Sea Dog Sailing – Lake Michigan/Milwaukee
Set sail on beautiful Lake Michigan and take in Milwaukee’s iconic shoreline—complete with stunning architecture, a 5-mile-long protected break wall, and panoramic city views. Whether you’re ready to relax on deck or take the helm, this private sailing experience is perfect for families, couples, or small groups of up to 6 guests.
Your vessel is a spacious 34-foot Catalina Mark II, featuring a 12-foot beam for added comfort. Outfitted with modern amenities like air conditioning, an audio system, inside/outside speakers, a refrigerator, and a fishfinder, it’s ready for your perfect day on the water. Below deck, enjoy a cozy cabin, a full kitchen, and a private head.
Led by USCG-certified Captain Matt Scott, you'll enjoy safe, memorable sailing, eco tours, or romantic sunset cruises. Sit back under the bimini, soak up the sun on the bow, or explore the onboard navigation gear, including GPS, autopilot, radar, and chart plotter.
Alcohol and children are welcome aboard. Optional add-ons include drinks and snacks to enhance your cruise.
Don’t just visit Milwaukee—experience it by sail. Book your unforgettable lake adventure today!
Set sail on beautiful Lake Michigan and take in Milwaukee’s iconic shoreline—complete with stunning architecture, a 5-mile-long protected break wall, and panoramic city views. Whether you’re ready to relax on deck or take the helm, this private sailing experience is perfect for families, couples, or small groups of up to 6 guests.
Your vessel is a spacious 34-foot Catalina Mark II, featuring a 12-foot beam for added comfort. Outfitted with modern amenities like air conditioning, an audio system, inside/outside speakers, a refrigerator, and a fishfinder, it’s ready for your perfect day on the water. Below deck, enjoy a cozy cabin, a full kitchen, and a private head.
Led by USCG-certified Captain Matt Scott, you'll enjoy safe, memorable sailing, eco tours, or romantic sunset cruises. Sit back under the bimini, soak up the sun on the bow, or explore the onboard navigation gear, including GPS, autopilot, radar, and chart plotter.
Alcohol and children are welcome aboard. Optional add-ons include drinks and snacks to enhance your cruise.
Don’t just visit Milwaukee—experience it by sail. Book your unforgettable lake adventure today!

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The charter operator canceled on trip date. This is an automated posting.
The weather was suspect all day and despite a touch of fog, light winds and some on and off again sprinkles of rain, everything about our sail was picture perfect! Captain Matt was a gracious and personable host, and let us (literally) take the helm the entire time. Brought out my 81-year old dad and mom for dad’s birthday, and it was a priceless experience all around. Anytime you need a second (third and fourth) mate, Captain Matt, you call us!! Thank you!!
Meet Capt. Matt Scott, a seasoned sailor based in Milwaukee who proudly operates a Catalina Mark II. With a deep passion for the water and the environment, he offers unforgettable sailing tours, sunset cruises, and eco tours on Lake Michigan. Capt. Matt is dedicated to providing a relaxing, scenic experience while sharing his love for sailing and nature.
Meet Capt. Matt Scott, a seasoned sailor based in Milwaukee who proudly operates a Catalina Mark II. With a deep passion for the water and the environment, he offers unforgettable sailing tours, sunset cruises, and eco tours on Lake Michigan. Capt. Matt is dedicated to providing a relaxing, scenic experience while sharing his love for sailing and nature.
Security deposit is not required
A refundable deposit is not required by the charter operator.
Deposit non-refundable
If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.
Reserve with a 15% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 15% booking deposit to guarantee your reservation.
The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:
Cash
Visa
Mastercard
American Express
Bank transfer
When paying the remaining balance with a credit card, an additional 2.5% charge will apply.