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
Thursday, July 20, 2017

Lake Pepin Sailing Weekend Forecast: July 20-23, 2017

Friday: rain
Saturday: High 80s, breezy
Sunday: High 70s, steady wind

David Sheridan
David Sheridan
Monday, June 19, 2017

Sweet sailing weather ahead

Great sailing weather is forecast for this week...
Book early to avoid losing prime dates and times!            715-442-2250 or info@sailpepin.com.