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    Find The Best Boat Rentals in Wisconsin.

    5.0
    (405 Reviews)

    Page 2 of 2 • 37 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!
    Events in Milwaukee · 30 guests

    Vintage AMERICA'S CUP Racing Sailboat (Up to 30 Guests). Voted Best Boat!

    New
    $500/hour
    SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother
    Sailing in Kenosha · 6 guests

    SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother

    New
    $175/hour
    Geneva Lake WI. Regal 35 Yacht Charter
    Events in Fontana-on-Geneva Lake · 6 guests

    Geneva Lake WI. Regal 35 Yacht Charter

    New
    $300/hour
    Lake Michigan Fishing Charters and Cruises on 36' Tiara Yacht
    Fishing in Muskegon · 4 guests

    Lake Michigan Fishing Charters and Cruises on 36' Tiara Yacht

    New
    $150/hour
    28ft Cutwater Cruiser Party Pontoon Charter Boat in Madison WI!
    Powerboats in Madison · 12 guests

    28ft Cutwater Cruiser Party Pontoon Charter Boat in Madison WI!

    New
    $200/hour
    Lake Boat with attached Jet Ski
    Powerboats in Superior · 7 guests

    Lake Boat with attached Jet Ski

    New
    $100+/hour
    Family boat rental or pleasure cruise, its up to you!!!
    Powerboats in Wisconsin · 9 guests

    Family boat rental or pleasure cruise, its up to you!!!

    New
    $125/hour
    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
    Sailing in Milwaukee · 6 guests

    Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

    New
    $120/hour
    Fully Chartered Fishing Trips on Lake Michigan for salmon and trout.
    Fishing in Two Rivers · 6 guests

    Fully Chartered Fishing Trips on Lake Michigan for salmon and trout.

    New
    $130/hour
    2023 Yamaha AR220 with the best stereo on the water
    Powerboats in Wisconsin · 10 guests

    2023 Yamaha AR220 with the best stereo on the water

    New
    $175+/hour
    Instant Book
    Charter Fishing On 34ft Silverton Sports fisherman Yacht in Algoma, Wisconsin
    Fishing in Algoma · 6 guests

    Charter Fishing On 34ft Silverton Sports fisherman Yacht in Algoma, Wisconsin

    New
    $113+/hour
    24’ Yamaha Boat with Captain for Rent
    Powerboats in Madison · 8 guests

    24’ Yamaha Boat with Captain for Rent

    New
    $225+/hour
    Instant Book
    Captained Charter 30' Sailboat in Milwaukee, Wisconsin
    Sailing in Milwaukee · 6 guests

    Captained Charter 30' Sailboat in Milwaukee, Wisconsin

    5.0
    Snoozed - Active 02 Jan 2026

    Top Destinations Nearby

    Wisconsin Reviews

    1. JW

      Jessica

      Captained Charter 30' Sailboat in Milwaukee, Wisconsin

      Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!

    2. TG

      Taylor

      Captained Charter 30' Sailboat in Milwaukee, Wisconsin

      Scott was incredibly kind and accommodating to our photoshoot. I highly recommend him and his boat.

    3. EM

      Emily

      Captained Charter 30' Sailboat in Milwaukee, Wisconsin

      Captain Scott provided an enjoyable adventure. We would highly recommend

    4. Emily

      Emily

      Captained Charter 30' Sailboat in Milwaukee, Wisconsin

      Scott made everything easy. His sailboat is beautiful, so relaxing!

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