The Best Boat Rentals in Milwaukee

Most Milwaukee rentals run about $125–$175 per hour for pontoons and bowriders, $150–$250 per hour for many sailboats, $100–$150 per hour for fishing charters, and $300–$500 per hour for larger captained cruisers and small yachts. Weekend and holiday pricing can be higher. Your total usually includes required safety gear; fuel, captain’s fee, taxes, and gratuity may be included or listed as add‑ons in the listing. Always review the listing for what’s included before you book.

You’ll find easygoing pontoon boats for the rivers, sporty bowriders and center consoles for lake and harbor cruises, classic sailboats for scenic sails on Lake Michigan, and mid‑size cruisers/yachts for celebrations. Fishing charters are also available seasonally for nearshore trips when conditions are right.

If you choose a captained charter, you don’t need a license—your licensed captain does the driving. If you plan to operate the boat yourself, Wisconsin requires a boating safety education certificate for operators born on or after January 1, 1989. Age and supervision rules apply for younger operators, and everyone must follow local boating laws. If you’re unsure, booking with a captain is the most stress‑free option.

Common departure points include McKinley Marina on the lakefront, the South Shore Park Boat Launch in Bay View, the Riverfront Launch in the Harbor District near South Water and Bruce Street, and the transient slips at Lakeshore State Park by Discovery World. Your captain or owner will confirm the exact pickup spot after booking.

Typical routes showcase the Milwaukee skyline, the Santiago Calatrava–designed Milwaukee Art Museum, the Daniel Hoan Memorial Bridge, and the Summerfest grounds at Henry Maier Festival Park. Out on the lake you can often spot the red Milwaukee Pierhead Light and the Milwaukee Breakwater Light, glide past Bradford Beach, and then return through the Milwaukee River to take in the RiverWalk’s bridges and public art.

Yes—families are welcome. Boats carry U.S. Coast Guard–approved life jackets for every passenger, with child sizes available on most listings. On Lake Michigan and other federally controlled waters, children under 13 must wear a life jacket while underway, and it’s a good idea on the rivers, too. Let the owner know your kids’ ages and approximate weights so the right sizes are ready at boarding.

Most boat owners allow you to bring snacks, picnic fare, and beverages. Many provide a cooler and Bluetooth speaker; some restrict glass or red wine to keep decks safe and clean. If you are the operator on a self‑drive rental, designate a sober driver—Wisconsin law prohibits operating a motorboat while impaired. For captained trips, moderate BYO is typically fine; confirm details in your booking.

Pet policies vary by listing. Many hosts welcome well‑behaved dogs, sometimes with a cleaning fee, while others are pet‑free to protect upholstery. If you plan to bring a dog, message the owner before booking and bring a properly fitted pet life jacket, a towel, and a leash.

Lake Michigan weather can change quickly, and captains make the final safety call. If conditions are unsafe, trips are typically rescheduled or refunded according to the owner’s stated cancellation policy on the platform. Because each listing sets its own terms (and holiday weekends can be stricter), check the cancellation policy before you pay and build a little flexibility into your plans.

Peak boating season runs roughly May through October, with the warmest, busiest stretch in June–August. Memorial Day, July 4th, and Labor Day weekends book up early and carry premium pricing. For calmer water and easier parking, choose weekday outings or morning departures. Sunset cruises are popular on clear evenings; mornings are usually smoothest on the lake.

Absolutely. Pontoons are great for casual celebrations on the Milwaukee River, while larger cruisers and small yachts work well for milestone birthdays, proposals, or corporate groups. Most boats list a maximum guest count—often 6–12, depending on the vessel—and many captains can recommend routes, photo stops by the Art Museum or Hoan Bridge, and timing to avoid the heaviest traffic.

Pick a captained charter if you want a turn‑key experience: the captain handles routing, docking, and Lake Michigan’s changing conditions while you focus on your guests. A self‑operated rental can be a good fit if you’re experienced, familiar with the river and harbor, and meet Wisconsin’s boater‑education requirement. For most group events, captained trips are the easiest and most relaxing option.

Yes—the WaterStone Bank Milwaukee Air & Water Show returns to the lakefront July 19–20, 2025, and is spectacular from the water. Summerfest and other lakefront festivals also energize the harbor area, though they increase marina and parking congestion. If you’re targeting these dates, book well in advance and budget extra time for meeting your boat.