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Meet our Captains & Crew

Come be part of our Superior Crew! 


We are looking for amazing staff!

If you’re an adventurous, hard-working and detail-oriented individual who wants to try something different this summer, inquire about our openings!  We always take applications throughout the year, so submit your application, reach out to us on facebook or call!

We’re Hiring Crew for 2024!

Our Captains

Our roster of captains are all USCG licensed and strive to provide a great experience while developing new sailors, teaching docking or providing some last minute information during your dockside briefing. 

If you want to join our roster of Captains, contact us, and she can let you know all the information we will need.  

Captain Mike Simon


Captain Mike has been sailing the Apostles for over 10 years and really loves to share his interest in local history, geology and Lake Superior.  He’s a patient teacher who is called on for all types of instruction, but he specializes in catamaran training.

Captain Dave Olson

Close up of Captain Dave Olson

Captain Olson lives here year round.  He also loves sailing on the Big Lake, that’s why on his days off, you can find him on his own 42’ sailboat or the tall ship schooner Abbey Road.  You’ll meet him during your dockside briefings and checkout trainings.

Captain Kristine DeVinck


Kristine grew up learning all about sailing from her dad while cruising Lake Superior. She’s definitely an enthusiast for sailing and the Apostle Islands. She teaches for her full-time job, so getting new sailors on the water and turning them into skippers is her new passion.

Captain Jim McKie

a man standing in front of a boat next to a body of water

Captain Jim has been a long-time sailor in the Apostle Islands and we’re happy to have him join our crew. He is a great youth leader who excels at teaching about sailing and the local area.

Captain John Barker

Captain John Barker headshot

Captain John has finally given up the 9-5 and is learning to relax more while on his boat in Bayfield. A proud Jeanneau boat owner for years, you’ve likely seen John with us at boat shows in the past.

Captain Gary Stang

a man smiling for the camera

Captain Gary is a recently retired salesman who has tons of experience sailing the Apostle Islands and the Caribbean. He’s spent 25 years as a ski instructor, so teaching is not new to him. You’ll love his sense of humor and his many sailing stories.

Captain Merritt P

a man holding a baseball bat

Captain Merritt was first a charter customer at Superior Charters, but after learning to sail he worked on getting his captain’s license.  He is great at honing the skills of a novice sailor and giving them some great experience on the water.

Captain Vicki Staudte

a man standing in front of a boat next to a body of water

Captain Vicki has been sailing for over 20 years in places such as Croatia, Greece and Tahiti, but she still loves sailing the Big Lake, Lake Superior.  Consider her your tour guide for an adventure in the Apostles.

In Loving Memory: Captain Dave Skoro

Captain Dave Skoro headshot
July 20, 1952 – April 3, 2021

Captain Dave was a fixture of Bayfield and the Apostle Islands for years. While he is no longer with us, his dedication to sailing is proven by the hundreds of skippers he has trained over the years, including our owners, Dick and Cindy Kalow. We honor him as Captain Emeritus at Superior Charters.

Captain Dave’s Obituary


Our Crew



We call her Red Fox Leader, because this powerful lady-boss leads her strong team year after year.  A great inspiration for those that work with her, she’s followed her bliss to Lake Superior where she’s made a business out of a hobby.



Alec grew up at Superior Charters, working first as a dinghy wrangler to his position now as Fleet Manager. As Dick and Cindy’s son, he’s been helping run the family business for years. In his spare time, you’ll see him working on the Superior Charters sponsored race boats, because going fast is fun.


a person sitting in a boat on a body of water

Kailee is a born and raised local gal who grew up on the shores of Lake Superior. After moving away for a decade for school and work, she returned to the area to raise a family of her own on the Big Lake. She serves as our Director of Operations which basically means she’s the CEO of GSD (getting stuff done!)


a person sitting on a dock next to a body of water

Brian’s story is really interesting…but it all started with getting to know him and his amazing work ethic while at boat shows in Annapolis and Miami. We recruited him and he decided to leave the hot Florida summer behind to join us in Bayfield for an exciting year on fresh water. He’s since been promoted to Fleet Engineer and is our go-to for anything that needs fixing. Self-coined “Team OCD” Brian keeps up with all the boat details and makes sure our fleet stays in tip-top shape throughout the season.


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Tabbi is our Fleet Housekeeping Manager, which means it’s her job to make a great first impression. She’s been at Superior Charters for years now and knows every boat inside and out. We’re lucky to have such an experienced and detailed crewmember.


a person holding a kite in a boat on a body of water

Tia was born and raised on Lake Superior & has lived in Washburn most of her life. She has tried (a few times) to move out of the area to check out new cities but the Big Lake always seems to pull her back. Tia is a dog lover and in her free time you can find her spending time with her black lab Archie. Tia is our Operations Coordinator, and she will be the smiling face that greets you when you come to visit us!


a man standing next to a boat

Joey brings a TON of experience to the crew at Superior Charters. Joey is a Coast Guard veteran, commercial salvage and recovery diver, USCG Licensed Captain and diesel mechanic. He acts as our Fleet Captain, and you might even be lucky enough to have him as your instructor when you visit us! 


Crew member Joe standing next to sailboat

Joe Radtke represents Superior Yacht Sales as our resident boat broker. Joe was previously the manager of Barker’s Island in Superior, Wisconsin.  That means all those years of experience with boats only makes him a greater resource for our boat buyers and sellers.