A Pirate Looks at Fifty

Synopsis

#1 NEW YORK TIMES BESTSELLER  This is the ultimate Jimmy Buffett philosophy on life and how to live it, "like sitting with Buffett at a beachside bar, listening to him spin tales" (Time).

"Buffett took his family on a three-week trek around the Caribbean. . . . His colorful travelogue is interspersed with memoirs of his youth and music career-both of which revolve around his continuing search for the perfect fishing spot."-USA Today

For Parrotheads, armchair adventurers, and anyone who appreciates a good yarn and a hearty laugh, here is the ultimate backstage pass. You'll read the kind of stories Jimmy usually reserves for his closest friends and you'll see a wonderful, wacky life through the eyes of the man who's lived it.
 
Jimmy takes us from the legendary pirate coves of the Florida Keys to the ruins of ancient Cartegena. Along the way, we hear a tale or two of how he got his start in New Orleans, how he discovered his passion for flying planes, and how he almost died in a watery crash in Nantucket harbor. We follow Jimmy to jungle outposts in Costa Rica and on a meandering trip down the Amazon, through hair-raising negotiations with gun-toting customs officials and a three-year-old aspiring co-pilot. And he is the inimitable Jimmy Buffett through it all.

Summary

Chapter 1: The Long Goodbye

* Jimmy Buffett reflects on reaching the age of 50 and feeling a sense of nostalgia for his youth.
* He reminisces about his early days as a musician and his journey to becoming a successful singer-songwriter.

Real-life example:

Buffett recalls a performance he gave at a small club in Key West, Florida in the early 1970s. He played his guitar and sang for a small crowd, and the atmosphere was intimate and unforgettable.

Chapter 2: Pencil Thin Mustache

* Buffett explores the theme of identity and the importance of embracing one's individuality.
* He reflects on his own unique style and persona, including his trademark pencil-thin mustache.

Real-life example:

Buffett describes a photo shoot where he was asked to pose without his mustache. He was initially reluctant but eventually agreed, and the resulting photos were surprisingly flattering. This experience taught him to be confident in his own appearance and not to conform to societal expectations.

Chapter 3: Son of a Son of a Sailor

* Buffett explores his family history and the influence of his father, a naval officer, on his life.
* He describes the adventurous spirit that he inherited from his father and his own experiences sailing and exploring the world.

Real-life example:

Buffett recounts a sailing trip he took with his family to the Caribbean. They sailed through stormy seas and experienced amazing sights, including a pod of dolphins that swam alongside their boat.

Chapter 4: Desperation Samba (Halloween in Key Largo)

* Buffett shares his experiences living and working in Key Largo, Florida.
* He describes the characters he has encountered on the island and the adventures he has had while fishing, sailing, and partaking in the local festivities.

Real-life example:

Buffett describes a Halloween party he attended in Key Largo where he dressed up as a pirate. He danced with a beautiful woman and had a memorable night filled with music and laughter.

Chapter 5: Volcano

* Buffett reflects on the ups and downs of his career and the pressures of fame.
* He uses the metaphor of a volcano to describe the intensity and challenges of his experiences.

Real-life example:

Buffett recalls a concert he gave at a large arena where the crowd was particularly enthusiastic. He felt a surge of adrenaline and excitement that was both exhilarating and exhausting.

Chapter 6: One Particular Harbor

* Buffett expresses his love for Key West and the sense of community he has found there.
* He describes the island's unique charm and the people who make it special.

Real-life example:

Buffett describes a sunset cruise he took with friends around Key West. They watched the sun dip below the horizon and enjoyed the beauty of the island's natural surroundings.

Chapter 7: Cuban Crime of Passion

* Buffett reflects on the Cuban Missile Crisis and the lessons he learned about the fragility of life and the importance of peace.
* He also explores the theme of love and loss in the context of his own relationships.

Real-life example:

Buffett recounts a trip he took to Cuba after the missile crisis. He visited Hemingway's house and reflected on the author's life and work. This experience deepened Buffett's appreciation for the importance of living fully and embracing every moment.