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All listings in Lake Michigan

Incredible sailboat rentals in Lake Michigan, United States.

Page 1 of 225 listings

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
$220/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Best of 2025
$200/hour
7 to 13 passenger Lake Michigan Sailing Charter
Sailing in Chicago · 13 guests

7 to 13 passenger Lake Michigan Sailing Charter

5.0
$550/hour
Sail & Swim from a Luxury Sailing Yacht
Sailing in Chicago · 7 guests

Sail & Swim from a Luxury Sailing Yacht

5.0
Superowner
$300+/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

5.0
$150/hour
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$120/hour
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200+/hour
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Best of 2025
$375+/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
$225/hour
Instant Book
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour
Instant Book
2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Day Sail from the port of South Haven Mi. on a Catalina 36

5.0
$175/hour
Instant Book
Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.
Sailing in Chicago · 6 guests

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

5.0
$450/hour
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0
$140/hour
Instant Book
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

New
Best of 2025
$175+/hour
Catamaran Sailing Lessons Chicago
Tours in Chicago · 6 guests

Catamaran Sailing Lessons Chicago

New
Best of 2025
$350+/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

New
$200/hour
No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit
Sailing in Chicago · 12 guests

No tie-ups: 39' Sailboat, Catalina 380 with huge cockpit

New
$245/hour
Instant Book
SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother
Sailing in Kenosha · 6 guests

SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother

New
$175/hour
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!
Events in Milwaukee · 30 guests

Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!

New
$500/hour
Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan
Sailing in Holland · 6 guests

Sail Lake Macatawa and cruise past the lighthouse, Big Red onto Lake Michigan

New
$150/hour
Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
Sailing in Milwaukee · 6 guests

Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

New
$120/hour
1986 22ft Catalina Sailboat in Holland, Michigan
Sailing in Holland · 6 guests

1986 22ft Catalina Sailboat in Holland, Michigan

New
$75+/hour

Sailing Reviews in Lake Michigan

  1. DV

    Danielle

    Sail & Swim from a Luxury Sailing Yacht

    We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

  2. S

    Sandra

    Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

    Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

  3. J

    Jeff

    Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

    What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

  4. Federica

    Federica

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I was so happy to do this experience but I didn’t know that I was going to like it so much ! I would recommend having this boat for a 2 date or double date ! The owners are really lovely but the best part is going to the pope and sitting there ! Make sure you bring wine, glassware and whatever you want to have ! 2 hours was a perfect time for us! Us we were lucky enough to have of the best sunsets of the season !

  5. vp

    vadim

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    I want to thank Nijole for her work . Everything was perfectly organized, swimming and sailing. My daughter got seasick and we received full support from the captain. There was also a miracle dog on board ! Dog swam with us and gave us a good mood! Thank you very much! If you want to have a wonderful time sailing, then you are definitely to Nijole! With respect, Vadim Pliss!

  6. AL

    Adam

    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    We loved our experience with Nijole. They took us all around the lake and we loved every minute of it. We even got to swim! They are also a very fun time to hang out with and enjoy the day. Definitely recommend and we will be booking with them multiple times this boating season.