Our keelboats offer exceptional stability and safety, making them easy to handle and ideal for quick learning.
Ideal 18
With convenient features like a furling, self-tacking jib and a self-bailing cockpit, the Ideal 18 is easy to rig and fun to sail. Stable and enjoyable with up to three people, the Ideal 18 is a no-hassle, well-balanced sailboat.
Monroe Harbor
Three boats
Rhodes 19
Sail Chicago's fleet began with brand-new Rhodes 19s in the late 1950s that grew to nearly a dozen at its peak. As these boats aged, most were replaced with Ideal 18s and Colgate 26s — though the Rhodes 19 remains a solid, well-built design you can still enjoy sailing today.
Monroe Harbor
Three boats
Colgate 26
Sail Chicago's most versatile boat is the Colgate 26, which combines the amenities sailors love with the simplicity and handling of a small vessel. Designed for instruction, the Colgate 26 excels as a day sailor and racing boat. Features include an outboard motor, large cockpit, furling jib, and small storage cabin.
Monroe Harbor
Eight boats
Hunter 34
Sail Chicago's 34-foot “Priorities” features a diesel engine, sleeping berths, head, and galley, accommodating up to seven guests and is popular for bareboat charter training. Some of Sail Chicago's cruising classes are taught aboard Priorities.
Belmont Harbor
One boat
Ericson 34
Calypso is Sail Chicago's 1993 Ericson 34 cruising sailboat built by Pacific Seacraft. She is a beautiful cruising boat, stiff in a good breeze and nimble in light winds. Calypso sleeps five and features an inboard diesel, head, and fully functioning galley. Some of Sail Chicago's cruising classes are taught aboard Calypso.
Burnham Harbor
One boat