The Wind Sends You Home

As sure as the wind whispering “go” at the back of my neck, I knew my buddy Dan wouldn’t want us to delay our sailing trip to the Keys. Not with a forecast predicting fair winds for days. Not when our 32-foot Catalina sailboat was fully provisioned and ready to go. Nah. He'd be raising a cold one in heaven.

“Red sky at morning,” my wife Jeanne said as she handed me her duffle and climbed aboard. I finished the phrase in my mind: Sailors take warning. “I don’t like leaving on a Friday either,” she added for good measure, although we often went on weekend trips that started on Fridays.

She’s not a pessimist. What she was trying to say was, “Let’s wait.” Dan’s crazy sister refused to have a memorial service, but two of his ex-wives and some cousins arranged a “celebration of life” in two weeks. I did not want to put off this trip that long, and Jeanne knew it, so she kept mum. Ish. She was acting like she always does. Dan’s unexpected death gave her a new excuse for her reluctance, that’s all. I’d be lying if I said Jeanne loves sailing.

The sunrise was burnt orange leaning into pink. I assured her that whatever weather a red dawn portended was not in any forecast, and she shouldn’t worry about leaving on Friday. “That’s only for ocean voyages,” I said. On our first day, we’d sally from Clearwater to Gulfport. If the wind wasn’t right, we could putter down the Intracoastal Waterway and never raise a sail.

“Loophole,” she said, and we smiled at each other as old couples do, understanding.

Sure, it was unsettling to leave Dan with no formal goodbye, cremated without ceremony. But we were carrying on the way he lived. He single-handed his Bristol sloop from St. Petersburg to the Keys more times than either of us could count. “Life’s too short to wait around,” I could hear him saying. “You gotta go when the wind is right.”

We motored out into the Gulf for a beamy, balmy sail southward. I cracked open two cans of Beach Blonde Ale and handed one to Jeanne. “For Dan,” I said.

“For Dan,” said Jeanne.

Dan had been an inveterate drinker, his motto alternating between “it’s 5 o’clock somewhere,” and “a little hair o’ the dog cures what ails you,” depending on the depth of the previous night’s indulgence. He saw no redeeming value in fruit or vegetables, but much joy in anything fried, particularly grouper, or charred, particularly steak. The booze and grease did him in before his time.

We had planned to meet him at O’Maddy’s in Gulfport that very night for fried fish and cheap 20-ounce drafts before sunset. He’d be sailing beside us to the Keys, visiting his favorite drinking establishments along the way, except his heart had other plans.

I missed him to my bones.

I guzzled that ale to ease the tight feeling in my throat. Jeanne took one swallow and set her can down. She would probably let it go warm. We had a rule about drinking while sailing, which was: no alcohol until the anchor is set.

“Dolphins!” she called, pointing, nearly knocking over her beer. Bottlenose dolphins are not unusual in these waters, but this was a whole pod – at least six, maybe seven, of them. Dan would’ve loved this. His YouTube channel was loaded with dolphin clips, which he posted the way some people post cats doing dumb things. Dolphins in the wild don’t usually do tricks like you see at an aquarium, so Dan’s videos were mostly them swimming alongside his boat, but he had a few classics of breaches at his bow. The dolphin pod next to my boat was getting annoying. They were unusually active: crossing our bow, diving under the keel and swimming so close to starboard it felt like they were trying to push us out of the channel. Jeanne either ignored or didn’t notice my irritation. Which also bugged me. I kept sliding closer to the shallows until I had to turn sharply to avoid running aground. I almost hit one and it leaped right next to us.

“Oh wow,” Jeanne said, and pointed her phone at the water. I wish she’d thought of it sooner, because as soon as she started filming, those dolphins became elusive, as if they weren’t signed on to this movie and hadn’t been paid to take part.

“Dan was so lucky with the dolphin videos,” she said. “I give up.”

“It’s fine,” I said.

*

After we passed the last channel marker, we turned south and picked up a steady 10-knot wind out of the west. A few puffy clouds dotted the horizon. We set both sails, turned on the autopilot and leaned back. My irritation dissolved in the breeze.

Jeanne had been up on the foredeck to sun herself, but on her way back to the cockpit, she stopped. “Greg, check the mainsail. What’s it doing?” I cocked my head around the bimini for a better view. A string was flapping from one of stays above the first reef. A gap of sky peeked through the sail.

“Holy shit. The stitching is coming out!”

We had to lower the main completely and continue with only the foresail to move us, which slowed us down. I turned on the motor to add speed, which turned out to be a good move. Those bulbous clouds grew thicker and grayer as the afternoon progressed. The wind started gusting, tossing the boat side to side. We rolled in all but a small triangle of the foresail for stability. We’d weathered worse, but I don’t like a storm on our first day out. 

We limped into Boca Ciega Bay at sunset, sodden and sour-stomached, and dropped anchor near Gulfport pier. We had a decision to make: Wait here for a sail repair or motor back, ending our trip. Jeanne said go home, but I couldn’t see why. I called a marine seamstress who had given me her card at some sailing event, and she met us at the fuel dock the next day, promising to have the sail back in a day or so.

Jeanne went to the Gulfport library and shopped and paddled our inflatable kayak in Clam Bayou. I sat at O’Maddy’s drinking until I couldn’t stand the noise anymore. Dan was supposed to be here. Man, I’d give anything to hear his latest theory about whatever the hell was on his mind. One time he tried to convince me that Atlantis was real, and its king was a dolphin. Said government scientists knew about it but their dolphin communication experiments were top secret. Shit like that. Just to see what I’d say.

Our sail got repaired and, anxious to be off, we pulled up anchor in a morning fog. I thought it would burn off. Instead, it grew thicker. And then, as if to prove my mistake, our diesel blew a belt. Fuck. Visibility couldn’t have been more than 10 feet. There was no wind and no place to drop anchor – we had just passed under a bridge at an intersection of channels. We rolled out the jib and Jeanne held the boat steady with the sail slack and maneuverability next to nothing. I forced a new belt onto the pulley using more adrenaline than muscle, cursing to relieve the tension, afraid my wife could be knocked overboard from the impact of some hot-shot powerboat that didn’t see us bobbing there. I didn’t tell her that.

We crossed Tampa Bay in light wind, diesel running. I focused on the engine, hoping my quickie repair would hold. The sad truth was this: I was glad to get my mind off Dan.

We anchored that evening off Cortez, a fishing village where we liked to stop for fresh shrimp. Later, we were jarred awake by pounding on our hull. “Wake up! You’re about to get hit!” I hustled out of the cabin in my skivvies. A guy in a little flat boat was between us and one of the many half-derelict boats that litter anchorages everywhere you look in Florida. “That one’s loose!” he called, pointing. It was drifting toward us in the current. I turned our engine on, and Jeanne took the helm while I hauled up anchor faster than I’ve ever hauled in my life. She maneuvered our boat away from the threat, avoiding running us aground, which was a feat, given we were surrounded by shallow shoals. We re-anchored close to the channel, away from other boats, but I couldn’t sleep after that. I sat in the cockpit watching fishing boats racing out in the dark. Our boat rocked all night from the wakes. Dan thought all powerboaters were scoundrels. “Stinkpots got no manners,” he liked to say.

The next day, the wind clocked southward and hit us on a close reach, an uncomfortable point of sail, too close to the wind. The seas had picked up too, and our old Catalina was pounding against the surf.

In my haste to get away from Cortez, I had not secured the anchor on its pulpit. Jeanne heard it falling when she went down below to the head. She came tearing back up the companionway, tugging her shorts, hair flying. “The anchor’s loose!” she screamed, scrambling forward. She hauled it back in and tied it up before I knew what was happening. She might not want to be a sailor, but, damn, she’s good in an emergency.

We hoped to find hot showers and a nice meal that night in Venice, but the docks at Crow’s Nest were full, so we puttered about a mile north and dropped anchor in Blackburn Bay. Jeanne was sullen about that – no place to go ashore, another boat shower – and my bum knee was acting up again. I could not get comfortable sitting, standing or lying down. It just hurt. “Don’t let the old man in,” Dan used to say whenever I complained of aches or pain. It was his way of telling me not to focus on what I was losing, but to be grateful for the moments I had.

Jeanne and I drank our sundowners in silence – ginger beer and Gosling’s dark rum, a concoction beloved by sailors called “dark and stormy.” Exactly how I felt.

I still can’t believe what happened next. A dolphin poked its head out and I swear it talked to us, chirping and trilling the way dolphins do. Like Flipper.

 “Can you imagine if Dan had been here for that?” Jeanne said. “He would have gotten the video.”

Yeah. Another bitter reminder that we would never meet up in some anchorage, never share drinks on our boats, and never again swap sailing tales, which was a crying shame because Dan would have loved the stories from this trip already. Mainsail rip, surprise squall, diesel blowing a belt in dense fog, bum boat making us re-anchor in the middle of the night, anchor taking a dive and Jeanne rescuing it. And a god-damned talking dolphin.

*

The morning air was still again the next day, a wall of humidity despite the forecast for moderate westerly breezes. We raised the sails anyway and tried to sail. I preferred the quiet, even if the going was slow. Jeanne put on music, some millennial indie junk. I took a nap and let the autopilot drive while Jeanne kept watch. By the time I awoke and checked the charts, I realized we were going nowhere. We would not reach our anchorage before dark unless I turned on the engine.

They say the gods laugh at sailors’ plans, and I was beginning to think somebody on Mount Olympus or wherever was having a party shredding ours. We’d been out nearly a week and should have been 100 miles closer to the Keys by now, somewhere off the Everglades. Instead, we dropped anchor a day’s sail north of Fort Myers. We dropped anchor outside Pelican Bay. The entrance to that lovely, protected harborage is narrow and unnervingly close to shore, nothing to mess with at the end of a long day.

Jeanne had been trying to warn me all afternoon about water leaking from the engine, but there wasn’t anything I could do about it when we were underway. Turns out it was more than a drip. Our galley floor was covered in soaked towels – Jeanne sopped up water with every towel on the boat – and the bilge was full. The engine’s cooling pump was shot. Like all good sailors on old boats, I carry parts. But l did not want to spend the next few days playing diesel mechanic.

Jeanne poured us a stiff rum and Coke while I ran the bilge pump. We would wait until morning to do another thing. Dan would like that decision.

That night I heard the distinctive clicking, ringing and warbling of dolphins, their vibrations bouncing off the hull. It’s an eerie sound until you realize what it is, but even when you know, the sound is strange enough to steal your sleep. I lay in my bunk, trying to understand what they were saying. They are social creatures, like people. They need each other. I wondered if Jeanne was hearing the same thing in the V-berth. She likes the breeze up there and she says she feels claustrophobic in the wide stern berth where I sleep. I get it. It has a low ceiling. Sit up too fast and you’ll hit your head. I called out: “Hear that, Jeanne? Honey?” She didn’t answer.

At sunrise, sipping my coffee in the cockpit, I felt a breeze tickle the back of my neck – more wind than we’d seen in days. I licked my finger to judge the direction. Southerly. On our nose if we kept going.

“You know what,” I said to Jeanne, “with this wind, we could be home in 24 hours.”

“In time for Dan’s party,” she said. Our eyes met. She nodded. She didn’t need to say it. I knew I should be there.

“But can we go with the engine like that?” she asked.

I shrugged. “People have been sailing without motors for thousands of years,” I said. “I think I can fix it enough to work if we need it, but we’ll have to sail.”

“Let’s sail, then.”

*

We tacked out the channel and turned north. When we raised the main, the boat lurched forward and flew as if it had wings. We slept in shifts for a day and a night as that blissful southeast wind filled our sails. The sea was smooth. The sun shone. We laughed and sang along to old 70s rock. We rested and read our books, and we never saw another dolphin until we tied off at our home dock. And then, the minute I stepped off the boat, a huge one breached, his port-side eye gleaming. I swear I saw that thing smile.

*

I wore my Hawaiian sailboat-print shirt and flip-flops to a sandy-shoes bar in Madeira Beach for Dan’s “celebration of life.” I still didn’t want to go. But it felt right to be among Dan’s friends in a bar he loved listening to a guy with a guitar playing Buffet.

“I just got home from the worst sailing trip of my life,” I said to start my toast. “There was no wind or too much wind and everything broke. But the last day, coming back here, was the best sailing of my life. I don’t know where you are, Dan-My-Man, but you sure let me know where you wanted me to be.”

Dan’s sister Donna cradled a white cardboard box in her lap through all the toasts. Inside were four bottles of gray ash. She handed one to me. “You know what to do with this.”

“I do.” Dan was supposed to be laid to rest near his mom up in Maine – among the wildflowers, not in the sea. “Good thing I’ll be in the ground,” he said, his mouth curling the way it did when he was about to make a joke. “Water’s too damn cold. I’d freeze to death.”

He thought people who were buried in one place had it all wrong, though. He also wanted his ashes in the Gulf, where the water is always warm. It wasn’t like he knew he was dying, but somehow he’d made his wishes known.

Another vial was for his second ex-wife because he said she never wanted anything to do with him when he was alive. She loved him, though, you could tell. She cried when Donna gave her the vial.

“Where’s the fourth bottle going?” I asked.

“Where do you think?” Donna said.

Could only be one place. Dan had to join the sailors and drinkers at Mile 0, end of the road.

“He wanted to be sprinkled over the meditation labyrinth in the Key West Botanical Garden,” Donna said. “He liked the view.” 

 “I’m surprised he didn’t ask you to hide him in a bar,” Jeanne said.

*

A week later, we sailed out of Clearwater pass at sunset, engine repaired and humming, with Donna and a few others aboard. We passed around a bottle of Flor de Caña rum, each of us taking a swig for Dan.

When the dolphins appeared, as I knew they would, I turned into the wind. The mainsail flapped as Jeanne tossed white rose petals from the stern. I lifted the top off the vial and let Dan’s ashes swirl upward. He landed amid those petals. At that moment, a dolphin snorted and dove into the slurry, pulling Dan into the deep, to rest at last.