Where are they sailing now? A Start Sailing Now update.
For more than 10 years SpinSheet’s Start Sailing Now page has brought you inspiring stories of sailors who took up the sport as adults. Here we catch up with Jason O’Mara, whom we originally interviewed in 2022, and revisit Thomas and Terri Sands’s 2019 interview in which they shared how visiting the Annapolis Sailboat show launched them into the sailing lifestyle.

Double the fun: underway with twin boys.
When we first met Jason and his wife, Ellie, the couple had recently moved up from a 1980 MacGregor to a 1981 Tartan 33 named Lindquist. They had spent nine months refitting the boat, which was located in New Jersey, and sailed her from Sandy Hook to the Chesapeake, where they planned to fine-tune their sailing, provisioning, and weather routing skills in preparation to one day sail down the East Coast to the Caribbean.
In August, Jason shared with SpinSheet this happy update: “Six months after we last spoke, my wife gave birth to beautiful twin boys. Seven months after that, our boys were indoctrinated into sailing life with their first sail. Now three and a half years old, their imaginative play revolves mostly around boats and water—and sailing is one of their favorite things to do. We’ve stayed relatively close to our home port in Middle River, MD, over these past few years, but now that our boys are a bit older and more independent, we have plans to sail further and aspire to eventually make it down to bluewater.”
Launching into the sailing lifestyle at the Annapolis Sailboat Show.
As the Annapolis Sailboat Show approaches (October 15-18), we thought it would be a good time to revisit a new sailor profile from 2019, when Thomas Sands explained how a visit to the show launched him and his wife Terri into the sailing lifestyle.

Thomas explained, “I stumbled on the flyers for the Annapolis Sailboat Show, and while I was [at the show], I was taken by the boats, the people, and the atmosphere. The magic moment happened after I stepped onto a new Seawind 1160 Lite Catamaran. I was met by Tommy Smith and Amy Michaud of Sail Away Catamarans. After speaking to them and the owners of the boat, I was convinced that the liveaboard life would offer the adventure and freedom Terri and I were looking for in retirement. I concluded my day at the show with a Sail Away demo on a Lagoon 420 on the South River. Terri hadn’t been with me at the show, but it did not take much to convince her; she was ‘onboard’ from the start.” Thomas went on to explain, “[Sailing] opened a whole new world for us. We were not just buying a boat… we were buying into a lifestyle.”
The Annapolis Sailboat Show welcomes all types of sailors, including those who are just getting started or even just curious about sailing. Team SpinSheet encourages new and would-be sailors to make a day of it in Annapolis. Inside the show gates you may board the boats, learn about chartering opportunities (no sailing skills needed if you hire a captain), meet with representatives from local sailing schools, and talk to experts on financing a boat purchase. If you’re looking for a hands-on introduction to sailing, check out the show’s First Sail Workshop. Participants start with a 45-minute classroom overview of sailing basics followed by 90 minutes of on-water learning with a certified instructor. All these opportunities and more will unfold in a lively, festive, and welcoming atmosphere. If you go, be sure to stop by the SpinSheet booth and say “hello” to our team.




