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The Best Sailboat Rentals in Lake Michigan
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Lake Michigan
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$150-$1,170
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,135
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$80-$690
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$480
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$520
Kayaks
Who says you need a motor to have fun on the water?
$20-$300
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$75-$175
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$60-$940
Canoes
A classic option for leisurely paddling
$65
Diving
Explore the ocean depths with trained boat operators
$630
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$200
Top Sailboat Rental Locations Near Lake Michigan
Milwaukee, Wisconsin
10 boats to rent
Holland, Michigan
8 boats to rent
Lake Geneva, Wisconsin
13 boats to rent
Williams Bay, Wisconsin
8 boats to rent
Chicago, Illinois
287 boats to rent
Madison, Wisconsin
8 boats to rent
Glen Lake, Michigan
12 boats to rent
Torch Lake, Michigan
21 boats to rent
Toledo, Ohio
7 boats to rent
Detroit, Michigan
36 boats to rent
Saint Clair Shores, Michigan
22 boats to rent
White Bear Lake, Minnesota
11 boats to rent
Minneapolis, Minnesota
23 boats to rent
Minnetonka, Minnesota
26 boats to rent
Wayzata, Minnesota
10 boats to rent
Excelsior, Minnesota
10 boats to rent
Lake Minnetonka, Minnesota
60 boats to rent
Spring Park, Minnesota
14 boats to rent
Recent Reviews in Lake Michigan
WK
William
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!
AA
ADOLFO
Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
This was an amazing boat! It’s HUGE!! Captain Lester was a true professional who catered to all are requests. This was the best day of our summer. I would highly recommend this boat! Truly great!
Aisat
38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!
Captain Russell & his team were so nice and helpful and accommodating and the vessel was perfect for a group of 10-12. We had the right vibes and experience and would highly recommend!
Eric
Sailing Lessons with Chicago's #1 Rated Sailing School
I had a four hour private lesson with Doug and small crew. All were very helpful and knowledgeable, it was a great learning experience. I look forward to joining them again.
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!
JD
Jorge
No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
Captain Dennis and Kate were great hosts. Everything was perfect
Top Sailboat Rental Locations in the United States
Los Angeles, California
376 boats to rent
San Francisco, California
80 boats to rent
Miami, Florida
1092 boats to rent
Marina del Rey, California
134 boats to rent
Oakland, California
46 boats to rent
Honolulu, Hawaii
43 boats to rent
San Diego, California
107 boats to rent
New York, New York
78 boats to rent
Annapolis, Maryland
48 boats to rent
Dania Beach, Florida
237 boats to rent
Fort Lauderdale, Florida
258 boats to rent
Chicago, Illinois
287 boats to rent
Charleston, South Carolina
128 boats to rent
Hitchcock, Texas
51 boats to rent
Texas City, Texas
42 boats to rent
Tampa, Florida
404 boats to rent
Saint Petersburg, Florida
269 boats to rent
Houston, Texas
53 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!
Dive into Our Journal
April 17, 2024
Boating Regulations on Lake Michigan
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April 17, 2024
Boating Regulations in Torch Lake, MI
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The Top Boating Lakes in the US - Getmyboat
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December 17, 2019
Great Lakes Boating Guide - Getmyboat
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August 01, 2023
10 Boating Adventures of a Lifetime
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October 03, 2022
Getmyboat's Guides to the World of Boating
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