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We finished our preparations and set sail for Ibiza. My crew were college students taking fall semester off. Nick, Charlie Junkerman’s son, had suffered up the California coast with me two summers earlier, on the way to my first charter season in the San Juans with Grendel. I had promised him and his parents that this trip would be better, an enjoyable cruise through the Med and then an easy downwind sail across the Atlantic and Caribbean to the Yucatan. Emi had been a student in one of my undergraduate courses. She was from Homer, Alaska, and had spent many seasons working on her family’s commercial fishing boat. Her boyfriend Matt, also an Alaskan commercial fisherman, had joined us even though I wasn’t paying him.

The trip through the Strait of Sicily was rough. So when we pulled into Ibiza after three days at sea, I was tired. A beautiful harbor, with a huge castle on the point, but also an overcast, blustery day. As I entered the narrow fairway to the marina, the wind was gusting at over thirty knots from behind, which made our entire boat act like a sail. I had the engines in reverse as I was blown down the fairway past dozens of multimillion-dollar motor yachts.

I saw very little of Ibiza. It’s a famous party town, one of the most famous in the world. Clubs that pound all night. We were seeing it in mid-October, though, after the high season, so it was quieter. The castle was magnificent and much better preserved and more accessible than any other I had visited in the Mediterranean. I felt the full enchantment of the place at night with Nancy, walking the fortified walls lit in green and white, following mazes down inside the castle, stone passageways that twisted and turned and finally emerged in some new vista of lights overlooking the harbor and city. I longed to have just a little more time, but I was on a schedule, meeting people in Gibraltar, the Canaries, and St. Lucia, and I had to keep the boat running. I had to arrive in Mexico on time for my new permits and licenses and other preparations for the winter charters.

So we sailed for Gibraltar, Nancy and the crew and I. No guests. And we hit no weather at all. It was flat calm. Reflective, like a mountain lake, with no boats and no wind. Even when I had hit a huge calm in the Pacific a thousand miles out from Hawaii on Grendel and seen a blue whale, I had been able to detect a very gradual swell, but on this trip there was no swell at all. We motored without sails across endless glass, laughing with each other at the oddity of it. Our last night, we passed through an enormous fishing fleet, lights everywhere on the water, like fireflies. Off in the distance were two lighter patches of sky that over the hours became the two Pillars of Hercules, Gibraltar and Europe on the right, Morocco and Africa on the left. Two such different worlds so close to touching. We could see the lights of individual buildings on both shores, and heavy shipping traffic in between. Scores of tankers and freighters were anchored in the shallows, our radar dotted up for miles.

We entered the Bay of Gibraltar, passing just southwest of the famous rock, which was lit by spotlights, and waited half an hour or so for daylight to make our approach into a marina. I felt lucky to be experiencing all of this, voyaging from one end of the Mediterranean to the other, and I think the crew felt the same way. In the future, though, I wanted to have the luxury of visiting every port. We had passed so close to Tunis, an African port, but the schedule hadn’t allowed a stop. We had passed Sicily, also, without stopping. We had sailed close enough to see these places, the outline of their mountains, had studied them through the binoculars, knowing we were missing everything. I missed Turkey already like a second home, ached for it despite all the hassles. And what about these other countries, if only I could spend some time in them?

In Gib, as the locals refer to it, we were joined by Barbara, one of my lenders who had already been on trips in the San Juan Islands, the British Virgin Islands, and Mexico. She was happy to be on vacation, away from the responsibilities of her law firm and kids, and she was anxious to head out.

My three crew were busy roaming Gibraltar for various spares and offshore equipment. The entire country is only three miles long and a mile wide, a warren of small shops that seem nearly invisible but are known, without exception, by every Gibraltarian. And the landmarks are houses and neighborhoods, rather than streets. “That’s near Imossi House, just before Irish Town,” they’ll say. Gates and walls are also used as landmarks. The walls run everywhere, large stone structures with various important gates commemorating war. The whole country a small wart on Spain’s backside (which Spain would like to have removed), but it looks nothing like Spain, and it even has its own weather, because of the Rock, which catches what is usually the only cloud for hundreds of miles and then manages to squeeze some rain and cold out of it, while Spain remains sunny and hot.

The main chandlery in Gibraltar was Sheppard’s, very near our marina. They can boast the highest prices for marine hardware anywhere in the world, combined with the very worst customer service. They can offer all this because they have no competition, a condition guaranteed to continue into perpetuity because of tight, nepotistic control over business licenses.

Gibraltar, all in all, is a dark and depressing little place. The bright spots are the pasties and the megayachts. The pasties at Dad’s Bakehouse are extremely cheap and tasty. Delicious pastry filled with the classic beef, potatoes, carrots, and onion, or variations with chicken or veggies. I was also fond of several fish-and-chips shops. And you can’t beat Gibraltar for megayachts. Everyone stops in Gibraltar on their way in or out of the Med, and these largest yachts tend to make their transits every year between the Med and the Caribbean. Boat International, the magazine that features them, is the only magazine I treasure, and for each megayacht that pulled up, Nancy and I would pull out the appropriate issue and stroll the dock to gaze at the exterior and check out the interior and specs in the magazine. Megayachts are a ridiculous waste of money, costing twenty million dollars or even ten times more, but they are also among the most beautiful and amazing objects created by humankind. Our favorite was a long blue hull of classic design with a high bow and a narrow stern, a varnished deckhouse and other classic brightwork combined with an ultramodern rig and underbody. The perfect fusion of the traditional and the modern, and as large as three city buses placed end to end.

We made good progress on our work, despite the distraction of these yachts parked right next to us, but the weather turned sour and delayed our departure. It was cold and squally, with a lot of rain and no weather window appearing.

I spent more and more time in the Internet café, fighting Amber. She assured me she had paid bills correctly after we received the $150,000 loan from Rand and Lee. But when I called my various cards to verify, I found she had mispaid my bills by an astounding $48,000. On my biggest AmEx card, she had paid $18,000 more than I had asked. This was $18,000 that didn’t need to be paid until the next month. She paid over $10,000 on another bill that wasn’t yet due. And she didn’t pay anything on a $12,000 bill that had to be paid immediately. I couldn’t understand how she could be so incompetent. I had written down the details very clearly and reminded her to double-check when she paid. She was a Stanford graduate, not an idiot, so the only explanation was that she didn’t care. She had already informed me she was moving on to a new job at the end of the month. A friend of hers had started a dot-com with millions of dollars, so she was getting a job as a product manager, even though she had no idea what that role entailed. And she didn’t care if my business went straight into the toilet.

I felt trapped. I should have been in California, saving my business, but I also had to stay with the boat and deliver it to Mexico. The winds were increasing, the weather turning foul, so I couldn’t have left the boat even if there had been no deadline for getting to Mexico.