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The Box Wine Sailors: Misadventures of a Broke Young Couple at Sea
The true story of a young couple who quit their jobs and set sail for a year on the ocean with no boating experienceAmy and Jimmie were not sailors. Their experience included reading a few books, watching a couple of instructional videos, and sailing once a week for a year. They were land-lubberly, middle-class twentysomethings, audacious and in love. All they wanted was to be together and do something extraordinary. They quit their jobs, bought a boat that was categorically considered "too small" for ocean sailing, and left Portland, Oregon, for the Sea of Cortez.The Box Wine Sailor s tells the true story of a couple's ramshackle trip down the coast, with all the exulting highs and terrifying lows of sailing a small boat on the from nearly being rammed by a pair of whales on Thanksgiving morning and the terrifying experience of rounding Punta Gorda--hanging on to the mast for dear life and looking about at what seemed like the apocalypse--to finding ultimate joy in a $5 Little Caesar's pizza. It also tells the story of two very normal people doing what most people only dream of, settling the argument that if you want something bad enough you can make it happen.
255 pages, Kindle Edition
First published November 1, 2015
About the author
Amy McCullough
6 books7 followersAmy McCullough is the former music editor of Willamette Week, Portland, Oregon's Pulitzer Prize–winning alt-weekly newspaper. She has also written for SAIL magazine, Eugene Weekly, Loyola magazine, Edible Austin, and Finder (a magazine-style guide to Portland).
In addition to writing, she makes independent music, music videos, and movies with her partner and former shipmate, Jimmie. The duo's first feature-length production, Operation: RAVEN—which stars McCullough as tough-as-nails detective Sheila Raven—premiered in association with the Austin Film Festival in February of 2014. Their follow-up, Beast Lover, premiered the following November at Zed Fest in Burbank, California. Amy and Jimmie are also semi-famous for their ongoing series of ridiculous Christmas cards.
Amy holds a Bachelor of Arts in Creative Writing from Loyola University Chicago and a Master of Arts in Geography from the University of Texas at Austin. She is currently a writer and editor for the Lady Bird Johnson Wildflower Center. The Box Wine Sailors is her first book.
In addition to writing, she makes independent music, music videos, and movies with her partner and former shipmate, Jimmie. The duo's first feature-length production, Operation: RAVEN—which stars McCullough as tough-as-nails detective Sheila Raven—premiered in association with the Austin Film Festival in February of 2014. Their follow-up, Beast Lover, premiered the following November at Zed Fest in Burbank, California. Amy and Jimmie are also semi-famous for their ongoing series of ridiculous Christmas cards.
Amy holds a Bachelor of Arts in Creative Writing from Loyola University Chicago and a Master of Arts in Geography from the University of Texas at Austin. She is currently a writer and editor for the Lady Bird Johnson Wildflower Center. The Box Wine Sailors is her first book.
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Displaying 1 - 26 of 26 reviews
June 6, 2016
(Reprinted from the Chicago Center for Literature and Photography [cclapcenter.com]. I am the original author of this essay, as well as the owner of CCLaP; it is not being reprinted illegally.)
It's funny that the basement-press books Newlyweds Afloat by Felicia Schneiderhan and The Box Wine Sailors by Amy McCullough should both randomly end up coming into my life at the same time, because on the surface they both deal with the same subject -- female big-city hipster decides to ditch her urban existence in order to live on a small boat full-time -- although in Schneiderhan's case, she mostly still spends her time in Chicago while living on a houseboat already owned by her new sailor-veteran husband, while McCullough ends up selling all her Portland possessions so to attempt to sail from there to Mexico with her equally untrained and unexperienced boyfriend. Unfortunately, though, while it's easy to get into Schneiderhan's story and end up rooting for her, this is much more problematic with McCullough, simply because she's not a very pleasant person, not usually an issue with authors of fiction but a major disruption when a memoirist is telling a true story; unwittingly loaded down with all kinds of Portlandia-type stereotypes about creative-class entitlement, McCullough spends a huge portion of her book self-righteously ranting against all the people who (correctly) warn her how dangerous her untrained trip on a too-small boat is likely to be, takes full credit for her "intelligence" and "resourcefulness" when the trip accidentally turns out okay anyway (while conveniently blowing off the half-a-hundred near-crashes that were avoided out of sheer randomness), and on at least half a dozen occasions proudly details the times she and her boyfriend flagrantly break the law because they have little money and therefore "deserve" to (such as, for one excellent example, routinely dumping the fecal matter from their toilet directly into coves where people swim, because they don't want to pay the $20 fee to legally dump it in a septic tank).
Also, while Schneiderhan uses her boating experiences mostly just as a jumping-off point for grander and more poetic essays about growing older, giving up societal expectations, and other universal subjects that all of us can relate to, McCullough spends the majority of her page count actually detailing in tech-heavy terms the literal sailing trip they took down the American west coast, which for a non-sailor like me gets tedious fast; and while Schneiderhan and her husband tend to do interesting things that are fun to read about when not on their boat itself, McCullough and her boyfriend tend to do nothing while offshore but eat pizza, drink the cheapest liquor they can find, and endlessly listen to the more pretentious side of the indie-rock spectrum. (McCullough was formerly the music editor for Willamette Week who now lives in Austin, and the snotty attitude and immature slang that comes with rock "journalism" shines through here on every page.) Now, all that said, there are still some fun and interesting things to be gleaned from this book, plus the sheer scope of the trip itself makes it worth checking out, which is why it's still getting a decent score today; but unfortunately you have to work hard to overcome all the weaknesses mentioned above, which is why it's not getting a better score than it is. It should all be kept in mind before deciding whether or not to pick up a copy yourself.
Out of 10: 7.1
It's funny that the basement-press books Newlyweds Afloat by Felicia Schneiderhan and The Box Wine Sailors by Amy McCullough should both randomly end up coming into my life at the same time, because on the surface they both deal with the same subject -- female big-city hipster decides to ditch her urban existence in order to live on a small boat full-time -- although in Schneiderhan's case, she mostly still spends her time in Chicago while living on a houseboat already owned by her new sailor-veteran husband, while McCullough ends up selling all her Portland possessions so to attempt to sail from there to Mexico with her equally untrained and unexperienced boyfriend. Unfortunately, though, while it's easy to get into Schneiderhan's story and end up rooting for her, this is much more problematic with McCullough, simply because she's not a very pleasant person, not usually an issue with authors of fiction but a major disruption when a memoirist is telling a true story; unwittingly loaded down with all kinds of Portlandia-type stereotypes about creative-class entitlement, McCullough spends a huge portion of her book self-righteously ranting against all the people who (correctly) warn her how dangerous her untrained trip on a too-small boat is likely to be, takes full credit for her "intelligence" and "resourcefulness" when the trip accidentally turns out okay anyway (while conveniently blowing off the half-a-hundred near-crashes that were avoided out of sheer randomness), and on at least half a dozen occasions proudly details the times she and her boyfriend flagrantly break the law because they have little money and therefore "deserve" to (such as, for one excellent example, routinely dumping the fecal matter from their toilet directly into coves where people swim, because they don't want to pay the $20 fee to legally dump it in a septic tank).
Also, while Schneiderhan uses her boating experiences mostly just as a jumping-off point for grander and more poetic essays about growing older, giving up societal expectations, and other universal subjects that all of us can relate to, McCullough spends the majority of her page count actually detailing in tech-heavy terms the literal sailing trip they took down the American west coast, which for a non-sailor like me gets tedious fast; and while Schneiderhan and her husband tend to do interesting things that are fun to read about when not on their boat itself, McCullough and her boyfriend tend to do nothing while offshore but eat pizza, drink the cheapest liquor they can find, and endlessly listen to the more pretentious side of the indie-rock spectrum. (McCullough was formerly the music editor for Willamette Week who now lives in Austin, and the snotty attitude and immature slang that comes with rock "journalism" shines through here on every page.) Now, all that said, there are still some fun and interesting things to be gleaned from this book, plus the sheer scope of the trip itself makes it worth checking out, which is why it's still getting a decent score today; but unfortunately you have to work hard to overcome all the weaknesses mentioned above, which is why it's not getting a better score than it is. It should all be kept in mind before deciding whether or not to pick up a copy yourself.
Out of 10: 7.1
May 17, 2018
I can't get over how young, educated Americans (from a liberal area no less!) could be so environmentally destructive. Dumping raw sewage - hello?! Their poor diet choices and tendency to get wasted made me like them less and less. They "should" know better but yet they seem to flaunt the kind of lifestyle I would expect from a college freshman. Ugh. If I wasn't interested in sailing or this book was much longer, I would have tossed it. To top it off, the ending was anti-climatic and nothing seems learned.
January 5, 2016
I feel like this falls into the "I'll do something that can be dangerous while wholly under equipped so I can write a book about my great insight" genre that has become popular. Overall, intensely unlikable. Also pumping out your head while near shore is disgusting and illegal.
November 20, 2025
wonderful book by a very talented person I had the pleasure of moderating for one time at a screening of theirs (did you also know Amy & Jimmie make movies, truly a Renaissance couple).
Amy does a swell job capturing the freedom, challenges, and day to day mileu of a life casually thrown to the sea. it's one of those enjoyable travelogues that successfully puts the wanderlust in the reader. while I think some of the flashbacks to minor incidents to add context to future/current events of their journey occasionally overcomplicates the structure, it's hard to deny that Amy paints a vivid account of her and Jimmie's journey from the coasts of Oregon to that of Mexico.
Amy does a swell job capturing the freedom, challenges, and day to day mileu of a life casually thrown to the sea. it's one of those enjoyable travelogues that successfully puts the wanderlust in the reader. while I think some of the flashbacks to minor incidents to add context to future/current events of their journey occasionally overcomplicates the structure, it's hard to deny that Amy paints a vivid account of her and Jimmie's journey from the coasts of Oregon to that of Mexico.
November 9, 2015
I won a copy of this book from Good Reads. Here's what I thought:
Amy relates her first-time sailing experience, travelling with her boyfriend Jimmie on a not-quite-big-enough boat down the West coast to the Sea of Cortez. In a way, it was just what I expected: They have some interesting experiences, a handful of scary and dangerous ones, mixed in with a lot of less riveting periods of days or weeks. It was usually fun to follow along with where they were and what the weather was like and how that affected their progress. But I got a little bored at times with the minutiae of their daily routines, like descriptions of what passed for their meals. I guess this goes with the territory - it's a journal of their experience, after all.
Amy and Jimmie are only in their twenties, and that youth shows in the writing. Some of the slang and expressions like "JB was a fucking champ" and adding "-ass" to various words for emphasis seemed childish to me. But, it's not overdone, and overall she comes across as mature and smart for her age. And it was refreshing to read about a couple with no hint of doom about their relationship. When something goes wrong, no blame or anger or even much frustration develops; instead they just find a solution and move on.
I'm glad I read this book, but it wasn't spectacular enough for me to re-read.
Note to publisher and oddballs like Lynne Truss: The book had no proofreading errors that I noticed, except for the glaring missing-hyphen one on the cover, the same one that almost everyone is making nowadays. Sorry Academy Chicago publishers, but "The Box-Wine Sailors" needs that hyphen. If it doesn't make sense to say "The Box Sailors" or "The Wine Sailors", then the hyphen is needed. How difficult is this, really? Arrrgh. Aside from that, good job.
Amy relates her first-time sailing experience, travelling with her boyfriend Jimmie on a not-quite-big-enough boat down the West coast to the Sea of Cortez. In a way, it was just what I expected: They have some interesting experiences, a handful of scary and dangerous ones, mixed in with a lot of less riveting periods of days or weeks. It was usually fun to follow along with where they were and what the weather was like and how that affected their progress. But I got a little bored at times with the minutiae of their daily routines, like descriptions of what passed for their meals. I guess this goes with the territory - it's a journal of their experience, after all.
Amy and Jimmie are only in their twenties, and that youth shows in the writing. Some of the slang and expressions like "JB was a fucking champ" and adding "-ass" to various words for emphasis seemed childish to me. But, it's not overdone, and overall she comes across as mature and smart for her age. And it was refreshing to read about a couple with no hint of doom about their relationship. When something goes wrong, no blame or anger or even much frustration develops; instead they just find a solution and move on.
I'm glad I read this book, but it wasn't spectacular enough for me to re-read.
Note to publisher and oddballs like Lynne Truss: The book had no proofreading errors that I noticed, except for the glaring missing-hyphen one on the cover, the same one that almost everyone is making nowadays. Sorry Academy Chicago publishers, but "The Box-Wine Sailors" needs that hyphen. If it doesn't make sense to say "The Box Sailors" or "The Wine Sailors", then the hyphen is needed. How difficult is this, really? Arrrgh. Aside from that, good job.
July 12, 2016
Amy and her boyfriend Jimmie want to figure out a way to take a year off work and have an adventure. They decide that the cheapest way to do that is to buy an old sailboat and sail from Oregon to Mexico - neither of them grew up sailing or have any real training. They watch a few DVDs, read some books, and spend a year sailing once a week to prepare. They saved as much money as they could in a year and lived as cheaply as possible in their year of sailing. While I admire them for going for their dream right now and not waiting until retirement or a "better" time, it seems like their year of sailing was more stressful than relaxing or fun. They ate really cheap, crappy food and never really slept much or well. After it was over and they spent their first night off the boat Jimmie said it was the first night of real, restful sleep he had had in over a year. Not to say they never had fun or a relaxing time, but it really seemed like a LOT of their time was very stressful. Overall, it was good, but it definitely didn't inspire me to want to do anything similar!
Some quotes I really liked:
"It turns out the only difference between bravery and stupidity is a happy ending. If we had died, if our soggy carcasses had washed up on some California beach months after our departure, everyone would have said that we were foolish. Or at least they would have thought it. Sailing the Pacific on a twenty-seven-foot boat, with no experience? Figures... But we lived. And so we are brave." (p. 1-2 of "Sensible" Cruising)
"Often, the thing that is the scariest is not the actuality of your situation but what your imagination sees as its potential amplification. The unknown. The unknown. The unknown. It haunts you. And it can never be answered until it is already happening. And then, an already worse unknown has formed in your brain." (p. 12 of Desperately Seeking Social)
Some quotes I really liked:
"It turns out the only difference between bravery and stupidity is a happy ending. If we had died, if our soggy carcasses had washed up on some California beach months after our departure, everyone would have said that we were foolish. Or at least they would have thought it. Sailing the Pacific on a twenty-seven-foot boat, with no experience? Figures... But we lived. And so we are brave." (p. 1-2 of "Sensible" Cruising)
"Often, the thing that is the scariest is not the actuality of your situation but what your imagination sees as its potential amplification. The unknown. The unknown. The unknown. It haunts you. And it can never be answered until it is already happening. And then, an already worse unknown has formed in your brain." (p. 12 of Desperately Seeking Social)
July 7, 2016
This book reminded me of our honeymoon, after we eloped, when we backed packed through Europe for three months well before a smart phone existed and the euro. You had to use an actual travel book and info centers. People thought we were crazy, but 20 years later we still look back with fond memories of our amazing experiences. Also, this books reminds me of our 12 years of boating in the sometimes cruel New England weather, but when you get one of those days like they had at the end of this book, it is so worth it. Just to be clear, box wine is almost always safest to have when boating. Cheers!
September 16, 2018
While the love that this couple shares is awesome, after 85 pages I am tired of feeling like a vouyer to it. The "we" language is so prevelant I found myself wondering at times if she had independent thoughts, feelings, or actions. Here is how I would sum what I read before I was completely apathetic about if they reached their destination...
Two young hipsters on an adventure: "so we were really ignorant, and really poor, and we were mad at all the haters who said it couldn't be done, and we were mad at the Coast Guard who didn't help us when we needed it. Furthermore, we've earned a badge for our fiscally conservative ways, which I remind you of throughout this book, namely by making frequent references to ramen and other cheap freeze-dried foods, but also by calling anything above 99 cents an indulgence. We nearly died, which I will emphasize multiple times and throw in a few F bombs to get the point across about the scariness of the waves. I'd also like someone to see through this sub-par writing and offer me movie rights. I'm tired of ramen, after all."
Two young hipsters on an adventure: "so we were really ignorant, and really poor, and we were mad at all the haters who said it couldn't be done, and we were mad at the Coast Guard who didn't help us when we needed it. Furthermore, we've earned a badge for our fiscally conservative ways, which I remind you of throughout this book, namely by making frequent references to ramen and other cheap freeze-dried foods, but also by calling anything above 99 cents an indulgence. We nearly died, which I will emphasize multiple times and throw in a few F bombs to get the point across about the scariness of the waves. I'd also like someone to see through this sub-par writing and offer me movie rights. I'm tired of ramen, after all."
January 10, 2018
This is truly a fantastic book and I'm not just saying that because I work down the hall from the author! My fiancé and I read this aloud together over the course of a couple of road trips and enjoyed everything from the musical infusion (read it and you'll see what I mean) to the pure humor and honesty of the entries. The book balances backstory and "real-time" action in a way that enriches the journey and never got confusing. We were rooting for Amy and Jimmie and all the while appreciating that they took this journey and that Ms. McCullough wrote about it ... so we don't have to.
October 30, 2017
What a fabulous story of a couple that set out for an adventure, taking a year to sail from Portland, Oregon, to the Sea of Cortez. I loved reading this and enjoyed the stories of the people and landscapes they encountered along the way. I appreciated how McCullough detailed what they ate and drank along the way. What an adventure!
April 6, 2020
As one half of a former “broke young couple at sea”, this book is an excellent peek into what life is really like as a liveaboard with a budget. Granted, we sailed from New Jersey to the top of the Bahamas and these guys did Oregon to Cabo, but many of the difficulties and laughs were incredibly similar to our story. Loved it!
April 22, 2025
it was fun reading about their adventures other sailboat. I will say it was hard to get thru some of the parts that referenced different parts of the boat and weather conditions on the water. I spent a lot of time asking Alexa what certain things were lol
March 9, 2017
Couldn't finish. Just didn't find it very entertaining. Its not really about sailing. more about a couoples adventures.
September 22, 2025
A fun and adventurous read! I enjoyed reading a sailing book from a woman’s perspective.
October 11, 2016
This is the story of two young people who are very lucky to be alive after they spend a lot of money and a lot of time on a really dangerous and uncomfortable sailing excursion. I love sailing, so I found some parts of this book interesting, but a few chapters in, the author disclosed that they left their dog for an entire year while they went on this dream trip, and I just couldn't like them after I learned that.
December 21, 2015
Beware: after reading this book, you'll have the urge to do wonderful, stupid things. This book makes you want to live, but like REALLY live. It makes you want to change your life, to take risks you never thought you had the courage to take. Because that's what Amy and Jimmie do. So many people talk about living a life of adventure, disregarding the pressures and demands of mainstream society, but how many actually do it? Answer: almost none. And the thing about this book that will get under your skin is that it's not that hard. These guys didn't know jack about sailing, didn't have six figures in the bank, didn't have a backup plan. They just bought a boat and hit the high seas. Is that advisable? Nope. Could they have died? It sounds like that could have happened on several occasions. But they're here to tell the tale. The Box Wine Sailors is a wake-up call to a generation of apathetic hipsters sitting at home pretending life is meaningless.
June 5, 2016
Reading this book has been like having a long conversation with your coolest, smartest, most adventurous friend; the one who's going to do all those things you just talk about doing. Actually, I never even talk about sailing anywhere since the few times I've been, I've found it to be vaguely terrifying. That's why I find what they've done to be so hugely impressive. It's hard to wrap my brain around these two young people sailing alone in a too small boat in the unforgiving Pacific but there it is. They fell in love, figured out how to be together 24/7 and they made it happen for themselves. And even bigger than that they stuck together despite the many, many, (many) hardships they faced. They crammed a whole lot of living into that one year and the book that came out of it is engaging, humorous and deeply insightful. Bravo!
November 2, 2015
I received an arc of this book in exchange for an honest review.
Entertaining tale of a couple of inexperienced sailors traveling from Oregon to Baja, Mexico. Admittedly amateurs, unfamiliar with their sailboat but wanting a cheap adventure, Jimmie and Amy go through a lot of unexpected, sometimes dangerous, circumstances. Perhaps not the smartest way to go out into the northern Pacific, but they sailed many miles without much damage, and a lot of life experience.
Entertaining tale of a couple of inexperienced sailors traveling from Oregon to Baja, Mexico. Admittedly amateurs, unfamiliar with their sailboat but wanting a cheap adventure, Jimmie and Amy go through a lot of unexpected, sometimes dangerous, circumstances. Perhaps not the smartest way to go out into the northern Pacific, but they sailed many miles without much damage, and a lot of life experience.
October 29, 2015
As someone whose partner is obsessed with sailing I found this interesting just to get an idea of what life at sea would be like. It confirmed that I do NOT want to have the kind of terrifying close to death experiences these two people described in the book.
April 17, 2016
The story was definitely a coming of age story about two young non sailors. The writing would have been better without the sprinkling of profanity but overall it was a light interesting travelogue of coastal cruising.
August 25, 2016
I really enjoyed it... funny, heartfelt, engaging, and at times delightfully irreverent. Their's was a very risky undertaking for neophyte sailors, but through sheer grit, love and teamwork, Amy and Jimmy pulled off an unforgettable adventure.
January 18, 2016
What they went through is incredible. Some people might view it as stupid, but I find this couple's motivation and determination brave and astounding.
January 25, 2016
I loved the adventure/ love story of this book. Ups and downs, challenges and problem- solving. Love and triumph.
Well-written. So good.
Well-written. So good.
April 1, 2016
This was good book if you were into sailing. I lost interest in it.
December 14, 2016
Funny people on a minimalist tack
Well written with a great voice. A book about sailing to live, great experiences and moving to the next adventure. Fun.
Well written with a great voice. A book about sailing to live, great experiences and moving to the next adventure. Fun.
April 3, 2017
Interesting story of two Non-sailors who sail a 27 foot Newport from Oregon down to Cabo San Lucas, Mexico. Easy read. Mariners will cringe at the risks they took.
I won this via Goodreads.
I won this via Goodreads.
Displaying 1 - 26 of 26 reviews