We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

All listings in Michigan

Incredible sailboat rentals in Michigan, United States.

5.0(Average of 641 reviews in this area)
Page 1 of 2 (29 listings)
Captained Charter 30' Sailboat.
Sailing in Milwaukee · 5 guests

Captained Charter 30' Sailboat.

5.0
$150hour
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
Best of 2022
$220hour
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
$150hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200hour
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
$115-120hour
37' Luxury Sailboat with Captain in Chicago, Illinois
Sailing in Chicago · 10 guests

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0
Superowner
$250-350hour
46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests 30% Off Weekends!
Events in Chicago · 12 guests

46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests 30% Off Weekends!

5.0
Best of 2022
$280hour
Instant Book
46' Spacious Portofino Party Yacht For Every Occasion
Sailing in Chicago · 12 guests

46' Spacious Portofino Party Yacht For Every Occasion

5.0
$250hour
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
Superowner
Best of 2022
$200hour
Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
Sailing in Chicago · 6 guests

Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois

5.0
$225hour
41' Morgan Classic Sloop in Muskegon, Michigan!!! Min $135 pp 2 persons
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!! Min $135 pp 2 persons

5.0
$89person
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200hour
38' Sailing Catamaran, Chicago's Largest!
Sailing in Chicago · 12 guests

38' Sailing Catamaran, Chicago's Largest!

5.0
Superowner
$440-500hour
Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
Sailing in Chicago · 4 guests

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

5.0
$202hour
Super Spacious Silverton Express Cruiser in Chicago, Illinois
Events in Chicago · 12 guests

Super Spacious Silverton Express Cruiser in Chicago, Illinois

5.0
Superowner
$250hour
 🌊🚣 Explore Grand Rapids Waters with Our Kayak Rentals! 🌊🚣
Adventures in Grand Rapids · 2 guests

🌊🚣 Explore Grand Rapids Waters with Our Kayak Rentals! 🌊🚣

New
$15-20hour
Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin
Powerboats in Wisconsin · 8 guests

Glastron GX185 Bowrider Rental in Saint Germain, Wisconsin

New
$500day
38' Catalina Sailing Cruise in Chicago
Sailing in Chicago · 6 guests

38' Catalina Sailing Cruise in Chicago

5.0
$250hour
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
$115hour
Learn Kiteboarding in Chicago, Illinois
Adventures in Chicago · 1 guest

Learn Kiteboarding in Chicago, Illinois

5.0
$120hour
Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
$300hour
*Fall Special: Buy 3 hours, get the 4th hour Free on our 43' Tiara
Events in Chicago · 12 guests

*Fall Special: Buy 3 hours, get the 4th hour Free on our 43' Tiara

New
$550hour
Sail Lake Michigan Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan Racine, WI

5.0
$220hour
37’ Rinker Yacht - AFFORDABLE and GREAT for Parties up to 12 guests (KMB #12)
Events in Chicago · 12 guests

37’ Rinker Yacht - AFFORDABLE and GREAT for Parties up to 12 guests (KMB #12)

New
Superowner
$250hour

Sailing Reviews in Michigan

  1. LS
    Liz
    46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests 30% Off Weekends!

    Everything with our rental was perfect. Nasco was very responsive with our booking and any questions we had. He also helped by providing several captain recommendations. The boat itself was perfect for our group of 12. We had plenty of room to sit, move around and the lily pad was great for those of us wanting to go into the water. We will definitly use this boat in the future and recommend it to anyone else looking for a Boat in Chicago!

  2. 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!

  3. 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!

  4. RJ
    Robert
    Set Sail with 36' Sailing Boat in Downtown, Chicago

    Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.

  5. JL
    John
    Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

    Had a great outing on a windy day, learning the details of the boat and watching the beautiful Chicago skyline from the best vantage point around. Ben was a great captain and provided a great sense of confidence and enthusiasm.

  6. NC
    Nataly
    46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests 30% Off Weekends!

    Nasco was very communicative and reliable and even recommended a reliable and great list of captains to hire. The boat was clean and exactly as shown in the pictures and as described. We had a great time with the boat! Would definitely recommend to other friends.