S2.30 - From Mooring Balls to Big Decisions: USVIs to Puerto Rico

Dec 27 – First Time in US Waters!

We enjoyed a slow, relaxing morning, having booked massages on a floating spa—until a last-minute staffing hiccup sank those plans. No worries. We cast off and headed to Francis Bay in the US Virgin Islands. Lucky Enough officially entered US waters for the first time! ⛵️🇺🇸

We snagged a mooring ball with ease—something we’ve gotten downright good at. Hard to believe when we think back to Aug 30, 2023 (S1.20 of the blog) and our almost disastrous “first solo date with a mooring ball.” What a difference a year makes! We’ve come such a long way and truly grown into a strong team.

Later, we took Ugh out for a spin. Our first stop: the Pay Station, run on the honor system and guarded by the resident “enforcer bird.”

Then, along the beaches, including the iconic Cinnamon Bay, we searched for Kenny Chesney’s legendary “Old Blue Chair.”

Didn’t find it—but we did thank him for the soundtrack to our adventures.

Dec 28 – Shifting Winds, Shifting Plans

The winds picked up today, so we stayed put and let Lucky Enough rock gently on her mooring. Most of the day was spent booking flights and scouting hotels in Puerto Rico. Why? Because life is full of Plan B’s (and C’s).

We had been told it could take 8–12 months to sell a boat like Lucky Enough, which is why we decided to list her now—thinking it would give us plenty of time for one more season of adventures in the Carribean before taking delivery of Lucky Stars (our Privilege 650) in January 2026. But after just one phone call, a potential buyer immediately showed interest. Suddenly, the timeline we had carefully mapped out shifted beneath our feet. Instead of a slow goodbye stretched over months, we now find ourselves hurrying toward Puerto Rico, preparing for the possibility that our time with Lucky Enough may end much sooner than we ever expected.

If she sells quickly, it’ll mean an unplanned year on land—Ryan tackling airplane projects, me catching up with family (and maybe, finally, a pedicure after two years!). If not, spring sailing remains on the table. Either way, we’ll adapt.

Dec 29 – Pizza Dreams & Surreal Realizations

We said our farewells to Francis Bay,

and set out through the Durloe Channel, famous for its ripping currents,

with a plan to experience something uniquely Caribbean—“Pizza Pi” at Christmas Cove, a floating sailboat-turned-pizzeria where hungry sailors raft up, swim up, or dinghy in for hot slices of cheesy goodness.

The thought of salty air, cold drinks, and a fresh pizza in hand had us practically drooling.

We dropped anchor nearby to plan our afternoon, but the spot was a little unnerving.

Just a few meters away, a shipwreck lay crumpled against the rocks—a stark reminder of how unforgiving the sea can be.

It’s a sobering contrast:

…one boat serving pizza joyfully to sailors,

another left battered by bad luck or poor judgment.

Lucky Enough has carried us safely through so much, and moments like that make us appreciate her all the more.

As we checked into the details, we realized we’d need a cruising permit to be here, and since Pizza Pi wasn’t opening for a few more hours, it didn’t make sense to linger. In true Lucky Enough fashion, “Plan B” kicked in—we pulled up anchor and kept moving westward.

As the sails filled, we both found ourselves unusually quiet, soaking in the view. The realization hit us: this might be our second-to-last sail on Lucky Enough. It’s one thing to plan a transition months down the line, but quite another to feel it pressing close. Every sight felt sharper, every sound more resonant—the slap of water on the hull, the hum of the wind in the rigging.

We passed the dramatic Luxury Villa Windsong,

perched proudly on a St. Thomas cliff,

and later, Sail Rock, a jagged outcrop that’s both a notorious navigational marker and an underwater haven for divers.

The area is home to the WIT Shoal II, a WWII landing ship sunk nearby, now alive with marine life—sharks, turtles, schools of fish. We didn’t dive it, but just knowing it was below us added weight to the passage: layers of history and mystery beneath the waves.

After 30 nautical miles (about 4.5 hours), we arrived at Bahia Tamarindo Grande, Culebra. By day it was crowded with local day boats, music and laughter drifting across the bay. But as the sun sank lower, they vanished, leaving the water calm and quiet again. We re-anchored in the middle of the bay for a peaceful night—our last at anchor aboard Lucky Enough.

One of our neighbors that stayed was this beautiful old tall ship,

now a school for upcoming young sailors.

There’s a photo of her lit up at night just a bit further down this post.

As we settled in for the night, it struck us that this was likely our final anchorage on Lucky Enough. She has carried us across oceans, sheltered us in bays, and rocked us gently to sleep under countless skies. To think this chapter might be drawing to a close felt both surreal and humbling. We didn’t need to say much—just sitting in the cockpit together, watching the stars bloom over Culebra, was enough.

This wasn’t goodbye, not yet. But it was a night to savor every ripple, every breeze, every quiet heartbeat of the sea.

Dec 30 – Puerto Rico Arrival & Marina Magic

At 8am, we set off for Puerto Rico. Border clearance was modern and surprisingly painless—FaceTime with a US border agent. A first for us!

Our destination: Safe Harbor Marina Del Rey in Fajardo. With 1,200 slips, it’s the Caribbean’s largest marina. Ryan had carefully chosen it for Lucky Enough’s post-crossing haul-out. But instead of just routine maintenance, we’re suddenly also preparing her for potential buyers.

The docking maneuver was a new challenge (at least my part): Ryan backing us into a finger slot while I tried to secure us to the dock while also lassoing two 7-foot bow poles. (Anyone who knows me knows my aim isn’t exactly Olympic.) Thankfully, help arrived in the form of Alex (Captain of Sisu - another Privilège 510) and our Atlantic-crossing crewmate Roa. Proof there is, in fact, a Mooring God.

Now begins a whole new chapter—getting Lucky Enough polished and ready for her next potential owners.