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Race to Hawaii: The 1927 Dole Air Derby and the Thrilling First Flights That Opened the Pacific

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Today, a trip to Hawaii is a simple six-hour flight from the West Coast. But almost a century ago, the first flights to Hawaii required a nerve-wracking and uncertain twenty-six-hour journey to isolated and elusive islands located in the middle of the world's largest ocean. Pilots prayed they would encounter land after flying a full day and night across 2,400 miles of the open Pacific.Race to Hawaii chronicles the thrilling first flights to Hawaii in the 1920s, during the Golden Age of Aviation. These journeys were fraught with danger. To reach the tiny islands, fearless pilots flew unreliable and fragile aircraft outfitted with primitive air navigation equipment. The first attempts were made by the US Navy in the flying boat PN-9 No.1, whose crew endured a harrowing crossing. Next were Army Air Corps aviators and a civilian pilot, who informally raced each other to Hawaii in the weeks after Charles Lindbergh landed the Spirit of St. Louis in Paris.Finally came the Dole Derby, an unprecedented 1927 air race in which eight planes set off at once across the Pacific, all eager to reach the islands first and claim a cash prize offered by Pineapple King James Dole. Military men, barnstormers, a schoolteacher, a Wall Street bond salesman, a Hollywood stunt flyer and veteran World War aces all encountered every type of hazard during their perilous flights, from fuel shortages to failed engines, forced sea landings and severe fatigue to navigational errors. With so many pilots taking aim at the far-flung islands in so many different types of planes, everyone wondered who would reach Hawaii first, or at all.

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Published August 1, 2018

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Jason Ryan

32 books14 followers
Librarian Note: There is more than one author by this name in the Goodreads database.

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Displaying 1 - 22 of 22 reviews
672 reviews58 followers
June 6, 2022
Audible.com 11 hours 56 min. Narrated by Keith Sellon-Wright (A)

Just about everyone knows the name of Charles Lindberg, the first American to fly solo across the Atlantic to Europe (Paris.) But have you ever thought about who was the first to fly from America across the Pacific? In 1927, shortly after Lindberg's successful flight, James Dole, the "Pineapple King," one of the richest men in Hawaii offered a cash prize of $25,000 to the first plane to fly from California across the Pacific and land in Hawaii. This was huge amount during the tough days of the Depression. Dole hoped Lindbergh would accept his offer; he didn't. However Dole was unprepared for the tremenous number of other applicants who did! This became known as "Dole's Derby." The Navy was already interested because of their Naval base at Pearl Harbor. This is the thrilling story of the aviators who attempted the feat of flying to Hawaii, a group of small islands, not a huge land mass like Europe.
Profile Image for Denise.
7,544 reviews138 followers
November 1, 2023
Interesting look at a piece of aviation history I knew next to nothing about prior to reading this.
Profile Image for Shrike58.
1,475 reviews27 followers
May 14, 2024
The Dole Air Derby of 1927 is an event that I've been aware of forever, but it's also the case that it's been literally decades since I've really thought about it, so my interest perked up immediately when I saw that there was a new book on the topic. This account is rather different in that the author is coming at the topic not as an aviation enthusiast (which he was not at the start), but as a journalist, so he's more concerned with context and how the events were covered in real time. Be that as it may, what I knew of the story was that the actual race was regarded as a bloody fiasco, and it was, but not necessarily for the reasons that concerned period commentators. They tended to be fixated on the demise of Mildred Doran, the flying mascot of the plane "Miss Doran," a young woman who wound up being the Christa McAuliffe of her time, and how this enterprise seemed to represent the barnstorming phenomena taken to its logically stupid conclusion.

While this is true to a degree, the basic point is that while the best practice of aeronautical engineering had produced aircraft that were viable enough to make the flight from the United States to Hawaii (this is all taking place in the excitement of Charles Lindbergh's flight across the Atlantic); the hard part was that navigation techniques had a long way to go before they were truly reliable. The aircraft on the cover was not one of the Dole Derby competitors, but the Army Air Service machine "Bird of Paradise," that was purposely sent out as an "x-plane" to test long-range navigation methods and technology. The cream of the Dole competitors did their best to learn from the previous Hawaii flights (which included a USN flight of flying boats and the first civilian crossing made by the "City of Oakland"), but the margins were very narrow between success and failure. Much of the rationale for the the Dole Derby was to entice Lindbergh into making another record flight, but he wanted nothing to do with the whole enterprise!

Originally written: September 1, 2018.
Profile Image for Martin.
457 reviews45 followers
July 16, 2018
I love books on the early days of flight and this is one of the best I’ve read. Imagine flying for 2400 miles with dodgy instruments for around 20 to 30 hours and trying to find a series of small islands. There isn’t a dull moment in this book. Highly recommended
770 reviews39 followers
May 6, 2021
What I find so amazing about early aviators is their unabashed fearlessness. Regular injuries from crash landings is no big deal. Very interesting story.
Profile Image for Tim Martin.
878 reviews51 followers
September 2, 2023
Very enjoyable popular history of the first flights to Hawaii. Divided into three sections, author Jason Ryan told these gripping stories with a novelist’s flair. Section one tells of the first ever attempt to cross the 2400 miles from San Fracisco Bay to Oahu, this attempt being made with three U.S. Navy flying boats in 1925, with only one ship (airplanes were called ships back then), flying boat PN-9 No. 1. (PN flying boats were twin-engine biplanes used by the U.S. Navy in the 1920s and 1930s) commanded by John Rodgers making it…kind of. It was a gripping story of survival and daring that I really enjoyed.

Section two tells of two flights on June 28-29, 1927, one military, one civilian, that took off almost at the same time. The military one was the Bird of Paradise, an Atlantic-Fokker C-2 tri-motor transport United States Army Air Corps aircraft crewed by 1st Lt. Lester J. Maitland and 1st Lt. Albert F. Hegenberger The civilian one City of Oakland, crewed by Ernest L. Smith and Charles R. Carter. One of the crews became the first to make it successfully to land on Oahu, though both are very interesting and well-told adventure stories.

The third section details the Dole Air Race or the Dole Derby, an air race from Oakland, California to Honolulu sponsored by pineapple king James D. Dole in August 1927. In a gripping section filled with some amazing personalities and fun (and also tragic) stories, the author detailed who won a race that originally began with eighteen entrants, eight actually participating in the race, but only a fraction of these eight actually landing in Hawaii. I won’t spoil the results of the race as I sure didn’t know who won and more importantly, who survived before reading the book (as you either finished the race, washed out pretty near the beginning and returned back to Oakland, crashed before even getting to the Pacific Ocean, or took off successfully but were never seen again).

Really great read/listen, I learned a lot about early aviation and though it was a little bit of padding to include sections on World War I combat aviation, post-World War I military aviation in the U.S., Charles Lindbergh and his famous flight, barnstorming, early use of stunt pilot and planes in Hollywood, air mail, and the story of James D. Dole and his pineapple empire, they were fascinating padding that I enjoyed. I liked how the author followed up with the principal individuals after the events of the book and detailed a tiny bit about the history of aviation to Hawaii after the Dole Derby. It was fascinating also to realize how early in aviation history these great feats were attempted, as instrument flying and even the use of radios and radio beacons was still relatively new.
Profile Image for Gregory Howe.
75 reviews
November 14, 2018
This single book is really three different stories. There is some overlap in the telling of these histories so a small part is redundant (that's why it's only four stars). When one considers the state of the art of long distance flying at that time, it's to me amazing that any of these pilots lived. The writing is descriptive and compelling. The stories and characters are endearing. I read most of the book flying to and from San Francisco, I regret not being able to visit the Oakland site from where these planes took off as I was too busy for any sightseeing. It's amazing that the exploits of these pioneers are not more well known, at least I had not heard of any of them. Their exploits are truly amazing, their bravery is astounding or maybe they were all just crazy.


Read this book, you won't be disappointed.
Profile Image for C. Patrick G. Erker.
297 reviews19 followers
February 20, 2019
Exciting story of the first aviators to make the trans-Pacific flight from the San Francisco Bay area to Hawaii. Three separate sets of pilots, three separate, though interwoven plots.
One forgets how remarkable human progress can be in a few short generations. For us, hopping on a flight across the world requires a few hundred dollars and a willingness to endure jetlag. For aviators in the 1920s, it meant risking death and personal bankruptcy.
I listened to this book while on a trip from San Francisco to Oahu, so found the settings particularly relevant: Crissy Field, Bay Farm Island, the hills of SF packed with people, then Honolulu, Kauai, Molokoi, etc. I finished the book on my flight home over the Pacific.
170 reviews
October 8, 2018
This was always going to be an emotional read for me, because everything about aviation reminds me of my late father, who was a pilot and flew to Hawaii many times in his career. But I think this book would have held my interest even if I didn't have these associations, because it's a great story and very well written. It helps that the stories of these flights--some successful, some not--are exciting, that they took place during a very dashing time in aviation history, and that many of the pilots were colorful characters, but the author deserves a lot of credit for showing the rest of us how non-fiction should be done.
Profile Image for Betsy.
165 reviews1 follower
June 22, 2019
I enjoyed this book. Very detailed, with obvious research put in to make sure facts and such were included. At times, the read was a little belabored because of the historical backstory that was necessary to include. But overall, I enjoyed this book and didn't want to put it down...a good read for history buffs, those interested in airplanes, and an interesting add on to my knowledge of US history.
Profile Image for Chandra.
265 reviews2 followers
July 9, 2024
This historic exploration of early flight was both endearing and oddly exciting. The pacing and narrative style are aligned with a Lauren Hillenbrand style, with an emphasis on quirky personalities and details. Who knew a non-stop flight from the mainland to Hawaii once captured the imagination of the nation? Or that it was achieved under such crude, rudimentary conditions? A fun and interesting read.
Profile Image for Cal McCormick.
35 reviews
January 2, 2025
It’s stories like these that makes the “age of exploration” feel a lot closer than the times of Columbus or Captain Cook. Pilots who dare to accomplish never before feats relying both on the newest technology of the age and techniques that would not have been out of place centuries earlier.

The writing was clear and made it easy to follow the many different stories of individuals who set up the contest and made the journey
Profile Image for Kent District Library.
972 reviews67 followers
April 17, 2019
“What is now a flight of a few hours was once only traversed by steamship. A thrilling tale of aviation between WWI & WWII. Dead reckoning, danger, and 2,400 miles of the vast Pacific Ocean.” – Grahm at KDL’s Service Center
Profile Image for Tony Bartelme.
Author 10 books22 followers
February 4, 2019
Jason Ryan wove a fascinating yarn about a pivotal period in aviation history. In the mid 1920s, just 20 years after Kitty Hawk, pilots began flying across oceans. In some ways, the Pacific was a more formidable barrier than the Atlantic. Ryan begins with a powerful story about a military flight to Hawaii, an adventure that's a book in its own right. He follows up with equally compelling stories, building up to the climactic race itself. The pace of innovation during this period is amazing, made all the more impressive because failures could be deadly. A great read.
Profile Image for Kenneth Flusche.
1,066 reviews10 followers
March 2, 2019
3 stories in one book, remines me of the old Boys Life Magazines, Amazing that anyone survived those first flights from California to Hawaii
47 reviews1 follower
September 10, 2019
At times it was a bit too much "history of aviation" and not enough narrative, but it had good parts too. And the history of aviation bits were sometimes quite interesting.
Profile Image for Joshua.
107 reviews2 followers
January 20, 2020
I had never heard the story of the first flight from continental USA to Hawaii. I enjoyed the adventure Jason Ryan took me on in this recounting of those thrilling first flights.
50 reviews
March 4, 2021
Interesting story about a part of aviation history that I didn't know much about. All stories from the Golden age of the aviation are fun and interesting though. Such an amazing time.
Profile Image for Layne Ruble.
Author 2 books3 followers
August 30, 2022
Jason really paints a picture that truly lets this story, take off
Profile Image for Karla.
1,691 reviews
May 22, 2024
An interesting bit of aviation history involving some of my favourite islands. A little bit slow in the middle
Displaying 1 - 22 of 22 reviews

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