"Any damn fool can navigate the world sober. It takes a really good sailor to do it drunk." - Sir Francis Chichester when asked why he carried so much alcohol on his solo sail around the world.


 2020 Bootlegger Races (tentative)

(Only race dates shown. For delivery dates consult the calendar page)

 LMSS Doublehanded Championship (June 11 - 13)

Visit Port Washington -

GLSS Chicago - Mackinac Island Solo Challenge (June 20 - July 2)
(May enter the Super Mac and Back) (Race registration and more)

82nd Queen's Cup Race (June 26 - 27)
(Postponed Until ?)
Probably with crew, maybe doublehanded

Plan now to enter the 82nd challenge of one of the most storied yacht races on the Great Lakes. This year’s night race across Lake Michigan departs from Milwaukee, WI for Grand haven, MI on June 26, 2020.
Both Milw
aukee’s South Shore Yacht Club and the Grand River Sailing Club will provide an experience worthy of this 82nd Queen’s Cup Race.

START: festivities, friendly accommodations and the traditional over-the top pre-party at SSYC’s Harbor of Hospitality on Thursday June 25th, plus Milwaukee’s world-famous SUMMERFEST music festival.

FINISH: the day begins with brunch, transitions into lunch, followed by the awards ceremony, an evening dinner buffet, and finally a great party until midnight.

The race is open to all boats with a valid 2020 Lake Michigan Performance Handicap Racing Fleet (LM-PHRF) rating certificate and Offshore Racing Rule (ORR) rating certificates. We will continue to have starts for the shorthanded fleet (with a limit of two crew per boat) and a cruising fleet for non-spinnaker monohulls.

We are looking forward to increasing the participation of one design boats such as the J/105, Beneteau 40.7, Beneteau 36.7, and Tartan 10s. The racing between these boats and other one design boats has been close in prior years.

Get the latest updates at and ...
Follow us on Facebook

37th HOOK Race (single-handed or with crew  (July 18 - 20)

LMSS Solo/2X2 (August 14 - 15)

"SOLO / 2X2 – a singlehanded race run since 1981 (now with a double handed section)—takes place usually every other year on the third Friday of August.  The next race date is Friday, August 14, 2020.  This singlehanded challenge is intended to encourage adventure, self reliance, and competition in the tradition of singlehanded sailing.  While also a race, the primary focus of this challenge is accomplishing the goal of completing the course – relying on oneself, yet enjoying the camaraderie of like minded sailors.
We include a separate division—the doublehanded 2X2—as an introduction to the spirit of the singlehanded challenge.

Course: From the starting line, Racine, Wisconsin, around Buoy “R 4” seven nautical miles due east of Glencoe, IL, around the NOAA Southern Mid Lake Weather Buoy (Station 45007), around Buoy “G 1” at Milwaukee Harbor, around the Wind Point North Shoals Lighted Buoy #14 near the Wisconsin shore and return to finish line at Racine. A distance of approximately 135 nautical miles. The “R 4”, NOAA Mid Lake Weather Buoy and “G 1” must be left to port. Wind Point North Shoals Lighted Buoy #14 must be left to Starboard.

Personal Qualifications: Solo entrants must be experienced sailors. Entrants who have completed previous Solo races are automatically qualified. Other entrants must provide evidence of experience, including a documented singlehanded passage of at least 50 miles and including a statement of other experience sailing or racing offshore. New entrants will have until August 1, 2020 to complete the 50-mile passage.

Notice of Race: Please see the previous 2020 Notice of Race (pdf) for further details, yacht eligibility, and a printable entry form. Alternatively, you can fill out our online entry form, optionally attaching scans or photos of your race documents, and even send payment via PayPal.

Race Date: Friday, August 14, 2020

Entry Deadline: August 1, 2020. Late applications will be accepted up till August 11, but may not include the free shirts or a participation flag."

Tri-State Regatta - Chicago to St Joseph, MI (Sept 4 - 6

Louie's Last Regatta (Sept 26)