High School Sailing

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The Basics of Sailing

Sheridan Shore Sailing School is dedicated to teaching the basics of sailing and sportsmanship. We are enthusiastic to have students of all ability levels join the program, because beginning sailors often go on to become some of the best racers in the Midwest. 

The Fall & Spring Seasons

Fall is a unique and exciting time to sail. In addition to 420’s, single-handed boats called Lasers join the mix.  Fall sailing is fleet racing orientated. Sailors may have the chance to participate in regattas against schools throughout the Midwest. The team’s main focus in the fall is preparing for the two major regattas: the Cressy National Championship and the Great Lakes Championship. Spring sailing fosters a team atmosphere through competition and extreme conditions. The season is orientated around the two national Championships: the Toby Baker Team Race National Championship and the Mallory Championship.

The Collegiate 420 Sailboat

The  collegiate 420 is a double-handed dinghy that has two sails. Named for the hull’s dimensions of 4.2 meters, it is one of the fastest growing double-handed dinghies in the United States. It is most commonly used for college and high school sailing. Regattas consist of an estimated twenty-five races each of which lasts approximately 15-20 minutes.

 Fleet Racing

Fleet racing is a very classic type of sailboat racing. For high school competitions, fleet racing is held in a two-division format composed of an "A" and "B" division. The objective in fleet racing is for each boat to perform at its best. A boat's place in its division is determined by the sum of its finishes. Each school's A and B division scores are combined to determine the overall winner of the regatta.

Team Racing

Team racing is a relatively new format of sailing competition. Unlike fleet racing, only two schools, with three boats each, compete at a time. The sum of the three boats' finishes for each school determines which school wins that race. Over the course of the regatta, each school will compete against every other team at least once. The winner of the regatta is the school with the best record. This type of competition allows sailors to use unique tactics, strategies and teamwork, which results in close finishes and suspenseful racing.


Loyola Academy Timeline

1991 - Founded:Andy Grohe & Dugan Okean
1996 - Baker Nationals
2000 - Cressy Nationals Vincent Porter
2000 - Baker Nationals
2001 - Cressy Nationals Vincent Porter
2001 - Baker Nationals
2002 - Cressy Nationals Vincent Porter
2002 - Mallory Nationals
2005 - Cressy Nationals Andrew Criezis
2006 - Baker Nationals
2009 - Mallory Nationals
2010 - Mallory Nationals
2011 - Cressy Nationals Alex Post
2011 - Mallory Nationals
2014 - Mallory Nationals
2014 - Baker Nationals
2015 - Keelboat Nationals
2015 - Cressy Nationals RJ Porter
2015 - IL State Champions
2019 - IL State Champions (2nd Place)


Varsity and Junior Varsity


Competing on the state, regional, and national levels, the Loyola Academy sailing team is one the most competitive and highly achieving teams in the nation. Loyola has qualified for Mallory, Cressy and Baker National championships. The JV and Varsity teams, comprised of 20 sailors, compete each weekend at regattas spanning the seven states that comprise the Midwest region of the Interscholastic Sailing Association. 

The team sails out of Sheridan Shore Sailing School, which is located at Wilmette Harbor in Gillson Park on Sheridan Road. The team sails on collegiate 420’s, which are provided by the sailing school. During the fall season students may also sail in Lasers, which must be privately owned. The coaching staff determines placement based on sailing experience and performance. 


Sailing Club

For the past eight years, the Loyola Academy Sailing Club has been the largest single high school sailing program in the nation. The coed sailing team usually consists of approximately 70 students, and includes all grade levels. The team has two seasons, Fall and Spring, and a student can participate in one or both. The team welcomes both new and experienced sailors. Additionally, many JV and Varsity sailors attend the Sailing Club practices to help develop the skills of less experienced sailors. Also, a number of Club team sailors will have the opportunity to travel to regattas in the Fall. 

Evanston Sailing Timeline

1999 – Founded
2013 – Shepherd Cup Champions
2019 - IL State Champion



The Evanston Township High School Sailing Team was found by only a few sailors in 1999. The Varsity team, now comprised of 8 members, competes each weekend at regattas spanning the seven states that comprise the Midwest region of the  Interscholastic Sailing Association. Since 1999, the team has competed in several national qualifying regattas, won the Shepherd Cup Championship, and consistently performs well in the Midwest region. 


Orange Blue

Named after the school colors, "Orange Blue" is the Evanston club sailing team. The team welcomes both new and advanced sailors. Additionally, many Varsity sailors attend the Club team practices to help develop the skills of less experienced sailors. The team finished the spring season of 2015 with 20 members, which makes it one of the largest sailing teams in the Midwest.   

Beacon Academy

Beacon burgee.png

Beacon Academy Timeline

2015 - Founded
Fall Scramble

Varsity and Junior Varsity

The Beacon Academy sailing team competed in its first MISSA regatta in the fall of 2015 and since then, sailing has become one of the most popular sports at Beacon.  The team has two seasons, Fall and Spring, and students can participate in one or both. The team welcomes new sailors as well as experienced sailors. The varsity team competes in MISSA regattas most weekends in the spring and fall.


Midwest Inter-Scholastic Sailing Association

The Interscholastic Sailing Association (ISSA) governs secondary school sailing in the United States, in both independent and public high schools. Sailor eligibility starts at the ninth grade and there are no age limits. As in college sailing, there are seven district associations which schedule events, as well as a system of national championships. While ISSA had its origins in the preparatory schools of the Northeast in 1930, it is now a nationwide organization with active districts in Northeast (NESSA), Mid-Atlantic (MASSA), South Atlantic (SAISA), Southeast (SEISA), Midwest (MISSA), Pacific Coast (PCISA), and Northwest (NWISA).

MISSA was established as the regional governing body for high school sailing in the Midwest. Their objective is to further the sport of sailing in Midwest secondary schools, and to provide a standardized set of rules and procedures for competition. Currently, there are 55 member schools. This number varies from year to year but has been fairly steady for the last several years.

Schools schedule dual meets for team racing and compete in open and closed fleet racing events, mostly in double-handed dinghies. There is some single-handed competition, and there is a National Single-handed Championship (Cressy Trophy). School teams reach the Nationals by competing successfully in district championships. Other National Championships are the Baker Trophy for team racing and the Mallory for two-division fleet racing in double-handed dinghies.

MISSA Pipeline


Sheridan Shore Sailing School will be continuing the MISSA Pipeline this fall due to the positive responses of the last couple years. The program introduces 6th, 7th and 8th graders(Junior High School) to High School Sailing.  MISSA (Midwest InterScholastic Sailing Association) is the Midwest governing body for High School sailing in the United States.

The MISSA Pipeline will be held 10:00 am – 2:00 pm every Sunday starting September 10th through October 15th. We will not have a lunch break, but bringing a snack and refillable water bottle is highly recommended. The program has ten available slots. Sailors that participated in the summer only need to fill out the Application Page. The Pipeline coach is one of the assistant coaches for the nationally ranked Loyola Academy and Evanston Township High School sailing teams.  The course will focus on advanced boat handling techniques, sail trim, and beginner racing rules and tactics. This program gives sailors the opportunity to improve their skills and get informed on what high school racing involves.