Originally published in Overnight Buses; included in The Best Travel Writing, Volume 10

Feliz Cumpleanos, Jose Luis

It’s late afternoon, and Erin and I have occupied the sunny courtyard of La Canchanchara for hours, drinking cervezas and taking turns dancing with José Luis. Now he’s tutoring Erin on the güiro, a traditional Cuban instrument made from a hollow gourd. He leans close as he teaches her the rhythm, locking eyes with her, and in unison they scrape thin sticks over the carved ridges of their instruments: cha, cha, chachacha, cha, cha, chachacha. The band plays son, and the sweet smoke from his hand-rolled cigar encircles our heads. As the sun crosses the sky and we order another round, José Luis takes my hand and begins serenading me in Spanish, soft and low. I sing back. Across the table Erin grins: missions accomplished.

Four days ago she picked me up at the Calgary airport. “I’ve been in a foul mood for months,” she said, backing her car out of the snowy airport parking spot. “I promised Drew I’d come back with an attitude adjustment.”

Erin is my best friend, and Drew is her Canadian husband. We met him in an Australian backpacker bar ten years ago and shared a pitcher of beer, and within minutes I knew he would marry her. What I didn’t realize was that he’d whisk her away to the cold plains of Canada, after which the only way I’d ever see her would be to bribe her with sunshine.

“I’m sick of my job,” she said, driving us toward the spray-tan salon where we had appointments to turn our grayish skin bikini-ready. “And this weather isn’t helping.”

She looked sideways at me, apologetically, as if I might judge her. Erin and I had been friends for twenty-five years; if I didn’t judge her when she was our high school’s head cheerleader, it was unlikely to happen now.

“Don’t worry,” I said. “We’ll find you a new attitude.”

The last time we traveled together I drank so much Tecate with two guys named Miguel that at the end of the night I decided to sleep in my Subaru outside our rented casita. “Are you crazy?” she’d hissed, holding the car door open. “I am not letting you sleep in a car, alone, in the middle of Mexico.” Now, three years later, we were off to Cuba—Erin in search of a new attitude, me in search of a cure for the insult of turning forty. At least if we failed, we failed together.

Our flight to Cuba kicks off with two complimentary glasses of champagne, and following Erin’s announcement that it’s my birthday, two more appear. While she reads a guidebook, I study “See It and Say It in Spanish,” enlightening her occasionally with useful phrases like Caramba! Eso es ridiculo. No tengo un gorilla en casa. Inexplicably—alarmingly—she appoints me our official translator.

I have never in my life taken a Spanish lesson, and even if I had, my brain isn’t as absorbent as it once was. But I did bring this handy kindergarten-level language book, along with several Lonely Planet and Rough Guides, whose glossaries should at least add some practical vocabulary to supplement “See It and Say It in Spanish” gorillas, geraniums, radishes, and accordions.

In addition to the dried-up sponge in my head and other obvious indicators of age—gray hair, wrinkles, sunspots, flabby waistline, unforgiving hangovers—one area in which it’s clear that forty is old is when packing for a trip. Between the ever-expanding first-aid kit, ugly-but-comfy shoes, just-in-case jackets, healthy snacks and emergency provisions, guidebooks and back-up documents, packing has turned complicated. In my twenties I could squeeze three weeks in Vietnam and Cambodia into a tiny zip-on daypack. Now I feel chastened each time I lift an overstuffed pack onto my shoulders or—so very much worse—admit defeat by opting for the expandable rolling bag.

But this time was easy. My boyfriend Dan had just returned from Cuba (his guys’ trip to my girlcation) and called to offer advice. “Cuban women wear skin-tight spandex and low-cut shirts,” he said, “but if you don’t want to get whistled at and have men following you around making kissing noises, dress modestly. Wear jeans.”

“Right,” I said, tossing tiny tank tops, skimpy sundresses, skirts, bikinis, and shorts into my pack—and leaving the jeans on my closet floor. I was turning forty: damn straight I wanted men following me around making kissing noises.

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Man’s mind, once stretched by a new idea, never regains its original dimensions.” –Oliver Wendell Holmes, Jr.