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All listings in Milwaukee

Great sailboat rentals near Milwaukee, Wisconsin.

Page 1 of 14 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
Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!
Events in Milwaukee · 30 guests

Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!

New
$500/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
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
Snoozed - Active 02 Jan 2026

Sailing Reviews in Milwaukee

  1. Van A.

    Van A.

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    A great Milwaukee skyline sail with an old sailor and his 8 and 5 year old grandkids. Patrick was totally accommodating and I was very happy. Toby “loved the ride” And Betty feigned boredom. I know they both loved the experience. Patrick our skipper was great. The boat clean and well cared for.

  2. DE

    Deborah

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik was definitely a solid sailor. We had a very smooth initial start and as we came back into the harbor, we had a quick change into very strong winds and that’s when things got FUN! Our captain kicked it into high winds experience mode and we got to see how much knowledge he had for the situation! Was really exciting!

  3. QR

    Qais

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrick has great experience and very knowledgeable with sailing. Great value and time well spent in the boat definitely worth it.

  4. MH

    Mike

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik was a great captain! Very knowledgeable and friendly and taught us a lot about sailing!

  5. JM

    Jill

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik did an exceptional job in our planning and implementation of our trip. Our need was to release ashes into the lake and I was very pleased with how the day went. He was cordial and hospitable. I would definitely recommend Patrik for a sailing trip. Thank you!

  6. RS

    Renata

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik was very easy to communicate with throughout the whole process and was extremely punctual. He did an awesome job answering any questions we had while we were out on the water and was super nice and easy to talk to. We did a sunset cruise from 6-8 pm in the middle of May and it was stunning! There was just enough wind to put up both sails and experience it all.