“Where it all ends I can’t fathom my friends/If I knew I might toss out my anchor/So I cruise along always searchin’ for songs/Not a lawyer a thief or a banker/but a son of a son, son of a son, son of a son of a sailor…” –Jimmy Buffett

Sailing runs deep in our family–Jay’s grandpa (Alfred James the first) was a sailor, Jay’s dad (Alfred James the second) was a sailor, and Jay (Alfred James the third) is a sailor. Our family’s holiday tradition since we bought Take Two in 2008 has been to do a buddy-boat “Turkey Day Cruise” with Jay’s dad and stepmom, Al and Mary, to spend Thanksgiving in Pelican Bay near Cayo Costa State Park, not far from the Boca Grande entrance to Charlotte Harbor, Florida. I’m not sure I can express how much I miss them both since Mary passed in October of 2022 and Al in September of 2025. Holidays just aren’t the same without them. I found these old pictures in his attic–photos Mary took on film the first year we did the Turkey Day Cruise together. They bring tears to my eyes–we were so young, so foolish (that infamous day we almost ran aground under full sail and the day the wave knocked the turkey soup off the counter!), and so happy.

Although I wrote a formal obituary for the Naples Daily News (see below), there was so much left unsaid, so here is my addendum. Al, a.k.a. “Skipper,” was an integral part of our family’s sailing adventures, from our first trip to the Dry Tortugas aboard Double Entry as newlyweds in 1998 to our last trip in 2023, a buddy-boat cruise with our oldest son Eli aboard Lovely Cruise as his grandpa’s first mate. He and Mary came with us to Fort Lauderdale the first time we went to look at Take Two, and they supported our sailing dream every step of the way. We went sailing together, we went to boat shows together, and we planned future buddy-boat trips together. He and Mary met us in various exotic locations to either charter a sailboat or visit Take Two. They shared our love of wind and water and exploration. Al even supplied the bottomless cups of coffee that helped me write about our family’s travels on this blog and, eventually, in an award-winning memoir, Leaving the Safe Harbor. I owe him a deep debt of gratitude.

It is hard to imagine a world without Skipper in it. We had Thanksgiving this year at his house, cooking in the kitchen he had recently renovated, without him. He would have been so happy to see Jay spatchcocking and grilling a turkey on his big green egg and Eli baking pumpkin pies in his new oven–he loved to cook. We all spent many happy hours with him on the back deck grilling or standing beside him in the galley or kitchen fixing good things for family dinners. He ate and drank with gusto, and he told great jokes. He and Rachel had a regular Wordle habit, and before that, a morning Sudoku tradition whenever we were together. He did the NYT crossword and was one of the most intelligent people I have ever known.

He spent the last couple of years trying his best to recover from a series of setbacks that meant not getting to go sailing in his retirement as he had hoped and planned. Despite hospital stays and illness, he managed to maintain his good sense of humor–I learned a lot about this kind of everyday courage while caring for him. It would have been easy to be bitter or grumpy about the circumstances, but he chose gratitude and joking instead. I’m so glad we spent so much time with him the last couple of years–I feel fortunate to have known him and to have made so many happy memories together. I will miss him every day, but especially during the holidays. Merry Christmas and Happy New Year from the Crew of Take Two!

Alfred James Hackney II 1948-2025 Alfred James Hackney II, 76, of Naples, Florida, passed away at Avow Hospice September 12, 2025. The eldest of eight children born to Alfred James Hackney and Sandy Teston, he has four surviving brothers, Charlie, Steve, Horace, and George Hackney, and a sister, Lisa Cox, all of Florida. Though he was born in Clewiston, he moved with the family to Naples in 1955. Al graduated from Naples High School in 1966 and received a football scholarship to Georgia Tech, where he got a degree in business management. His MBA was completed at Georgia State University. He was a CPA in Naples for five decades and a member of the Rotary Club. A lifelong sailor, he was a member of Naples Sailing and Yacht Club for many years and spent time on his boat in the Bahamas and the Florida Keys. Al is predeceased by his second wife, Mary Tanner Hackney, with whom he built a house in Bocas del Toro, Panama. He is survived by ex-wife Allison Bowes Kitchens and two sons, Jay and Jeff Hackney, as well as seven grandchildren. His hobbies included golf and bowling, and he enjoyed cooking and spending time with family. An intelligent man with a great sense of humor and an extensive vocabulary, he will be remembered fondly by those who knew him. If you would like to honor Al Hackney, a donation can be made in his name to Avow Hospice.