Incredible sailboat rentals in Lake Michigan, United States.

Sailing Reviews in Lake Michigan

1. CM

   Caley

   Beautiful Ranger 22 Sailboat for rent in Chicago 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!

2. 

   Ben

   Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

   Ben was an awesome captain and a pleasure to be around during our two-hour trip. His boat is the perfect setting for a romantic date night, and I highly recommend experiencing the sunset on board, the views were absolutely amazing!

3. 

   Brittany

   Charter this beautiful Catalina from Milwaukee, WI - Captain Included

   Patrik was so kind! We absolutely loved our sunset cruise around Milwaukee. He was so friendly and had great areas to go by! We loved every part of our engagement session and can’t think of a better skipper 🥰

4. MJ

   Meneka

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

   Sailing with Nijole and her husband was an incredible experience! From the start, they were very responsive in communication and flexible with our requested times, even allowing us to extend once on the water. Their knowledge, warmth, and passion for sailing made the trip both safe and fun, with stunning views that we’ll never forget. Highly recommend!

5. 

   Van A.

   Charter this beautiful Catalina from Milwaukee, WI - Captain Included

   A great Milwaukee skyline sail with an old sailor and his 8 and 5 year old grandkids. Patrick was totally accommodating and I was very happy. Toby “loved the ride” And Betty feigned boredom. I know they both loved the experience. Patrick our skipper was great. The boat clean and well cared for.

6. SN

   Sergey

   Private Cruise onboard Hunter Legend Sailboat in Chicago

   We (myself and 5 of my friends) had a private boat tour with Captain Mitch, and it was a greta experience. We did plenty of swimming in the open lake (outside the harbor) and did a quick tour along the shoreline. Mitch is very knowledgeable about the lake and the city, and many other things - it was both entertaining and educational to chat with him. Highly recommend!