The Best Boat Rentals Near Benton Harbor

20' Lund Bass Boat for 3 in Chicago, Illinois

I honestly didn’t expect to walk away from this trip with a whole new hobby, but here I am—hooked for life. Guy has this way of making the entire experience feel effortless and exciting, whether you’re a total beginner or someone who’s been at it for years. From teaching the basics with real patience to creating an atmosphere that’s both laid-back and full of energy, he made it easy to fall in love with fishing. The way he explained the gear, read the water, and shared his stories made every moment out there on the water feel like something special. You can tell he truly loves what he does, and that kind of passion is contagious. I went in thinking this was just a one-time adventure, but now I’m already planning my next trip—and buying my own gear. Can’t thank Guy enough for turning what was supposed to be a relaxing weekend into the start of a lifelong obsession. If you’ve ever been on the fence about trying fishing, let Guy be the reason you dive in—you won’t regret it.

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.

Sail & Swim from a Luxury Sailing Yacht

We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

70' EXCLUSIVE Motor Yacht NEW to Chicago

Boat is amazing. Best set up to host a group of people. Multiple large areas to gather. Boat is well kept and made for the BEST boat day we have ever had!

Book a Private Charter to cruise on Lake Kalamazoo with a U.S.C.G Master Captain

We had a group of 12 for a bachelorette and had so much fun!! This was the perfect boat. Rich couldn’t have been nicer or more accommodating! We loved being able to get in and swim at the cove!

26 ft. Chaparral SSX257 Luxury Vessel

We had an amazing time! The captain was super friendly, kept our safety a priority, and ensured we had fun. The boat was perfect for our group of 9!