The Best Sailboat Rentals Near Grapevine Lake

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

This was 1000% the way to go for boat rental! Derrick was absolutely incredible. We found him through a Gemini AI search and we couldn’t be happier! The boat was well maintained and came with everything we needed including complementary gas and tubes so we could just enjoy our time on the lake! He was so flexible with drop off and pick up and made the experience so relational and positive for our family!

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!

13 person 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.

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

Patrik was awesome! We did an engagement photo shoot on the boat and he helped us to get the perfect shots! Would highly recommend to anyone looking for a unique date night or fun photo shoot location!