Sail Chicago owns and maintains a fleet of 12 keelboats for instruction and private use. These boats provide excellent stability and safety with simple layouts designed for easy handling and quick learning.  

Rhodes 19

The Sail Chicago fleet began with the purchase of a brand new Rhodes 19 in the late 1950's. At its peak of popularity, we had close to a dozen operating out of Monroe and Montrose harbors. As these boats have since aged and required more maintenance, we have replaced most of them with Ideal 18's and Colgate 26's. But because the Rhodes 19 design remains solid and well-built, you can still enjoy sailing our remaining ones out of Monroe harbor.

The Rhodes fleet is moored at Monroe Harbor.

Ideal 18

With several convenient features like a furling and self-tacking jib, and a self-bailing cockpit, the Ideal 18 is easy to rig and fun to sail. This is the only boat in our fleet on which we allow single-handed sailing with certification. Stable and fun to sail with up to 3 people, the Ideal 18 is a no-hassle, balanced sailboat. 

The Ideal 18 fleet is harbored at Monroe Harbor.


Colgate 26


Sail Chicago's most versatile boat is the Colgate 26. With an outboard motor, large cockpit, furling jib and small cabin for storage, these boats have all the amenities that sailors love, with the simplicity and handling of a smaller boat. The Colgate was designed for instruction, but also serves as a solid day sailor and racing boat.

The Colgate fleet is moored at Monroe Harbor.

Hunter 34

Priorities is Sail Chicago's 34-foot cruising boat. With a diesel engine, cabin with sleeping berths, head (aka toilet), and a kitchen, it is is a popular choice for those interested in preparing for bareboat charters or simply interested in taking a group of up to 7 people out for an afternoon sail.

The Hunter 34 is located at Belmont Harbor. 

Ericson 34

Calypso is Sail Chicago's 1993 Ericson 34 cruising sailboat built by Pacific Seacraft. She is a beautiful cruising boat that is stiff under a good breeze and ghosts along in light winds. Similar to Priorities, Calypso has sleeping room for 5, an inboard diesel, head, and fully functioning galley. Some of Sail Chicago's cruising classes are taught on Calypso. 

The Ericson 34 is located at Burnham Harbor.