In my experience, the most important decisions tested my courage far more than my intelligence.
– Ben Horowitz
Recently Robie and I were forced to reevaluate our plans.
The test came from an unlikely source.
When we met Alec and Angela at The Black Marlin in Sarandё, we had no inkling of the trouble they’d make. After all, the friendly couple enjoying a drink on the patio in the cool dusk of early March seemed innocent enough.
Until they threw a monkey wrench in our roving retirement.
When Robie and I left the States last summer we had a plan for the remainder of the year. We’d start in Liverpool where the weather was cool and wet, a welcome change from the Texas heat before migrating south to spend the holidays on a remote Greek island. But after December, our trajectory was less certain. We knew I’d be in Spain to walk the Camino de Santiago in August with my sister, but we didn’t know where we’d spend the first seven months of 2025. As for 2026 and beyond, we had only half-notions and a dim, hazy vision.
Despite the limitations inherent to living out of suitcases, once in Europe Robie and I quickly realized we weren’t returning home anytime soon. And it wasn’t long before we envisioned a multi-year itinerary that would keep us moving ever eastward after we left the Schengen zone.
But upon meeting the newcomers, those plans were nearly derailed.
Sitting on the patio at The Black Marlin that evening, Robie and I heard the unmistakable lilt of English where people use words like “prawns” in place of shrimp, say “dunny” instead of toilet, slap you on the back with a hearty “good on ya” for “job well done” and refer to small sailboats bobbing in the harbor as yachts.
Aussies Alec and Angela had just bought a “yacht” in Sardinia and were waiting for the endless Italian red tape outside Schengen. But since this was a Jubilee year, the paperwork to transfer title of their boat was taking longer than usual – even by notoriously lax Italian standards. Then just as they thought they were getting close to securing their boat the Pope died, and Italy effectively shut down.
Over the months Angela and Alec waited in Sarandё, they ventured daily to the waterfront to sip coffee and admire the boats coming in and out of the harbor dreaming of the day they would board their new home and set off across the Mediterranean.
The new sailboat wasn’t their first yacht. Alec and Angela had raised four children in places like Türkiye, Italy and Indonesia. Along the way they owned several pleasure crafts and spent vacations and long weekends visiting nearby anchorages. They even chartered catamarans and spent lazy days in Spain’s Balearic Islands. So when they retired in 2024, the couple dreamed of buying another yacht and making the Great Loop.
Starting in Florida, the Great Loop circumnavigates the eastern United States and Canada traveling through intercoastal waterways before crossing into the Great Lakes via the Hudson and Erie canals then south through inland rivers like the Illinois, Mississippi, Ohio, Cumberland, and Tennessee before returning to Florida. While some Loopers – the name given sailors who complete the journey – make the trip in a few months, for others the passage can take years.
But when Angela and Alec arrived in the United States in late 2024, they discovered that their Australian dollars didn’t stretch very far. Struggling to find a vessel to make the 6,000-mile loop, they hopped a flight to Barcelona to check out boats in Europe. And while sitting on the balcony of their Spanish hotel staring out at the blue water, they felt a familiar pull.
The allure of the Mediterranean is legendary. A body of water where rich natural beauty meets vibrant cultures and ancient ruins combine with diverse culinary experiences – all touched by stunning turquoise waters, picturesque coastlines and charming, white-washed towns. Suddenly, Alec and Angela’s dream changed from making the Great Loop in a trawler to wandering the Mediterranean on a sailboat.
When Robie and I overheard them talking at their table on Black Marlin’s patio, we couldn’t help eavesdropping on their plans. And soon the four of us were sitting together swapping tales as Robie and I described our sailing adventures in the Caribbean and the two years we spent swimming with dolphins, dining on fresh-caught lobster, visiting Mayan ruins, seeing the remains of forts sacked by Francis Drake and sets for Pirates of the Caribbean.
Reveling in the camaraderie of like-minded sea people, the four of us got together often after that first evening. We met in town, had tea and cake in the rain, and commented on boats in the harbor while sipping wine or quaffing beer at local cafés. And each time I listened raptly as Alec described pristine bays in Türkiye, cheap tavernas in Greece and friendly villagers in Italy.
That’s when I felt a disturbance in the force and heard the siren song of the sea, an allure, once tasted, that’s hard to resist.
Soon I imagined Robie and I sailing the Mediterranean, wind in our hair, crisscrossing islands from North Africa to Asia. But such musings were interrupted by Robie attempting to reel me back in. He reminded me of the time we lost the dinghy in St. Kitts and dealt with a roach infestation in Grenada. He recounted the water valve that burst off the coast of Venezuela flooding the salon and nearly sinking us. He reminisced about the litany of things we lost overboard like silverware, grill regulator, clothes, towels and sunglasses and recalled the times we got boarded by the U.S. Coast Guard and robbed in Colombia. But mostly he reminded me of how we were constantly on edge about the weather.
“That was in the Caribbean during hurricane season,” I pushed back. “Not the Med.”
I reminded him of the underwater beauty we found while snorkeling in the Jacques Cousteau Marine Park off Guadeloupe and the Tobago Cays in St. Vincent and the Grenadines, how we celebrated New Year’s Eve with friends in Cartagena, played in the lazy river at Atlantis and learned to sail surrounded by footprint-free beaches in the Bahamas. And I recalled swimming through waterfalls in Dominica, eating fresh baguettes in Martinique and wall diving in the Bay Islands.
But were we really prepared for another sailing adventure?
Life on the boat had been harder for Robie than for me. While I was responsible for tracking the weather, looking after the cats, navigating, meal planning and cooking, he took care of everything else. And that meant anything that went wrong on a thirty-year-old boat – the bilge pump, the jib sail, the hydraulic line and windlass, the head, water valve and dinghy. Because something as simple as changing the oil in the engine was a sweaty, five-hour ordeal.
Then I started looking more closely at our surroundings in Sarandё and noticed for the first time the subtle wind changes that turned boats in the harbor 180 degrees and a new arrival’s difficulty finding a place to anchor in the bay. I watched the monohulls rocking from the waves in the broad, open port and saw the catamarans wobbling awkwardly as speedboats and jet skis skimmed through the anchorage. I recalled the swirling meltemi winds that blew gale force winds on Ikaria and the island’s lack of natural harbors. But mostly I noticed how the boats in Sarandё never stayed long.
When we sold our home last summer and set out on this vagabond life, many of our friends asked if we were planning to buy another boat, and we honestly responded that we were hoping for a different adventure this time. But after a few short weeks around Angela and Alec I was again contemplating another home on the water.
So what’s changed? I asked myself.
The answer was simple: our friends’ enthusiasm was infectious. And while another voyage was compelling, buying a sailboat and tootling around the Mediterranean also meant giving up our current dream.
Sailing the Med meant not spending three months in Morocco or renting an apartment outside the temples of Luxor and Karnak in Egypt. It meant we wouldn’t be able to spend time watching the annual migration in the Serengeti or visit Sri Lanka, wouldn’t have the chance to see Angkor Wat in Cambodia, explore Ha Long Bay in Vietnam, travel across Australia by train or spend a spring surrounded by cherry blossoms in Japan. We wouldn’t someday ride horses across Argentinian Pampas, explore the Amazon or eat Uruguayan beef. Because while I knew I’d adore checking out every bay and inlet from Gibraltar to Alexandria, it came down to a choice between getting an in-depth view of a small region of the world or exploring more of the Big Blue Marble.
I chose more.
Angela and Alec left Sarandё a month ago with the title to their yacht waiting on board. All that was left was to outfit their new home and reregister it. But while they’re setting out for ports unknown, Robie and I will forgo sailing around the Mediterranean for now and continue this slow, deliberate path across the globe with long-term stays and excursions that let us explore, dive deep and look into as many corners of the world as we can.
Hopefully someday we’ll meet up with our friends on a yacht of our own. But not now.
Until then, bon voyage, mates!