The Best Sailboat Rentals Near Me

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

Took our three grandchildren on a sailboat excursion with Captain Andy. Such a great, peaceful experience. Let the waves and breeze carry your troubles away. We’ve spent a good bit of time on the water but never in a sailboat and had me wanting to learn more. Such great hospitality, beautiful day, and magnificent lake. Dreading returning to the heat!

Luxury Stylish Poontoon

Our trip with Michael was fantastic! My family of 6 booked a trip with him on the 4th of July, and we had a great time relaxing on the water in his beautiful boat. He took us to some of the popular coves on Lake Norman until we finally settled on a sandbar. We parked and enjoyed the water with locals until our trip came to an end. 3 hours was the perfect amount of time for our group. We would certainly book with Michael again!

20ft Bayliner VR5 Boat in Rockville, IN

First time renting a boat through this platform - would definitely do it again. HIGHLY recommend Peter. Communication was excellent from the get go... easy to schedule, easy to pick up/meet, boat and equipment was in great condition...we had everything we needed for a great day on the lake. Would DEFINITELY rent from him again. As we stopped past the marina to fill up, the worker said, "nice boat." When we told him it was a rental he was shocked and said it was way nicer than anything they rented out. Highly recommend!

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

Amazing experience with top-notch communication from start to finish. Super responsive and incredibly knowledgeable—especially helpful for first-timers in Chicago. They guided us around the lake and to the perfect fireworks viewing spot, even capturing great photos for us. The captain was skilled and professional, and the music made the ride even better. Highly recommend!

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

Patrik was definitely a solid sailor. We had a very smooth initial start and as we came back into the harbor, we had a quick change into very strong winds and that’s when things got FUN! Our captain kicked it into high winds experience mode and we got to see how much knowledge he had for the situation! Was really exciting!

Sail & Swim from a Luxury Sailing Yacht

This is an iconic trip in Chicago. I have always been on the river walk or on a kayak looking at people boats and thought "Those lucky kids." So this time I rented a sailboat to go out on the lake- even luckier! The operators are very organized and helpful. Everything was as expected from the site. Communication throughout was excellent. Thanks for lovely and memorable sail. I'm coming back to jump in the lake when the water temperature is a bit warmer :)