Captain Doug Stein

I love what I do with a passion that shows in every moment on the water. I have a knack for reading the group and adjusting to the vibe so everyone feels comfortable. Guests enjoy free sea-sick patches, keepsake photos, and videos captured on my Insta360, creating lasting memories. I bring portable batteries, floating saddles, and even juggle or refresh drinks while navigating Chicago’s locks and finding the best fireworks spots. Every charter is designed for fun, comfort, and a little extra flair that makes your trip unforgettable.

Whether it’s a weekday cruise or a special event, I go above and beyond with thoughtful touches that guests love. I am proud to be one of Chicago’s most five-star reviewed captains, known for energy, humor, and attention to detail. Learning new skills, like drone photography, allows me to capture unique moments for your group. Every trip is planned for comfort, adventure, and endless memories, so all you need to do is relax and enjoy the water.