The Best Cruising Catamaran Rentals Near Chicago

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

We can’t thank Captains Dave & Joe enough. From the communication with Bailey, to the overall experience.. everything went smooth and easy. I booked for my friend’s Bachelorette Party and they made our time worth while. I definitely recommend for any occasion. Both Captains Dave and Joes made sure we were equipped with everything and comfortable during our sailing. My favorite part was swimming and lounging on the floatable pools.. oh, and seeing dolphins! Overall 10/10 experience!

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay

Booked Captain Terry's boat for my wife's birthday. Everything went perfectly!! Captain Terry suggested a sunset cruise and plotted out a great itinerary. We ended up singing happy birthday as the sunset in the background. The boat itself was beautiful and very stable. For those who get seasick, the boat does not rock very much. Captain Terry and his First mate Wayne were fantastic. Very friendly and took care of everything. This boat is all about having a great time with your friends!

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

The captain and crew were amazing! The sunset cruise was the perfect end to a great weekend with friends. I definitely would highly recommend to anyone looking for a wonderful evening.

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

Our sunset cruise exceeded expectations. Cannot recommend this boat and its crew enough. Overall great experience that we will always remember.