Summer Guide: Let’s Go Boating in Metro Milwaukee!

Summer Guide: Let’s Go Boating in Metro Milwaukee!

Your guide to party on the water.

It’s mid-July, and the late afternoon sun is bright. You cross a bridge Downtown and look out at the river below. Amid the window glare and shadows cast by tall buildings on either side, you see … boats. So many boats! There’s a double-decker cruiser packed with 100 very happy people. A gaggle of friends sitting in tiny hot tub boats, all holding a cold one. People playing bags or cards on pontoons gussied up in themes such as “Gilligan’s Island.”


READ MORE OF OUR 2026 SUMMER GUIDE HERE.


The common denominator: Everyone’s happy. No one’s scrolling their phones. And few of these folks, if any, actually own the boats they’re in. “There’s so many [rental] options to choose from now,” says Lindsay Schwegler, director of operations for Edelweiss Cruises. “You can get on the water without having to buy your own boat.” So, Milwaukee, no more excuses. Those people you see floating by having all the fun? That’s soon going to be you.  


Tell us who you’d pick to be a Betty this year!

 

Milwaukee or Lake Country?

One major difference: Boats on the Milwaukee River and interior of Lake Michigan can’t stop – local regulations don’t allow it. So the party is always in motion, and the partiers always on board. On inland lakes and rivers, you can drop anchor or tie up. Wear your swimsuit – there will be jumping in the lake, or just wading. 


Where to Rent a Boat

Milwaukee: 

  • Riverwalk Boats: You-drive pontoons, plus private charters driven by a boat captain. Board at Pere Marquette Park. 
  • Edelweiss: Chartered boat tours and one “PonTiki” pontoon. 
  • Rigged & Ready MKE: You-drive powerboats and fishing boats of various size. Board at McKinley Marina. 
  • Duffy Boat Rentals: You-drive electric cruisers. Board at Boone & Crockett Cocktail Lounge on Water Street. 

Lake Country and Beyond:  


Oh My, Okauchee

Of all the lake party boat scenes in the region, Okauchee Lake in Waukesha County has the biggest reputation. The lake has many shallow areas, perfect for tying up multiple boats for a boozy soirée, and of course Party Island near the lake’s eastern shore, which for decades has hosted the region’s largest tie-up party the third Saturday in July.

Photo by Nate Vomhof

Lexi Krahn, who operates Okauchee staple The Hideaway with her father, Scott, says they’ve had people come from as far as Europe. A party “barge” boat shows up every year, with revelers on it playing beer pong and other games. Last year, a pontoon boat had a stripper pole attached to the deck – and yes, it was utilized.

Scott Krahn, who’s owned The Hideaway since 2015, says he’s confident they’ll bring back the tavern’s lakeside bikini contest this summer after a lull due to construction. Add the lake’s reputation as being a meeting spot for swingers, and you get a wild scene. “It got too rowdy for us,” says longtime Okauchee-area resident and boat aficionado Julie Brewer-Mathews. “It got to be a real big drunken fest.”


How-To: Dock a Boat

1. Take it slow.
2. Have another person onboard get near the front of the boat to help guide it in and tie up the ropes.
3. Make sure your bumpers/buoys are hanging from the side that will be flush against the dock.
4. Drive straight at the dock, slowly.
5. About 15 feet out, turn the boat sharply, to get it roughly parallel to the dock.
6. Keep the engine running, in neutral.
7. Let the waves and wind gently guide the boat toward the dock.
8. Don’t be afraid to throw it gently into reverse to steady the boat and avoid overshooting the dock – or running into it! 


(Not-So) Booze Cruises

Not long ago, the 20- and 30-somethings among us went on river and lake cruises to get smashed and do questionable things with their friends (which still seems to be the case on Okauchee Lake). The cruises ran late at night. Oceans of alcohol went down. In the past decade or so, that scene has changed.

Photo courtesy of Edelweiss

Boat tour companies such as Edelweiss have shifted to earlier cruises framed around themes such as history and architecture. They trend toward families and retirees. Booze cruises still happen, but with less booze and earlier in the evening; this generation no longer wants to get hammered. “As opposed to being your destination party, we are now your pre-party,” says Lindsay Schwegler of Edelweiss. “You come hang out with us, and then we release you out to Water Street and Third Street.”

Yacht Rock: This cruise emphasizes the adult in adult contemporary. The oft-wild Monday night excursion is just $15 and includes “your first beer,” as Milwaukee Boat Tours puts it. Tickets go on sale each Tuesday morning and sell out quickly.


How-To Catch a Perfect Sunset
Check your weather app to find out what time the sun sets, then plan to have your boat in viewing position about 25 minutes prior – the lead-up to official sunset is typically the spectacular part. Gawk, ooh, ahh – and linger for five minutes afterward for the dusky afterglow. If you’re on Lake Michigan, proceed to the Hoan Bridge for the light show that follows.
Photo Courtesy of Visit Milwaukee

This story is part of Milwaukee Magazine’s June 2026 issue.

Find it on newsstands or buy a copy at milwaukeemag.com/shop.

Be the first to get every new issue. Subscribe

Daniel Simmons grew up in St. Paul, Minn., the “good twin” city. He started his writing career covering the midsection for the Mayo Clinic. Since then he’s written about human smuggling by sea in San Diego, the coyote invasion of Chicago and the political circus in Madison. He also got to write about his childhood idol, Larry Bird, for Runners World. He’s the managing editor.