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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 2022!

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 Bravo, 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

Captain Vicki Staudte headshot

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.

Captain John Mayers


A local resident, and longtime professional mariner, Captain Mayers holds a 100 Ton Masters license and specializes in big boat and catamaran handling.

Deliveries and instructions have taken him to the Atlantic, Pacific, Caribbean, Mediterranean, Gulf of

Mexico, and the Great Lakes Great Loop.

In sailing, John enjoys a mix of instruction, exploration, and has a relaxed and empathetic style, eager to make crews in any situation feel comfortable with new skills.

Captain Gordy Ringberg

a man sitting in a boat on a body of water

In a maritime career spanning over four decades, Captain Gordy has skippered all types of vessels from a 7′ Opti to a 112′ square rigged brig.  This laconic sea captain with a heart of gold enjoys in sharing the his love of sailing with new friends.

Captain Lauren

a person sitting on a boat

Lauren has a deep love for sailing, and you can tell when you talk to her! She’s been working in the Apostle Islands for years, so she knows all the great spots for anchoring and exploring.

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

Cindy 'Bravo'

a woman sitting on a bench

Bravo joined Superior Charters in 2014 and worked her way from the back office to front-and-center with each and every customer. Her voice is the first one you’ll hear when you call the office to ask a question or book a charter. She’s originally from the area and can’t seem to stray very far from the Big Lake.

Cindy Kalow


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 Operations 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.


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Tabbi is our senior boat detailer, 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.



What started as a fun summer job has turned into many summers of adventure for Molly. When not working on the Madeline Island Ferry, you can find her working tirelessly on her own sailboat. Who said owning a boat was easy?!


Cara Sailing

Cara loves hospitality (she majored in it!) and the water. This job is perfect for her! She’s always at the desk or on our boats with a smile on her face and she really brings the energy to our entire staff.


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.


a man standing on a dock near a pole

Cohl has very quickly become a mascot of Bayfield and the marina. After he sailed his Erickson 27′ here in August 21′, he’s found a home, friends and a new family here at Superior Charters. He loves sailing and is always happy to hear new stories about adventures on the water.


a man standing next to a boat

Joey brings a TON of experience to the crew at Superior Charters. A  Coast Guard veteran, commercial salvage and recovery diver, USCG  Licensed Captain, diesel mechanic and all around handy guy. We can’t wait to get him working on our boats!



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.



Gabe is joining us for the summer on Lake Superior all the way from Memphis, TN. He usually spends his winters in Aspen working on ranch, maybe he’ll like Bayfield so much that he comes back every season!



Cassidy is a college student at Minnesota State University – Mankato where she’s studying International Business. She loves to travel and always has a positive attitude. She’ll be working at keeping our boats spiffy clean all summer.