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The Best Sailboat Rentals Near Madison
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Madison
Fishing Charters
Let a captain do the driving while you do the fishing
$70-$160
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$70-$185
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$110-$200
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$170
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$80
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$225
Top Sailboat Rental Locations Near Madison
Williams Bay, Wisconsin
7 boats to rent
Lake Geneva, Wisconsin
11 boats to rent
Milwaukee, Wisconsin
10 boats to rent
Lake Michigan, United States
349 boats to rent
Chicago, Illinois
261 boats to rent
Holland, Michigan
8 boats to rent
Glen Lake, Michigan
12 boats to rent
White Bear Lake, Minnesota
9 boats to rent
Minneapolis, Minnesota
21 boats to rent
Minnetonka, Minnesota
20 boats to rent
Torch Lake, Michigan
21 boats to rent
Wayzata, Minnesota
7 boats to rent
Excelsior, Minnesota
10 boats to rent
Lake Minnetonka, Minnesota
60 boats to rent
Spring Park, Minnesota
15 boats to rent
Toledo, Ohio
8 boats to rent
Detroit, Michigan
35 boats to rent
Saint Clair Shores, Michigan
22 boats to rent
Recent Reviews in Madison
AH
Alexandra
38-ft Hunter 376 Sailing Adventure in Annapolis
Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.
PM
Prince
Affordable Yacht 27' Doral in Toronto
Had an amazing experience on the yacht — but honestly, the real highlight was the captain. Super friendly, very patient, and knew exactly where to go for the best views and photos. Even when we were running late, he didn’t rush us at all and made sure we still got the full experience. You can tell he genuinely cares about giving people a good time, not just finishing the trip. If you’re booking this, you’re in safe hands. Highly recommend.
BF
Bruce
38-ft Hunter 376 Sailing Adventure in Annapolis
This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.
W
Wilber
Fun time Jet Ski Rental at Lake Norman, NC near Charlotte
Highly recommended. She’s knowledgeable sincere and friendly. Never tried to outsell us Also great value for the price.
LD
Logan
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
Great weekend on the boat from Derrick, would highly recommend. Derrick was very responsive and helpful, boat was in great condition and big enough to fit our family comfortably.
Kevin
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
The entire boat rental process was wonderful. We will definitely reach out to Derek again in the future when we are in need of a boat rental.
Top Sailboat Rental Locations in the United States
Los Angeles, California
362 boats to rent
San Francisco, California
75 boats to rent
Miami, Florida
1026 boats to rent
Marina del Rey, California
132 boats to rent
Honolulu, Hawaii
46 boats to rent
Oakland, California
43 boats to rent
San Diego, California
112 boats to rent
New York, New York
77 boats to rent
Annapolis, Maryland
47 boats to rent
Dania Beach, Florida
236 boats to rent
Fort Lauderdale, Florida
255 boats to rent
Chicago, Illinois
261 boats to rent
Hitchcock, Texas
52 boats to rent
Texas City, Texas
42 boats to rent
Charleston, South Carolina
128 boats to rent
Tampa, Florida
420 boats to rent
Newport Beach, California
124 boats to rent
Houston, Texas
52 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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