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Sailing Wisconsin

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By Kevin Revolinski | Photo courtesy Travel Wisconsin – Mike Tittel

With an abundance of water, including two Great Lakes, Wisconsin unsurprisingly has a thriving sailing community. Whether you’re experienced, looking to learn or just want to be along for the ride, you have a wide variety of options for setting sail.

COME SAIL AWAY

It doesn’t matter if you’re out for a sunset cruise or a multi-day tour, sailing the Great Lakes is always an unforgettable experience. Time out on Lake Michigan or Lake Superior is in league with facing the open sea, and an experienced captain makes all the difference.

For Lake Superior, head to Bayfield, the gateway to the Apostle Islands. These 22 pristine isles and the facing sandstone cliffs and sea caves on the mainland make up the Apostle Islands National Lakeshore, the setting for your trip. Some tours offer swimming opportunities or access to some of the remote beaches.

To head out on Lake Michigan, you can find tour companies in Milwaukee and Kenosha, as well as up in the Door County Peninsula. Milwaukee and its harbor offer the city skyline and the iconic Quadracci Pavilion at the Milwaukee Art Museum. Door County is a bit wilder, with towering bluffs and forested islands on the Green Bay side, and exposed limestone cliffs on the open lake side.

The season runs from May through late September. Most boats accommodate six passengers, but larger vessels might take up to 28.

The most popular tours are day trips and sunset cruises, lasting from about 90 minutes to two hours. Private charters are common so you can have the boat to yourself. 

Some cruises may include refreshments, otherwise be sure to pack at least water. Be aware that despite the heat of summer you might need to bring a jacket when you are out on the Great Lakes. Even in summer water temperatures can be chilly. Nonslip footwear (not flip-flops) and sun protection are recommended as well. While sailing is often a gentle ride, the lake may have its own ideas: Anyone prone to motion sickness might consider taking dimenhydrinate (Dramamine) before boarding. Trips may be canceled for unpleasant weather, but a light rain won’t stop the sail.

LAKE SUPERIOR

Bayfield

  • Superior Charters provides captained and bareboat (you’re the captain) multi-day trips aboard two- and three-cabined sailboats. superiorcharters.com
  • All Hands Sailing offers 2.25-hour, full-day and overnight excursions. allhandssailing.org
  • Lake Superior Tall Ships sails Abbey Road, a 52-foot schooner for morning, afternoon or sunset cruises or even multi-day trips. Passengers can participate a bit with the sailing tasks. lakesuperiortallships.org
  • True North Sailing Charters runs 2.25-hour sails on a 33-foot clipper and half- and full-day trips on a catamaran. truenorthsailingcharters.com

LAKE MICHIGAN

Milwaukee

  • Sea Dog Sailing provides fully customized itineraries on their 34-foot Catalina, sailing in Milwaukee Harbor as well as out onto the open lake. seadogsailingmilwaukee.com

Door County

  • Sail Door County based in Sister Bay offers day tours, sunset sails, private charters, and special event sails. saildoorcounty.com

Kenosha

  • Sail Away Charters offers two-hour sails and hosts special events. (up to 6 passengers) sailawaycharterskenosha.com
  • Red Witch Sailing offers sailing adventures on the 55-foot Red Witch II. (up to 28 passengers) redwitch.com

LEARNING HOW TO SAIL

Take a person sailing, they’ll enjoy the day. Teach a person to sail, and they’ll enjoy a lifetime out on the water. Wisconsin offers a wealth of sailing instruction, on small lakes and Great Lakes. “People have a perception of sailing that it is sort of a rich man’s sport, something that they can’t do,” says Holly Church, Director of Milwaukee Community Sailing Center (sailingcenter.org), one of the nation’s premier, community-based, educational sailing organizations. The center helps make lessons affordable and available to people of all ages, means and abilities. Anyone can become a member. Also in town, Milwaukee Yacht Club (milwaukeeyc.com) offers a Junior Sailing Program that serves kids as young as 4.

HOOFER SAILING CLUB AT UW-MADISON

One of the activity clubs at the Wisconsin Union on the shores of Lake Mendota at the University of Wisconsin-Madison campus, Hoofers is open to anyone who becomes a Wisconsin Union annual or lifetime member, including non-students. Club members have access to free unlimited lessons and the club’s fleet of more than 120 boats of 15 different craft types. Members can register their children for the Youth Sailing Program courses. Sailing lessons take place from mid-May through late October and provide ratings for members to check out the club’s boats. American Sailing Association (ASA) certifications are available for a fee. Additionally, members can opt to take part in intra-club sailing competitions.

SAILING LESSONS

Founded in 1897, ILYA, the Inland Lake Yachting Association (ilya.org), united ten Upper Midwest yachting clubs to enjoy and promote sailing. Today, in Wisconsin alone, there are 15 chapters offering sailing instruction to youth and adults.

American Sailing Association was founded to develop international standards for sailing instruction; it has 8 primary certification levels. Six schools in Wisconsin, including Hoofer Sailing Club, offer ASA-certificate courses. americansailing.com

THE RACE IS ON

The word regatta comes from the Venetians, a people once known for their mastery of the seas. It means “boat race” and typically refers to sailboats in particular. There are more than a dozen regattas throughout the state each summer.

YACHT CLUB REGATTAS

  • 2025 C-MIR
    Delavan Lake Yacht Club – June 7
  • 2025 Wisconsin MC Championship
    Delavan Lake Yacht Club – June 21
  • 2025 ILYA C Scow Invitational Regatta
    Hartford, WI – July 18
  • 2025 ILYA No Tears Optimist Clinic
    East Troy, WI – July 21
  • 2025 ILYA Annual A-E-C Championship Regatta
    Oshkosh, WI – August 10
  • MKE OD/ILCA Great Lakes Masters
    Milwaukee Yacht Club – August 10-11
  • Sunfish Masters Championship
    Milwaukee Yacht Club – August 16-18
  • 2025 ILYA MC Annual Championship Regatta
    Pewaukee, WI – August 21

CATAMARAN RACING ASSOCIATION OF WISCONSIN REGATTAS

crawracing.org

  • Rock & Roll Regatta
    Lake Mills, WI – May 17-18
  • Madtown Throwdown Regatta
    Madison, WI – July 5-6
  • Sheboygan Regatta
    Sheboyan, WI – July 19-20
  • Trivers Trap Out Regatta
    Two Rivers, WI – August 1-3
  • Windjammers Regatta
    Green Bay, WI – August 16-17
  • Barnum Bay YC Regatta
    Petenwell, WI – September 13-14
Author

Kevin Revolinski is a Wisconsin outdoors and beer writer and author of "Backroads and Byways of Wisconsin" a guidebook to the best paddling throughout the Badger State. See his website at themadtraveler.com.

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