Heather Richard is a skilled sailor, an exceptional teacher, a great storyteller, and a kick-ass mother! As a high school graduation present for her son, they double-handed in the Pacific Cup Race to Hawaii, aboard the boat on which she raised him! Heather and I talk about prepping for this race, the crossing, and the long sail back. We discuss why she’s decided to sell her boat and what she’s looking for next. After hearing her story, you can sail with Heather at Fine Day for Sailing.

Raffi Patatian is one of the most conscientious, careful, and knowledgeable sailors I know. He set off for Mexico aboard his Hallberg Rassy 43, Wind River, in the fall of 2023. Since then, he has sailed many miles down the West Coast and across the Pacific Ocean, mostly singlehanded. He’s an entrepreneur who ran his own IT business in the Bay Area before heading off cruising. Raffi and I caught up at his Sausalito home when he briefly returned from Fiji to pick up some boat parts.

Jamie and Behan Gifford have been sailing their Stevens 47, Totem, around the world for more than a decade. They raised three children aboard but are now empty nesters, planning the next chapter of their cruising life. Lauren and I joined them aboard Totem to discuss life afloat, upgrades to their beloved boat, their successful coaching business, and their upcoming sailing plans. (Photo by Jill Hearne)

Jon Bilger is the director and founder of PredictWind. Jon founded the company after working on forecasting for the Alinghi Americas Cup team. The technology has revolutionized accessibility of weather forecasting and routing for both racers and cruisers. I talk to Jon about his own sailing background, how he developed Predict Wind, some new exciting tools - like 100 meter accuracy tidal current modeling for San Francisco Bay - and more.

John Taussig is the founder and executive director of Backcountry Medical Guides and the subsidiary Maritime Medical Guides. He’s a career paramedic who’s worked on helicopters, in ambulances, on ski patrol, as a ranger, and as a captain on boats. He’s a surfer, climber, kayaker, mountain biker, snow boarder, sailer, and and all around adventurer based in Bellingham Washington. John and I talked about responding to bear attacks in Yellowstone, commuting to work from Santa Cruz to Monterey via sailboat, flying on choppers through the Sierra as part of a air medic team, his trip paddling and sailing a kayak from Washington up the inside passage to AK, and more.

Michael Rohde is rebuilding - bow to stern, keel to masthead - a late 70s Cape George 36 named Akela. He welcomed me aboard the boat last August when it was on the hard at Napa Valley Marina. He’s jumped into this major project with both feet and is making good progress. Inspired by other YouTubers, he’s documenting the entire refit on his channel RohdeSoda.

Andre Lay is licensed Captain from the Bay Area who is in the process of circumnavigating North America in a compact trawler. He’s currently in Barra de Navidad on the Mexican mainland and is soon headed for El Salvador. He is doing this trip simply to prove too himself he can, to meet people, and to see what’s out there. He’d also like to raise awareness for Chronic Fatigue Syndrome, but as Andre says” I’m not trying to change the world by going around it. I’m just out there to experience it.”

Scott Racette and Ashley Gremel met sailing in San Francisco Bay in 2016. Five years later they sailed under the Golden Gate Bridge together aboard their Pearson 365, Azimuth, to begin a trip from the San Francisco Bay to the Chesapeake Bay. Along the way they adopted a cat, transited the Panama Canal, fixed leaking through-hulls, and learned a whole lot. I talk to them about the adventure.

Brendan Borrell is a corespondent for Outside Magazine. Along with photographer Tom Fowlks, he recently paddled from the Central Valley of California to the headwaters of the San Francisco Bay. Taking advantage of a very wet winter last year, which led to the reformation of Tulare Lake, they paddled over flooded farmland, up irrigation ditches and down rivers, braving putrid water, a sinking boat, being shot at, and nearly being arrested. An article about the adventure titled My Wild Wet and (Sometimes) Miserable Paddling Trip Through the Heart of California, with words by Brendan and photos by Tom, appears in the November/December issue of Outside Magazine.

As my wife, two daughters and I prepare to move aboard and sail south aboard Dovka, our 1981 Hallberg Rassy 352, the four of us sit down with my parents Sid and Rebecca shaw to talk about the boat--which they used to own--and our coming travels. Follow our trip at www.Dovka.com