The Best Boat Rentals Near Saint Joseph

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 :)

Private Cruise onboard Hunter Legend Sailboat in Chicago

We had an amazing time sailing around Lake Michigan with Captain Mitch! The marina was super easy to locate/get to, the boat was the perfect size for our group of four, and we really enjoyed our time on the water. I would highly recommend booking a trip with 3rd Coast!

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.

43ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

Kevin had great communication and was very transparent leading up to us actually getting on the boat. My guest and I had such a great time and it was amazing vibes. The Captain (Capt Jim) we had on board was very attentive, had we needed anything while on board. It was a very clean boat. Pictures are very accurate. I'd definitely book 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.

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!