History of Chicago Sailing

Chicago Sailing was originally formed as Bill Gladstone’s Sailing, Inc. in 1986. Operating out of a phone booth Bill began adult sailing lessons with a single J22 serving as his sailing school. Each year his business grew as demand for quality sailing instruction and boat rentals increased. By the mid 90’s his fleet included six J22s and its first J30. Things were hopping in the 40’ houseboat that served as the BGS office in Belmont Harbor.

It did not take long for BGS to become the premier adult sailing program in the Midwest. When Belmont harbor added new docks, Bill seized the opportunity to acquire as many slips as necessary to house his fleet of eight J22s and three J30’s and houseboat. At the same time Bill changed the name to Chicago Sailing Club to reflect the friendly atmosphere of his operations.

By 1999 the fleet had grown to twelve J22s and four J30s, but Bill’s business and family ties drew him back to Connecticut. When it became clear that he would be unable to devote full attention, Bill reluctantly turned over Chicago Sailing Club a new owner. Alan Veenstra, a former options trader and lifelong sailor, seized on the opportunity to make a business out of his passion. With renewed vigor, Chicago Sailing Club expanded and improved the fleet to include 14 J22s, five J30s, 3 Hunter 326s, a J24, and a 50’ houseboat/office. All these were in addition to a 53’ charter sailing vessel, “Bumblebee” and Alan’s personal Valiant 47, “Parvenu”.

Having a large fleet is one thing, but having a thriving sailing program is quite another. Chicago Sailing Club has always succeeded because of the people it attracts. From our incredibly committed staff, led by manager Ronan Adams, to our loyal following, we have been continually blessed. So in 2004, after long and careful consideration, we decided to drop the ‘Club’ from our name and became simply ‘Chicago Sailing, Inc.’ The new name is simpler and more immediately descriptive of who we are, a broadly inclusive organization with no membership requirements. And while our name changed, our atmosphere has not. Everyone is a special ‘member’.

Today, Chicago Sailing is one of the larget and most respected sailing facilities in the nation. Each year we proudly instruct over one thousand sailors to the highest certifiable standards in our industry, those of US SAILING, the governing body of the sport of sailing in America.

Chicago Sailing remains focused on the needs of sailors and the boating community. We continually evaluate our programs and offerings to make certain that each one delivers the highest level of quality, safety and value. Most important, we promise to share our passion and support your lifetime of adventure.