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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
$65-$750
Fishing Charters
Let a captain do the driving while you do the fishing
$35-$780
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$35-$935
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$35-$500
Kayaks
Who says you need a motor to have fun on the water?
$30-$225
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$500
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$100
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$60-$225
Top Sailboat Rental Locations Near Wisconsin
Recent Reviews in Wisconsin
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 🥰
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.
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.
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!
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.
Top Sailboat Rental Locations in the United States
Los Angeles, California
377 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
137 boats to rent
Miami, Florida
915 boats to rent
Honolulu, Hawaii
58 boats to rent
Oakland, California
42 boats to rent
New York, New York
89 boats to rent
Annapolis, Maryland
49 boats to rent
San Diego, California
101 boats to rent
Newport Beach, California
133 boats to rent
Charleston, South Carolina
119 boats to rent
Baltimore, Maryland
44 boats to rent
Chicago, Illinois
280 boats to rent
Dania Beach, Florida
247 boats to rent
Southampton, New York
67 boats to rent
Noyack, New York
46 boats to rent
Palm Beach, Florida
127 boats to rent
Riviera Beach, Florida
120 boats to rent
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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Real reviews from happy Getmyboaters.
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