The Best Sailboat Rentals Near Torch Lake

Welcome Aboard Optimystic! Create a beautiful memory on the water.

Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

Charter 42' Lagoon Catamaran in Annapolis, MD

We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

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

Nijole was a wonderful captain with great communication and flexibility. The change in plans due to weather was seamless. We had a great time on the lake with Nijole, Remus and Piper and will chose her again if we are back in Chicago and want to go out for a sail. Thanks again Nijole!

Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

This was an amazing boat! It’s HUGE!! Captain Lester was a true professional who catered to all are requests. This was the best day of our summer. I would highly recommend this boat! Truly great!

38ft Catalina Gemini Sailing Yacht Chicago Weekday Special 4th Hour Free!

Captain Russell & his team were so nice and helpful and accommodating and the vessel was perfect for a group of 10-12. We had the right vibes and experience and would highly recommend!

Sailing Lessons with Chicago's #1 Rated Sailing School

I had a four hour private lesson with Doug and small crew. All were very helpful and knowledgeable, it was a great learning experience. I look forward to joining them again.