The Best Boat Rentals in Kenosha

Expect small captained powerboats and sail outings to start around $90–$175 per hour, while private Lake Michigan fishing charters commonly run about $650–$800 for a 5–6 hour trip and roughly $950–$1,050 for a full 8-hour day. Prices usually include a licensed captain or guide when applicable, fuel, basic safety gear, and—for fishing trips—use of tackle plus fish cleaning and bagging. Taxes and platform fees may be separate, and gratuity for your captain or crew is customary.

You’ll find offshore-capable powerboats and cruising yachts for relaxed lakefront cruises, classic sailboats for scenic sails, and purpose-built sportfishing boats targeting salmon and trout on Lake Michigan. Pontoons are less common on the open lake due to waves and weather, so most Kenosha options emphasize stable hulls and seaworthy designs suited to Great Lakes conditions.

Most trips here are captained, especially fishing charters and larger cruisers, which makes the day easy and stress-free. A limited number of smaller boats may be available for experienced renters to operate themselves; if you were born on or after January 1, 1989, Wisconsin requires boating safety certification or an approved temporary rental certificate for motorboats. Always check the specific listing’s rules before you book.

The primary departure points are Southport Marina by the harbor mouth near downtown and Simmons Island Marina on the protected harbor side of Simmons Island. Depending on your booking, some captains also arrange convenient pickup along the HarborPark waterfront; your confirmation will specify the exact dock and meeting spot.

From the lake you can take in Kenosha’s signature red North Pierhead Light and the historic Southport Lighthouse above Simmons Island, wide beaches at Simmons Island and Pennoyer Park, and the modern HarborPark shoreline. On a very clear day the Chicago skyline can appear to the south, while longer runs north may reveal Wind Point Lighthouse near Racine. South of town the Kenosha Sand Dunes and Chiwaukee Prairie shoreline add a natural backdrop.

Passengers on captained trips do not need any license. If you plan to operate a motorboat yourself, Wisconsin law requires a boating safety certificate if you were born on or after January 1, 1989; visitors without a certificate may qualify for a state-approved temporary rental certificate for that rental period. Personal watercraft have stricter age rules and are typically not part of Kenosha’s lakefront charter scene. Bring photo ID and any safety card your captain requests.

Yes, families are welcome. Boats carry U.S. Coast Guard–approved life jackets for every passenger, with child sizes available when requested in advance. Children under 13 must wear a life jacket while underway on federal waters like Lake Michigan. Let your captain know ages and sizes ahead of time so the right gear is ready when you arrive.

Most captains allow you to bring snacks, picnic meals, and non-alcoholic drinks, and many permit beer and wine for guests of legal age. Glass containers and red wine may be restricted to keep decks safe and clean, and hard liquor is often discouraged on the open lake. Coolers with ice are fine on most boats; confirm specifics with your captain and consider simple, packable items to keep setup easy.

Pet policies vary by boat. Some captains welcome small, well-behaved dogs with advance notice, while others prefer no pets for safety and cleanliness on open-water trips. If your group includes a pup, ask before booking, bring a non-slip mat and water bowl, and plan for a properly fitted pet life jacket.

Lake Michigan can change quickly, and captains closely monitor marine forecasts. If conditions are unsafe—think strong winds, storms, or dense fog—your captain will reschedule or cancel according to the platform’s and operator’s policies. Summer pop-up showers sometimes shorten outings; mornings are often calmer, so choosing an early departure can improve your odds of smooth water.

Absolutely. Private charters are ideal for celebrations, offering reserved space, a set itinerary, and the ability to bring decorations, cupcakes, and a playlist. For the easiest day, choose a captained cruise, share your headcount and vibe with the captain, and ask about add-ons such as coolers with ice or a photo stop by the lighthouses. For larger groups, multiple boats can cruise together if you book early.

Peak boating season runs roughly from late May through mid-September, with the most reliable lake conditions in June, July, and August. Major boating holidays—Memorial Day weekend, July 4th, and Labor Day—are extremely popular on the lakefront and around HarborPark, so reserve well in advance. Kenosha’s HarborPark Jazz, Rhythm & Blues Festival typically lands in mid-August and draws big lakefront crowds, which can affect parking and pickup timing. For smoother water and easier logistics, consider weekday outings and morning departures; afternoons and weekends see more wind, chop, and harbor traffic.

Fireworks are staged at Celebration Place along the HarborPark shoreline, and the surrounding streets and Simmons Island access often have traffic controls before and after the show. If your charter overlaps with the holiday period, build in extra time, follow your captain’s meeting instructions closely, and expect dock areas near HarborPark to be busier than usual.

It’s possible with careful planning. Milwaukee’s WaterStone Bank Air & Water Show is scheduled for July 19–20, 2025, and Chicago’s Air & Water Show is slated for August 16–17, 2025. Both create very heavy marine traffic near their show boxes, and transits from Kenosha are long and weather-dependent. If you’re set on watching by water, book a full-day captained trip well in advance, be flexible, and understand that safety zones and lake conditions will dictate how close any boat can get.