S2.31 - Farewell to Lucky Enough: The Final Chapter

Dec 31 – Jan 6: Sorting, Packing, Letting Go

Happy New Year from Puerto Rico!! 🥳

…though ours began in a whirlwind of boxes, bins, and sticky notes. For seven mind-boggling days, we lived in a cycle of decisions: keep, give away, or leave on board. Every single item on Lucky Enough had to be touched, evaluated, and either packed into luggage, gifted to new hands, or inventoried and stored neatly for the buyers, or for our return assuming the boat did not sell.

We gave away a lot: our treasured massage table, pounds of frozen meals, cans of provisions, spices, clothes, spare parts, and home goods. The marina was sprinkled with happy new owners of our donations—everything essentially fresh and new, now given a second life.

Thankfully, Alex and Roa dove in to help. With Ryan under the weather, their support was invaluable. Alex’s local knowledge and mechanical expertise, paired with Roa’s familiarity with Lucky Enough’s rhythms and details, kept us moving forward. By week’s end, the watermaker was serviced, engines polished, the interior scrubbed and staged, and the exterior gleaming. Exhausted but proud, we stepped back and admired: our little floating home looked amazing.

Jan 7: Meeting the Buyers

The day came. We moved off the boat, loading all of our personal belongings into a rental van and settling into a nearby Airbnb (down a dock so long, each trip felt like a hike).

That afternoon, we finally met Jim and Susan—the couple who had fallen in love with Lucky Enough before even seeing her. From the very first hello, we knew they were the right fit. They were thrilled with the boat’s condition and presentation, and after dinner together, it was clear: they really wanted this boat.

Our first night in the Airbnb, though, was less dreamy. Desperate for hot showers, we discovered there was no hot water. Then came our loud, new nighttime companions: the Puerto Rican coquí frogs. Their 90-decibel serenade—think lawnmower at bedtime—kept us wide awake.

Fun fact: the males’ “co-quí” call both scares off rivals and woos the ladies. Impressive, but not exactly lullaby material.

Jan 8–9: Systems, Secrets & Sticky Notes

The next two days were spent walking Jim and Susan through Lucky Enough’s systems, quirks, and secrets—everything from “where to find” to “how to do.” We also introduced them to Alex, though his Captain schedule won’t line up with their training needs. Another name, Arturo, soon surfaced as a possible fit.

We were leaving Lucky Enough fully equipped—absolutely everything they could possibly need to start their journey was on board: household items, bedding, supplies, spare parts, water toys, fat boys, all scuba gear, kitchen appliances and dishes, beach-day supplies, alcohol, even our emergency medical kit. All Jim and Susan really needed were their clothes and some groceries, and they could sail away.

Meanwhile, our to-do list seemed to multiply. Sticky notes covered every surface with reminders for sea trials, survey prep, and final shutdown before our January 15 flight home. Regardless of whether the sale actually went through or not, Lucky Enough would be sitting for at least two months—either waiting for Jim and Susan to take her over or for us to return for another season—so she needed to be properly “put to bed.” Still, we couldn’t get ahead of ourselves; the survey and sea trials were yet to come, which meant an entirely new list of tasks would be waiting on the other side. Thank goodness for Advil PM to muffle the chorus of coquí frogs.

Jan 10–11: Decisions and Manatees

With the contract signed and funds in escrow, Ryan and Jim hashed out whether Lucky Enough should remain floating in the marina or go “on the hard” until delivery.

On one of our endless treks to and from the dock, we spotted manatees swimming among the slips…

….a magical first for us.

These gentle giants, related to elephants, swam upside down and squeaked to each other. We didn’t get photos, but the memory is etched forever.

That same afternoon, Jim and Susan arrived with friends. Eight of them!! Twelve people onboard at once! For Ryan and me—who are not crowd lovers—it was a bit of a shock. In fact, the new boat we’re building is intentionally designed with just three cabins (when most Privilege 650s would have four or more). One of those cabins is permanently reserved as our “snore room”—a marriage-saving feature that has already proven its worth more than once. The setup means we’ll never host more than one other couple at a time, which is exactly how we like it: small, quiet, and personal. So seeing Lucky Enough suddenly filled with ten guests felt like a floating cocktail party we hadn’t RSVP’d to. I cringed as polished stainless collected fingerprints, but in the end, laughter and good company won out.

Later that evening, Jim and Susan came back to the boat, and the four of us returned to our comfort zone, where Ryan and I introduced and shared our favorite “Lucky Enough” tradition: patio wine at sunset, comfortably laid back on the fat boys, raising a glass to new beginnings.

Jan 12–13: Sea Trials & Survey — The Last Ride

By Jan 12, our checklist was complete, and Lucky Enough gleamed inside and out. The next morning, we were back at the marina at 7 a.m., nerves buzzing. This was the day: the official survey and sea trial.

Roa joined us again (forever our right-hand man), along with Arturo, the local Captain we had interviewed, and Anna, the surveyor. We were grateful for the team around us—familiar, trusted faces who knew boats and knew us. It felt like a final send-off crew.

The survey itself was meticulous, as it should be. Anna inspected every corner: the hull, deck, rigging, mechanical systems, steering, fuel, electrics, safety gear—you name it. As Roa shadowed Anna through the inspection, opening and closing every hatch, locker, and access point, we stayed just out of the way—quietly proud of how immaculate Lucky Enough looked. After all, we had cared for her meticulously inside and out, and if anything did come up, we knew it would be an easy fix.

Then came the haul-out. Watching your boat rise out of the water, suspended by straps, is always a heart-stopping sight, especially after an ocean passage. The underwater inspection stretched nearly ninety minutes. Thankfully, Lucky Enough passed beautifully, her bottom clean and her systems sound.

Roa lightened the moment by grabbing a few cold cervezas while we waited on the hard—our unofficial “survey sundowner.”

The sea trials, though, were the emotional core of the day. Split into two parts—before and after the haul-out—they tested everything: sails, engines, performance, rigging. The wind filled the canvas, and she carried herself like the champion she is.

Once sail inspections were complete, Ryan packed away the main sail, and I couldn’t help but feel the sting in my eyes. This wasn’t just another sail; it was the last one.

Sadly, Jim’s schedule didn’t allow him to join any of the sea trials, though Susan was there to witness Lucky Enough in all her glory. We wished Jim could have felt her pull, her grace, her steadiness. At least Susan saw firsthand what had made us fall in love with her.

As Ryan and Arturo turned Lucky Enough back toward the marina, the truth pressed down:

the sea trials weren’t just a test for the buyers—they were also our final farewell sail.

Every wave, every tack, every gust of wind carried a little piece of memory with it. I logged a “cry count” of three that day, though honestly, I lost track.

By the time we tied her back in her slip, Lucky Enough had once again proven herself. Survey passed. Sea trial complete. Buyers happy. All boxes ticked. And yet, instead of celebration, what lingered was a heavy silence in my chest: this chapter of our lives was truly coming to an end.

Jan 14: A Final Goodbye

Our last day was spent buttoning her up—tying dock lines, securing sails, protecting against weather and swell. The rituals felt familiar, like when we winterized her after Season 1 (S1.29). But this time, there was no “see you in spring”. This time, it was goodbye forever.

As parting gifts, Ryan left his beloved No Shoes Nation hat for Jim,

- a small nod to the Kenny Chesney spirit that has followed us through so many island days.

And I left my Lucky Enough bracelet,

a gift from Kristy that had traveled with me since the beginning of our journey.

It had become a quiet talisman, worn every single day as a reminder of courage, gratitude, and the magic of the sea. I passed it on to Susan with a handwritten note, sharing the story of how it was meant to be worn, cherished, and eventually passed forward again. My hope was that it would bring her the same sense of comfort, connection, and protection it had given me—keeping a little piece of Lucky Enough’s spirit alive as she begins her own adventure.

Two seasons. Nearly 400 nights aboard. 10,894 nautical miles. Countless sunsets, storms, and stories. Lucky Enough was more than a boat; she was our home. A place where Ryan and I grew closer, where our marriage deepened, where dreams stretched into reality.

We’re comforted knowing she’s going to loving hands, and we’re excited to turn the page toward our next chapter aboard Lucky Stars. But oh, the ache of walking away.

Jan 15: Heading Home

Roa, ever loyal, drove us to the airport after spending one last night at our Airbnb. He returned the van for us, took the last of our groceries, and waved us off.

Exhausted, we sank into our seats.

Hours later, we landed in Phoenix, greeted by Len and Kristy—familiar faces, warm hugs, and a mountain of luggage in tow.

We were home.