Highlanders

What happens when you send a Penthouse Pet, a reality-TV star, and two regular joes to compete in an adventure race in the rugged north of Scotland?
By John Bolster
Photos by Rodrick Cox

We drank like champions, witnessed three nearfistfights, and narrowly missed uprooting a crosswalk light with our vehicle. And that was just on the ride to the airport.

A quick word to the wise about Drambuie, the honey-and-herb-flavored Scottish liqueur with a legendary 250-year history: Don’t let its pleasing taste and smooth character distract you from the facts that (a) it’s made of malt whisky, (b) it’s 80 proof, and (c) if you down it like it’s some kind of peach schnapps–style girl drink, it will fuck you up.

That was a lesson our group learned right off the bat. Well, most of our group, anyway.

There were 40 of us, and we were headed overseas, as guests of Drambuie, to participate in the Drambuie Pursuit, a nine-stage adventure race in the fairy tale–beautiful Scottish Highlands.

Our teams of four would be shooting arrows, riding speedboats, hiking up mountains, canoeing, biking, running, and, in some cases, puking. Team Penthouse consisted of 2007 Penthouse Pet of the Year Heather Vandeven, former Bachelor contestant Charlie O’Connell, an agent named Brian, and a broken-down Penthouse editor with a trick knee. We would span 180 miles of land and water in the event, which is a reenactment of Bonnie Prince Charlie’s legendary escape from the English in 1746. After a failed attempt to reclaim the British throne for his father, the Scottish prince fled through the Highlands, protected by the region’s clans. As an expression of his gratitude, the story goes, the prince gave his secret recipe for Drambuie Liqueur to James Mackinnon, captain of the Highland clans.

After a send-off party at the Penthouse Executive Club in Midtown Manhattan, we boarded the bus to the airport for our flight to Glasgow. People were ready to take it to the next level. Bottles of Drambuie made the rounds and were tipped heavily, and the company motto—“Enjoy our good taste with your good judgment”—went right out the window, with painful results in some cases. One woman began the bus trip as a fresh-faced, bubbly blonde, only to finish it wandering blotto and cadaverous looking through the airport terminal without her luggage.

Fortunately, she figured it out and went a little easier on the stuff for the remainder of the trip (and someone found her luggage). One guy failed so spectacularly to learn the lesson that he got booted from the trip when we landed in Glasgow.

But once he was gone, and everyone else got their sea legs, the trip rocked. From Glasgow, we made the short voyage to Edinburgh, the historic capital of Scotland. After a day of sightseeing and a welcome party, we boarded a bus the next morning for the Highlands—Braveheart country.

Anyone who slept on that two-hour journey missed some of the most spectacular scenery on the globe, one majestic vista after another: snow-capped peaks, lush valleys and meadows, and the sprawling Loch Ness.

The scenery functioned as a direct counterpoint to the cuisine, which we’re pretty sure has inspired no poetry, except maybe a dirty limerick or two. Most of the food looks like something you might eat on a dare. Have you ever tried black pudding? You should know that the term pudding here is a total smoke screen. Not since sweetbreads has a euphemism been employed more brazenly. Black pudding is in fact a sausage made by cooking blood until it is thick enough to congeal when cooled.

There was a lump of it sitting on our plates on the morning of the big race, and since we’ll try anything once, we gave it a go. Our reaction? Let’s just say we’ve crossed “choke down a piece of blood sausage” off our bucket list, and never speak of it again. Now it was time to suit up for stage one of the event, a Zapcat powerboat race.

Zapcats are two-person inflatable speedboats; one person drives (Drambuie provided us with professionals) and the other functions as dynamic ballast, also known as “hanging on for dear life in the front of the boat and trying not to get tossed out by the g-force as you round the turns at top speed.” We all took a turn in the Zapcat, and, needless to say, this stage was awesome. Even though our boat’s engine died right out of the gate and we had to scramble for a new one, Team Penthouse rallied to escape a lastplace finish.

Stage two had two parts: One team member made a three kilometer uphill bike ride to the foot of a mountain, then the remaining three teammates climbed the mountain on foot. Our man Charlie O’Connell was on the hike team, and he was so gassed by the end that he had to crawl the last 20 yards. Two teams passed him where he lay. “I felt like the snail that gets overrun by two turtles,” he said. “It all happened so fast!”

After the climb, we traveled 40 miles to some rapids for a white-water raft race. Let the record show that Team Penthouse’s white-water-rafting skills were not up to snuff. We’re not sure what the problem was, exactly, but we stunk so bad that, after seeing us in action, our guide simply stopped giving us pointers. Apparently, we were beyond help. Luckily, the river had a current, so we eventually did reach the finish line. We’re pretty sure we placed last in that stage. Dead last.

Next, we biked two miles up a mountain, then barreled back down on an off-road trail. Given the all-USA lineup of participants, this brutal descent had international incident written all over it. It was really steep, and it plunged through mud, stones, tree roots, and hairpin turns. The whole white-knuckled way down, the main thought in our heads was, How the hell is Heather Vandeven going to come out of this alive?

Amazingly, Heather not only made it down in one piece, she also finished ahead of fellow Team Penthouse members Charlie and Brian.

With only three stages left, Team Penthouse was in good position to achieve the two objectives it set after taking stock of the rest of the field. Goal No. 1: Have a good time. Goal No. 2: Defeat at least one of the other nine teams. No. 1 was in the bag-we were having a blast-and No. 2 was within reach, as we were in ninth place.

We held that position until the final stage, a one-mile run through the city center of Inverness. But the tenth-place team, the Rusty Nails, was nipping at our heels. O’Connell looked like he might not make it. But as we labored toward the finish line at Inverness Castle, just a short uphill sprint away, he and Heather made one last heroic push, putting a few crucial yards between us and the Nails. Then, just to be sure, Brian grabbed them both and shoved them over the line.

Goal No. 2 accomplished.

O’Connell collapsed on the ground in the finish area, and we can’t say we ever saw him get up. We’re not saying he perished there, but we didn’t see him rise. When all was said and done, it was a spectacular event (a team of Idaho smoke jumpers—guys who parachute into forest fires, on purpose, to fight them—ended up winning, by the way), and worth it for the scenery alone.

If you happen to see a few Drambuie representatives at your local watering hole some time soon, offering chances at a free trip to Scotland, sign up and give it a shot. You won’t regret it. See PursuitOf1745.com for more on the Drambuie Pursuit.