The Client & the Most Dashing Yachtsman on Capri
Swoon-worthy destinations, luxury hotels, an adventurous client hellbent on finding love. What could go wrong? Oh, everything.
The following is a true story, but some identifying details have been changed.
Today, walking down to the sea, I passed a handsome man with salt-n-pepper hair, who reminded me of the Most Dashing Yachtsman in Capri.
And that got me thinking about my former client, wealthy “Phoebe” from Miami Beach (let’s say) — a fun-loving, two-time divorcee, who had everything to do with why I encountered the Most Dashing Yachtman on Capri.
I met Phoebe a while back, just as she was launching a new health-oriented enterprise that showed great promise. I wrote articles for her new company’s website, but a few months into it, Phoebe decided that she wanted me to ghostwrite a book for her.
She had in mind a memoir about bouncing back from divorce — a book about the joys and challenges of jumping into dating in a vastly altered landscape. Phoebe wanted a dating book that would land her on the talk shows, a book that was both extremely insightful and laugh-out-loud funny.
I figured if all went well, we could knock it out in six months.
Except there was a hitch.
From the first time she mentioned it, I pointed out that there was a big problem with her idea for a dating book: she wasn’t dating anyone. That snag would be quickly addressed, she assured me. In the meantime, she had me write up five chapters about her previous marriages and where they had gone wrong.
The Search for Love Begins
To remedy her lack-of-a-social-life impediment, Phoebe and I flew to a ritzy ski resort, where she believed she was certain to have a whirlwind romance or three — since, she claimed, the ratio of men to women was 14 to 1.
Upon arrival in the pristine mountain getaway, I was shocked: it seemed that the ratio of men to women was actually about 593 to 1.
The ski town was simply awash with handsome guys — and the very few women we saw were inevitably with husbands. Strangely, whenever Phoebe, who is attractive and dresses seductively, flashed a smoldering look at one of the men, they looked away.
After a few days, we discovered why her “come-hither” looks were met with blank stares: unbeknownst to her when she booked our stay, it was “Gay Ski Week.”
A Fresh Stab
When she returned to Miami after that non-romance-filled vacation, Phoebe, who was pushing 50, embarked on a series of amorous affairs with 20-somethings — a handyman here, a surfer dude there.
While “the younger man” theme arguably has a place in a modern dating book — under the heading “Lessons Learned and Not to Be Repeated” — these sounded like trivial, empty encounters, none involving stories remotely worth capturing; nevertheless, I duly took notes and wrote up chapters, feeling like the slumber-party confidante of a hormone-crazed teen.
But then Phoebe decided to backburner the dating book idea and instead make the memoir about her recently launched business, which both an astrologer and a “seer” predicted would be a phenomenal success.
When she flew to an exotic country in Asia to meet with a potential investor, Phoebe invited me along — wanting me to document how charming yet business-savvy she was.
However, there was a catch: she didn’t want the potential investor to know she was writing a book. So she would tell him I was her PA.
Let me be clear: I am a quirky, bohemian writer, not that perky, organized, fresh-from-college person whom you’d hire as your personal assistant. From the get-go, I was committing serious gaffes and blunders worthy of immediate dismissal of a PA — including accidentally making off with the prospective investor’s car keys, which remained in my purse all night, forcing him to get a hotel room — a faux pas that both he and she thankfully laughed off.
That trip was rich with rip-roaring adventures, but when I’d agreed to act the part of her personal assistant, the dynamics changed. With rare exception, such as the Car Keys Incident, Phoebe kept barking orders at me and acting imperious.
Even though the setting was dreamy, I was elated when that journey, and my stint as her faux PA, came to an end — all the more because her dazzling suite was on the 23rd floor of a luxury hotel. I get woozy with heights and the elevator was glass, and my stomach wrapped around my throat every time we ascended in the see-through elevator.
The morning we were checking out and I stepped out of the glass elevator into the hotel lobby, I felt tremendous relief knowing that I’d never have to step into it again.
Unfortunately, in the hotel lobby, Phoebe realized she’d left jewelry in the hotel room. “Go get my ring, Melissa!” she demanded.
So I warily hopped back on the glass elevator, alone, pushed the button for floor 23, and braced myself. Mid-ascent, the elevator got stuck between floors and remained stuck for 15 minutes, prompting a panic attack. When it finally violently jerked and then started moving again, the elevator did not take me to floor 23 but thankfully returned me to the lobby, where I ran out and over to Phoebe.
“You can go back and look for it yourself,” I told her, in hyperventilating voice, my heart still pounding, “because I’m not setting foot in that elevator again.”
“No need,” she said with a laugh. “I found my ring!”
More Bumps
After many months of having me write the book about her start-up venture — we were nearly done, except for the chapters on its astounding success, which hadn’t happened — Phoebe’s business appeared to be floundering. Her partner, whom I’d interviewed extensively, artfully weaving his tale into her book, suddenly pulled out, so did the investor, and her staff up-and-quit.
Phoebe decided to ditch that book idea and go back to the dating book.
Alas, she still wasn’t dating anyone.
Which is how we ended up on Capri, where love would assuredly blossom.
Phoebe had gone to Capri on her first honeymoon nearly 30 years before, visiting frequently since. The enchanted isle to the west of Italy, where depraved Roman Emperor Tiberius fled and where Jackie Kennedy vacationed (wearing Capri pants, of course), was her most adored place in the world. Magic would soon unfold, she assured me. Especially since we were starting off our trip not on the island, but in the gorgeous village of Ravello on Italy’s heart-stopping Amalfi Coast.
On the (Coastal) Road Again
At the airport in Naples, a driver from the Ravello hotel — who looked like a movie star — picked us up in a flashy Mercedes. Phoebe sat in the passenger seat and when I slid into the back seat, I noticed paper puke bags tucked into the pouch — understandably.
The necklace of mountain villages strung along the breathtakingly beautiful Amalfi Coast are connected by a narrow road of high-altitude hairpin turns overlooking the crashing Tyrrhenian Sea, which one tiny little itsy-bitsy steering miscalculation will have you plunging right into.
I’d traveled along the Amalfi Coast Road a decade before, a harrowing ride on a bus, which — whenever it met another bus on the road — backed down the curves in reverse, each time prompting all onboard to launch into solemn prayer.
So I was relieved that this time the vehicle was much smaller, negating the need for reverse curves and praying, I hoped. I settled back, erroneously believing that this time I would enjoy the ride and the views spilling below.
However, every time there was another spine-tingling curve in the coastal road along the perilously high cliffs, Phoebe very shrilly SCREAMED at the top of her lungs — as though on a roller coaster — and forcefully grabbed the chaffeur’s right arm. Although the driver requested that she stop doing that, around every impossible bend in that hour-long drive she’d scream and again yank his arm.
Pro though he was, even he broke out in a sweat during the drive (that amazingly didn’t turn into a dive) until finally we pulled up to the charming villa hotel in Ravello.
The cliff-perched village, where writer Gore Vidal once owned a sprawling villa, was stunning — craggy, but lush, and its commanding panoramic views were intoxicating. But unlike the ski resort during Gay Ski Week, Ravello wasn’t exactly swimming with men.
Outside of the driver, who — apparently catching the lascivious look in Phoebe’s eye — volunteered that he was married, we hadn’t laid eyes on one guy under age 95. At lunch we finally spied a man without a walker: the middle-aged restaurant owner, who did a double-take when he caught the ample cleavage spilling from Phoebe’s plunging-neckline dress.
A view as beguiling as the Amalfi Coast Road, his eyes seemed to say.
When Phoebe paid for our meal with her black American Express, the restaurant owner, who was not the slightest bit debonair, was even more intrigued — plunking down a bottle of limoncello and pulling up a chair.
Phoebe mentioned that she was looking for someone with a boat to take us to Capri the next morning. He had a friend who would assuredly take us there for a fantastic price, he said.
Then he began grabbing at Phoebe’s bosom, which she laughingly endured, while I kept vainly making “time out” signs across the table and flashing her horrified looks.
When he finally left to call his friend, I suggested that she not let men paw her, especially in Italy, especially somebody like the creepy restaurant owner.
“I was just making sure that we get a great price for the boat trip!” she replied.
While the owner was on the phone with his friend, his 20-something son made a beeline for Phoebe, pulled out a chair, and three seconds later began making out with her — with me right there across the table, yelling, “Oh, for crying out loud, cut it out!”
As his father approached, the young upstart fled, and the owner announced that his friend would take us to Capri — for a mere 600 euros (about $700) — a price too steep even for Phoebe, although I’m sure the price inflated after he caught the smooching with his son.
A Steep Descent into Positano
That evening Phoebe booked the hotel driver to take us to a beachfront restaurant in Positano, a much more lively town 20 minutes away. Having previously stayed in that gorgeous village tumbling down a hill, I was elated to return.
When we met in front of the hotel, I noted two things: our chaffeur was not the dashing driver from the morning. His portly replacement explained the original driver had been called away at the last minute.
The second thing: Phoebe, clad in a tight dress with an even more revealing neckline, was wearing red, very spiky high heels.
“Phoebe,” I said, “I don’t think those are great shoes for Positano. We’ll have to walk down a steep stone path to get to that beachfront restaurant…”
She’d been to Positano before, she said, I didn’t have to explain anything to her. She’d have the driver drop us off in front of the restaurant.
I noted that cars couldn’t enter the village — we’d have to walk down. Phoebe rolled her eyes at my insolence. Then she realized she’d left her phone in the hotel room.
“Go get my phone, Melissa!” she demanded. I was about to point out that I was no longer her faux PA, when she became enraged. “Get my phone, now!” she yelled. “We’re already late!”
She snapped her fingers at me and pointed toward the hotel.
Normally, I would have told anyone who snapped their fingers at me to shove it. But, uncharacteristically, I bit my tongue and retrieved her phone. However, I was fuming and didn’t say a word the whole ride there — during which, thankfully, she didn’t once scream or grab the driver’s arm, probably because this chaffeur wasn’t hot.
At the very top of Positano, the driver stopped. Phoebe commanded him to drive directly to the restaurant. He said he couldn’t drive through the village: we’d have to hoof it through the pedestrian-only town center.
“Well, I’ve never heard of such a thing!” Phoebe said, miffed, as we got out. She looked before us at the steep, uneven cobblestone path that wound down to the sea. If I’d been bigger or stronger, I’m sure she would have insisted that I carry her down.
“Take off your shoes and walk barefoot,” I said. But she was determined to wear those red stilettos with the 6-inch heels. She took my arm and slowly teetered down the mile-long path — amazingly, never once falling — though every eye at every terrace restaurant that we passed fell upon us, some onlookers openly laughing, pointing, or shaking their heads in disbelief.
The dinner was only so-so, but afterward we walked — Phoebe teetering along — to a groovy club built into a cave, where we saw two interesting-looking 30-something guys. They ignored us.
“Who cares,” said Phoebe. “I’m waiting for the men in Capri!”
The Boat
The next morning we boarded a hydrofoil that stopped at Positano, Sorrento, and Capri. As we pulled up to the first port, the ferry hand yelled out “Positano!” and disembarked. Nobody got on to replace him.
“How long until Capri?” I asked as we headed across the sea. I was already feeling queasy.
“Two more stops!” said Phoebe. “It’s the last one.”
When we pulled up to the next stop, nobody yelled out anything and I was feeling pretty sick. “Isn’t this Capri?” I asked her. It looked like the photos I’d seen of the island.
“Melissa, I’ve been to Capri six times! I know exactly where we’re going!”
By the third and final stop, another half hour away, I felt horrible — and that was before they called out the name of the port.
“Sorrento! Last stop! Sorrento!”
The previous stop indeed had been Capri. By the time we got back to Capri, my stomach was sloshing around in the vicinity of my ankles.
Capricious Capri
“I’d sure love some lunch,” I told Phoebe as we set off through the town center. But first she wanted gelato, then to find her favorite restaurant, which took an hour of wandering to locate; by the time we found it, they’d stopped serving.
On and on we hiked in the blazing sun, passing closed trattoria after closed trattoria, until finally, down a secluded lane of stunning villas, we found a restaurant where the door wasn’t locked. Upon entering, my eyes fell upon a quartet of handsome, nattily dressed men in their 50s. The one with salt-n-pepper hair was particularly easy on the eyes, I thought. He looked over and winked.
“This place is perfect!” I said.
The kitchen, however, was closed. I was surprised that the quartet, who were clearly checking us out, didn’t invite us to join them.
“I wanted to talk to those guys!” I said as we left.
“Oh, this island is small — we’ll see them again,” said Phoebe. “They’re probably yachters. The ‘little marina’ where yachts moor is right below.”
I mentioned that it would be perfect for her book if she were wined and dined by a yachter, who told her about his adventures at sea over dinner, perhaps even sailing her back to Miami.
“Oh Melissa, all of those guys were way too old for me!”
I did not point out they were only slightly older than she was, if at all.
The Search for the Yachter Begins
That night, we met some of Phoebe’s friends from Miami, all couples clad in designer clothes and most of them snobs. I left to stroll across the terrace and through the restaurant, looking for the Yachter with the Salt-n-Pepper hair. But he wasn’t there.
When I returned to the table, one of the friends was lecturing Phoebe.
“Why do you keep chasing after younger guys?” the friend asked.
“I’m not chasing after them! Young guys are chasing after me!”
“Get over it with the kids, Phoebe. You need to go for marriage material — older men with money!”
That night, we sat at a terrace bar people watching. The streets, lined with designer stores, were filled with gorgeous men, every one of them strolling with gorgeous women at their sides.
I scanned the crowds for the Dashing Yachtsman, but didn’t spot him.
The Non-Sommelier
At the terrace bar, we met an Irish couple on their honeymoon. Aidan was a white-haired 50-something business owner and his new wife, Riley, was a daycare worker in her 20s. They were riotously funny — and we met them for dinner the next night at another fancy-schmancy place of Phoebe’s choosing, where yet again I did not see the Dashing Yachter.
“Why is it that society is fine with marriages between older men and younger women, but everybody freaks out if the situation is reversed?” Phoebe asked.
Aidan said it had been plenty uncomfortable when they first started going out; before their first date, he’d even asked permission from her parents.
And then he launched into a mystical story. He said that the year before he’d checked into the hospital with enigmatic health problems, and the doctors, after running tests, told him that he didn’t have long to live. Alone in his hospital room, he began yelling at the universe. Fifteen minutes into his fit, a strange light flashed in the room and a male voice boomed out saying, “I’m in control here!”
I wondered if it had been somebody just messing with him over the intercom, but even though Aidan wasn’t at all religious, he suddenly believed that his future was in divine hands.
Ten minutes later, the doctors entered his room — carrying an altogether different set of test results and giving an entirely different prognosis — and he had minor surgery and has enjoyed fabulous health ever since. Aidan said that the experience changed his outlook on life — and he no longer worried about “the wee things.” He also decided to marry Riley, regardless of what Irish society thought.
“Quite the inspirational tale!” I said, thinking Phoebe would pipe in.
But she didn’t. She was staring across the restaurant.
“Look, look!” Phoebe whispered to me. “That guy keeps checking me out!”
“Who?”
“The sommelier!”
“What sommelier?”
She gestured across the terrace at a kid who vaguely resembled a very young Tony Danza.
“Phoebe, he’s a child!”
“How can he be a child if he’s a sommelier?”
Turns out, he wasn’t a sommelier — he was an 18-year-old busboy. We learned that after we moved over to the adjoining gardened patio for an after-dinner drink. As the restaurant cleared out, he appeared for an after-work smoke, and Phoebe demanded I ask him to join us.
Unfortunately, the busboy didn’t speak English, requiring that I translate everything Phoebe wanted to say to him — and vice versa.
I felt like a procurer — and one in a precarious situation. Because the busboy was trying to hit on me, probably simply because I could speak his language. I clarified in Italian that Phoebe was the one who was keen on him, asking if he knew any yachters with salt-n-pepper hair. He didn’t.
“What’s he saying?” Phoebe asked when he launched into another cliché-ridden attempt to woo me.
“I’m not sure,” I said, again telling him in Italian that Phoebe was the one who was hot to trot, not me.
Ticked that he kept talking to me and wasn’t even trying with her, Phoebe stood and wrapped her leg around a nearby pole, appearing ready to break into a pole dance for the young lad. That grabbed his attention all right.
“He says you have the most beautiful eyes,” I told her. “And he really likes your scarf.”
“Tell him I’m taking him out to eat wherever he wants!”
He said he’d stop by the hotel at 2 the next day.
As my many attempts to convince Phoebe to return to the restaurant where we’d seen the yachters had proved unsuccessful, I decided I’d head there on my own — right around 2 the next day.
The Ridiculous Nadir
However, the following afternoon when I announced I was going out on my own, Phoebe had a fit. “You can’t leave — you know I can’t speak Italian!” she said.
“Just use Google Translate on your phone,” I suggested. “Besides, you’re fluent in the international language of love.” And pole dancing.
She insisted that I stay — to take notes on what would be a thrilling chapter in her book.
“Pursuing an 18-year-old busboy, Phoebe, is not thrilling. It’s cheap, tawdry, questionable, and doesn’t show you in a good light.”
We’d write him up as a 30-something sommelier, she said. And besides, she reminded me, I was her guest and I had to do what she wanted. Like I needed reminding of that.
At 1:55, Phoebe was messing around with her hair and makeup, and still not dressed. “Go down and wait for him,” she commanded.
I sat on a couch on the patio, praying that he’d stand us up. He didn’t. When he saw me, he ran over, kissed me on the cheeks, and told me how happy he was that I’d changed my mind — because it was me that he longed for, not Phoebe.
“She’s the one taking you to lunch — not me,” I told him.
He went off on another spiel that included such key phrases as “bellissima,” “amore,” and “te voglio bene.”
“Basta,” I said, sickened by his professions of fake love that seemed out of a book.
Just then, Phoebe stormed over. Even though she didn’t speak Italian, she’d gotten the gist of Romeo’s pronouncements of bs. She glared at me. “Ask him where he wants to go for lunch,” she hissed.
He said, in Italian, that he wanted to eat in the hotel room. I told him that wasn’t an option.
“What’s he saying?” she asked.
“That he wants to order room service in the suite. I told him to forget it.”
“But that’s a brilliant idea!”
“Phoebe, clearly he just wants sex.”
“Fine by me!”
“Well, then go for it,” I said with a shrug. “I’m leaving.”
“Oh no you’re not! We’re going up to my suite and having a three-way,” Phoebe informed me. “It’s going to be the steamiest chapter in the whole book!”
Now it was my turn to glare. “Phoebe, I am writer. I am not a call girl, not a slave, not your PA. I’m not going to sleep with you or with Junior, separately or together. And I am leaving right now.”
“Don’t you dare, Melissa!”
“Ciao-ciao,” I said and stomped off.
The Search Continues
I hustled to the restaurant where we’d seen the yachters, but it was closed. I walked along the Marina Piccola, then the Marina Grande, I checked out terrace bars and boating stores — and anywhere else the Dashing Yachtsman might go. But I couldn’t find him.
I looked into getting my own hotel room — but it was high season, Capri was filled up. I considered taking a ferry to Naples and catching the next flight out, risking sleeping at the airport.
Finally I trudged to the hotel where Aiden and Riley were staying. Happily, they were there at their cottage — swimming in their private pool. I told them what had happened — and that I was in a jam.
“I realize that you’re newlyweds and this is weird — but if worse comes to worst can I spend the night here? I’ll sleep outside on one of the pool chairs…”
Just then Aidan’s phone rang. It was Phoebe. “Yep, she’s here,” he said. “Sure, we’ll meet you for dinner. Is your boyfriend coming?”
Thankfully, he wasn’t.
On the walk to the restaurant, I kept searching in vain for the yachter, wondering if he’d sailed off to Naples or Positano or Timbuktu.
Phoebe was in charm mode when we met at the restaurant.
“Are you all right?” she began, feigning concern. “We looked everywhere for you! Nothing happened between us, of course…”
“Of course.”
“He was too young anyway…”
“Think so, Phoebe?”
“I can’t help it if the 20-somethings flock to me…”
“He was 18. I suggest you aim a little higher than busboys, Phoebe. And a little older, too.”
However, that night as I surveyed the restaurant — again not seeing the yachter — and when we later went out for drinks because Phoebe again wanted to “people watch,” I realized what the problem was. Capri may be the isle of love, but it’s best to byo lover.
“This isn’t people watching, Phoebe,” I said. “This is couple watching. Nobody here — including your friends from Miami — is single. It’s all honeymooners and second-honeymooners. We really should find those yachters.” Although they probably had wives, too.
To her credit, Phoebe was on good behavior with me for the rest of the trip — no snapping fingers, no barked orders, no demands for three-ways, no new crushes on 20-somethings, and no forcing me to procure them.
She even acted open to my idea for a new outline for her book: meeting one man different ways for each chapter— a dating service, Tinder, a church group, a blind date, a personals ad. And if none of them worked out, she could conclude that love and romance were overrated and that she was better off alone.
“Huh, hmm, interesting!” she said in response.
The Unexpected Final Shebang
For our final meal in Capri, we lunched with Aidan and Riley at Da Giorgio, which peers down over the Sea of Naples from cliffs — Phoebe’s favorite restaurant that she’d wanted to check out that first day we arrived.
It was my last chance to encounter the handsome boater with salt-n-pepper hair. I checked out the other diners—all couples, of course.
“Guess I’ll never see that dashing yachtsman again,” I said. I’d really thought that I would.
Despite his absence, it was the best meal we had in Capri — huge bowls of spaghetti laden with lobster and crab — and our waiter, a handsome, middle-aged guy named Sergio, kept doting on us, asking our names, and, upon learning that this was our final meal in Capri, he brought desserts on the house, and, of course, limoncello. We stayed for hours, being the last table to finish.
Finally, we stood to leave. Phoebe, Aidan, and Riley were already out the door, when Sergio called me back. When I turned, he handed me a piece of paper with his phone number.
“Meleeza, you must return to Capri!” he said, and then, before I saw it coming, he grabbed my face and gave me a passionate kiss. “Come back to Capri, Meleeza, come back!”
“Highly unlikely,” I mumbled and headed out the door.
When I caught up with the others, Phoebe asked what that was all about. I shrugged.
“Took me by surprise,” I said. “I never did meet the dashing yachter with the salt-n-pepper hair, but I did meet a handsome waiter with salt-n-pepper hair…”
And then I started cracking up.
“What’s so funny?” Phoebe asked.
“I just put it together — that was him! The guy I was looking for all week. We assumed they were yachters because they were dining late at the restaurant by the marina. But they were just off-duty restaurant employees.” I couldn’t stop laughing. “What does Capri mean anyway?” I asked. “Isle of playboy waiters?”
That set us both roaring.
“Whatever it means,” said Phoebe, “you have to admit that we both made out much better here than we did at the ski resort during Gay Ski Week.”
And we couldn’t stop laughing all the way to the ferry back to Naples.
After five years of working on Phoebe’s memoir, years during which she changed the topic, plot line, and characters involved in her tale a dozen times, I finally said “Arrivederci.”