From Trail to Tide: One Man’s Journey Around the World
Jon, with the fitting trail name of Salty, is a triple crowner from Pensacola Florida. In August of 2024 he set sail from Pensacola Florida to Guatemala on the first leg of his circumnavigation of the globe. On his next leg of this adventure, he sailed Guatemala to Honduras to Panama where his ship, Serena, awaits her next voyage through the Panama Canal, to the Galapagos Islands, possibly Easter Island, and across the Pacific to French Polynesia.
What is your sailing experience?
I grew up in and around the water. My parents mostly had center console fishing boats, so I spent a lot of time offshore fishing. But I also had friends with sailboats and would occasionally go sailing on the bay. I always dreamt of one day traveling to far-off, exotic places that I’d read about or seen on fishing or dive shows.
As I spent more time on the water, I started working on charter fishing boats and entering some tournaments. Eventually, I landed a job aboard a 130-foot private luxury yacht and spent seven years traveling the Caribbean. The experience broadened my horizons and started a passion for travel that stayed with me for years. Still, despite all that time at sea, my actual sailing knowledge remained basic.
As time passed and my dreams grew, I decided to learn more about sailing. I signed up for an American Sailing Association course in the Virgin Islands with my dad and a friend. We rented a 47-foot catamaran and completed ASA 101, 103, 104, and 114 certifications.
With this new knowledge and hands-on experience, I bought a sailboat in Tampa, Florida. I sailed down to Key West and then back to my home port of Pensacola, in the Florida Panhandle. Since then, I’ve crossed the Gulf of Mexico, sailed south to Belize and Guatemala, explored the Bay Islands of Honduras, and continued on to Panama—where my boat awaits to transit the Panama Canal and head across the Pacific Ocean.
What sailboat are you currently captaining?
I’m currently sailing a 2002 Bavaria 47 named Serena
Do you carry any special equipment or gear on your sailboat?
In addition to the usual assortment of safety gear—like GPS, autopilot, wind instruments, chart plotter, anchor and chain with a windlass, and bilge pumps—I carry several key upgrades that make long-distance cruising more self-sufficient.
One is a water maker, which uses reverse osmosis to convert saltwater into fresh drinking water. The other is Starlink, which provides high-speed connection even in the middle of the ocean. That’s been a game-changer for weather forecasting and staying in touch with friends and family.
I also carry a dinghy for getting ashore when anchored and a life raft for emergency situations.
What’s your most memorable time sailing?
As with most adventures it’s not about the journey but about the people you share it with. For me, sailing is a way to explore the world and create meaningful moments with others.
That said, two stand out as especially memorable. The first was reaching Key West with my dad. That place has always held a special meaning for my family, and to sail there as captain of my own vessel and to share it with my dad was quite special.
The other was making my first solo landfall after a 500-mile crossing between Roatán, Honduras and Providencia, Colombia. I sailed alone for five days without seeing land and navigated through known pirate waters.
What made it even more surreal, thanks to Starlink, is that I was able to share it with a good friend. Literally within 30 minutes I hooked a beautiful mahi-mahi, spotted a pod of whales, and saw the island rise up out of the ocean on the horizon.
What trails have you hiked?
For someone who loves and lives on the water, I’ve spent a surprising amount of time on land. Long-distance hiking has been a huge part of my life and has shaped the way I approach adventure whether it’s on trails or at sea.
I have thru-hiked:
Appalachian Trail (twice)
Colorado Trail (twice)
Florida Trail
Pinhoti Trail
Tahoe Rim Trail
Continental Divide Trail
Pacific Crest Trail
Long Trail
Arizona Trail
What are your goals for sailing around the world, and what’s the next leg of your trip?
There’s a saying in boating: “Any good voyage is one you return from.” In that regard as captain I am responsible for my crew and vessel. I always want to return to port safely.
Beyond not sinking, what do I want from this journey? I want to see what lies beyond the horizon, travel to new countries, experience other cultures, explore beautiful places, and meet incredible people. For me, sailing is simply a means to those ends.
As Captain Jack Sparrow once said:
"Wherever we want to go, we go. That’s what a ship is, you know. It’s not just a keel and a hull and sails... that’s what a ship needs. Not what a ship is. What a ship really is... is freedom."
Sailing is freedom.
And as for the next leg? Serena is currently in Panama, and the plan is to transit the Panama Canal and set sail into the Pacific to the Galapagos, Easter Island, and French Polynesia.
Any wildlife you’ve encountered while sailing?
I’ve been fortunate enough to see whales on just about all my trips. Dolphins regularly surround the boat and play in the wake as I travel. I’ve been diving with whale sharks…. and tigers, and hammerheads.
While docked I always take time to explore the area. I’ve seen wild monkeys, sloths, coatis, capybaras, and all kinds of exotic birds. I even saw a “black panther” which is really a melanistic Jaguar.
What’s been the most “butt-clenching” situation you’ve found yourself in while sailing?
Man I remember it like yesterday! We ran into a hellacious storm while anchored off the Everglades. I had just taken possession of Serena, and we were on our maiden voyage down to Key West. We stopped to anchor for a few days of exploration among the mangroves.
Just as we got the anchor set, a violent storm, packing hurricane-force winds, hit. The anchor didn’t hold, and we started drifting. I tried to motor out into deeper water, but the wind would not allow me to turn. With no steerage and only an undersized spare anchor, it looked like we were going to end up on the beach.
Luckily, Serena has a 6.5-foot draft, and I was able to ease her gently onto a sandbar instead of the shoreline. It looked like we might lose the boat. But fortunately, we were able to salvage her and continued with our trip. Adrenaline was straight pumping. The experience was raw.
What’s been the most rewarding experience you’ve had while sailing?
Probably that same storm near the Everglades.
Throughout the storm, we remained calm, worked problems out as they arose, and ultimately came out the other side with a huge sense of pride and relief. Adapt, overcome, and achieve.
Any advice for future sailors getting into sailing?
Go simple. Go small. Go now.
There is some truth to that. You don’t need a 50-foot yacht with every gadget imaginable to have an incredible experience. You might never even need to cross an ocean. One could spend a lifetime cruising the Caribbean on a 30-footer and never grow weary of it.
That said, I wouldn’t recommend doing what I did buying a boat and setting off on a 1,000-mile voyage within the first week. I had prior boating experience, but even then, it was a steep learning curve.
I’d suggest learning to sail first and making sure it’s something you actually enjoy. If and when you buy a boat, begin with day sails while returning to your home port each night. Do that for six months to a year to build confidence and experience. Then, move on to overnight trips. Anchor out. Get used to life aboard. Build from there. And remember, a ship is freedom.
