About Sailing Lady Jane
Sailing Lady Jane follows Ryan and Jennifer, two near-beginners — one of us a Type 1 diabetic — as we sell our house, choose a Catalina 445, and learn to sail it through the Caribbean with a senior dog and a puppy aboard.
Who we are
We're Ryan and Jennifer — an ordinary couple with very little sailing experience and one big plan. One of us lives with Type 1 diabetes, which turns "go sailing" into a real logistics problem most cruisers never face. We're not hiding that. It's part of the reason we're doing this at all.
Why we're doing this
Life is short, and we'd rather learn something hard than wonder about it. We're selling a house to buy a boat, trading the certain thing for the one we actually want. We're documenting the whole process honestly — the real costs, the real mistakes, and the decisions along the way — so anyone thinking about the same leap can see how it actually goes, not the highlight reel.
The boat: a Catalina 445
We're choosing between two Catalina 445s: one that's turnkey and ready to sail today, and one that's a project we'd upgrade ourselves. Ready-made freedom, or build-it-yourself and learn every system on the boat? That decision is the spine of our first season — and we're letting it play out on camera.
Sailing with Type 1 diabetes
Insulin that can't overheat. Redundant supplies for when the nearest pharmacy is two days away. Glucagon aboard and a crew that knows how to use it. Blood sugar management while standing a night watch. This is the part of cruising nobody makes videos about — so we will. If you're a Type 1 diabetic who's been told to play it safe, this channel is the counter-argument.
The crew
Two dogs come with us: a 15-year-old mini Aussie who's seen it all, and a one-year-old Maltipoo who thinks every beach is his to roam. Life jackets, foredeck potty training, keeping a senior dog cool and safe offshore, and the very real paperwork of moving pets between Caribbean islands — it's all part of the show.
Follow along
New videos land on YouTube, and every one gets a companion post here with the real numbers, gear, and details that don't fit in a video.
FAQ
Can you sail the Caribbean with Type 1 diabetes?
Yes — with planning. Type 1 diabetes offshore comes down to keeping insulin cool, carrying redundant supplies (roughly twice what you think you need), having glucagon aboard and teaching the crew to use it, and managing blood sugar hundreds of miles from a pharmacy. We document how we handle it, honestly, on every leg.
Do you have sailing experience?
Almost none. We are near-beginners learning on camera — which is the whole point. If you have ever wondered whether you could do this with no experience and a chronic illness, you are watching the honest version.
What boat are you sailing?
A Catalina 445 — a roomy, well-regarded production cruiser. We are choosing between two: one that is turnkey and ready to sail today, and one that needs upgrades we would do ourselves. Which one we pick is the story of our first season.
What about the dogs?
Two crew members come aboard: a 15-year-old mini Aussie and a one-year-old Maltipoo. We cover the real logistics — dog life jackets, potty training on the foredeck, keeping a senior dog safe offshore, and Caribbean island-to-island pet paperwork.