It’s hard to be friends with Howard Scott. Yes, he’s a fun, generous, music-loving, story-telling guy with whom I’m made lots of wonderful travel memories – jet skiing in the Bahamas, hiking in Sun Valley and strolling the cobblestoned streets of Nantucket.
The problem isn’t being with Howard. It’s when my husband, Chris, and I are not with him that it gets a little harder. See, I’m often glued to my laptop in my office, then I take a break to mindlessly scroll through Facebook. And there’s Howard, with photos of himself enjoying another gorgeous Caribbean day, jumping off his yacht, dining outdoors at some fabulous seaside restaurant or sharing scenic views from the top of a mountain he has climbed.
Yes, I am aware of the irony that as a travel writer, I often post similar photos. However, those are intermittent episodes in my life, which lead to the hours spent hunched over the computer. Those moments are Howard’s life. He and his wife, Valerie, spend about 75% of their time on their boat, Capricho, wintering in Florida and the Caribbean then cruising up the east coast when the weather gets warm.
A typical day for him may involve anchoring off a remote island and swimming to a beach, snorkeling along a coral reef and as he says, being “beholden only to the wind and the current.”
It wasn’t always this way. Howard was a hard-working lawyer in his hometown of Athens, Georgia, for decades, working insane hours in the legal practice he took over from his father and legendary attorney, Guy Scott. Stories from his legal practice are the basis of his first book, an often-hilarious murder suspense novel, “Rascal on the Run.”
I caught up with Howard recently to hear what inspired him to write the book, the challenges of living on a boat full-time, where his favorite places are and the story of how they rescued some people from the Dominican Republic who were stranded in the water beside their capsized boat.
When You Can’t Decide Where to Retire
Unlike the character is his book, Critter Stillwell, Howard didn’t always plan to live on a boat. When he first contemplated retirement he knew he wanted to find some place warm and scouted places in South Florida. “I was worried I’d get bored and realized if I had a boat, I could travel from place to place,” Howard says.
They spend the winter south of Florida aboard their 1987 Burger motor yacht, staying in the Bahamas, the Yucatán Peninsula, Cuba, Belize, Guatemala, the San Blas Islands and sometimes as far south as Trinidad. He has plans to travel through the Panama Canal and up the Pacific Coast of Costa Rica.
Some of his favorite places include two islands in the Grenadines, a group of islands north of Grenada. “We love Bequia and Mustique, a small island with private estates where people like Mick Jagger have a home. There is no marina, just a tiny airport and the world-famous Basil’s Bar. “When we last visited there was a blues festival going on and I ran into all these blues musicians I knew.” (Howard is also the co-founder of the Legendary Rhythm & Blues Cruise — the world’s only fully chartered blues cruise.)
Another favorite is a group of islands off Guadeloupe called Ille Saintes. “It’s where the French go to get away. There’s a parade almost every night as musicians pour out of bars into the street, beating on homemade instruments. There’s an amazing French restaurant. You can’t dock there, which creates a more authentic environment as there aren’t as many tourists.”
In the warmer months, they cruise up the coast of the U.S. When we spoke, they were docked in Baltimore Harbor. “It a surprisingly beautiful place,” Howard says. “A smaller version of New York City, especially gorgeous with the full moon.”
Other places they have discovered include Chestertown, Maryland. “It’s a beautiful little colonial restored city on the Chester River, the site of Washington College, the first college chartered in the United States,” Howard says. “We also love Beaufort, North Carolina, and Tangier Island in the Chesapeake Bay, an island that time forgot. It’s only accessible by air or water and we could barely get our boat in there. We hired a local woman to give us a tour and it was a blast.
“A beautiful thing about boating in the United States is that the water was the earliest highway so there are all these incredibly historic towns on the water that have blossomed into modern cities or remained small and quaint.”
If you’re wondering how you can have a social life when you’re constantly on the move, no worries there. They have made friends all over the U.S. and in the Caribbean. “Boating people are generally pretty social and adventurous,” Howard says. “And most are in same boat we are. They travel from place to place and want to share experiences, so we may learn about a museum we need to check out. We’ll have drinks together and take a walk along the waterfront. We have a network of people.”
The Challenges You Face When Your Home is a Boat
While it may sound idyllic, cruising from sunny port to sunny port and never driving in traffic, living on a boat does have its challenges.
“Our biggest challenge is dealing with the unexpected every day, the things that can go wrong with a boat. When your home and its electrical and mechanical systems are surrounded by saltwater, things go wrong continuously even if you’re doing constant maintenance,” Howard says.
His second biggest challenge? The weather. “Sometimes we’ve been confronted with unexpected bad weather and difficult seas. We have left one island and after difficult weather set in, had to turn around and go back because the sea was too rough.”
The biggest challenge he’s ever faced was a rescue at sea in January 2021. They were about 100 miles south of the Turks and Caicos on their way to Puerto Rico when Howard spotted a flare about five miles away with no land mass anywhere close.
“We went to take a look, although it occurred to us there could be pirates waiting to board our boat and rob us. We searched in the dark and found four people floating in the water and there were three others trapped underneath a 160-foot long capsized freighter,” Howard says. “We rescued the four men in the water, who had been there about 9 hours, and raced back to the Turks and Caicos to get help for the three others trapped underneath. We gave the men, who were from the Dominican Republic, food and water and then they just collapsed on the floor and slept, exhausted.”
Walking Away From Your Career
Howard doesn’t miss his former career. “The practice of law and politics are similar in that the measure of success is winning,” he says. “You don’t get paid to lose. As such, it’s self-corrupting and you start crossing lines of moral behavior and ethical considerations. You may start out a profession with noble ideas, but when you are enticed to win at all costs, lines start getting blurred and you start lying to yourself and others. You wake up 20 years later and you don’t like yourself.”
Howard reached the point that he didn’t want to live that life. He attributes positive changes in his life to giving up alcohol when he was 33. “I never got in trouble with drinking but I could see myself heading there.” He had watched his father, a hard-drinking man, die of alcohol-related causes at the age of 58, and he didn’t want to be that person.
“After I quit I began making better decisions and I had more energy to devote to my career,” he says. “Maybe I traded one compulsion for another, but this one was healthier. I started making more money and investing in real estate.”
He realized he had enough income from his investment properties to retire and travel so he sold his law practice and began a new life.
“Making money can be wonderful thing if you use it in right manner. I didn’t want to use it to buy mega mansions to show off. That’s the wrong purpose for me. I wanted to invest to have the freedom to do what I wanted to do, which is to experience cultures in different parts of the world and pursue passions.”
The Story of Rascal on the Run
He’s living his best life. So why write a book? It all started, as many good stories do, with a dinner party. He was the new guy at the table of old friends, and when asked about himself, told a few wild and colorful stories about his life and law practice in Athens.
That led to some people in the movie business wanting to work with him to develop a screenplay. After several years of working with different collaborators, he had a version he was happy with. “We pitched it all over but couldn’t get anyone interested enough to put money into it,” he says. He shelved the idea for several years.
Then he read “Where the Crawdads Sing,” did some research on the author, Delia Owens, and learned that she had also grown up in Georgia, attended the University of Georgia around the same time he did, and that this wildly successful novel was her first book.
That gave him the motivation to get to incorporating his stories into his book, “Rascal on the Run,” inspired by actual cases navigated by Howard and his father, the late attorney Guy Scott.
One of his early reviewers described it as “The genial style of Rick Bragg meets the pathos of Pat Conroy in ‘Rascal on the Run’ – a touching, often laugh-out-loud tale brimming with wry language and knee-slapping metaphors.”
I loved the book and found myself laughing out loud several times at the interwoven stories of the Dixie Mafia, unsolved murders, brothel visits, rowdy party scenes and the family dynamics of the Stillwell family, based on Howard’s own.