The Best Boat Rentals Near Portage

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!

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 :)

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.

27' Sea Ray Sundancer – Extended Swim Platform

Our charter cancelled at the last minute and Alex came in like a super hero and saved the day! We had a phenomenal time aboard his boat. He’s very friendly and accommodating. I will definitely recommend.

Luxury 29ft Crownline Bowrider 285 SS

Mark and crew were excellent. We arrived to a friend my crew that guided us each stop of the way. Boat was clean and well maintained. We had a great trip.

SeaRay 310 Sundancer for Rent on Chicago's Lake Michigan

My group enjoyed our time out on the water. Edward was great at communication and we all felt very safe out on the water. Would definitely book again.