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Every two years, thousands of white people congregate in Newport, Rhode Island, hop on sailboats, and race each other to Bermuda. They are vying for the chance to get to the Royal Bermuda Yacht Club first, belly up to the bar, get wasted on Dark ‘N Stormies, and spend the night dancing to the house band’s cover of “Disco Inferno.”
Normally somebody with my level of sailing expertise (novice to quite novice) would not be invited to sail in the Newport-Bermuda race. But as Jimmy Buffett once sang about me in his 1978 album, Son of a Son of a Sailor, I am the son of a son of a sailor.
My grandfather taught himself how to sail in a little skiff while reading a sailing textbook, and thus officially converted our family from Judaism to Protestantism. Fine – technically speaking, we are not Protestant. We’re not even Anglo-Saxons because none of us have English blood and only one of us, a second cousin, ever played the saxophone in his junior high band. But we are White, and we are Asshole Sailors, and we are People, so we are White Asshole Sailor People, which is just another version of W.A.S.P. In the sailing community, this makes us members of the sailing community.
My dad grew up sailing too, and for a short while in my childhood and early adolescence we owned a 33’ sailboat. I liked the boat, but I didn’t love the boat. I just never thought it was worth the effort. First, you had to get the boat ready to sail, which usually consisted of way too much cleaning, tying, untying, and varnishing. Then you had to actually sail the thing, which is a very complicated procedure, especially if you’re trying to go up wind, in which case you CAN NOT GO WHERE YOU WANT TO GO. Instead of traveling in a straight line, you have to “tack” back and forth, much the same way your car has to zig zag its way up Mt. Washington because some drunken posse of idiot road workers couldn’t figure out how to lay a straight line of asphalt between base camp and the summit.
But the most frustrating thing about sailing is the speed, or lack thereof. If you’re lucky, in a sailboat you move at the pace of an overweight middle-aged pregnant water buffalo jogging in ski boots.
All that being said, I do enjoy sailing in small doses, so I was glad that my dad was able to convince his college buddy, Captain Mark, to bring me along for the race. And I had an awesome time.
Sailing is a sport where team chemistry is very important, and our team was a tight one. We had a good captain, a good navigator (my dad, “Cold Eddy” White), and I had a skilled and patient watch captain (Andy, who broke the record for most Heinekens in a race without getting drunk). Andy, for example, didn’t care that whenever he asked me to tie a knot, I would make two bunny ears and start looping them around each other like I was fixing my shoe lace. Or I guess he did care, but he would just re-tie the knot for me, and I was allowed to go back to reading The Beach.
We also had a great computer technician, Jeff, who wisely (or maybe not-so-wisely) brought along all fourteen editions of Girls Gone Wild. I’m pretty sure we became the first boat in the 100-year history of the Newport Bermuda-race to watch soft-core porn on deck, while sailing.
My role on the boat, other than buying groceries before the race, staying out of the way, and working on my sunburn, was to keep the older crew members up-to-date on porno terminology. I realized there was a need for this when we started using spinnaker bags as seat cushions. After a couple hours of sitting on the spinnaker bag, the spinnaker would get flat, and the bag would be in need of fluffing. When Lew, the eldest member of our crew and a true gentleman, fluffed the bag, someone told him he was a good fluffer. I thought this was hilarious, but nobody else knew what I was laughing at, so I had to explain. Then everyone got the joke so they laughed, too. And then I made a hat out of a cardboard box for Captain Mark that said “BOYS GONE WILD – #1 FLUFFER.” He wore it proudly for two minutes, and then he threw it into the Gulf Stream.
Probably the best thing about our boat was that we weren’t like other boats. We sailed on a very nice Swan ’51 called Tonic, but it didn’t have all the glossy painted curly-cues and matching flags that some of the other boats had. When we pulled up to the Royal Bermuda Yacht Club (illegally, by the way – we didn’t have a reservation, so they kicked us out after seven minutes), I felt a little like Han Solo slipping the Millennium Falcon into the Death Star, except I wasn’t driving and we weren’t on a space ship and the Royal Bermuda Yacht Club probably isn’t equipped with a laser beam that can blow up small planets.
The guys on the other boats – they just looked like nerds.
Question: Who, exactly, are these nerds?
Answer: They are rich white people who, if their lives were turned into movies, would all be played by Phillip Seymour Hoffman (unless they are older than fifty-six, in which case, they would be played by Phillip Seymour Hoffman in a lot of makeup).
Usually, due to constraints on available oceanfront property, sailing people are spread amongst rough neighborhoods like Newport, Nantucket, and Annapolis, although occasionally they all congregate for reunions in the Hamptons. But nothing brings them together like a Newport-Bermuda race. You can’t blame them – everyone wants to hang out with their friends from time to time. It’s the same reason Muslims go to Mecca, Hollywood stars go to the Cannes Film Festival, and fat RV-owners from Pennsylvania go to Maine McDonald’ses for lobster rolls.
If you’ve never seen a sailor up close, this is what he looks like, from toe to head:
Feet: Brown leather Topsider boat shoes.
Legs: Very tan, not muscular.
Shorts: Nantucket red.
Shit: Somehow, perhaps thanks to an inherited genetic mutation, odorless.
Belt: Cloth, with dozens of yacht club flags embroidered at one-inch intervals. But you can only see the back half of the belt because the front half is covered by the…
Beer Gut: Fat and droopy, like an overfilled water balloon.
Shirt: Polo, with the name of a boat and that boat’s sail number on the left breast. Some boat owners, feeling festive I guess, issued matching Hawaiian shirts to their crew members. And one guy wore a mock turtleneck, but he also had a long gray mullet, so it’s hard to say if he was actually at the Royal Bermuda Yacht Club on purpose, or if he was just passing through on his way to an adult league hockey game in Moose Jaw, Saskatchewan.
Face: Phillip Seymour Hoffman
Hair: Floppy and windblown, or alternatively, bald with patches of floppy and windblown
Sunglasses: Wraparound with Croakies.
Face coloration: Red from sun and alcoholism, except for a white band around the eyes in the shape of wraparound sunglasses.
Hat: Red Mount Gay hat from some regatta around Block Island or Buzzard’s Bay.
General demeanor: Relaxed, ready to party through the end of vacation, yet all-around better-than-you.
These are the type of men who fill the Royal Bermuda Yacht Club’s bar and dock for the annual post-race party. Neither my dad nor I really wanted to be associated with them, but they were fun to watch as they got fall-down drunk and bragged about their boats. It was like when you go to the zoo and all the monkeys have been drinking all day, and it’s right before closing, and they’re all hammered and throwing poop at each other. As long as you don’t get hit with the poop (i.e. get roped into a conversation about some New York I-banker’s boat), it’s entertaining.
The next day my dad left for the airport, but before he went, he showed me his belt. He had only packed one belt, and it was navy blue cloth, with Cruising Club of America flags embroidered at one-inch intervals. But the belt was inside-out. He didn’t want to look like one of the other sailors. He didn’t want to look like a nerd. But he still did because he’s my dad.
Just kidding. He’s not a nerd because that would make me a son of a nerd. And if my grandfather were a nerd, I would be a son of a son of a nerd. But I’m not. I’m just a son of a son of a sailor. (Ask Jimmy Buffett).
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