Welcome to Sail Pepin and the Breakwater Wine Bar.

Join us for a Lake Pepin cruise aboard the splendid sister ships Messenger, Dragonfly and Sunshine.

Now in our 20th year, we sail from Pepin, Wisconsin and Lake City, Minnesota. 

Relax ashore on Pepin’s charming waterfront at our Breakwater Wine Bar. Enjoy fine wine, craft beers, small plates and live music.


Our offerings include:

  • Fun family & group sailboat rides
  • Couples' Special private reservation for two
  • Sailing instruction
  • Weddings & wedding parties
  • Bachelor & bachelorette parties
  • Family & personal events
  • Client & staff appreciation
  • Corporate & youth teambuilding
  • Waterfront meetings & receptions

Sail Pepin

We operate four daily scheduled Lake Pepin sailboat cruises from our Pepin and Lake City locations.

These charming river towns are superb gateways to beautiful Lake Pepin, home to exceptional outdoor and cultural activities – all just 45-90 minutes from Minneapolis/St. Paul, Rochester, La Crosse, Winona and Eau Claire.

We’ve been providing sailboat rides, sailing instruction and corporate and youth sailing teambuilding programs since 1997. We serve the sailing communities in Minneapolis/St. Paul, greater Minnesota and western Wisconsin by offering a wide variety of Lake Pepin sail boat charters, sail boat rentals and sailing programs.

Breakwater Wine Bar

Sail Pepin and the Breakwater are headquartered in our historic 1867 Breakwater building on Pepin’s charming waterfront. The Breakwater also offers a wine bar, light food and live music, plus options for corporate meetings, weddings, wedding parties and other personal events.

Join us on the Pepin waterfront with fine wine and craft beers, exceptional food, live music – and our famously stunning sunsets!

Latest News


Sail Pepin Blog


David Sheridan
David Sheridan
Saturday, October 14, 2017

Music at the Breakwater tonight!

We can't imagine a better way to wrap up our 2017 music season than an evening with The Beavers, starting at 8:00. These songbirds deliver indie folk and rock better than just about anyone on our horizon. Yay!

David Sheridan
David Sheridan
Friday, October 6, 2017

October music at the Breakwter

We wrap up our 2017 season this month with this fine music:
  • Saturday, 10/7 -- innovative psychedelic rock and Americana from Trempeleau starts at 8:00.
  • Saturday, 10/14 -- the Beavers push out indie rock starting at 8:00.
Our outdoor Firefly Lounge will also be open weekends as long as weather permits.

David Sheridan
David Sheridan
Friday, October 6, 2017

Autumn's Golden Days Arrive

Some of the season's best sailing is upon us!

Lake Pepin's fall colors start to peak this weekend and continue through at least the following week. Temps and winds are forecast to be comfy -- if not downright primo -- right through the 20th.

We run right operate thru Sunday, 10/29 before tucking "the girls" away for the winter right away in November.
Book early to avoid losing prime dates and times!            715-442-2250 or info@sailpepin.com.