Captain Jack
Sailor • USCG Master Captain • Merchant Marine Deck Officer
MY SAILING STORY
My name is Jack, and sailing has been a major part of my life for more than 25 years.
My connection to sailing began long before I ever imagined I would hold a professional captain's license or cross an ocean. In my early twenties, I had my first real taste of sailing on a Hobie Cat in Key West.
Something happened that day.
I was completely fascinated by sailing, but looking back, I think it was more than that. Somehow, from that point forward, I developed a connection with the sea that I’ve never really been able to explain.
Being on the water just feels right to me.
The strange part is that I don’t always notice that feeling when I’m there. I notice it when I’m away from it. After enough time on land, something starts to feel like it’s missing—almost like a part of me isn’t where it belongs.
The closest comparison I can make is Jill. When she’s beside me, I don’t spend every minute thinking about how important her presence is. I just know everything feels right. But when she isn’t there, just like with the sea, I notice that a part of me is missing.
That is what the sea has become for me.
It isn’t simply something I enjoy. It feels like something that has worked its way into my soul, and I seem to understand that most clearly when I’ve been away from it too long.
Years later, life took an unexpected turn. In my early thirties, a serious spinal injury left me unable to walk for nearly a year, with only about a fifty-fifty chance that I would walk normally again.
During that period, I made myself a promise: one day I was going to sail around the world.
Recovery took determination, patience, and a lot of work. Looking back, many of the same lessons I learned during that time—preparation, persistence, problem-solving, and refusing to give up when circumstances become difficult—are the same qualities that have served me at sea.
Over the years, sailing changed from something I enjoyed into a way of life.
I have spent more than two decades sailing throughout the Caribbean and have gained extensive experience in the Gulf of Mexico, Intracoastal Waterway, near-coastal and offshore waters, and the Atlantic Ocean.
Eventually, that lifelong dream led to Keep the Faith, our 44-foot pilothouse sailing yacht.
The boat was completed and commissioned in the United Kingdom, with extensive hands-on involvement in outfitting her systems and preparing her for offshore cruising.
One of the defining experiences of my sailing life was taking Keep the Faith across the Atlantic from England to the United States.
Every passage brings another lesson. Every problem solved adds experience. And every safe arrival reminds me why preparation, judgment, and seamanship matter.
Today, Jill and I live aboard Keep the Faith full-time. We continue cruising, learning, maintaining and improving the boat, and working toward the dream that began many years ago—extended worldwide cruising.
Through Captain's Jack and Jill, we want to share not only where we travel, but what we learn along the way: the successes, mistakes, repairs, weather, navigation, beautiful anchorages, difficult passages, and everyday reality of living aboard a cruising sailboat.
PROFESSIONAL MARITIME PROFILE
My years on the water eventually led me to formalize that experience through professional maritime training and licensing.
I am a United States Coast Guard Licensed Master Captain with an Auxiliary Sail Endorsement and hold credentials as a Deck Officer in the United States Merchant Marine.
My professional training complements more than 1,500 verified days of sea service accumulated aboard vessels up to 44 feet in inland, near-coastal, offshore, and ocean waters.
SEA SERVICE & SAILING EXPERIENCE
My experience includes:
More than 1,500 verified sea-service days
More than 25 years of sailing experience
More than 20 years of Caribbean sailing experience
Atlantic crossing from England to the United States
Extensive Gulf of Mexico cruising and offshore passages
Extensive Intracoastal Waterway cruising
Near-coastal, offshore, and ocean passagemaking
Passage planning and weather routing
Navigation, radar, AIS and marine communications
Anchoring and docking operations
Watchstanding and offshore operations
Liveaboard vessel operations
Offshore provisioning and voyage preparation
Vessel maintenance and troubleshooting
KEEP THE FAITH
Keep the Faith is our 44-foot pilothouse sailing yacht and our full-time home.
I was extensively involved in completing, commissioning, outfitting, and preparing the vessel in the United Kingdom for offshore cruising. That experience gave me hands-on familiarity with many of the systems required to keep a cruising yacht operating far from home.
My experience aboard includes diesel propulsion, electrical and lithium battery systems, solar and wind generation, Raymarine navigation electronics, radar, AIS, communications equipment, anchoring systems, sail handling, and the countless maintenance jobs that come with operating a long-distance cruising vessel.
Keep the Faith eventually carried us across the Atlantic from England to the United States and continues to serve as our home, cruising vessel, and platform for the adventures ahead.
WHY WE SHARE THE JOURNEY
Captain's Jack and Jill isn't intended to be only a sailing résumé or a collection of vacation photographs.
We want it to be a place where people can follow the real journey.
We'll share the destinations and beautiful days, but we'll also share the repairs, mistakes, difficult decisions, weather, navigation, equipment, preparation, and lessons that are part of actually living and traveling aboard a sailboat.
And for anyone facing a difficult period in life where the future seems uncertain, I hope part of my story demonstrates something I've learned both ashore and at sea:
Sometimes you can't see the entire route from where you're standing. You simply have to find the next safe course and keep moving forward.
I'm Captain Jack.
Licensed mariner. Sailor. Navigator.
And this is our journey aboard Keep the Faith.