Captain Roland Senn

MEET YOUR CAPTAIN

Captain
Roland Senn

Your Lake Michigan Adventure Starts Here!

Meeting point
31st Street Harbor on J Dock

About Me

Meet Captain Roland — Your Lake Michigan Adventure Starts Here!

Originally from Texas and now cruising the waters of Lake Michigan, Captain Roland brings a perfect mix of Southern charm, local knowledge, and a love for life on the water. Whether you're looking for a laid-back cruise, a skyline sightseeing tour, a birthday celebration, or just an excuse to get out on the lake, he’s here to make your day unforgettable.

Offering private 3–4 hour charters, Captain Roland specializes in creating fun, personalized experiences for groups of all kinds. From soaking up the sun and snapping photos of Chicago’s iconic skyline to enjoying great company and lakefront views, every trip is designed around making memories.

Fluent in both English and German, Captain Roland welcomes guests from around the world and makes everyone feel right at home from the moment they step aboard.

Safety is always the top priority, but that doesn’t mean you can’t have a fantastic time. With a steady hand at the helm and a passion for hospitality, Captain Roland ensures every cruise is smooth, relaxing, and filled with good vibes.

So gather your crew, bring your favorite drinks, and get ready to experience Lake Michigan from the best seat in the city. Adventure, relaxation, and unforgettable views are waiting aboard with Captain Roland!

Interests & experience

  • Speaks German
  • Skyline cruises
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NEXT STOP: THE WATER

Start with your boat.

Book your bareboat charter, then choose and arrange your captain through the post-checkout portal. Captain fees are paid separately, and availability depends on your date and vessel.

Booking a COI passenger charter? Your captain and crew are included and assigned by our team.

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