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To Cuba and Back

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A first-hand look at what life was like in Cuba from the author of Two Years Before the Mast. This book has entirely redesigned for the modern reader in a larger more readable font.

103 pages, Kindle Edition

First published August 14, 2007

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About the author

Richard Henry Dana Jr.

93 books64 followers
Dana was born in Cambridge, Massachusetts on August 1, 1815, into a family that first settled in colonial America in 1640. As a boy, Dana studied in Cambridgeport under a strict schoolmaster named Samuel Barrett, alongside fellow Cambridge native and future writer James Russell Lowell. Barrett was infamous as a disciplinarian, punishing his students for any infraction by flogging. He also often pulled students by their ears and, on one such occasion, nearly pulled Dana's ear off, causing his father to protest enough that the practice was abolished.

In 1825, Dana enrolled in a private school overseen by Ralph Waldo Emerson, who Dana later mildly praised as "a very pleasant instructor", though he lacked a "system or discipline enough to insure regular and vigorous study". In July 1831, Dana began his studies at Harvard College, though he was suspended for six months before the end of his first year for supporting a student protest. In his junior year, he had a case of measles which also caused ophthalmia and his weakening vision inspired him to take a sea voyage.

Rather than going on a Grand Tour of Europe, he decided to enlist as a common sailor, despite his high-class birth. He left Boston on the brig Pilgrim on August 14, 1834, on a voyage around Cape Horn to the then-remote California, at that time still a part of Mexico. On the 180-ton, 86.5 foot-long Pilgrim, Dana visited a number of settlements in California (including Monterey, San Pedro, San Juan Capistrano, San Diego, Santa Barbara, and Santa Clara and San Francisco). He returned to Massachusetts aboard the ship Alert on September 22, 1836, after two years away from home.

He kept a diary, and after the trip wrote Two Years Before the Mast based on his experiences. The term "before the mast" refers to sailor's quarters -- in the forecastle, in the bow of the ship, the officers dwelling near the stern. His writing evidences his later social feeling for the oppressed. After witnessing a flogging on board the Pilgrim, he vowed that he would try to help improve the lot of the common seaman.

After his sea voyage, he returned to Harvard to take up study at its law school, completing his education in 1837. He subsequently became a lawyer, and an expert on maritime law, many times defending common seamen, and wrote The Seaman's Friend, which became a standard reference text on the legal rights and responsibilities of sailors.

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Displaying 1 - 6 of 6 reviews
Profile Image for Pam.
765 reviews170 followers
November 3, 2025
This book was first published almost 20 years after the book Dana is usually remembered for, “Two Years Before the Mast.” Dana was from Massachusetts, an attorney, politician and advocate for better conditions on sailing vessels. His first book is dramatic and caused a sensation leading to reforms.

This book is missing some of that advocate or muckraking spirit and is less dramatic. By the time of his Cuban book Dana is no longer young and appears to be on a fact finding mission to Cuba. A group of pre-civil war southerners had been tossing around the idea that the United States could buy places where slavery already existed or could be introduced. That was to change the balance of power by adding more slave states. Dana mentions the “30 millions bill” which was an attempt to have congress buy a part of Mexico and possibly Cuba. The reader is expected to know what was going on.

Dana takes a ship from the States to Cuba and begins to tell you all about Havana and then rural areas. It starts as a travel book—local color, his lodgings, food, customs and business. He then investigates sugar plantations and slavery. It is interesting. There is much to learn.

Ultimately he lets the reader know that the two cultures would not be a suitable combination. There was no good reason for the United States to buy Cuba. Coming from an abolitionist family from Massachusetts this is really a foregone conclusion but the right one.
Profile Image for David Partikian.
362 reviews34 followers
July 11, 2026
While I generally shy away from travel books, Richard Henry Dana’s Two Years Before the Mast (1840) contained enough detailed and compelling descriptions of the California coast and early pioneers to make me wonder about his later work, To Cuba and Back (1859), written when he was the United States Attorney for the District of Massachusetts, a few years before the Civil War. It also helped that I always wanted to own and read a Ticknor & Fields book, and I managed to grab Dana’s late offering off the internet in a first edition (disputed) second state, for $50. I felt like I was not only reading a relic, but enjoying his views of a bygone colonial Cuba, complete with descriptions of the sale of both Chinese coolies and African slaves as well as the sugar economy. Although Dana’s account is over 150 years old, it is surprisingly readable and, hands down, more entertaining than most travel narratives.

While the book is uneven, with weaker sections dealing with the author’s daily routine and an excursion from Havana to the interior, the better sections are worth the effort. These include Dana’s views, as an ex-mariner, of the short cruise on the steamer, Cahawba from NYC to Havana; the bustle of embarking and disembarking, especially in NYC where touts fight for fares; the ridiculous sanguine idiocy of bullfights (Hemingway fans take notice); and the economy of Cuba, which relied heavily on slave labor and coolies. As a lawyer in Boston, Dana took cases of runaway slaves prosecuted under the Fugitive Slave Law. Despite his humanitarian inclinations, he gives a dry, matter-of-fact description of the institution of slavery in Cuba that doesn’t betray how he feels about the subject. His aim is to report, not convince the reader of his opinion on slavery. Dana visited the island in February of 1859 while there was a failed attempt by the Southern states in the US Congress to annex (i.e. purchase) Cuba for the Union as a slave state to better perpetuate the institution of slavery in the USA. Dana often mentions this “30 millions” bill as an aside but never mentions whether the Spanish crown, which still possessed the island, was open to any sale.

The more I revisit and read for the first time the works of Richard Henry Dana Jr., the more I am intrigued by him. This book fits well with accounts of Colonialism in the Caribbean. Astute readers will comprehend how this sleepy province which depended on slave labor becomes such a thorny subject in modern Realpolitik.
Profile Image for James.
177 reviews
June 21, 2019
Once you get past the author's views about certain issues, it's a very interesting book that tells about a Cuba long past. I found it very informative, if a bit of a short read compared to some of his other writings.
Profile Image for Duncan.
285 reviews8 followers
November 8, 2019
Some good information on the Cuban scene in 1859 but otherwise not the great work of journalistic literature that Dana's Two Years Before the Mast is. It's very good reporting about a short trip to a tropical colony of the Spanish Empire mid 19th century but otherwise not a significant work of art.
20 reviews19 followers
February 15, 2024
An interesting, but admittedly random read. I picked it up at a used bookstore years ago and finally made it through. The details about the sugar and coffee manufacturing were fascinating. Overall much more readable than expected, but really only recommended if you're interested in this time period or Cuban history.
Profile Image for Hal Brodsky.
856 reviews13 followers
August 17, 2021
Doesn't hold a candle to "Two Years Before the Mast" , but this does provide a contemporary feet on the ground travelogue about life and attitudes in Cuba in 1859 when Spain ruled with an iron fist and the economy ran on slaves.
Displaying 1 - 6 of 6 reviews