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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-$750
Fishing Charters
Let a captain do the driving while you do the fishing
$35-$305
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$35-$465
Kayaks
Who says you need a motor to have fun on the water?
$30-$210
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$50-$200
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$90
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$60-$210
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$230-$320
Top Sailboat Rental Locations Near Wisconsin
Recent Reviews in Wisconsin
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.
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.
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!
Top Sailboat Rental Locations in the United States
Los Angeles, California
396 boats to rent
Miami, Florida
974 boats to rent
San Francisco, California
76 boats to rent
Marina del Rey, California
142 boats to rent
Oakland, California
43 boats to rent
Honolulu, Hawaii
50 boats to rent
New York, New York
87 boats to rent
San Diego, California
102 boats to rent
Charleston, South Carolina
123 boats to rent
Annapolis, Maryland
44 boats to rent
Chicago, Illinois
280 boats to rent
Newport Beach, California
138 boats to rent
Long Beach, California
91 boats to rent
Hitchcock, Texas
56 boats to rent
Texas City, Texas
38 boats to rent
Dania Beach, Florida
256 boats to rent
Southampton, New York
65 boats to rent
Noyack, New York
46 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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