From family sailing to captaining respite sails for other families, you never know where sailing will take you.
When Bob Holman and his wife Teresa joined their young sons for a sailboat ride during “parent day” at Boy Scout Camp in 2010, little did they know that the experience would open a door to years of family sailing, boat ownership, and, for Bob, serving as a volunteer captain for the nonprofit Sails of Hope Chesapeake. Below Bob shares in his own words some of the ways in which sailing has enriched his life, including observing the window of relief that sailing can provide to those battling cancer.
Sailing during “Parent day” at Boy Scout camp.
Bob: My first experience with sailing was when I was about 42 years old. My two sons were working on their sailing merit badges with the Boy Scouts at Camp Rodney near the town of North East, MD. The boys learned basic sailing skills aboard Sunfish and Flying Scots. On “parent day” the boys could take their moms and dads out and show them their new sailing skills. We had such a good time that during our family vacation later that summer, we signed up for a family sail day on Lake Wallenpaupack in the Pocono Mountains. It was an afternoon for the whole family to have an introduction to sailing with an American Sailing Association (ASA) instructor on a 28-foot O’Day sailboat.
We were hooked on sailing!
After our experience with the scouts, my wife, Teresa, and I were hooked! We took a weekend ASA 101 class in St. Michaels, MD, followed by an ASA 103/104 combo class near Fort Myers, FL. We also got our ASA 118 Docking Endorsements. Once we felt experienced enough, we started renting daysailers whenever we could. Living outside of Philadelphia, we did most of our sailing on the Chesapeake, usually in the Havre de Grace, Annapolis, or St. Michaels areas.
When we could, we would take winter sailing vacations, sailing out of Burnt Store Marina on Charlotte Harbor near Fort Myers. In addition to the O’Day, we sailed a Colgate 26, and a few Hunters 27s. Later, I sailed a Beneteau 31 near Kent Narrows quite a bit.
Teresa and I had our sailing ambitions interrupted when she was diagnosed with advanced ovarian cancer in 2014. She fought it courageously for more than seven years, defying her original prognosis of one to two years. Throughout her battle, whenever she felt up to it, one of her favorite things to do was sail. When time allowed, we would travel and often incorporated sail days into our trips. Sailing brought peace to Teresa and a brief escape back to better days that helped to sustain her during her fight against cancer. Our last sail together was on San Fransico Bay where we sailed out under the Golden Gate Bridge.
Sails of Hope Chesapeake
A few months after Teresa passed away in 2022, my long-time colleague and friend, Janet Zebleckes, and her husband, Joe, invited me to do some sailing with them on their Beneteau 40, Anneliese, in Annapolis. One weekend when we were sailing, Joe asked if I could stay on another day. He needed crew for a sail he was doing for a local nonprofit that offered sailing excursions to those being challenged by cancer. I happily agreed and found myself serving as first mate on an outing for the newly formed organization that eventually became Sails of Hope Chesapeake.
On the sail, I saw our guests experience the same relief, peace, and joy that Teresa and I had on our sails together. I immediately volunteered and served as a crew member through 2023 and 2024. The following year, as I continued to serve as crew, in August, I qualified as a captain.
Today I volunteer as captain and crewperson with Sails of Hope Chesapeake and was honored to be named lead captain for maintenance and upkeep of Annelise, which was donated to the organization by Joe, in a final act of tremendous generosity, before he passed away from lung cancer in 2023.
When Irish eyes are smiling: sailing into the future with family and friends.
Two years ago, I purchased a Catalina 320, which I keep on Kent Island. Her name is Sùile donna (pronounced Soola dōna), Irish for Hazel Eyes. She is named for my two granddaughters, both of whom have hazel eyes. I want to share the experience of sailing with my family and friends.
I plan to continue to support Sails of Hope Chesapeake and our mission to bring hope, healing, renewal, and joy to those struggling with cancer and their loved ones.
Perhaps, eventually I will become a sailing instructor to help people discover the pleasure of sailing the way I did. Over the past couple of years, I have continued to build my sailing skills. I completed ASA 105 in 2024 and ASA 106 in 2025, sailing from Punta Gorda down the Gulf Coast to the Everglades.
Advice for someone interested in learning to sail.
Don’t wait to get started, and once you start, keep going. For me, it was important not to let too much time pass between outings so that I did not have to re-learn skills or struggle to “shake the rust off.” Classes are great, but it is the time on the water practicing skills where the real learning happens; so, when you take a class, don’t let time pass before you get out there and practice what you’ve learned. Like most things, the more you do it the better you get.
