Jamie Rosman: Sailing in Wisconsin, Mexico and Ports in Between

Recently we shared the story of our two newest Golden Ticket winners: Brian Natov from Davis, CA, and Jamie Rosman from Nevada. While we shared Brian’s sailing story, we were waiting to hear back from Jamie about his sailing life. We now know more about Jamie and have learned that he’s a lifelong sailor with many miles and dozens of ports under his keel.

Jamie was just a kid when he learned to sail at summer camp in northern Wisconsin. There he sailed X boats, Sunfish, Hobies and MC Scows. He moved away from sailing a little when he was in his teens to late 20s, but reconnected with the sport on San Francisco Bay. “I had a coworker who had a friend that took people out sailing on Friday evenings. He was restoring a stripped-out 40-something IOR race boat and needed a bunch of crew to sail the boat, and I got invited to go. Within about eight weeks of going out on Friday nights, my coworker and I pretty much ran the boat while the skipper took care of the wine and snacks. I realized that this was something I loved and could actually do myself, so I decided to get my own boat, which was my Sabre 34 Freedom Rider.” That was 1992. “I sailed the s**t out of that boat all over S.F. Bay and the Delta and up and down the local coast,” Jamie adds.

In May 2000, Jamie and his then girlfriend, now wife, Elaine Lutz, bought the Taswell 49 TARDIS in Puerto Vallarta. They had spent five months crewing on a friend’s boat, going from San Diego to Acapulco, then back to Puerto Vallarta. After buying TARDIS, they took her back to Alameda, where they lived aboard for six years. “My wife, Elaine Lutz, was the marina manager at Grand Marina for much of that time. In 2006 she took the manager’s job at Cabrillo Isle Marina in San Diego. The job came with an apartment above the office, so we moved off the boat.” But that wasn’t the end of their sailing. The couple sailed the boat all over Southern California from Ensenada to Santa Barbara, with numerous visits to Catalina and the Channel Islands. Then, in 2012, they cast off from San Diego and cruised on and off, splitting their time on the boat between Mexico and SoCal until 2023.

Though they never joined a yacht club, as such, the couple were honorary members of Encinal YC when Elaine was manager at Grand Marina. “I would say we were more yacht club hanger-on-ers,” Jamie says. “We had lots of friends who were active members of Encinal, Alameda, Saint Francis, Silver Gate, San Diego and Pacific Maritime Yacht Clubs and we hung out a lot at those clubs as guests.”

Jamie recalls crewing in the 2007 Baja Ha-Ha Cruisers Rally* aboard his friend Mike Scheck’s (of Scanmar International) Jeanneau 45 No Worries. “It was the year many of us slept on the beach in Santa Maria since the waves at the bar were too big even for the panga drivers to take people back out to their boats after the beach party.

“Doing the Ha-Ha was a lot of fun,” Jamie continues, “and I am glad I did it, but in my opinion, the most underrated cruising in Mexico, BY FAR, is the Pacific side of Baja. I have made 10 trips in total up and down the coast, and we always go as slow as possible, stopping in all the anchorages. On one trip down, we took two-and-a-half months to go from SD to San Jose del Cabo, exploring and hanging out. My recommendation is to go on the Ha-Ha as crew to both have fun and gain the experience for sailing Baja. Then, when it comes time to head south yourself, take your time and enjoy a slow trip down the coast, experiencing all that the Pacific side of Baja has to offer. Amongst the many fantastic experiences we have had [on] the Pacific Baja, perhaps the highlight was meeting our now lifelong friends Jose Angel Sanchez Pacheco and Melanie Lamaga, owners of Cedros Outdoor Adventures, and Victor and Carolina Aguilar, a local lobster fisherman and abalone diver and their boys on Isla Cedros.”

Jamie counts the friends they have made and the people they have met among their favorite aspects of sailing. And for being on the water, Jamie says, “I love how it slows you down, keeps you in the moment, connects you to nature, and always teaches you something new no matter how long you have been at it.” He can recount many moments that would serve as his most memorable: “(S)ailing through a megapod of dolphins, having a humpback whale swim under the boat setting off the depth alarm, and gazing at a ‘bazillion’ stars while listening to coyotes howl while at a deserted island in the Sea or Cortez.” But the most memorable was when he crewed for his friend Rodney Pimentel aboard his Leopard 49 catamaran Azure II (also of the Cal 40 Azure).

“We were crossing the Atlantic, and the wind was blowing 40+ knots. We were way overpowered and we were going WAY too fast. We needed to reef ASAP. As we let the main down, one of the full battens got stuck in the lazy jacks, preventing the sail from dropping and us from slowing the boat down. It was a potentially very dangerous situation. Without thinking I scrambled up on the bimini and with one foot on each of the 1-inch support bars attempted to free the batten while we tried to come up into the wind to raise and re-lower the sail. Even using both motors at full power it was near impossible to keep the boat into the wind. I don’t know how long I was up there but it seemed like an hour, while getting the crap beaten out of me with the flogging sail and wildly swinging boom, all the while worried that one slip and I would fall down straight through the bimini into the cockpit from about eight feet up. Did I mention it was two in the morning? Because of course it was. We eventually got it all sorted. I was buzzing on adrenaline for hours after. It was a moment I’ll never forget.”

These days Jamie and Elaine split their time between Las Vegas and TARDIS in Marina del Rey. “Due to a health issue, our long-distance cruising days are over, but we still enjoy daysails and trips out to Catalina,” Jamie adds.

Thanks, Jamie, for this excellent bio of your sailing life. We hope it inspires others to take the leap and cast off to go cruising, or even daysailing. Readers, if you’re looking to do the Ha-Ha on someone else’s boat, check out the Baja Ha-Ha here (registrations for the 2026 rally are open), and sign up for the crew list here.

You can also come to the Latitude 38 Crew List Party being held on March 5 at the Golden Gate Yacht Club. Details here.

* Read the full story of the 2007 Baja Ha-Ha beach sleepover here.