Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Getmyboat Logo
    Captained Charter 30' Sailboat in Milwaukee, WisconsinCaptained Charter 30' Sailboat in Milwaukee, WisconsinCaptained Charter 30' Sailboat in Milwaukee, WisconsinCaptained Charter 30' Sailboat in Milwaukee, Wisconsin

    Milwaukee Sailboat Rental - Private 30' Captained Charter on Lake Michigan

    With Captain

    5.0(7 reviews) ·
    8 bookings
    ·
    the United States,Wisconsin,Milwaukee,Sailing

    • Looks Good

      This date is available.

    Enjoy a private sailing experience for up to five guests (children 12+) along the Milwaukee beautiful lakefront. Kick back, relax, and let your US Coast Guard licensed Captain treat you to stunning views of Milwaukee's spectacular skyline. Make memories, not landfill, is my motto. As a former Navy Search and Rescue Swimmer your trip will not only be enjoyable but safe. Things offered: - Sunset cruse - Take the helm and learn to sail. - Anchor and go for a swim. - Comfortable seating in the cockpit or at the bow. - Electric Toilet. - Alcohol allowed. - Blue tooth speaker to enjoy your favorite music. - Let me know if you have any special request.

    Scott

    Scott

    8 total bookings
    Capacity
    6 guests
    Sailing
    Cruising Monohull

    Reviews

    5.0 (7 reviews)

    • Listing Accuracy

      Awesome

    • Departure & Return

      Awesome

    • Vessel & Equipment

      Awesome

    • Communication

      Awesome

    • Value

      Awesome

    • Itinerary & Experience

      Awesome
    1. Captained Charter 30' Sailboat in Milwaukee, Wisconsin
    2. Captained Charter 30' Sailboat in Milwaukee, Wisconsin
    3. Captained Charter 30' Sailboat in Milwaukee, Wisconsin
    3 photos have been added by reviewers who booked this listing.

    1. JW

      Jessica

      Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!

    2. TG

      Taylor

      Scott was incredibly kind and accommodating to our photoshoot. I highly recommend him and his boat.

    3. Emily
      Emily

      Scott made everything easy. His sailboat is beautiful, so relaxing!

    4. EM

      Emily

      Captain Scott provided an enjoyable adventure. We would highly recommend

    5. JH

      Jessica
    Scott

    Scott

    8 total bookings

    Active Sailor

    Features & Details

    • O'Day
    • 302
    • Capacity: 6 people max

    Safety Equipment

    Life Jackets (1)

    Operating Equipment

    GPS ChartPlotter

    Guest Amenities

    Cabins (1)
    Sun Protection
    Toilets (1)

    Leisure & Entertainment Equipment

    Sound System

    Departure Location

    The boat's approximate location on a map

    You’ll get helpful information for your departure after your booking is confirmed.

    Street Address For Arrival

    Street Address For Arrival

    643 East Erie Street
    Milwaukee, Wisconsin, 53202
    United States
    Departure Location

    Departure Location

    Same as Street Address

    Cancellation Policy

    Free cancellation up to 1 day before your trip.

    Similar Listings

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included
    Sailing in Milwaukee · 6 guests

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    4.8
    $150/hour
    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
    Sailing in Milwaukee · 6 guests

    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

    New
    $120/hour

    Top Destinations Nearby

    Currently Snoozed(Out of Office)

    This listing will be active on 02 Jan 2026.

    You’ll be able to get in touch with the owner when they return.

    About

    1. About Getmyboat
    2. Careers
    3. Media Inquiries
    4. Terms of Use
    5. Privacy Policy
    6. Cookies Policy
    7. Accessibility Statement
    8. Member Interface Agreement
    9. Contact Us

    Learn More

    1. How It Works
    2. For Owners
    3. Mobile Apps
    4. Safety

    Experiences

    1. Boat Rentals
    2. Jet Ski Rental
    3. Fishing Charters
    4. Houseboat Rental
    5. Pontoon Rental
    6. Yacht Rental
    7. Sailboat Rental
    8. Bachelorette Party Boat Rental
    9. Party Boat Rentals

    Journal

    1. Company News
    2. Lifestyle
    3. Experiences Guide
    4. Destinations
    5. Tips for Renters and Owners

    Popular Destinations

    1. Miami
    2. Lake Lanier
    3. Lake Tahoe
    4. San Diego
    5. Lake Travis
    6. Newport Beach
    7. Chicago
    8. Lake Norman
    9. Key Largo
    10. Destin
    11. Marathon

    24/7 Live Support

    1. Help & FAQs
    2. +1 818 927 2148
    3. support@getmyboat.com

    Real reviews from happy Getmyboaters.

    4.9 out of 5! 500,000+ reviews

    • Download on the App Store
    • Get it on Google Play
    © Getmyboat 2025
    TermsPrivacy