10 Books To Read If You’re Dreaming of Sailing Off Into the Sunset

When I first started to get the “itch” – the urge, on a regular basis, to quit my corporate job and sail off into the sunset – I started reading like crazy.  After a colleague, in her early 40s, moved aboard a sailboat and worked from port, after her kids left for college, I realized it really was possible.  A few years later, she and her husband quit their jobs entirely and retired to roam the world full-time.  And I realized that time was running out – that every day I spent sitting in my desk chair was a day I was missing out.

I took to Amazon, looking for books to inspire my own transition.  I started with Amazon primarily because I’ve had a Kindle Unlimited subscription for several years.  If I was going to start locating real-world, down-to-earth accounts of people who have successfully sailed off into the sunset, Amazon seemed like a logical place to start.

Here is a list of my favorite books on this topic along with the reasons why each one made it onto the list.  There are literally hundreds of accounts of sailing around the world, quitting Corporate America to cruise full-time, and creating a gypsy lifestyle aboard a boat.  But each of these spoke to me in one way or another.  I’ve tried to include a variety of perspectives here, as well as varied approaches to the lifestyle.  Each of these books is available for free with Kindle Unlimited (or a free 30-day Kindle Unlimited trial), so you won’t break the bank while you save for that sailboat.

Readers have commented that this list doesn’t include some of the absolute must-read classics, such as Joshua Slocum’s Sailing Alone Around the World, written in 1956 about his 1895 solo trip around the world.  In this list, I’ve focused on more current accounts, particularly those in which the authors were escaping 9-to-5, debt and possessions-laden lives in favor of cruising.  I hope they help inspire your journey!

Salt of a Sailor: The true origins of a durable, but not-so-dainty sailor I think this was my favorite of all the sailing away books I read.  Possibly because I identified with the 30-something, coming-out-of-a-long-term relationship female author; or possibly because she’s real and gritty in a way that many authors gloss over.  Either way, it’s a great read – about making a major life change and finding some peace in the process.

 

 

Annie Dike’s next book,  Keys to the Kingdom: A rising young lawyer who found the key by losing the lock, also earns a place on the list.  Similar to the first, her honest continues to be refreshing.  And, her tales of the less-than-glamorous days onboard will help you get a picture of both the good – and bad – days as a cruiser.

 

 

 

Quest and Crew: A True Sailing Adventure This one earns a spot on the list for several reasons.  First, its detailed accounts of the areas they’re sailing are fascinating if you’re ever hoping to follow in their footsteps. The realism of day-to-day life aboard, both in perfect harmony and in total disarray, is compelling.

 

 

 

Quest on the Thorny Path: A True Caribbean Sailing Adventure (Quest and Crew Book 2) makes the list as well; continuing the story of a husband and wife who, later in life, alight onboard a sailboat and begin their adventures.

 

 

 

Get Real, Get Gone: How to Become a Modern Sea Gypsy and Sail Away Forever In a nutshell, this book is about cutting the bullshit and taking drastic action to move aboard.  It doesn’t pull punches, but it also provides a solid reminder that we’re all designing our days – either intentionally or passively – and we might as well design them well.  Pick up this book if you’re ready to stop dreaming and start doing.

 

 

Among the Multihulls: Volume One If, in any part of your sailing-into-the-sunset dreams, you see a catamaran or trimaran…this is a great place to start.  A combination memoir and history of multi-hulled sailboats from an early DIY multi-hull builder, it offers insights into the strengths and weaknesses of catamarans and trimarans as opposed to single-hulled boats.  Among the Multihulls: Volume Two continues the story.

 

 

This Is It: 2 hemispheres, 2 people, and 1 boat Told from a slightly more international perspective, this couple didn’t just quit their jobs and start sailing around the world – they flew overseas to start their journey by finding the perfect boat.

 

 

 

Leap of Faith: Quit Your Job and Live on a Boat This book makes the list because it goes into a bit more detail about just HOW to go from ho-hum to sailing the doldrums.  He talks about paying off debt, freedom, and many other topics that we love!

 

 

 

Alone Together: Sailing Solo to Hawaii and Beyond This book makes the list because of its focus on how sailing and solitude can turn your attention inward.  If you’ve ever wondered what you would think about if you couldn’t check Facebook every morning and watch the news every night, this book is for you.

 

 

 

Sailing the Great Escape—¡Qué Bárbara! This book, while not free with Kindle Unlimited, is just $2.99 for the Kindle Edition.  It makes the list because they’re sailing off into the sunset in a catamaran, but also because I enjoyed the perspective of a man whose dream was to sail away…and a wife whose dreams lay elsewhere, finding a common ground and starting off.

 

 

What are your favorite books about sailing off into the sunset?  Is there a particular book that helped motivate your own journey?

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