Caribbean overnight sailing between St. Croix and Antigua becomes a thirty-two-hour test of endurance.
Thursday, May 7, 2026, 8:59 am. Caribbean overnight sailing from St. Croix to Antigua is the last overnight of our season, and I am anxious to get it over with. We’ll be heading into the wind for the next 24 hours, so we’re motoring. The weather forecast looks good: calm seas and sunny skies. I tidy up down below before settling into the cockpit.
10:00 am. One hour down, twenty-three to go. The seas are a bit wonky. The waves are coming in from two directions, and the interval between them is short, maybe two or three seconds. The shorter the interval, the more uncomfortable it is. Instead of the waves rolling in from ahead or behind us, hobby-horse style, or swelling from either side, cradle style, they have more of a washing-machine vibe. My body can’t get into a rhythm. Dogs are not loving it, neither am I. I go down below to fetch the Trazodone. Sampson ate a calming chew before departure, but Sully, being part poodle, is picky and refused. I give Sully a quarter of a dose of Trazodone and try to calm him until it kicks in.
If my recent horoscope, Taurus is entering their “I become the threat” era, is correct, then I think the weather forecaster should be afraid.
12:30 pm I am miserable and bored and …miserable. I’ve eaten a handful of ginger and three packets of peanut butter crackers, the orange ones Dad used to call Nabs and always ate on road trips. I don’t feel any better. It’s a mystery to me why I am feeling lousy because I haven’t been seasick since we owned the boat, and we’ve been in far rougher conditions. Lee keeps talking at me, “It should be getting better soon.” Or “Once we get behind” … I know he’s trying to be reassuring, but I just want him to keep quiet. I can’t even respond.
Sampson is calm, and Sully is still restless but has short stints of calm. Lie down, get up, legs quaking, reposition, and lie down again. Pant. By one, he falls asleep. We motor through the waves, occasionally pounding through them and cringing at the sound. I doze intermittently.
3:34 pm. For hours, we’ve been alone in the sea. The waters are desolate this time of year, as most people have returned to, or are returning to, their home or storage ports far to the north or south of us for the impending hurricane season. Our storage port in Antigua is still eighteen hours away. We have not even reached the halfway point. All I see is the sky, the sea, and the delineating horizon line between them; the line that always looks like we’ll sail off the flat edge of the earth when we get there.
Caribbean overnight sailing sounds romantic until the forecast lies, the engine alarms start screaming, and Antigua keeps drifting farther away.
All day the horizon remained exactly where it had been, measuring distance not in miles but in patience.
Both Sampson and Sully are anxious, panting, their nails curled under, holding on for stability, to prevent sliding. I give them both Trazodone.
5:35 pm. I can see the silhouette of Saba Island, the first land we’ve seen in hours. It’s grand to break up the monotony, and it will take well over an hour to pass. The Saba Bank, a huge, shallow reef, is just off our starboard side.
6:22 pm. The sky is pinkening behind cotton-ball clouds. The motor hums along, and the seas are marginally quieter. I zip the dodger down, but am unable to snap the bottom securely. Lee climbs around and snaps them in place while I drive. Before we left St. Croix, we picked up a few chicken empanadas, so dinner is easily served. The sun sizzles into the water, an orange ball with hot, rough edges.
7:10 pm. It’s dark now. Lee has a strange allergy-type thing from either bread — or the preservatives and other crap in it —or Coke. He says he feels like he’s drowning in mucus and hacks up a lung and retches. It lasts for nearly half an hour but feels longer. It’s horrible enough to hear, let alone experience. After he recovers, he heads below to check on things. I drive. It’s pitch black. There is a little waning moon casting light on the water’s waves. I can see Saba Bank on the chart, and we are just outside of it. I feel lightheaded, almost like I am experiencing vertigo. And it feels like I am driving downhill, like I’ll go down into an enormous swirling sea drain. When I was recovering from Meningitis as a child, I remember hallucinating in my bedroom. Huge balls of string reached the ceiling and consumed the entire room. I couldn’t get out, get past them.
At nine years old, it was scary. The feeling now is not unlike that. My head is not my own. I try to look in other directions, distract my eyes and my mind.
When Lee returns, I sit in the cockpit, unmoving. “You okay?” Lee asks. I shake my head ever so slightly. “Sick?” he asks. I nod. I remove my glasses and head to the stern, but puke in my mouth just before I reach the lifelines to vomit overboard. And then it’s full-on heaving of the empanadas I’d eaten half an hour earlier. I reach for the shower hose and clean the deck. I lay down in the cockpit.
7:46 pm. An alarm goes off. It’s the engine overheating. Lee shuts it off. I’m back at the wheel while he investigates down below. He checks strainers, coolants and belts, and whatever else lurks behind those compartment doors I have no interest in learning about. We’re floating, drifting alongside the Saba Bank, and have turned back towards St. Croix. We set the jib and mainsail, get back on course, and sail away from the bank. I lay back down.
8:15 p.m., “ML,” Lee shouts to wake me. “We need to tack.” I sit up, man the winch, we tack. I lay back down.
8:26 pm “What the…?” I hear Lee say more to himself, the boat, and the sea than to me. We’re in a current that is dodgy and strong, and we’re making little headway. We have no option of motoring through. Our ETA has changed from 9 am to 9 pm. I’m still lying down; there is nothing for me to do. My mind begins to wander. Why is main sail pronounced main-sil? Why is a bowline knot pronounced bo-lin (not bowling, as I had thought as a child), but a bowline is enunciated as bowline? And if I go down actual stairs to the galley or cabins, why am I going down below? It’s considered bad form to say you are going downstairs…or upstairs. And honestly, it’s a kitchen; why call it a galley? And head? Really, where does that even come from? I am afraid to ask. I could Google that, but I feel like crap. Boredom and queasiness give way to sleep.
10:54 pm “ML,” Lee says, “time to tack.” I get up, man the winch, we tack. Nausea takes over again. I lean over the quarter stern, and my stomach hurls up nothing. It’s the kind of heaving that steals all your air, and it feels like your throat is turning inside out. Makes you wonder if you’ll ever catch your breath again or if your ears will explode. The event subsides. I’ve got the chills. I put a sweatshirt on over my windbreaker and sleep again.
Friday, May 8, 2026, 1:30 am. We’re slowly progressing, but because we are heading into the wind, it is a serpentine route, adding thirty miles or so to our original hundred and eighty. We tack endlessly; I sleep in between. Lee is vigilant. I don’t know how he can stay awake. I am having zero fun, but the stars are glorious when I gaze up through the bimini.
5:42 am The sun rises, and with it my spirits. Under sail, the boat is quiet and slips through the water more easily. The dogs are quiet, and I’m feeling slightly better. St. Kitts is just off the bow. The Bactrian camel-like top of the island is ensconced in clouds. The sky is visible in the valley between the two peaks, and the light is soft, yellow, and clear. I nibble on more peanut butter crackers and have a few sips of Coke. Sleep overtakes me again.
9:21 am Lee goes down below to check the engine. It has cooled. “Let’s try to motor,” Lee says. She starts up, and after a few minutes hearing no alarm, we furled in the jib and the mainsail. Our ETA drops from 9 pm to 4:45 pm.
11:17 am Mostly, I continue to sleep, rising when Lee needs help with something or the dogs need settling. They haven’t eaten anything since the night before we left, having refused breakfast before we set sail. And they’ve had almost no water. I trust they know what’s in their best interest at this point. I log in to the SailClear app, register our arrival with the customs office in Antigua, and WhatsApp the vet with our estimated arrival time. We have all the clearance forms and health certificates for them, but a vet needs to meet us at customs and examine them. And collect money.
2:09 pm The engine alarm sounds. We are 11.5 miles from Antigua. I can see it; I can see masts in the harbour. We are so close. Lee shuts her down and goes below. He checks all the things. I stand watch at the wheel, though there is nothing to be done. We have no forward momentum, so there is no steerage. We drift. I watch the radar change our distance-to- destination reading from 11.5 miles to 12.3 miles. At least there are no hazards on the chart and no other vessels nearby. Water bottles and Coke cans have piled up; I clear them away. I coil some lines, fidget. Lee calls our mechanic in Antigua and gets help troubleshooting. He removes the impeller for inspection, all good, and replaces it. He checks fluid levels, water filters, intakes, and whatever else I care nothing to know about. I watch the chart, the horizon, and the distance to shore grow. By some miracle, the engine starts again, and the alarm does not go off. As I clear out of Lee’s way and head back to my perch in the cockpit, I fall. Inside my head, I’m screaming profanities, vowing revenge on the seas, the weatherman, and anything else that seems culpable.
4:59 pm Thirty-two hours since our twenty-four-hour crossing started, we pull into Falmouth Harbour. We drop the anchor in front of Pigeon Beach, splash the dinghy from the deck to the water, and hustle onto shore for the dogs to finally relieve themselves. On the way back, we stop at Skullduggery. I order an espresso martini. I think I earned it.
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