High School Sailing

The Fall 2026 High School Sailing Season is scheduled to run August 31 - October 23. Regattas will run almost every weekend for SailMaine teams.

Registration will open July 31. If we reach capacity we will begin a waitlist. We encourage you to sign up as soon as you can to secure your spot on the team!

SailMaine raises money from the community to support sailing scholarships in an effort to keep the sport accessible to anyone who is interested. You can fill out the application form online with your registration. 

New to sailing dinghies? We have a Development Team to provide direct instruction to get you up to speed before joining your respective high school’s team.

7th or 8th grader looking to sail? Join the Development Team! Dev Team often splits into two groups, one for middle schoolers and one for high schoolers.

For more information on High School Sailing at SailMaine, email highschoolsailing@sailmaine.org.

Returning Registration

New Registration

Helpful Links for High School Sailing

  • FALL 2026 ALL-SAILOR’S MEETING: AUGUST 27th, 6pm, at SailMaine (regular waterfront location). All are encouraged to come.

  • 2026 Fall Regatta Schedule (coming soon)

  • Fall 2026 Regatta Scores (mostly Saturday races, Sunday races are rarely scored online) (coming soon)

  • NESSA Schedule

  • Gear Recommendations/Packing List

  • More info on the mainehighschoolsailing.com website (hosted by SailMaine)

“It’s helped shape me into the person I am today…”

Eva - Portland High School Racing Alum/Junior Program Coach

High School Teams

  • The Cape Elizabeth Sailing Team is a member of the New England Schools Sailing Association (NESSA), a division of the Inter-Scholastic Sailing Association (ISSA). The Capers have a strong sailing record with a young core coming up through the program.

  • The Cheverus Sailing Team is a member of the New England Schools Sailing Association (NESSA), a division of the Inter-Scholastic Sailing Association (ISSA). The Stags have participated in many regional regattas and are the original SailMaine high school team.

  • The High School Development Team is SailMaine’s learn to sail/learn to race program for 7th and 8th graders, as well as high schoolers who are new to the sport. The Development Team is for those who want more training before joining their high school sailing team.

  • The Falmouth High School Sailing Team is a member of the New England Schools Sailing Association (NESSA), a division of the Inter-Scholastic Sailing Association (ISSA). The Yachtsmen have a strong sailing record and recently qualified for the Atlantic Coast Championships in 2019.

  • The Greely High School Sailing Team is SailMaine’s newest team, formed in 2016. Greely is a member of the New England Schools Sailing Association (NESSA), and is continuing to grow.

  • In September 2006, students from Portland High School (PHS) and Casco Bay High School (CBHS) joined forces and successfully won school committee approval for a school sanctioned sailing team at Portland High School. In recent years, the Portland team has qualified and competed in the Atlantic Coast Championship, the National Keelboat Championship, Great Oaks Championship, and the Terk Team Race Championship.

  • Southern Maine High School Sailing Team (SMHS) is a comprehensive high school sailing program for any students in the greater Portland area whose school does not have a sailing team. Students come from Kennebunk to Freeport to participate. SMHS won the Levesque Trophy (ME State Team Race Championship) in May, 2021.

  • Yarmouth joined the SailMaine family as a recognized Varsity Team in the Fall of 2012. The Yarmouth Sailing Team is a member of the New England Schools Sailing Association (NESSA), a division of the Inter-Scholastic Sailing Association (ISSA). Yarmouth recently qualified for the Atlantic Coast Championship!

  • Deering Sailing is one of our newest teams at SailMaine!

    Deering currently practices alongside the Portland High team, and competes independently in regattas.

  • Waynflete is one of our newest teams at SailMaine!

    Currently, Waynflete practices with the Southern Maine team, but has the added opportunity to compete in official regattas.

All practices run 3-6pm and school transportation is typically not provided. Sailors can be dropped/picked up at the SailMaine gate and are welcome to come a bit early and use the space to study etc.

Regattas run on most weekends, typically both days. In many cases the experienced sailors race on Saturdays and newer sailors race on Sundays.

High School sailing costs $690/season.

Drysuits can be rented for spring sailing for $125/season. (REQUIRED for spring sailing)

Practice Schedule

  • Cape - T/Th/F

  • Dev Team - M/T/Th

  • Greevus - M/W/F (Cheverus and Greely)

  • Falmouth - M/T/Th

  • Yarmouth - M/W/F

  • Portland - T/W/F

  • Deering - T/W/F (same as Portland)

  • Southern Maine - M/W/Th

  • Waynflete M/W/Th (same as Southern ME)

Mon - Dev, Greevus, Falmouth, Yarmouth, SM, Waynflete
Tues - Cape, Dev, Falmouth, Portland, Deering
Wed - Greevus, Yarmouth, Portland, Deering, SM, Waynflete
Thurs - Cape, Dev, Falmouth, SM, Waynflete
Fri - Cape, Greevus, Yarmouth, Portland, Deering