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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!

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 great teacher and 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.

Captain Dean Kass

Profile photo of Captain Dean Kass

Captain Dean is a retired architect, and spends his free time staying active by biking across the country and teaching the next generation of sailors.

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 Nick Nelson

Nick Nelson

Captain Nick grew up on Madeline Island and began boating as a young boy. The big lake has taught him many lessons along the way to becoming a licensed captain. The Apostle Islands can be a challenging sailing grounds, but also very exciting.

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


Captain Mayers is joining us back on the water this year…the pull of the lake was just too much to stay away! A knowledgeable and interesting captain, he’ll tell you about his many trips on Lake Superior.

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 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 Dave Skoro

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

Captain Dave has been 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 interior boat cleaner, which means it’s her job to make a great first impression. She’s been around boats for years, but has really found her groove while racing sailboats.



What started as a fun summer job has turned into four summers of adventure for Molly. Working on getting her captain’s license, you can also catch her on the Madeline Island Ferry during the week as well. 



Cara was originally recruited from the Hospitality & Tourism Management program at UW-Stout. A college graduate as of May 2021, we are looking forward to her joining us full-time.


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 group of people on a boat in the water

Blake is a trained aviation mechanic, which means he’ll be working hard to fix up boats as they need it. Always ready with a smile and helping hand, we’re really excited to have him join our crew.


a person standing next to a body of water

Cohl has joined us mid-season to help us get boats ready for charters. He sailed here on his Erickson 27′ from his last stop in Marquette, Michigan and will sail on from here as well.



Andrew is a hard-worker that found his way to Bayfield to answer the call of the lake. While he may be new to the sailing world, he’s learning fast and loving it!

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