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Find The Best Boat Rentals in Wisconsin.

4.9

(463 Reviews)

Page 3 of 3 • 58 listings

Powerboats in Madison · 12 guests

Cutwater Cruiser Party Pontoon Charter Boat!

New

$200/hour

Adventures in Wisconsin · 1 guest

Kayaks for rent near Castle Rock Lake

New

$60/day

Adventures in Wisconsin · 1 guest

2 Kayaks for rent Jefferson WI

New

$60/day

Fishing in Two Rivers · 6 guests

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

New

$130/hour

Sailing in Kenosha · 6 guests

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

New

$175/hour

Powerboats in Wisconsin · 10 guests

2023 Yamaha AR220 with the best stereo on the water

New

$175+/hour

Instant Book

Events in Milwaukee · 30 guests

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

New

$500/hour

Fishing in Algoma · 6 guests

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

New

$113+/hour

Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0

Snoozed - Active 02 Jan 2026

Water Sports in Wisconsin · 3 guests

Experience the Thrill - Sea-Doo GTX

New

Snoozed - Active 02 Aug 2025

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Wisconsin Reviews

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!
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.
EM
Emily

Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Captain Scott provided an enjoyable adventure. We would highly recommend
Emily

Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Scott made everything easy. His sailboat is beautiful, so relaxing!