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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
$70-$400
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$35-$330
Fishing Charters
Let a captain do the driving while you do the fishing
$35-$145
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$35-$145
Kayaks
Who says you need a motor to have fun on the water?
$30-$205
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$95
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$65-$210
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$315-$390
Top Sailboat Rental Locations Near Wisconsin
Recent Reviews in Wisconsin
Doug
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Patrik did a great job getting us out on the water. There was a storm coming in and we had to cut the sail a little short but the winds did not disappoint. Great tour of the harbor and the city skyline. Patrik let us take the helm and experience sailing on the lake. Wish we had more time but better to be safe and dry.
KP
Kelly
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Captain John was so personable and shared many fun stories and provide a full-blown sailing experience
JK
Jessica
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Patrik was awesome! We did an engagement photo shoot on the boat and he helped us to get the perfect shots! Would highly recommend to anyone looking for a unique date night or fun photo shoot location!
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!
Top Sailboat Rental Locations in the United States
Los Angeles, California
362 boats to rent
San Francisco, California
83 boats to rent
Oakland, California
48 boats to rent
Marina del Rey, California
126 boats to rent
Honolulu, Hawaii
42 boats to rent
Miami, Florida
825 boats to rent
San Diego, California
106 boats to rent
New York, New York
83 boats to rent
Annapolis, Maryland
51 boats to rent
Hitchcock, Texas
54 boats to rent
Texas City, Texas
44 boats to rent
Chicago, Illinois
289 boats to rent
Houston, Texas
53 boats to rent
Clear Lake Shores, Texas
41 boats to rent
Kemah, Texas
44 boats to rent
Charleston, South Carolina
131 boats to rent
Tampa, Florida
378 boats to rent
Saint Petersburg, Florida
253 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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