Fishermen are drawn to exotic destinations like bugs to a light, and one of the beauties of owning a boat nowadays is that you can send her to those ports of call. For big-game fishermen, the island of Madeira off the coast of Portugal has become hallowed ground for giant blue marlin, and this glowing garden island cast her brightest beam on boat owner and big-game angler Mark O’Brien and me. The prospect of tangling with marlin weighing more than 500 pounds—and possibly 1,000 pounds—was enough for us to ship O’Brien’s 58 Merritt, Brier Patch, across the Atlantic. Specifically, we’d send the boat to Genoa, Italy, run her to Madeira, spend the rest of the summer chasing huge fish, take her through the Med, and then ship her back home from Genoa.

A voyage of this magnitude is a daunting task: It took four months of planning and preparation before Brier Patch was riding piggyback on the deck of a ship heading towards the Straits of Gibraltar. Getting the boat ready was a huge part of the equation—the administrative tasks alone were mountainous—so seeking the advice of those who’ve done it before was paramount.

Fortunately, I was able to draw from the experience of captains who have cruised the Med aboard yachts as well as some of the best big-game skippers in the business who had fished Madeira in her mid-1980’s glory. I also had two top-rate deckhands in Tim Mitchell and Ben Brownlee, who endured tedious preparation and anxious waiting as the arrival of our ship to Genoa, BBC Spain, was repeatedly delayed (eventually by more than a month).

There are two ways to transport your yacht to an exotic location aboard a ship. One way is to send her with a yacht-transport company like Sevenstar or Yacht Path International, in a cradle on the deck of a cargo ship. The second is to use a service like Dockwise, which utilizes semisubmersible ships set up specifically for moving yachts. The major difference between the two methods is that when shipped as deck cargo, your vessel is loaded on top of the ship with a crane, usually alongside containers and sometimes along with other boats. With Dockwise, you drive your boat into the semisubmerged ship. Once all boats are in place and jack stands and cradles have been affixed under them by divers, the water is pumped out.

We used both methods on our trip. We tried to get a berth on Dockwise sailing from Fort Lauderdale, Florida, to Genoa, but all its ships were full. Undeterred, we called another company and secured an on-deck spot complete with the crane-lift and deck-loading experience. We were instructed to make our boat sufficiently secure to withstand 70-knot winds, not that the ship actually would be encountering such conditions. However, foul weather and squalls with winds of 40 to 50 knots are not uncommon; coupled with the 15-knot speed of the ship, you’ve potentially got 55 to 65 knots of wind over the deck. So all canvas and cushions had to be stowed, flying-bridge cabinet lids and doors taped shut, antennas secured with wire ties, and everything inside fully secured. We also had to have chine blocks fabricated to protect her spray rails from being crushed by the crane’s lifting straps.

This article originally appeared in the March 2007 issue of Power & Motoryacht magazine.