Sea Dog Sailing – Lake Michigan/Milwaukee 

5.0/5 (2 reviews)
 North Lincoln Memorial Drive 1550, Milwaukee, WI 53202, United States

Sea Dog Sailing – Lake Michigan/Milwaukee 

Milwaukee, WI, United States
34 feet
6
5.0/5 (2 reviews)

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!

Matt Scott
Captain
Matt Scott
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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1 Hr –Sunrise Sailing Lake Michigan
Non-refundable
1 hour trip starts at 5:00 AM
Seasonal trip
(Fri, Sat, Sun)
US $200
Private tour: 2 people
2 Hr – Sailing Lake Michigan
Non-refundable
2 hour trip starts at 11:00 AM
Seasonal trip
(Thu, Fri, Sat, Sun)
US $260
Private tour: 2 people
2 Hr – Sailing Lake Michigan
Non-refundable
2 hour trip starts at 2:00 PM
Seasonal trip
(Thu, Fri, Sat, Sun)
US $260
Private tour: 2 people
2 Hr – Sailing Lake Michigan
Non-refundable
2 hour trip starts at 5:00 PM
Seasonal trip
(Thu, Fri, Sat, Sun)
US $260
Private tour: 2 people
2 Hr – Sunset Sailing Lake Michigan
Non-refundable
2 hour trip starts at 7:00 PM
Seasonal trip
(Thu, Fri, Sat, Sun)
US $290
Private tour: 2 people
There are 2 people looking at this charter.

Customer reviews

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Rating

5.0
(2 reviews)
5.0
Boat & equipment
5.0
Captain & crew
5.0
Experience

All reviews (2)

Showing 12 of 2 reviews
SCOTT RULAU
SCOTT RULAU
us
Florida, US
Member since 2026
The captain canceled
August 28, 2026
Trip was supposed to happen on August 28, 2026

The charter operator canceled on trip date. This is an automated posting.

Kevin Jacobson
Kevin Jacobson
us
Wisconsin, US
Member since 2026
5.0
Verified
New
Aye aye, Captain Matt!
2 Hr – Sailing Lake Michigan on September 17, 20266 adults

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!!

FAQs about Sea Dog Sailing – Lake Michigan/Milwaukee

Sea Dog Sailing – Lake Michigan/Milwaukee offers the following trips to customers:
  • US $100 per person - 1 Hr –Sunrise Sailing Lake Michigan (1 hour)
  • US $130 per person - 2 Hr – Sailing Lake Michigan (2 hours)
  • US $130 per person - 2 Hr – Sailing Lake Michigan (2 hours)
  • US $130 per person - 2 Hr – Sailing Lake Michigan (2 hours)
  • US $145 per person - 2 Hr – Sunset Sailing Lake Michigan (2 hours)
When you book a trip with Sea Dog Sailing – Lake Michigan/Milwaukee, you can expect the following amenities onboard:
  • GPS
  • VHF Radio
  • Radar
  • Chart Plotter
  • Depth Finder
  • Autopilot
  • Anchor
  • Wheel Steering
  • Life Jackets
  • Bimini
  • Kitchen
  • Bow Sundeck
  • Air Conditioning
  • WiFi At marina.
  • Audio System
  • Inside Speakers
  • Outside Speakers Bluetooth.
  • Refrigerator
  • Fishfinder
Trips booked with Sea Dog Sailing – Lake Michigan/Milwaukee include:
  • Snacks
  • Drinks
Sea Dog Sailing – Lake Michigan/Milwaukee offers the following activities:
  • Boat & Yacht Tours
  • Sailing, Catamaran & Gulet Tours
  • Sunset Dinner Cruises
  • Eco-Tours

Your operator

Matt Scott
Matt Scott
Matt Scott

Milwaukee, Wisconsin, United States

2 Customer reviews
Response time within an hour
Member since May 2025

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.

2 Customer reviews
Response time within an hour
Member since May 2025

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.

What the boat is like

Boat category
Other
Boat type
Sailing
Boat manufacturer
Catalina
Boat Model
Mark 11
Year built
1991
Boat length
34 ft
Capacity
6 persons
Number of cabins
1 cabin
Number of berths
2 berths
Number of heads
1 head
Number of toilets
1 toilet
Boat category
Other
Boat type
Sailing
Boat manufacturer
Catalina
Boat Model
Mark 11
Year built
1991
Boat length
34 ft
Capacity
6 persons

Which kind of activities are offered

Boat & Yacht Tours
Sailing, Catamaran & Gulet Tours
Sunset & Dinner Cruise
Eco-Tours

Which amenities are available onboard

GPS
VHF Radio
Radar
Chart Plotter
Depth Finder
Autopilot
Anchor
Wheel Steering
Life Jackets
Bimini
Kitchen
Bow Sundeck
Air Conditioning
WiFi
At marina.
Audio System
Inside Speakers
Outside Speakers
Bluetooth.
Refrigerator
Fishfinder

What's included in the trip price

Snacks
Drinks
Water ginger ale

What’s allowed on the boat

Child Friendly
Alcohol
Byob
Shoes
Liveaboard
Swimming
At captians discretion
Red Wine

What additional terms you should be aware of

Security deposit is not required

A refundable deposit is not required by the charter operator.


How cancellations work

Deposit non-refundable

If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.

More details

How you can pay

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.