Come with R&R and view the beautiful Chicago Skyline on a wonderful 37’ classic Chris-Craft sailing yacht. Enjoy a peaceful andrelaxing time out on the pristine waters of Lake Michigan. We offer private intimate charters along the Chicago’s lakefront as we sail where the wind permits.

Day Cruises

10:00 am - 12:30pm

1:00pm - 3:30 pm


1-5 guests

2 .5 hour cruises


Price includes captain and crew fees.

15%- 20% gratuity is much appreciated

Sunset Cruise

7:00pm - 9:30pm

1-5 guests

2.5 hour cruise


Price includes captain and crew fees.

15%-20% Gratuity is much appreciated

Wednesday Night Fireworks

7pm -10 pm

3 hour cruise

1-5 guests


Price includes Captain and crew fees

15%-20% Gratuity is much appreciated

Our Team

USCG Captain Rosalie

You are in good hands with the exceptional expertise offered by Captain Rosalie who also holds US sailing Keel Boat Instructor Certification. Rosalie grew up sailing in Europe, Caribbean, Bahamas, Gulf Coast, and Florida and has been sailing Lake Michigan  since 2012 on vessels ranging from 21’ to 50 ‘.

     " We lived in the UK when my dad built a 42' Catamaran and my mom asked me if I wanted to sail around the world. We moved aboard when I was 10 and I was helming  alone while my parents slept by the time I was 11 while  crossing the Atlantic Ocean. It was an amazing adventure seeing every sunrise and sunset for those 30 days at sea with nothing but water and sky and the wind in my face. We lived aboard for 6 years and I became an expert sailor and navigator before GPS was even invented" Captain Rosalie

USCG Captain Randy

Captain Randy has sailed the Caribbean, Florida, and across the Atlantic. He has been a U.S. Sailing level one instructor, and a Sea Scout Skipper. He knows his way around a boat having worked in service for years at the best boat yard on the Great Lakes. He loves to be on the water sharing good times.

Crew Members Moriah

Moriah has been crewing on various yacht charters in the Chicago area and is currently acquiring seatime to qualify for her USCG License. She is always happy to help with sailing and attending to the needs of our guests

Contact us 

Tel: 773 640 0116 - capt.rosalie@rrclassicsailing.com

31 st Street Harbor - 3155 S Lake Shore Dr Chicago IL 60616

Our aspiration is to share the wonderful relaxing experience of sailing with all those who enjoy getting out on the water.