Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in Wisconsin

Incredible sailboat rentals in Wisconsin, United States.

Page 1 of 18 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
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0
$140/hour
Instant Book
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$449/day
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother
Sailing in Kenosha · 6 guests

SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother

New
$175/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 Wisconsin

  1. Brittany

    Brittany

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik was so kind! We absolutely loved our sunset cruise around Milwaukee. He was so friendly and had great areas to go by! We loved every part of our engagement session and can’t think of a better skipper 🥰

  2. CS

    Corrie

    41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

    John recently took my family out on Lake Michigan and he made the trip a great experience - communicative, nicely kept boat and very competent as a captain! I appreciated how he answered my youngest questions and was so thoughtful with them. Would recommend.

  3. 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.

  4. 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!

  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.