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A Pirate Looks at Fifty by Buffett, Jimmy (1999) Mass Market Paperback

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Tales from Margaritaville (stories) and Where Is Joe Merchant? (a mystery) secured songwriter Jimmy Buffett's niche reputation as an affable, poetic beach bum. A Pirate Looks at Fifty, a travel-diary-cum-autobiography, features Buffett behind the wheel of his Grumman Albatross seaplane, safely piloting family and friends through a three-week trip around South and Central America and the Caribbean. He blends gentle scenic narration with rambling, unplugged life stories meant to convey that he's made peace with the whole aging process. For Buffett, turning 50 "can be a ball of snakes that conjures up immediate thoughts of mortality and accountability. (`What have I done with my life?') Or, it can be a great excuse to reward yourself for just getting there. (`He who dies with the most toys wins.') I instinctively chose door number two." On this tack, Buffett plans an opulent, laid-back trip for his brood and goes into so many details about his favorite possessions (three pages on knapsacks!) that the cheerful vagabond in flip-flops is nearly eclipsed by the rich, domesticated businessman/dad he's become. In addition, stinging losses and limitations--his dad's Alzheimer's disease, his own terrifying solo plane crash in 1996--creep into his cozy yarns. Yet Buffett's infectious, grinning attitude towards life eventually finds resurrection in extended riffs on fly-fishing, solo piloting over water, and surfing. In such passages, he earns his claim to a "saline psyche," a legacy inherited from his grandfather, skipper of a five-masted barkentine that ferried lumber from New Orleans to the Caribbean. Sailing and soaring over Atlantic, Caribbean, and Pacific seas, Buffett looks at 50 and sees a very good life.

Mass Market Paperback

First published June 2, 1998

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About the author

Jimmy Buffett

96 books472 followers
James William "Jimmy" Buffett (born December 25, 1946) was a singer, songwriter, author, businessman, and recently a movie producer best known for his "island escapism" lifestyle and music including hits such as "Margaritaville" (No. 234 on RIAA's list of "Songs of the Century"), and "Come Monday". He had a devoted base of fans known as "Parrotheads". His band was called the Coral Reefer Band.

Aside from his career in music, Buffett was also a best-selling writer and was involved in two restaurant chains named after two of his best known songs, "Cheeseburger in Paradise" and "Margaritaville". He owned the Margaritaville Cafe restaurant chain and co-developed the Cheeseburger in Paradise restaurant concept with OSI Restaurant Partners (parent of Outback Steakhouse), which operates the chain under a licensing agreement with Buffett.

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5 stars
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Displaying 1 - 30 of 371 reviews
Profile Image for Travis.
6 reviews
July 30, 2008
Oddly enough, this was an incredibly interesting and profoundly boring book at the same time. The story unfolds as Jimmy Buffett, now turning 50, is preparing for a tour of the Caribbean. It reads almost as a travel guide, interspersed with flashbacks in the form of short stories of his more adventurous past. The short interesting chapters of adventure are constantly interrupted by pages upon pages of tedium. For example, the entire chapter devoted to his search for the perfect backpack to carry all of his reefer and other miscellaneous crap. I would recommend skimming through this book and only reading what suits you, reading from cover to cover will only waste precious time that you could spend watching paint dry.
Profile Image for Ash Wilson.
111 reviews5 followers
September 29, 2023
I am a huge Jimmy Buffett fan. I’m a millennial Parrothead and not ashamed to say it! I LOVE his music, own all his records and concert dvds and consider him one of my all-time favorite musicians.

Because of that, I have been excitingly reading his books in order. The first two, “Tales from Margaritaville” tells of Jimmy’s ‘Semi-True Story’ adventures, and his well-known first complete work of fiction, “Where Is Joe Merchant” were both very fun and enjoyable reads that I loved nearly as much as I do his music.

Soooo naturally, I was SUPER stoked to read his third book and autobiography, “A Pirate Looks at Fifty”. I read A LOT of autobiographies and memoirs and assumed that no one could have as exciting stories of adventures and other cultures, rock and roll and the meaning of truly living life to the fullest as much as Mr. Margaritaville himself, right?! … Wrong. At least not that he was willing to write about at the end of the 90s.

I WANT to say that I liked this book, yet my main thoughts when I finished it are that it was extremely long/seemingly never ending, and that I had to force myself to keep pushing through it each time I picked it up.

I read another review on here that started off by saying that “oddly enough, this was an incredibly interesting and profoundly boring book at the same time.” SO TRUE.

I mean, if you’re looking for a Caribbean travel guide, or all you could ever want to read about fishing and seaplanes, this is the book for you. If you actually wanted to learn anything personal beyond the surface of Jimmy Buffett’s image, any real history on his songwriting, etc as you would hope to get from an autobiography or memoir, I guarantee you will be disappointed.

The book revolves around the Caribbean islands trip Jimmy took with his family and friends celebrating his fiftieth birthday right after Christmas in 1996/1997. Interspersed with that are some autobiographical stories of reflections on his life and his beginnings, (which were most of the best parts of the book). But a lot of the time, he would just ramble off into super boring nonsense. (He spent several pages walking us through the evolutionary timeline of his using backpacks, shoulder bags, man bags and back to backpacks throughout his life and why. … I wish I were kidding.)

Two other things that bothered me about this book besides all the wordy, boring nonsense, is I found him to be extremely repetitive. Mixing the same stories in together and telling us about the same people and places over and over again as if he hadn’t already explained them before.
I don’t know if that was an editing thing from his journals or just the fact that he never imagined anyone would actually attempt to read and not skim this entire book. Either way, it got annoying quickly and made the book all that much more boring.

Another thing that bothered me is the same feeling I had when I read Eric Clapton’s autobiography a few months ago – I started this book liking Jimmy Buffett as a person more than I liked him by the time I finished the book.

Whenever he mentioned his ‘swag bag’ that he would use giving out his tee-shirts and cds as bribes and payment(s) in different places he’d visit, and whenever he mentioned his fans, something about his tone in the words he wrote made him come off as extremely arrogant to me. Like he’s some beach God and has no time for his inferior Parrotheads who are really just weird, annoy him and get in his way during his travels unless they’re useful to him because they’re the proprietor of a hotel he wants to stay in or restaurant he wants to eat at, etc. That really turned me off.

He also mentioned late in his book that the two things that matter most to him are “planes and fishing, after, of course, my wife and kids.” But reading his autobiography, it REALLY didn’t seem that way.

During his birthday trip he brought a fishing buddy and his wife brought a girlfriend of hers and the women and men split up for many of the adventures and often didn’t even travel together and stay in the same places. Even when they did, they only seemed to be together to eat dinner. There were only one or two stories he told where he was actually spending any time at all with his wife.

He also came off throughout the story of his birthday trip like hanging out with his kids was a chore. Like he would come from an amazing day of ‘adult fishing’ and be burdened with taking them ‘kid fishing’ not because he actually wanted to, but because he had promised them he would.
They also had other people taking care of their children most of the time, so they weren’t even with them. And he spent very little time with them that he wrote about during the trip. At one point, his kids flew home because his party was going to the Amazon and they felt it was too dangerous. I don’t disagree there, but I was just bothered by how he made it sound at the beginning of the book like this great family adventure, and yet, never seemed to actually spend much time with (or at least talk about), his family at all.

So, it was at times interesting, at times funny when I could hear that classic Jimmy Buffett tone and sarcasm that all Parrotheads love and know well come out. I learned a few things. There were a few interesting adventures and people.
Mostly though, I was disappointed in this book and walked away with a slightly more deflated view of Mr. Buffett then I used to have. I will continue reading his books in order, but I’ll be needing a break for a while after this one.

He mentioned a few times throughout the book memoirs he may one day write. Now that he’s approaching 70 years old, I hope that he will do that and that it will read much more like “Tales from Margaritaville” and much less like “A Pirate Looks at Fifty” for Parrotheads still clinging to the Buffett dream like myself.
6,210 reviews80 followers
November 29, 2024
Jimmy Buffet hits 50, at the peak of his powers, with parrot heads abounding, best selling books, and a whole of other branding.

He talks a lot about his boats, his planes, and his travels. It's interesting, but not really exciting.
Profile Image for Caitlin Fisher.
365 reviews5 followers
September 11, 2023
If one man understood joie de vivre, it was Jimmy Buffett. There was a lot of facts about planes and fishing that I feel did not need to be here but all in all loved being in Mr. Margaritaville’s brain. RIP to a legend!
Profile Image for Richard Subber.
Author 8 books54 followers
April 21, 2019
Full disclosure: I’m not a Parrothead, but I’m related by blood and marriage to gen-you-wine Buffett fans, so I take the liberty of using familiar language, even though “the king of somewhere hot” has never seen me and isn’t likely to in this earthly paradise…
A Pirate Looks at Fifty is a memoir-ish book by Himself, written more than 20 years ago, I spotted it in the local library’s discarded book sale bin and I did the right thing.
Seems to me, for starters, no one should ever discard a book full of Jimmy Buffett stuff, he’s just so much in love with life and he is a magnet for vicarious attention, I dare you to read Pirate without getting at least a fleeting urge to head for the islands and see the world through Jimmy’s eyes.
You don’t even have to read the whole book (I confess, I didn’t), just read as much as gets the juices flowing and then get on with your regular life, and you can dip into it again any time you want. Buffett’s music and Buffett’s style are a buffet—grab what you want, anytime, sing along as the spirit moves, and go back for more whenever…
You don’t even have to like margaritas to get the full, slobbering, belly laugh, hijinksed, hot damn but mucho mellow effect when you sing along with Jimmy about the Mexican cutie and the lost shaker of salt.
I dare you to not sing a couple verses and the refrain right now, you have to, really…
Read more of my book reviews and poems here:
www.richardsubber.com
13 reviews
October 15, 2007
Want to feel bad about your life? Read this. Poor bastard has more money than he knows what to do with.
Profile Image for M.A. Kropp.
Author 9 books1 follower
July 12, 2013
I’ve been a fan of Buffett’s music for a long time. Some of it is just pure fun, and others cut a bit closer to Life. I have tried to make Changes in Lattitudes, Changes in Attitudes an anthem for myself, and Trying to Reason With Huurricane Season is another I find inspiring. So I have wanted to read his autobiography for a long time.

The exoskeleton, if you will, of the book is the occasion of Buffett’s 50th birthday on Christmas Day, 1996. It is part autobiography, part travelogue, and all fascinating. The book is structured in parts, with multiple chapters in each. Some of the chapters are no more than a page or two in length. Buffett talks about his family, his early years, his wild days, and his present life, which he seems quite happy in. His has been a storied life, and you’ll find them all here- the good times with family and friends, the dark times of drug and alcohol abuse, and his struggles to make it in the music industry. He doesn’t gloss over the fact that his fame and popularity leave him with the money and connections to do whatever he wants to, but he does not flaunt it, either. It is simply the way it is.

The writing is simple and straightforward, and fun to read. There is more than a little humor, and some poignant moments, as well. And it is all narrated with a voice that is unmistakably Buffett’s.

If you are a fan of Buffett’s music, and want to know what makes this self-proclaimed pirate tick, or just want a fun read about one of today’s most successful musicians, give this one a try.
Profile Image for Diane.
653 reviews2 followers
February 2, 2020
This is like sitting on a bar stool at a tropical bar, having some adult frosty beverages and chatting with the stranger next to you. His stories are random but fascinating, and you just don’t want him to stop talking.
Profile Image for Wayland Smith.
Author 26 books61 followers
May 1, 2019
I've enjoyed Jimmy Buffet's music for a long time, but I didn't really know much about the man. This book fit a slot I needed in a writing challenge, so I decided to take the opportunity to learn. It was a fun ride.

The book might annoy some with its format: it's not exactly linear. The overall notion is a recounting of Buffet's flight around the Caribbean around the time of his fiftieth birthday. Each little section sparks off earlier memories, and the book jumps around to different points in his life. I knew he was a sailor, but I hadn't realized he was a pilot, too. The man wears many hats, but he enjoys wearing them, and is a great storyteller. He's lived an amazing life, but he's smart enough to know how lucky he is, and realistic to tell stories on himself about the highs and lows of his life.

It's a fun, if meandering, read.
Profile Image for Nicholas.
19 reviews
December 15, 2025
Very solid 4.5 stars. In only ways that he could, Jimmy Buffett told tales of his early life, music, mistakes, successes, and travels. The first half or so of the book focuses mainly on him getting into music, his early career, his family, discovering his love for flying sea planes, and planning his 50th birthday trip with his family. The second half is mostly him traveling around different parts of the Caribbean for his 50th birthday trip. If you find island hopping/exploring boring, you may find the second half of the book a little boring. There is, of course, plenty on priceless Jimmy Buffett wisdom scattered throughout the entire book. I flew through the first half, completely loving reading about how he got started and how he got to where he was in life. I took more time with the second half of the book: when I wanted to feel like I was also exploring the Caribbean, I would pick the book up and read some pages. His writing style is so descriptive, funny, and truly genuine that I greatly enjoyed reading this book and felt like I was along for the journey with him - I have so many images in my head from this book and the scenes he painted. Jimmy Buffett was such a light in this world - I’m glad I got to read about some of his life’s adventures and stories in A Pirate Looks at Fifty. I recommend you do too🫧🦜
Profile Image for Ginny Muse.
913 reviews70 followers
October 25, 2025
I thought that this book would be so fun!
Unfortunately, I was not very interested in the stories and the way that they are presented in this book. So many details about unimportant info that didn’t draw me in.

I tried to come at it several different ways in spurts over the course of several weeks - audio, ebook, and both together - but I am abandoning ship at only 20% in. Maybe I will revisit it later, But for now, I am moving on. Changes in latitudes/changes in attitudes! 🤣

Jimmy Buffett is pretty fascinating! Many Parrotheads might love this book. What a journey! But I couldn’t invest more time trudging through for now. The audiobook is narrated by Don Johnson. I thought that could be great, but it wasn’t great for me.
Fins Up!
Breathe in, breathe out, move on -
Profile Image for Matt Blanchard.
42 reviews4 followers
September 19, 2024
As a massive Parrothead, this was a necessary read for me. Jimmy Buffett has had such an outsized influence on my life, so I expected this book to be interesting. It was incredible. I feel as though I know Jimmy better now, and he and I have more in common than I ever realized.

The tale of his trip around the Caribbean, his reflections on his life thus far, and his love of fishing and flying made for an absolutely brilliant read. Also, of course, Jimmy is hilarious.

Fins up!
159 reviews
June 7, 2024
Jimmy Buffet takes a family trip to celebrate his 50th birthday. As Buffet plans, prepares, packs, and pushes through the trip, he tells us many stories of his life leading up to 50. We get an image of his life but not in sequential order.

In this book, Buffet has two realities: growing up and starting out with little to nothing; and then having every toy available. What we don’t see is the years when he hit the big time and accumulates the toys.

This is not literature, but Buffet holds my attention well as he reels out his stories, his life.
Profile Image for Lillian Alvino Blanchard.
70 reviews2 followers
July 28, 2024
I feel like Jimmy held a lot of himself back with this one. Although not what I expected, the travel diary format was cute. I feel there could have been more about himself and less about the geography/history of the Caribbean/planes.

It was exactly as if your Dad, Jimmy Buffet, was dad-splaning his hobbies to you without telling you his youthful coming of age.
52 reviews
December 1, 2024
This book was painful to get through. Mind numbing passages, written in an intensely detailed way, describe the ins and outs of planes, surf boards, and boats. I agree with others that to get through this book, one has to skim at times. Jimmy was a good writer and interesting fellow, but the entertainment value of this book is minimal.
699 reviews6 followers
June 19, 2020
I enjoy Buffett’s music, love his humor and I read the book with the feeling that I would have done something similar had I lived in his circumstances. This has been a really enjoyable way to while away some time on the deck on a few warm, breezy spring days.
Profile Image for Kate Grumme.
17 reviews2 followers
January 1, 2022
His life was interesting and seems like a cool guy, but way way to many pages dedicated to fishing…
Profile Image for Erica Johnson.
134 reviews27 followers
May 24, 2023
This book dragged. I felt like easily half of his side tangents could have been edited out. I also felt like some elements had unrecognized privilege - I recognize this book was written in the 90s but in today's view point it left a bit of a sour taste.
Profile Image for Scott.
28 reviews
September 14, 2024
Most rock stars write about sex, drugs, and rock and roll. Buffett writes about wanderlust. I've never been more jealous.
Profile Image for Katie.
62 reviews1 follower
September 24, 2025
A solid ⭐️⭐️⭐️.
I do love me some JB. It was interesting to learn about his personal life as a traveler and pilot (rather than a musician). Some interesting facts, but jumped around a lot.
Listened on audio. Narrator did a great job.👏
Profile Image for Judy.
18 reviews
February 9, 2025
A great re-read. It definitely read differently this time. Fins up!
Profile Image for Jim Saunders.
87 reviews1 follower
August 27, 2022
Picked this up at a yard sale, was a good read about traveling around the islands and Latin America in a sea plane.
Profile Image for Brandon Robert Patton.
26 reviews
May 18, 2024
Love the book. I enjoyed reading about some of Jimmy's history and his travels he embarked on on his 50th birthday! I'd recommend for any Parrothead!!!
Profile Image for Tommy Harrison.
17 reviews
December 5, 2025
Jimmy B has a unique outlook on life and has lived it all. The man takes risks, has fun doing it, but feels like a very down to earth celebrity. I know the laid back, carefree vibe in his music but it was interesting to read about the 50 year old version of the legend with what seems to be his true passions as a traveler, pilot, fisherman, surfer, and connecting with people everywhere he goes.
Profile Image for Molly.
111 reviews3 followers
December 15, 2023
Have always loved Buffett and after his death I remembered this book and finally secured my copy from the library. Great insights into his life and what made him happy besides music. Jumped around at points but his insights on living and loving life will make his music even more special. Bubbles up!
Profile Image for Aaron.
262 reviews
December 27, 2011
I read about 80% of this book about 5 years ago, and for reasons that are unclear to me, I put it down. So, fast forward to now, and I have finally finished this book. A truly enlightening read about one of my most favorite musicians of all time. No surprise, he lives a pretty exciting life, and one that makes me long for the time and fortune that only few and select successful careers seems to afford. For, having the time and the money is half the battle. A theme of life we all know too well, isn't it? Still, Jimmy takes you on a journey, almost always by his own hands behind the wheel of his plane, to so many different places and people it's hard to keep track of it all. But every bit of it sounds as fun as the last. It's everything you would expect it to be, his life. Surfing, traveling, boating, fishing (my god, so much fishing) , flying, and of course, the music. (I did thoroughly enjoy the tidbits about some of his songs sprinkled throughout) This book makes me want to travel even more than I already want to, and there aren't may people I'd wish trade places with, but I have to think that Jimmy Buffett would have been one of them. His life fascinates me to no end, and probably always will.
Profile Image for Katie.
319 reviews55 followers
June 21, 2010
Jimmy Buffett is my favorite musician of all-time, hands down. His music always makes me long to lay on the beach with a boat drink and his book gave me the same intense longing. It was certainly not a typical autobiography that starts at the beginning and moves chronologically through the author's life. Instead, Jimmy primarily recounts on the trip he took with his family to celebrate his 50th birthday. Interspersed into his detailed descriptions of flight plans and fishing trips are little flashbacks of specific moments in his life.

At first I was disappointed because I felt like I was learning more about his seaplanes and fish species than about the author, but as the book progressed I got caught up in his descriptions of the tropical locales and was swept away. I realized that reading about his travels and passions painted a more accurate portrait of the real Jimmy Buffett than a "then this happened" format could ever achieve.
59 reviews1 follower
March 30, 2021
Jimmy Buffett is without a doubt my favorite musician of all time. I’ve been meaning to read some of his writing for a while and I’m happy to say that I was pleased with this one. This is a long read, maybe a little too long. There are some chapters that tell great stories, and I loved them, but there are some that describe a fishing trip in way more detail than would ever be necessary. Good chapters feel enriched by the details and minutiae that he provides, while others feel bogged down by it. I did love the way he frames the memoir, with the main story being a vacation he took with his family for his 50th birthday, interrupted by smaller stories that he tells along the way. At times, however, it felt like he was leaving out stories that I would have wanted to hear and opting to include another chapter on fishing instead. Overall I did really enjoy it and would recommend it to anyone who would call themselves a Parrothead.
Profile Image for Dan.
177 reviews2 followers
September 12, 2012
Being a huge Jimmy Buffett fan I wanted to like this book, but I had to force myself to finish it. While there is a lot of good stuff here, the writing is too often very dry and didn't hold my attention. It isn't without its adventurous moments, but sadly they are too few and far between. I like Buffett as a storyteller, but his ability to turn a tale is almost totally lacking here. None of the characters he meets in his travels are treated with any flare or presented colorfully. As for his philosophies of life - they are much better presented in his songs (his late 90's period of introspective songwriting was, in my opinion one of his best). Stick to his fiction, this one is a snooze.
Profile Image for Louann.
282 reviews
November 13, 2011
This was just ok. The first 150 pages was tedious because it dwelled on minute details of private planes, boats and fly fishing. He rambles a lot and takes you two stories away from what he started to tell you. He will eventually come back around, but you have to hang on for all the subject changes. I enjoyed the part about his lean years and the parts about his wife, kids, close friends and the places he has vacationed. He has at least 2 more books that he has alluded to in this one. I am not sure if I will read them or not.
Displaying 1 - 30 of 371 reviews

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