Ready for inspiration to start sailing now? SpinSheet helps build the Chesapeake's sailing community. In our pages and pixels experienced sailors see their own sailing journeys reflected, and new sailors gain knowledge and find encouragement.
For example, not long ago, SpinSheet contributer Gail Marcus sent a note to our editor writing, “Thank you very much for providing a place for people to exchange stories about some of our shared experiences. In an article by Betty Caffo in the November 2024 SpinSheet, Betty reported how her sailing career started, writing that her first sail was on a Sunfish during her honeymoon in the Adirondacks in 1967. Wow! My first sail was on a Sunfish on my honeymoon in 1968. (In my case, in St. Thomas, U.S. Virgin Islands.) But the similarity in our stories doesn’t stop there. Betty alluded to the fact that she and her husband knew very little about sailing and had a problem getting the boat back to where they’d started. My husband, Mike, and I were also novices, and our inaugural voyage did not go completely smoothly, either.”
We reached out to Gail and Betty, who both stuck with sailing (and their husbands) and today are accomplished sailors on much bigger boats. Here they share more about their sailing journeys.
Less than perfect honeymoon sails.
Betty: It took me years to realize why Blue Mountain Lake in the Adirondacks was chosen by my husband for our honeymoon in 1967. Al knew but didn’t mention the Sunfish we could use while there. He had a taste of sailing at Penn State and was hooked—but not skilled. My first-ever sail with him was decidedly unromantic. We were able to tack back and forth, but I noticed we were increasingly far away from the lodge. My new and optimistic husband said, “That’s okay, we have a paddle.” On the next tack, it went overboard, and my husband pleads forgetfulness about how we got back. Ah, young love.
Gail: In our case, while honeymooning in St. Thomas, an attempt to gybe a Sunfish went very wrong, and I ended up in the water under the sail. I wondered if my husband of one week was trying to kill me! When I freed myself, I announced that I would never get on a sailboat again. That’s one promise I’m glad I didn’t keep!
Advancing to big boats.
Betty: We went to grad school in Ohio where there was never mention of sailing—no real water there. But years later, we moved to Delaware, where Al and a friend went sailing at every chance. In 1986, we took our boys on a bareboat charter to the BVI; the only thing the boys and I knew was how to tie a proper cleat hitch. I loved our charters but had little interest in learning how to sail.
However, in 2001 with the kids grown, I “announced” that we should buy a boat. I would have preferred a beach house, but I knew my husband who by then had earned his captain’s license. He resisted for 10 minutes, and then we went shopping. Our first and only sailboat was a new 36-foot Dehler. Before it even arrived, I was urged to try just one race, and I was hooked before the first upwind mark! When we recognized that sailing was a way of life for us, we moved to Havre de Grace, MD, and Summer Semester is kept just two blocks away.
Gail: We also went on to grad school, and the only boating we did was on a small outboard Mike’s father had for fishing. But after moving to Washington, DC, three years later, and becoming drenched in sweat just sitting outside to read the Sunday paper in June, we decided we had to do something. We both had grown up near the Atlantic, but it was too far away to go there weekly, so I swallowed hard and said I’d try sailing—if we took some lessons. A one-weekend “instant sailor” course on a Rainbow (a stable boat, ideal for beginners) at Annapolis Sailing School removed some of my anxiety.
We were then going to rent boats for a year to see if we really liked sailing, but after one rental, we bought a boat. We started small, a Leisure 17. The twin keel satisfied my need for stability. Soon boat envy got to us, and we kept looking longingly at boats with more features. Over time, we moved up to a Morgan 24, a Jeanneau Attalia (32 feet), and now, an Island Packet 350.
Still sailing, after all these years.
Gail: Well, it seems that Mike wasn’t trying to kill me on our honeymoon because we are still together and still sailing on Silvergirl. We’ve never raced; we sail to relax, to commune with nature, and to enjoy the lovely small towns along the Bay. We’ve often invited friends or foreign visitors for day sailing. We love to cruise, and we have been all over the Chesapeake Bay and up to Cape May as well as to New England aboard a friend’s boat. We’ve also chartered boats, usually in the Caribbean (once for the 1998 eclipse!), but we’ve gone day-sailing or had short charter cruises elsewhere, too, most recently in New Zealand.
Betty: We are now 79 years old with copious stories. We introduced our sons and most of our nieces and nephews to sailing, two of whom bought their own sailboats. From the start, we balanced cruising with racing, although we took a hiatus from racing because we felt we were too old; but we are back at it, albeit with a change in attitude. We now teach others to sail and race and have been having great fun as the senior sailors that we are. We have a crew of five novice sailors who jump at the chance to join weekly races.
We have explored and enjoyed the Bay for sure, but we still chartered boats: BVI and USVI, Turkey, Croatia, and Italy. We sailed to New England four times. Our bucket list sail occurred in 2015 when we left our slip for a six-month sail to the Bahamas. With all of our adventures, the best one is still to anchor somewhere on the Bay, watch the sunset and the moonrise, and get awakened by Canada geese.
As told to Beth Crabtree
