Racing is Fun, it's Invigorating and it Tests Your Skills as a Sailor Like No Other Endeavor Can.


Wednesday Nights we race out of Monroe Harbor.

Join Us
to learn or test your skills against the best.

Click Here to Buy a Racing Five Pack and save $125. May be used for any Wednesday Night Race.

At Sailboat-X.com we not only teach you racing strategy but actually have you participating in Chicago’s highly competitive races, guided by our experienced crew members.

In our fleet we have our T-10, Eleanor Rigby. The T-10 fleet is the largest class sailing in Chicago with 51 boats registered. It is highly competitive with 20 to 30 boats showing up to major races. There is no complicated handicap needed to score the boats since they are all the same. First one over the finish line wins, It’s purely how great your crew works together and how well prepared you are.

We also have our smooth sailing J/35, Ob La Di!. With her lightweight, uncomplicated rig, and simple deck layout she’s the perfect boat to start your racing journey. She’s a fast boat with a responsive yet forgiving nature. It’s a great way to introduce the whole family to the fun, adventure and excitement of sailboat racing.

At Sailboat-X.com, we are always learning, always racing and always having fun. Here our crew really is your family. Sign up today to start your adventure of a lifetime.

We do the Chicago to Mackinac Race (starts Saturday, July 21, 2018) and we do the Tri State Race over Labor Day Weekend. Both of these races are by invitation only.

2018 Day Event Club Type Boat Call
July - 21 Sat  Chicago to Mackinac Island - Pic CYC Port-to-Port   9:00 am
Aug - 31 Fri Tri-State, IL to MI - Pic ColYC Port-to-Port   5:00 pm
Sept- 2 Sun Tri-State, MI to IN - Pic MCYC Port-to-Port   9:00 am
Sept- 3 Mon Tri-State, IN to IL - Pic JPYC Port-to-Port   9:00 am

Buckley's Quote

"Sailboat racing is analogous to
standing under a cold shower,
fully dressed, ripping up thousand
dollar bills."
      - William F. Buckley, Jr. - 1975

Baird's Quote

"Sailing is a game," says American's
Cup Winning Helm and Coach Ed Baird adding: "You have to be patient, you've got to make the right choices for the moment and then let time prove you right."



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You're Always Learning

Here is Your First Racing Lesson:

Be a part of the team. Leave your ego on the dock, know each position but do your job first and let your teammates do their jobs. Don't step on or over others, literally and figuratively.


Your Second Racing Lesson:

At any moment;categorize your teammates and yourself into one of two groups: One group is responsible at that moment for sailing the boat fast and the other group is responsible at that moment for changing the sail plan fast.
Now, when a situation comes up, as they always do, your first decision is to categorize this situation as in or out of your group's purview. If it is in, fix it. If it is out, keep doing your job and let the other group fix it.