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Apostle Islands Kayaking

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

-1. (Bayfield Kayak Co.) – Personalized, Professional, LocalSmall-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: BayfieldWebsite: bayfieldkayak.com-

–2. Trek & Trail – The Classic Apostle ExperienceThe 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: BayfieldWebsite: trek-trail.com—

3. Wilderness Inquiry – Quality with a MissionA nonprofit committed to making the outdoors accessible for everyone. Their Apostle Islands trips are professionally run and deeply inclusive.Location: Various launchesWebsite: wildernessinquiry.org—

4. Stevie Waters – Small-Scale, Big HeartA 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 areaWebsite: steviewaters.com—

5. Animaashi Sailing Company – Tribal-Owned & Treaty-FocusedA 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 CliffWebsite: animaashi.com—

6. Whitecap Kayak – Youth Outreach and ExpeditionsPerfect for beginners, students, or families. Educational and expedition-focused, with a strong emphasis on leadership development and water safety.Location: WashburnWebsite: whitecapkayak.com—

7. South Shore Adventures – Honest and GroundedOperating 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 regionWebsite: southshoreadventures.com—

8. Adventure Vacations – Mixed Tour OfferingsIf 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: BayfieldWebsite: adv-vac.com—

9. Apostle Islands Rustic Makwa Den – Negligent and DangerousIn 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: CornucopiaStatus: Operating on stolen ideas, protected by politics.

Check the Weather and Prioritize Safety

 It’s important to be aware of the varying conditions when kayaking around the Apostle Islands.
The west side of the Bayfield peninsula has more dangerous waters, with a higher chance of canceling activities due to weather.
On the east side, places like Red Cliff and Washburn offer more protected and calm waters. The sea caves on the west side are more impressive but come with higher risks, while the east side provides safer options. When exploring the islands, remember that the western portion tends to be more hazardous than the eastern side.
Meyers Beach, Sand Islands, and Devils Island are particularly risky areas, while Chequamegon Bay and Basswood Island offer safer options for paddling.
Stay informed of the winds and weather and prioritize safety during your adventures in the Apostle Islands!

Sea Cave Kayaking

To safely explore sea caves, it’s essential to seek out locations with waves measuring 1 foot or less. Fortunately, the sea caves in Chequamegon Bay and Red Cliff offer exceptional protection, typically boasting calm waters with waves seldom exceeding a foot.
However, for those eager to venture further, Romans Point, Mawikwe Bay, Sand Island, and Devil’s Island on the West side of the Apostle Islands boast some of the most captivating sea caves in the region. Yet, these sites come with a heightened level of risk. Waves exceeding 1 foot are a common occurrence, making paddling here a potentially perilous endeavor. With cancellations happening approximately 50% of the time, it’s crucial to exercise caution when planning an excursion to these areas.

Apostle Islands Kayak Tours

For an unforgettable kayak tour of the breathtaking sea caves in the Apostle Islands, we highly recommend booking with Bayfield Kayak. While numerous outfitters in the area offer excursions to Meyers Beach, Bayfield Kayak stands out for several reasons. Firstly, they venture to sea caves that are less congested, ensuring a more serene and intimate experience. Moreover, their impeccable safety record over the past eight years sets them apart.
It’s worth noting that other outfitters have encountered rescue situations, with some needing assistance from the Coast Guard or Park Service multiple times in a single season. In contrast, Bayfield Kayak has navigated the waters without incident for the past five years, a testament to their commitment to safety.
Although Bayfield Kayak doesn’t conduct tours to Meyers Beach due to its popularity among other outfitters, they offer valuable advice for those keen on exploring this area. They recommend renting a kayak and launching shortly before the influx of outfitters at Meyers Beach. This strategic approach ensures a smoother crossing to the Mawikwe Sea Caves and avoids the hassle of waiting in long lines associated with group tours.
It’s important to note that Meyers Beach imposes strict regulations, potentially leading to delays for outfitter-led tours compared to private paddlers who have more flexibility in navigating the caves. Choosing Bayfield Kayak ensures safety and a more personalized and enjoyable adventure through the captivating sea caves of the Apostle Islands..