News Archive

As we head into the dog days of summer it is never to soon to look ahead to Summer 2022. After a year that saw record interest in the Dragon Fleet, and with a past history of having a 90%+ renewal rate of returning skippers, Fairwind is now taking applications for next season. If you [continued…]

The Dragon Fleet made up for lost time in 2020 with a great summer of sailing. Fairwind Sail Charters now looks forward to 2021 for its 43rd year of providing the best sailing experience in Chicago. With a record renewal rate of returning skippers there are limited shares available for 2021, so if you are [continued…]

The Dragon Fleet is up and running for its 42nd year. Given the pandemic, Fairwind is taking all necessary precautions to ensure the mighty Dragoneers have a safe sailing experience. Unfortunately, Fairwind has closed its sailing school for this summer out of an abundance of caution and is limiting private charters to two passengers to [continued…]

This was a difficult season weather-wise, with most of May and June lost to rain. But it highlighted the exceptional value of Fairwind Sail Charter’s seamanship-based business model. Unlike other programs that pack their boats full, Fairwind leaves at least 30% of each of its boats open so that sailors have the opportunity to make [continued…]

The buds are on the trees, the crocuses are poking their noses up, and the sandhill cranes are heading back north. Spring is here and summer is around the corner. If you have always wanted to learn to sail, let 2019 be your year. Fairwind’s American Sailing Association certification classes begin in June. If you [continued…]

This year marks Fairwind Sail Charters’ 40th anniversary and my 20th anniversary as owner/operator. When I bought Fairwind in 1998 I started what has now been a twenty year experiment. Could you run a sailing business based on the principles of seamanship instead of maximizing profit? Could a business model based on the best of [continued…]

The newest addition to Fairwind Sail Charters’ legendary Dragon Fleet has left its nest in Marion, South Carolina, (dragons start out in nests) and is headed to its new home on Lake Michigan. To be christened Dragonfly, it is a sparkling new Beneteau 38.1, and, as you can see from the photo taken in Columbia [continued…]

Capt. Ben Sells’s latest book, The Tunnel Under the Lake: The Engineering Marvel that Saved Chicago, is featured in the Northwestern University Press 2017 Spring/Summer catalog and was chosen as the lead book in the new series “Second to None: Chicago Stories.” The book tells the remarkable story of the building of the first tunnel [continued…]

Fairwind Sail Charters celebrates its upcoming 39th year with Special Fall Pricing on a brand new 2017 Beneteau 38.1. The Beneteau 38.1 combines practical features, performance, and elegance on a beautiful yacht that epitomizes the cutting edge for family cruising. The innovative chined hull provides stability and speed and sets the standard for modern yacht [continued…]