Sneak a peek at the trip highlights from this past season with Heather on our Women's Sailing page.
At 8 years old, Heather Richard followed her gut and joined the Community Boating Center on the Charles River in Boston. For $1, she gained access to sailing dinghies with a diverse group of inner-city kids who also shared her adventurous spirit.
As she put it, “I found my tribe,” and little did she know that her life long career in sailing had begun.
Unlike most yacht clubs these days, this club was not full of wealthy sailing families. Heather and her new crew would end up soaking wet in their jeans and converse shoes after a day sailing on 15’ Cape Cod Mercury’s.
In the cold New England winters she describes how they would soak the jib sheets in antifreeze the night before and “...go out and sail until the antifreeze wore off and you couldn't un-cleat your jib sheet!”.
Her enthusiasm for the sport morphed into raw skill and soon she began winning races against the fancier yacht club kids. Seeing her talent, Heather was poached by the adults sailing the Rhodes 19’ and J24’s to be their foredeck ninja.
She then met Hatch Brown, a sailing coach at MIT who became her first true sailing mentor. With Brown, “Everything was always methodically explained in a calm voice, and I think I try to this day to teach that way,” she explains. In addition to the lessons learned from his demeanor, Brown also developed Heather’s technical understanding of sailing. She shared how “He’d take our rudders away and make us sail rudderless” and “we’d get blindfolded, and the crew had to tell the skipper where to drive.”
Knowing that she wanted to continue sailing, Heather got a job as a skipper with Sail Caribbean Voyages during her college summer breaks. In reflecting back on the experience, she laughs while explaining how unqualified she was for this role, being only 19 years old, and why she thinks they teamed her up with “Delly”— a legendary old salt and engineer who had worked in the harbor. He, being the oldest crew member, was appropriately matched with Heather, the youngest.
From the start, Heather confessed to Delly her fear of the mechanical side of the boats, and how...
“His way to get me over that fear of the engine room, was to start taking things apart and making me put them back together. It was more creative than I thought it would be and less of a mystery than I thought it was.”
This set the foundation for her skills as a Captain, where one of the most important things is owning the ability to fix the many things that can and always break on sailboats.
While most captains may not see fixing broken boat systems as creative, when Heather wasn't sailing, she was studying sculpture and education at Boston University. Her creative side came through in sailing when she got to use her hands, something that was very natural to her. After the kick start in the engine room with Delly, Heather has continued to cultivate this skill over years. To this day, she does her own mechanical work on her custom built solent rigged aluminum sloop, that she lives on full time in Sausalito with her three kids.
In addition to sailing and the arts, Heather had been studying education and was offered an opportunity to move to Japan and develop a recreational sailing course for the US Navy. She created a curriculum, and went to work to break through the shy demeanor of the Japanese girls she was training, who were not used to do anything co-ed, as the girls and boys were always segregated.
This experience made her more aware of the fact that being a woman skipper was unique, as otherwise evident by the lack of women sailors she encountered in her early career. She didn’t know another female captain for many years. Yet, what made Japan most unique was she learned from the start that differences between men and women meant success would depend on using different types of feedback and debriefing practices.
Outside of the course she was leading, she had the opportunity to sail aboard Steve Fossett's infamous trimaran that would sail upwards of 20 knots. She remembers looking up at the windward side of the trimaran flying an alma in the air, and thinking “I need to run 70 feet UP this boat to make it through the tack!”.
Through her lifelong career in sailing, she has always continued to push her limits, to take on new experiences and gain knowledge across a wide variety of vessels. Part of that can be attributed to an important decision she made in taking on so many sailing roles. She shares,
“I had to very, very consciously decide that I was capable of becoming a captain of a big boat and running a boat myself and running a crew and, you know, just wearing that hat. It was a very conscious moment where I was like- no, I'm not gonna just gonna be stuck in the female role forever.”
Since 2000, she has parlayed this narrative and diverse training opportunities into becoming the race coach at the prestigious Saint Francis Yacht Club, running solo charters on her own boat, cruising 5,000 nautical miles with her kids to Mexico, and Captaining the 100’ tall ship Matthew Turner all from her current home of the San Francisco Bay area. Additionally, she also serves her community in Sausalito as part of the Gailee Harbour co-op, where lives on her sailboat with three kids, and volunteers with the Spaulding Marine Center to offer craftsmanship and youth sailing programs. But perhaps what is most impressive, is her ability to break through norms and inspire women to find their own narrative and skillset to become sailing pros.
Really what she’s seen is the importance of women seeing women doing the things they want to do. And not just doing the thing, but really succeeding at it. With her generation perhaps more than with women today, she explains “they've spent their whole life taking care of other people, so it's hard for them to focus on the role that they're given in that moment.”
Motherhood, in addition to being a woman, plays a role as well. She’s seen that in women-only sailing crews,
“all the women are kind of caring for each other, the way women do that, you know, especially moms…it just sets the stage for more learning to happen.
Whereas if you're in a mixed group, often the women will be distracted, caring, or thinking about people's comfort and not learning what's being presented, and the men will pick it all up because they're not thinking about anything except what you're teaching them”.
Her role as sailor, artist, teacher, community organizer, woman, and mother all add up to make Captain Heather Richard who she is today. Her squeaky clean safety record, salty charm, and love for the ocean, is what has drawn people to her to teach Women Sailing Events with OCSC in Berkeley and is what will make Cruisers Academy’s Women's Sailing Courses in the Sea of Cortez, something not to be missed.
Heather will be running two trips out of Puerto Escondido, a protected bay sitting 30km south of the historical town of Loreto on the Eastern side of Baja. The goal of the course is to sail out to the nearby islands of Isla Carmen, Isla Danzante, or possibly to the Baja peninsula anchorage of Agua Verde. These islands offer protected anchorages from many angles that could include beautiful hiking, paddle boarding, or exploring a natural Salt Flat in addition to practicing sailing skills.
We'll be opening bunks for each leg, and accepting only 2-3 students for each passage to keep things personal. This will be a dynamic learning environment, with the opportunity to put to work any sailing experience you may already have with lots of room to include new lessons and first hand experience of living the sailor lifestyle. Students will be taking part in every crew role , from sailing and navigation, anchoring, jumping into the cooking rotation, taking care of Lintika, and learning how to be the best crew member possible.
Join Heather on a Women's Sailing Course in the Sea of Cortez this January 2025 by joining the waitlist here.
Topics covered in the 6 day sailing course will include… Weather forecasting
Passage planning
Essential safety offshore
Boat systems
How to keep watch both day and night
'Best Practices' aboard
International sailing logistics
Anchoring
Provisioning & cooking underway
Crew dynamics and responsibilities
Highs and lows of living aboard
Lots of time at the helm and working the lines
How to adapt to whatever Poseidon throws at us!
Women's Sailing Course in Mexico this upcoming season!
All courses will be taught on SV Lintika, Cruiser Academy's Passport 42'.
This blog was brought to you by Kira Kessel, a young Cruiser who sailed the South Pacific with her family and is enraptured by the cruising lifestyle!