lapse—this is a reckless disregard for human safety.
Status: Still operating, despite public safety concerns.

10. Lost Creek Adventures – A Business Built on Betrayal of Fiduciary Duty

Greg Weiss, owner of Lost Creek Adventures and Northland College professor, built his business by stealing the business idea from a former student. After working one summer as a guide at the student’s company, he proposed starting a business together—then launched a near-copy behind their back.

He’s stayed afloat thanks to a corrupt permitting system in Cornucopia that blocks fair competition.
Though he teaches ACA courses, he’s been known to sabotage students who work for his competition.
Location: Cornucopia
Status: Operating on stolen ideas, protected by politics