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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

5.0
$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
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$449/day
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
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
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. 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!

  2. 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.

  3. Emily

    Emily

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik was an excellent captain. He accommodated my trip request on short notice, was flexible with times and very responsive with communication. His sailboat is comfortable, he is a steady captain and he is an easy conversationalist. I would definitely recommend going out on the water with Patrik.

  4. CD

    Christina

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    He was so courteous and accommodating! It was very choppy at first, and he suggested another route and out trip was still amazing! While the quarters are small, the views are worth it! We were able to drink and smoke, play all of our music while seeing all of the shore! I would recommend him!

  5. ST

    Sara

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

    I booked this trip as a surprise for my dear friends Rob and Leslie. This was a first anniversary trip gift. John was amazing to work with and everything went smoothly. Rob and Leslie were so excited and said it is a memory for a lifetime. I would highly recommend John and his beautiful vessel!

  6. JW

    Jessica

    Captained Charter 30' Sailboat in Milwaukee, Wisconsin

    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!