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The Best Sailboat Rentals in Wisconsin
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Wisconsin
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$15-$750
Fishing Charters
Let a captain do the driving while you do the fishing
$15-$950
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$15-$1,075
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$110
Kayaks
Who says you need a motor to have fun on the water?
$10-$50
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$15-$195
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$145-$325
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$150
Canoes
A classic option for leisurely paddling
$35
Top Sailboat Rental Locations Near Wisconsin
Recent Reviews in Wisconsin
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!
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!
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.
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.
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!
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!
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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