Cookies!
We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.
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-$150
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$150
Canoes
A classic option for leisurely paddling
$35
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$325
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!
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!
CA
Calie
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
We had a perfect day sailing on White Lake. Captain John is very knowledgeable and experienced. You won’t be disappointed!
TG
Taylor
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Scott was incredibly kind and accommodating to our photoshoot. I highly recommend him and his boat.
EM
Emily
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Captain Scott provided an enjoyable adventure. We would highly recommend
Emily
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Scott made everything easy. His sailboat is beautiful, so relaxing!
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!
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
