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Sunday, October 5, 2025

SUNDAY REVIEW / LET'S GO SAILING WITH JENNIFER




Editor's Note: For the next year, this blog will publish stories by Jennifer Silva Redmond, a literary gypsy, who has lived aboard the yacht that she and her husband sail the Americas. A long time voice in book publishing, she recently launched a memoir of her own: Honeymoon At Sea, a romance with husband Russel and the sea. When we asked Jennifer for a paragraph long bio to launch the beginning of her posts with PillartoPost.org she submitted the following. Yes, it's a bit longer than we asked but life is full of surprises. Our 14-year-old daily blog is delighted Jennifer ignored our paragraph request. Please meet Jennifer Silva Redmond: 

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Jennifer and Russel
How did a 28-year-old young actress living in New York City end up spending the next 36 years of her life on a sailboat on the West Coast of North America? 

 Well, when Russel proposed to me we’d just spent the day sailing San Diego Bay on board his 26' Columbia, Watchfire, so I knew what I was getting into. He wanted to travel and had been preparing the boat to go cruising. I was living in New York City—not the ideal place for a sailboat. Russel said he was willing to move East and relocate his illustration business, since I was enjoying some hard-earned success as an actress in NYC, adding that he could ship the boat to Long Island and we’d sail when we could, while pursuing our careers in the city. I changed that sensible plan one day by asking the man I was about to marry what he would like to do more than anything. 

He answered that he'd like us to sail down Baja and up into the Sea of Cortez while he painted the area. It sounded so good—I was a California girl who loved the sun and the water and after six years, was getting a little tired of the Big City. However, I knew nothing about sailing. I'd only been a passenger on the boat in San Diego and it wasn’t clear if I could learn to love it as much as Russel did or even enough to enjoy myself. 

But it seemed an ideal way for us to spent a lot of time together building a strong foundation for our marriage as well as being productive for him and relatively inexpensive. We decided to do it. Nine months later, in November of 1989, after a wedding, dozens of boat jobs, and seemingly endless preparations, we untied the dock lines and sailed south. 


I learned to tolerate sailing and to enjoy what sailing meant—living in beautiful spots that were hard to get to—and more often inaccessible—by car. I fell in love with Baja and we ended up staying for a year in the Sea of Cortez, spending a majority of that time sailing and anchoring in the waters around Puerto Escondido and La Paz. 

Then we headed south, spending a few months along Mexico’s Gold Coast and Central America. We went through the Panama Canal and sailed up to Florida where we lived for a year in a marina near Sarasota, with Russel getting his paintings ready to exhibit, and me waiting tables and bartending. Then we sailed along the Intercostal Waterway along the US Gulf Coast to Texas, where we hauled little Watchfire out and trucked it back to San Diego. 

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Then, a couple of years later, in June of 1996, we sailed down to Baja again, and spent three more years in the Sea of Cortez. While we were there, we started a magazine called “The Sea of Cortez Review” which was a collection of stories and poems about Baja, beautifully illustrated and designed by the Uber-talented Russel. 

We did three annual versions, with the last issue in 2000 being published and distributed by Sunbelt Publications of San Diego, a small press that specializes in books about California, Baja California, and Mexico. 

I fell in love with Sunbelt and the feeling was mutual; I worked for them for 11 years doing marketing and acquisitions, and was Editor-in-Chief when I left to become a freelance editor. I am still their Editor-at-Large, always keeping my eye out for great San Diego publications and partnerships. 

Russel sold many paintings over those years, but also began teaching screenwriting at San Diego City College, where he is still an adjunct professor. 

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One sad note: In 2003, we were living aboard Watchfire up at a friend’s ranch in Harbison Canyon, near Crest. Our plan was to fix up the little boat and sell it along with the trailer we’d bought to transport it back from San Carlos, Sonora, Mexico back in 2000. 

Our friends had offered us a place to live and work in the shade of dozens of old oak trees in their home’s vast “backyard.” In October of that year, the Cedar fire began out in the backcountry and moved toward the city of El Cajon. Our friends evacuated their house and advised us to do the same, “just to be safe,” so we drove out in my new-to-me Nissan and our old Dodge RV, leaving Watchfire and our 1970 VW Van behind. 

The fire became a firestorm as it came down that valley and nothing in the canyon survived. We lived in the RV for a few months, then moved into a friend’s La Jolla home to housesit while she traveled, and one day while having tea on the patio I saw an ad for a 35 foot Coronado. I knew the boat was much like a big Columbia 26, so I pointed the ad out to Russel. 

We went up to Newport Beach and bought Watchfire 2 in August of 2004. After we moved it down to San Diego, we lived aboard in Harbor Island for 6 years, while I worked and Russel worked on the boat any day he wasn’t teaching. In the spring of 2011, after my jump into freelancing, we took off for Catalina, where we enjoyed being on a mooring in glorious Avalon. 

The rest of the summer was spent in Los Angeles, working on producing a screenplay that Russel and I had written that spring. The next few years were spent living on the boat in the winters, much of that time spent on a mooring in Coronado Island. 

We found our dog Ready, a small red rescue mutt, at PAWS in Coronado; she was little, with a big personality, and made a great addition to the crew. Being that close to my mom who lived in San Diego's historic North Park, I was able to take care of her after a stroke in 2011, and when she fell and broke her arm a couple of years later. 

 During the summers, when Russel was off school, we would sail up to Morro Bay or Monterey, rent a slip, and get to know the town by walking everywhere. My editing business was slowly becoming a viable support, and Russel’s teaching job now offered us both benefits. He started teaching hybrid classes, that met for a few sessions then transitioned to online. Eventually he was teaching exclusively online, and I was working exclusively online, except for teaching at a couple of local conferences. 

Life was good. 

Yet, in 2016, my mom started to show signs of memory loss, and was diagnosed with vascular dementia, as a result of her stroke. I spent a lot of time in her tiny North Park duplex, with my niece Emma living in the front half. Russel enjoyed having a garage and workshop for boat jobs and renovations, so we gradually became landlubbers. 

By 2018, my mom began to wander off and it was clear that she was unable to live in her house anymore. By then we were all sharing the tiny half-house, me, my mom, Russel, and Ready, who loved having a yard to run in. I was lucky enough to get my mom involved with PACE, and they found her a room at the Villa, a memory care facility located on the east side of Balboa Park, and run by the amazing people of PACE. (I can’t say enough about how great a resource PACE is for San Diego’s low income seniors!) 

We sold the North Park house and moved back aboard Watchfire in the summer of 2019. When my mom passed away in hospice in the fall, it was clear that nothing was keeping us tied to San Diego any longer. We made plans to leave in March of 2020. Yeah, no. That didn’t happen. The Pandemic hit and we got stuck on the boat through May. We stayed in the lovely Pier 32 Marina in National City, which afforded us great walks through mostly uninhabited neighborhood of industrial buildings. 

There was also a nearby boatyard to haunt out and fix up our rigging and some other boat jobs. Then in June we sailed north out of Mission Bay, stopping in Oceanside, Dana Point, Long Beach, and Oxnard where we visited with family. We sailed on to Morro Bay and spent a month there, enjoying the quiet of that normally bustling summer tourist town. Finally, we made it to San Francisco, sailing under the Golden Gate in August of 2020. We spent fall in South Beach Marina, right by the Giant’s ballpark, before heading east for a winter in the Delta, and then back for another summer and fall in the SF Bay area. 

In the winter of 2022, we trucked the boat up to Washington state and spent the summer exploring Puget Sound. During this relatively quiet couple of years, I had finally turned to finishing the Baja memoir I’d been promising myself I’d write since about 1993. I wrote and rewrote chapters, and shuffled them again and again, like someone doing a thousand-word jigsaw puzzle with no picture on the box. 

Finally, I was pretty happy with the first 50 pages, and I started thinking about looking for a publisher. One day on Instagram I saw a post about a new publisher looking for true stories about adventurous women, so I sent my query and the first fifty pages off to Rebecca Eckles at Re:Books of Toronto. 

 In January of 2023, I was in San Diego when I got the message that Re:Books wanted to publish my memoir, Honeymoon at Sea. I was thrilled of course, and spent that year editing, finalizing, copyediting, and anticipating the publishing of my book. I even recorded the audiobook in a sound studio in Seattle that summer. I had started my Substack, also called Honeymoon at Sea, earlier that year and I did a zillion podcasts and appearances of all kinds in Washington that summer and in Southern California during the winter and spring. 

Since then, we have spent another three summers up in Puget Sound and the San Juan Islands, with summer 2025 dedicated to exploring British Columbia’s Sunshine Coast. I have been posting occasional travel columns for Womancake Magazine for the last two years, and now—thanks to PillartoPost.org—I’m going to share them with you here. I’ll update them with info about how we got to each place, unless that is made clear in the piece, add more photos where I can, and I’ll be happy to take any questions from readers: Jsilvaredmond@gmail.com 

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Note: Jennifer's first article will appear next Tuesday: www.pillartopost.org 




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