Social & Competitive Sailing

Community Boating offers racing almost every day of the week! Racing is a fun and challenging way to get more out of the sport. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly and competitive community. Hone your boat handling through competition and learn racing rules and strategies through classes. See our different racing opportunities below and learn how get involved, whether you’re a seasoned vet or completely new to sailboat racing.

Friday Night Informal Racing

Members organize several short races most Fridays after work. Racing is informal, so boats can join at any point in the evening. A social atmosphere blending camaraderie, fun, sailing, and competition; meet new people and broaden your sailing horizons.

Who: All skill levels welcome; whether you’re a national champ or are just learning you’re encouraged to sail with us.
When: Rig anytime and head out to race as soon as a few boats are ready and a course is set — usually about 17:30. Racing ends at sunset, so come out even if you free up a bit later.
Where: Meet on the water. Look for a cluster of Mercuries, the nearby committee boat flying flags & sounding horns, and big red tetrahedrons.
What: You can race mainsail, sloop or spinnaker, solo or with friends, keel or centerboard, as long as it’s a Mercury.


See our blog below for updates, rules & racing tips, watermelon announcements, and hilarity. Sign up for email updates so you don’t miss a post; typically weekly or less:

Or join by sending a blank email to [email protected]

Unsubscribe by sending a blank email to [email protected]


Tiller Club Racing

Tiller Club is a community of CBI sailors with the goal to promote racing at all levels.

What: We run seasonal racing series, trophy regattas, single-handed events, and races in keelboats and dinghies, in boats provided by CBI.
Who: Skippers with knowledge of the Racing Rules of Sailing and the Tiller Club Sailing Instructions. Novice and experienced crews welcome. Come with a teammate, or connect with one at CBI (two sailors per boat unless specified).
When: Sunday mornings ~09:30 to rig/register before 10:15 competitors’ meeting. No race starts after 13:30 on series days, or 14:30 for trophy events. See schedule for details.
Where: CBI main dock, rain or shine.
Cost: $5 per boat to cover trophies and administrative expenses.

Getting Involved

Come down on race day! We can often connect you with an experienced skipper and get you racing on day one. Arrive ~09:30 and let us know you’re looking to race; we’re easy to find as we’re often the only group there so early!

  • Learn To Race class series for new racers, or those needing a refresher
  • get your Tiller Club rating by completing a test on the racing rules of sailing (CBI membership required)
  • regular, experienced participants are expected to assist with Race Committee occasionally; we’re volunteer driven
  • Like our Facebook page for weekly results, photos, etc.
  • Sign up for our Tiller Club Google Group for important updates or to connect with skipper/crew
  • With questions, email [email protected]
  • intermediate & advanced racers: CBI hosts offer a series of practices to sharpen your skills

Tiller Club Executive Board 2020

Commodore: Marcelo Pereira
Vice Commodore: Robin Weatherill
Steward: Cole Constantineau
Members at Large: Janne Nappe, Matt Hebert, Alisha Reppucci, Steve Albertelli

Documents & Links

Learn To Race

Tiller Club volunteers teach classes and clinics designed to introduce sailors to the competitive sport, and to expand the horizons of experienced racers.

Learn to Race Class Series

Our Learn To Race class series is designed to demystify sailboat racing for the intermediate sailor with little or no racing experience. The course is taught in three 90-minute chalk talks — Intro to Racing, Basic Racing Rules, and Basic Racing Strategy.

While all three lessons are on land, the instructor will also provide details on several opportunities to put your new skills to the test on the water, including those below and at

Who: Members with Mercury Yellow rating (Jib class suggested)
When: See schedule and sign up in advance through the Online Member Portal

Novice Racing Clinics

For first time racers, this companion clinic will help put new skills and knowledge from the Learn-to-Race classes into practice. Learn through practice starts, races with on-the-water support, and a debrief afterwards. Tiller Club members will help introduce first-time racers to the sport, directing them to understand the course, locate the marks, and comprehend the starting sequence in order to get around the course properly their first couple times.

Who: Members with Mercury Yellow Rating who have taken LTR part 1
When: See schedule and sign up in advance through the Online Member Portal

Intermediate & Advanced Instruction

CBI volunteer instructors run intermediate race practices geared towards regular CBI racers.

High Performance Racing

We’re a friendly group of CBI members interested in the speed and excitement of sailing and racing 420’s and Lasers. Our group is dedicated to improving our sailing skills, while having fun on the water through informal racing. Most weeks, we run several short races with no score-keeping, so boats may join at any point in the evening.

Who: Whether you were a college all-American or just learned the racing rules through CBI’s Learn To Race class series, you’re welcome to sail with us. A 420 or Laser rating is required to skipper. Crew may have any rating, but must match up with a skipper.
When: Monday evenings starting after 17:00. We head out to race as soon as a few boats are rigged and a course is set. Racing ends 30 minutes before sunset.
Where: CBI main dock, rain or shine. If arriving late, meet us on the racecourse.

Contact & Updates

To see important updates, ask questions, or match up with a crew/skipper, join our CBI High Performance Racing google group. Or subscribe by sending a blank email to [email protected].

Note that Google Groups allows you to control the frequency of emails as there is often a high volume on summer Sundays/Mondays.

Women’s Racing

The mission of Women’s Racing is to advance the sailing skills of women at CBI through racing and practice in a challenging, supportive, and social environment. We welcome women at all levels of experience interested in competitive sailing, as well as improving skills for coed racing and for recreational sailing. Women’s Racing complements CBI’s classes and other racing opportunities, and uses the Mercury, 420, or keelboat fleets depending on conditions and attendance.

Women’s Racing is a lot of fun and a great opportunity to meet other women sailors
When: Summer Thursday nights about 17:30
Where: Check our small white-board on the Bay 2 ramp for weekly updates

To receive updates about Women’s Racing join our Google Group at:

Keelboat Racing

An inclusive group of CBI members interested in the teamwork and power of sailing and racing Sonars and Ideal 18’s. We’re dedicated to improving our sailing skills and building camaraderie, while having fun on the water through informal racing.

Keelboat Racing is organized by CBI staff every Wednesday Night starting in May, and will race on Sonars and Ideal 18s. Sailors include members from both the Adult Program and Universal Access Program. We hold a competitors’ meeting at 17:30 to brief sailors about the course, rules, and answer questions. We return to the dock approximately 30 minutes before sunset and hold a debrief on shore.

All are welcome to attend; UAP members should RSVP below:


Intermediate Racing Practice

Geared towards experienced racers, these on-water practices are run by Tiller Club volunteers. Each practice will include briefingdebrief, a structured practice environment, and on-water feedback. Drills vary per attendance and wind conditions with focus on improving boat speed, boat-handling, tactics, and other racing techniques in Mercuries.

Who: Regular CBI racers with Mercury Red rating
When: See the schedule post on the blog
Where: Please be dressed and rigging on the front of the dock at the start of practice
Sign up each week after reading the day’s briefing in our blog below:

Friday Night REBOOT
Weekly on Fridays 17:30 – 18:30 We’re back at it by popular demand, with a revised format. Join Charlie and Niko to chat briefly about… Read More 
April 3, 2020 Fireside Chat w/ Sam P.
Fireside Chat Hi All, With CBI being closed until further notice due to COVID 19 I have been trying to think of a couple ideas that we could do to… Read More 
July 16, 2019 Practice Briefing
Last practice today. We’re going to work on starting practice and boat-handling. We’ll start with the starting practice, then do some boat… Read More 
July 2, 2019 Practice Briefing
Great breeze out there today. Should be fun on the water, and the temp is really nice too. I’d like to set up some two-boat speed testing, we’ll… Read More 
2019 Practice Schedule
We will have practice just a few weeks this year, on Tuesday evenings. Please be dressed and rigging on the front of the dock by the start of… Read More 
Windsurf & SUP Racing

The CBI Windsurfing Community is a diverse group of people, who share a love for water sports; world class windsurfers and beginners having fun and learning from each other. We race the BIC One Design 293 with a 7.8 rig, but you can go with a smaller sail if you feel more comfortable (or more competitive).

Who: All windsurfers with a yellow rating are welcome, whether you’re a pro or just learning the racing rules through CBI’s Learn To Race class series.
When: Every Wednesday evening between Memorial Day and Labor Day at 17:30 (rigging starts earlier). We will run several races, and go until sunset
Where: Meet at the windsurf shed. Don`t forget to check out at the dockhouse before rigging.

SUP Racing


Stand Up Paddling and Windsurfing is a great combination to stay in shape ?

Contact & Updates

To see important updates, ask questions or simply enjoy our community please join our Community Boating Windsurfers Facebook Group.