Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Lake Michigan, US Boat Rentals & Yacht Charters

Page 15 of 15354 listings

Chicago Lake Adventure on 24ft Former Military Willard Marine SeaForce Boat!
Powerboats in Chicago · 6 guests

Chicago Lake Adventure on 24ft Former Military Willard Marine SeaForce Boat!

New
$270/hour
Lake Michigan Fishing Charters and Cruises on 36' Tiara Yacht
Fishing in Muskegon · 4 guests

Lake Michigan Fishing Charters and Cruises on 36' Tiara Yacht

New
$150/hour
New Buffalo Shoreline and Sunset Yacht Cruises on 36ft Cruiser Yacht
Powerboats in New Buffalo · 6 guests

New Buffalo Shoreline and Sunset Yacht Cruises on 36ft Cruiser Yacht

New
$500/hour
Bostwick Lake Pontoon Rental -  20ft Bennington
Powerboats in Michigan · 7 guests

Bostwick Lake Pontoon Rental - 20ft Bennington

New
$100/hour
Carver Mariner 350 | Private Chicago Yacht Charter | Captain and Fuel Included
Events in Chicago · 6 guests

Carver Mariner 350 | Private Chicago Yacht Charter | Captain and Fuel Included

New
$275+/hour
1986 22ft Catalina Sailboat in Holland, Michigan
Sailing in Holland · 6 guests

1986 22ft Catalina Sailboat in Holland, Michigan

New
$75+/hour
Fully Chartered Fishing Trips on Lake Michigan for salmon and trout.
Fishing in Two Rivers · 6 guests

Fully Chartered Fishing Trips on Lake Michigan for salmon and trout.

New
$130/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
Explore Lake Michigan with the 27’ Bayliner Ciera Sunbridge Yacht from Waukegan
Powerboats in Waukegan · 4 guests

Explore Lake Michigan with the 27’ Bayliner Ciera Sunbridge Yacht from Waukegan

New
$350/hour
260 Sea Ray Sundancer for Overnight Stays
Powerboats in Angola · 6 guests

260 Sea Ray Sundancer for Overnight Stays

New
$300/day
Charter Fishing On 34ft Silverton Sports fisherman Yacht in Algoma, Wisconsin
Fishing in Algoma · 6 guests

Charter Fishing On 34ft Silverton Sports fisherman Yacht in Algoma, Wisconsin

New
$113+/hour
Explore the Beauty of Lake Michigan & Duck Lake by Kayak!
Adventures in Michigan · 2 guests

Explore the Beauty of Lake Michigan & Duck Lake by Kayak!

New
$35+/hour
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

4.9
Snoozed - Active 15 Jul 2026
Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests
Events in Chicago · 12 guests

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

3.8
Snoozed - Active 18 Jul 2026
Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago
Events in Chicago · 12 guests

Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago

4.9
Snoozed - Active 25 Jul 2026
51ft Sea Ray Sundancer Yacht at Diversey Harbor!
Events in Chicago · 12 guests

51ft Sea Ray Sundancer Yacht at Diversey Harbor!

5.0
Snoozed - Active 02 Jan 2027
27' Four Winns 225 Sundowner - Lake Michigan Charter Boat Rental with Captain
Powerboats in Chicago · 12 guests

27' Four Winns 225 Sundowner - Lake Michigan Charter Boat Rental with Captain

New
Snoozed - Active 22 Jul 2026
Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests
Events in Chicago · 10 guests

Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests

New
Snoozed - Active 02 Aug 2026

Lake Michigan Reviews

  1. Erica

    Erica

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    Ben is wonderful he is so passionate and knowledgeable about sailing and he made it a great time.

  2. CM

    Caley

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!

  3. Tonu

    Tonu

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    It was the perfect experience! Right from the beginning, I began steering, pulling the halyard and raising the main sail. I learned the basics easily and Ben is great to talk to because of his years of experience and pleasant demeanor. I very much enjoyed my time and even more so am happy to have learned so much so quickly. I highly recommend this for anyone trying to see what sailing is all about!

  4. YH

    Yousuf

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    Our experience sailing with Ben was great. He is a pro and is clearly very passionate and knowledgeable about sailing. This passion is infectious, and we learned plenty from him. He also allowed us to take an active role in the process given our interest in sailing. Ben was also very personable, interesting, and pleasant to converse with, which is an important quality when sailing with someone! Would highly recommend!

  5. Kimberly

    Kimberly

    Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

    Benjamin communicated quickly and clearly and was super flexible as our plans changed. We rented the boat without a captain and he also provided a super helpful instruction sheet with every single thing we'd need to know... from harbor bathroom codes to the color of the jib sheet! So thorough and helpful, and it set us up for a perfect afternoon on the water. Thank you!

  6. Devon

    Devon

    Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

    Arthur and his crew were great at accommodating us for an event at the playpen on one of the busiest days of the summer. Arthur was very responsive leading up to the day and even helped find another captain after ours cancelled. Communication the day of wasn’t the best as I believe there was another charter before us but we were able to finally link up and take off for the full allotted time. We had a blast!