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Sideways 3; Chile

Sideways 3; Chile! The advertisement caught my eye and immediately piqued my interest. Was this for real? The idea of Miles and Jack in Chile really excited me. How had I missed this?

Sideways, the movie, was fun, especially the intoxicating journey through California Pino Noir wines. But it was also a bit sad, due to Miles’ struggle with relationship demons and huge doubts he would ever score a decent book. Traveling companion and old buddy Jack, despicably on the prowl for sex no matter the time, the place, nor the target, certainly lent plenty of laughs to their week-long binge before he had to head back to what surely would be a marriage of doubtful longevity. Jack was clearly short changed on the faithful gene, but he did know how to arrange and enjoy debauchery.

Miles, Jack and Sideways boosted sales of PInot Noir wine in the US, at the expense of Miles’ nemesis Merlot, and precipitated a sea change in the way reticent Americans view and pursue the pleasures of tasting and enjoying wine. Sideways was transformative; wine sales in the US increased significantly as a result, and Americans are more thoroughly enjoying wine.

As Sideways ended, Jack’s sorry fate was predictable, but it appeared that Miles’ story might have a happy ending. Hooking up with lovely and well-grounded Maya, if he could harness the nerve and stay sober long enough, was what I, and probably everyone who saw the movie or read the book, wanted to happen. But we were left with the uncertainty of the future for these complicated, alcohol soaked buddies, and I must admit that flashbacks of the craziness of the Sideways adventure did occasionally over the past few years take me back to California’s Santa Ynes Valley.

But now I had discovered Sideways 3; Chile. Being a Chilephile, and a major investor (bottle by bottle, case by case) in Chilean wine, I immediately downloaded this book, anxious to see what Miles and Jack were up to now, and in my adopted country with my favorite wines. But as I did this, it began to dawn on me that if there is a third Sideways, there must be a second one, a sequel, so I hunted for it.

Colchagua Valley Vineyards

Colchagua Valley Vineyards

Sideways 2 is hidden under the title Vertical, which picks up Miles’ story after he has finally published a successful book (Sideways, of course, but in Vertical it goes by the title Shameless). Miles has become quite popular and is finally earning a healthy income he can splurge, aimlessly of course since he is still living alone, and still smarting from his divorce, and is as mercurial as ever. He is again, or probably still, drinking way too much and engaging in outrageous public performances as a well-sought-after speaker and companion for well-heeled, pleasure seeking wine tour groups.

Vertical is all about a trip Miles and Jack make through northern California, into the Willamette Valley of Oregon where Miles is to be the master of ceremonies for the hedonistic three-day International Pinot Noir Celebration near McMinnville. This journey by itself would be entertaining, but an additional emotional overlay results because Miles and Jack are also transporting Miles’ mother, very disabled by a stroke, her dog, and her Philippine caregiver to Wisconsin where she is to live out her years with a sister.

Vertical is a sad story of the failure of success, for not too surprisingly we find Miles squandering away his earnings and abusing the fame he has earned as an author of one successful book. But it is also a heartening story of a very confused man, alcoholic and unstable while well meaning, trying to please his mother, finally, by giving her what she most wants at this stage in her life. “Miles, please take me home”. This is one promise he delivers on.

So a year after Miles and Jack return to California, Miles cleans up his act, but still has not found that female companion he has searched for, unsuccessfuly, through Sideways (aka Shameless), and Vertical.

Here we pick up Sideways 3: Chile. Due to his newly earned fame as a writer, a major travel publication has engaged Miles to write an article on wine in Chile. Believing that this might be a grand opportunity to gather information and another experience upon which to write a second book, a sequel to Shameless, Miles accepts and takes off, alone, to Chile even though he does not like to fly, does not like being alone, and suffers frequently from panic attacks.

Author Rex Pickett does Miles a huge favor, and us too, by immersing him in Chile and Chilean wines not via the more well known industrial sized giant producers like Concha y Toro, Santa Rita, or San Pedro, but rather the exciting smaller, newer, boutique winemakers who, Miles concludes eventually, are “on the precipice of something astonishing, revolutionary, trailblazing” with winemaking in Chile.

Chile is relatively new at winemaking, especially when compared to the European experience of hundreds of years. Central valley Cabernet Sauvignon and Merlot have sustained the Chilean wine reputation to now, and truth be told, much of it is excellent, reasonably priced, and highly valued in the international market including the US. Most of the wine-drinking world knows, likes, and buys these bold, red Bordeaux varietals and simple blends from Chile. But this is not where Pickett wants Miles to direct his attention in Chile. Instead, Miles is introduced to the less well-known wines beginning to be produced not only in the central valley but also in the cooler coastal regions, the arid northern valleys like Elqui and Limarí where hillside Syrah is popular due to its high acidity and minerality, and further south in Colchagua and Maule.


Before Miles leaves Santiago to discover Chilean wine in situ, in fact his first night in Chile, he lands in the cozy Bocanaríz wine bar in the trendy Lastarria neighborhood where he begins to enjoy the new dimensions of Chilean wine: crystal clear Sauvignon Blanc from the Casablanca Valley and hefty Syrah, Pinot Noir, and Riesling from the cooler Leyda area closer to the coast.

When he finally gets out of Santiago, the huge, capital city where 40% of Chileans live, Miles discovers what is most attractive and intoxicating about Chile, the rural grape growing areas and down-to-earth people who are experimenting with lesser know grape varieties, but also returning to some of the traditional grapes and winemaking methods of the past. Miles is an overnight guest at the Lapostolle winery, that produced a few years back Wine Spectator’s Best Wine of the Year, Clos de Apalta. They, like most other wineries in the Colchagua Valley, are producing the mainstay of Chilean reds, Cabernet Sauvinon and Merlot, but also Cabernet Franc, Petit Verdot, Syrah, Carmenere, Carignan, and in whites, Chardonnay.

As we know from Sideways, Miles despises the Merlot grape, and interestingly enough, in his visit to Chile he also decides he has little good to say about Chile’s latest “flavor of the  month”, Carmenere. It makes sense that Miles has the same disdain for Carmenere he has for Merlot; for years Chileans had Carmenere and Merlot grapes confused with each other, mixed up in the vineyards and marketed as Merlot. What now is sold so successfully in the US as Chilean Carmenere, several years ago would have shown up as Merlot. Miles, on the other hand, believes Chile’s next super wine will be Syrah, if they can figure out where this grape grows best (probably cooler central coastal areas and the highly mineralized soils of the northern valleys south of La Serena in Chile’s 4th region), and are patient but diligent with their experimentation. Some wine experts also believe this, and having tasted recently some very interesting Chilean Syrahs, I’m convinced.

In a relatively forgotten, more isolated part of Chile, Maule east of the sleepy, old town of Cauquenes, about 400 kilometers south of Santiago, Miles discovers the Cinsault grape being fermented in large earthenware containers (tinajas). Also, vineyards of old vine País (mission grape) and Carignan are being rehabilitated on rain-fed hills. The wine from these grapes is pure Chile; earthy and unpredictable.

As Miles explores Chile, his persistent demon of companionship rears its ugly head more than once. Several women hook up with him, but the relationships don’t last. Even Jack flies to Chile to accompany Miles. Although Miles has his excessive drinking in better check in Chile, he is constantly in need of his crutch, Xanax, “crushed and placed under the tongue for faster action”. But he begins to be more comfortable and attracted to Chile, in spite of the “very disorganized, grossly unequal society”, the all too frequent earthquakes, and the ubiquitous Nescafe (“absolutely terrible’). He even is more at ease with the stray dogs found everywhere flopped down in the sun, sleeping off their Jack-like nocturnal carousing. Miles may even get comfort from these dogs, quiltro in Chile. They probably remind him metaphorically of his friend Jack.

As you read through this book, and you really should read all three of the Sideways series, you begin to wonder if Chile might just be the right place for Miles to settle down. He could, like so many of the rest of us, live part of the year in Chile, and part of the year in the US, avoiding winter altogether. Chile can exert an almost magnetic pull on visitors, and make you feel like you never want to leave.  Many don’t. “Maybe if I found a Chilean woman, I could find a way to a simpler life”, Miles mused in a melancholy, sober moment. Well, that could be, and I highly recommend it to Miles, but not because it would lead to a simpler life; interesting maybe, but definitely not simpler!

So where will Miles be when Pickett gifts us with Sideways 4? Another emerging wine producing region like New Zealand, Australia, South Africa? I hope he is still in Chile, making Pinot Noir, Syrah and Sauvignon Blanc wine somewhere in the Casablanca, Limarí or Elqui Valley. But if Pickett has not told us where Miles is by the time I make my next trip to Chile, I’ll be looking for him in Bocanaríz.

Tasting at Viu Manent wineries, Colchagua Valley

Tasting at Mont Gras wineries, Colchagua Valley

Posted on October 6, 2015, in Leesburg, Virginia.



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David Joslyn
David Joslyn, after a 45-year career in international development with USAID, Peace Corps, The Inter-American Institute for Cooperation on Agriculture (IICA), The Chicago Council on Global Affairs, and private sector consulting firms, divides his time between his homes in Virginia and Chile. Since 2010, David has been writing about Chile and Chileans, often based upon his experience with the Peace Corps in Chile and his many travels throughout the country with family and friends.
David Joslyn

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5 thoughts on “Sideways 3; Chile”

  1. Rex
    Rex says:

    Great post, David. You’ll be happy to hear that I might be doing a screenplay adaptation of my Sideways 3 Chile novel, and it could, unlike Vertical, be a movie, for reasons that are too complicated and convoluted to go into. Ciao, and grazie, Rex Pickett.

  2. Avatar
    Melica Heuser says:

    I LOVE this posting! Wow! Didn’t know about this book. I’m going to have to pick it up. Also, this makes me desperately homesick for Chile!! I miss the wine, empanadas, the street dogs (O’Higggins), Neruda, and of course……the people!!

  3. Avatar
    Floyd Thompson says:

    Dave, very interesting post. I hope you get to visit some of these wineries from Sideways Chile on this 2016/2017 stay in Chile. I have to agree with him that Camenere is overrated.
    Blessings to you and Ximena.

  4. Avatar
    Rick Duque says:

    Thanks for the post. My family is from post Pinochet chile, but I grew up in west Los Angeles California, visiting solvang frequebtly as a kid; and when I was mature and wine savvy enough after years of fine dining restaurant work during my humble Hollywood career, I would visit st Inez valley and envírons for the wine and culture long before the exceptional film adaptation of sideways put it on the global wine map. I returned to chile as a graduate student the year that movie came out to start a study on how the internet was shaping the scientific community here, an extension of a similar sociological project in sub Saharan Africa I had been working on. Over the past decade I have visited chile from Santiago to puerto Montt frequently to update my study, now focused more on University communities in disaster prone regions. And of course over these years I have incrementaly advanced my understanding of wine culture here, though I’m not nearly satisfied with my knowledge of It. I have to admit i have a bit of a Mendoza bias when it comes to South America wines . So, I find myself back in chile, my first summer here since I was a toddler – as an academic, normally I’d visit during June and August due to the longer school break. And I have a weekend to kill and I’ve been debating enduring the arduous bus ride over the Andes to finally feed my Mendoza Boudreaux fetish or to stay local and deepen my Chilean wine experience. The fact that I just discovered that Pickett chose to set the third installment of sideways in Chile was the “sign” I needed. Your blog identifying casa lapostle, a wine I poured at two Santa Monica restaurants I worked at before my academic career, as one of the wineries featured in this novel made it clear where to begin. Thank you. 🙂

    1. Avatar
      Rick Duque says:

      Correct spelling: Casa Lapostolle

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