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Sea of Gray: The Around-the-World Odyssey of the Confederate Raider Shenandoah

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The CSS Shenandoah commenced the last, most quixotic sea story of the Civil War. Before its voyage was over, 34 Union merchant and whaling ships and their cargoes would be sunk. Four months after the Civil War was over, the captain learned the war was over, and he had gone from being an enemy combatant to a pirate, a hangable offense.

448 pages, Hardcover

First published January 24, 2006

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About the author

Tom Chaffin

9 books13 followers
Historian Tom Chaffin is the author, most recently, of “Odyssey: Young Charles Darwin, The Beagle, and The Voyage that Changed the World" (Feb. 2022, Pegasus). The work, focused on the naturalist's five years of global travel aboard HMS Beagle, chronicles the the formative experiences of his youth.

Chaffin’s earlier books include “Revolutionary Brothers: Thomas Jefferson, the Marquis de Lafayette, and the Friendship that Helped Forge Two Nations," "Pathfinder: John Charles Frémont and the Course of American Empire," "Sea of Gray: The Around-The-World Odyssey of the Confederate Raider Shenandoah," and "Giant’s Causeway: Frederick Douglass’s Irish Odyssey and the Making of an American Visionary."

The author was was born and grew up in Atlanta and spent his early professional years in journalism, living in, among other places, Savannah, New York City, San Francisco, and Paris. Chaffin has taught U.S. history and writing at various universities. He holds a B.A. in English from Georgia State University, an M.A. in American Studies from New York University, and a Ph.D. in history from Emory University. His articles, reviews and essays have appeared in the New York Times Magazine, Time, American Scholar, Harper’s, The Nation, the Oxford American, and other publications. He was a frequent contributor to the New York Times‘ acclaimed “Disunion” series on the American Civil War. In 2012, he was a Fulbright fellow in Ireland.

Chaffin lives in Atlanta.

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Displaying 1 - 30 of 46 reviews
Profile Image for Al.
476 reviews4 followers
October 29, 2025
This was a gift book that I otherwise would never have read as I haven’t generally liked maritime/naval books. It has been on my shelf for years.

But it really is an interesting story and it’s told well. There’s a lot of detail and another author would probably slice 100 pages off of it. So it occasionally gets a bit dry but for the most part it’s quite readable and the story ends up being more interesting than one might expect.

The book (like a television show) starts with a shocking look at the action about to come, but then the story gets told. In 1864 during the American Civil War, the Shenandoah launches from London- it’s stated mission to go to Bombay for trading obfuscating its true goal which was as a Confederate Navy ship headed to Alaska to sink and pillage American (Union) whaling vessels.

The ship sailed to the Pacific, capturing a few American ships on its way to Australia, stopping in Melbourne and then stopping to visit the natives of the Caroline Islands. From there it eventually does make it all the way to Alaska. Here they do have their most successful moments. But things have changed. While they meet other ships and read newspapers, they find out that the Confederacy may have been defeated.

If this is true, are they still military raiders or have they become pirates? It is an issue that has dogged them from the beginning and dictates how the ship must be managed. But there are all kinds of questions now if there is no Confederacy to go back to

In fact, the Shenandoah makes raids after the War has ended, even after the final land battle - a post-Appomattox engagement in south Texas. Then it becomes a matter of what to do next- where and how to surrender without being shot upon.

This really could be a great little Netflix miniseries except the protagonists are Confederate soldiers- not something the studios would touch. That said, there’s no shortage of drama here and Chaffin captures all the particulars- Captain vs crew, Captors vs Captured, Boat vs Weather and so on. It really would make a great screenplay.
6,256 reviews80 followers
March 19, 2025
Lately, the Trump administration has been talking about reviving Letters of Manque, to go after the Cartels, making this more relevant than ever.

It's the premise of several westerns: A small unit is sent to execute an operation where there is money involved, only to find out the war is over after they're through. That's what happened in this case, where a ship full of privateers find out they might just be pirates after the war is over, and sail around the world.

Very interesting. I'm surprised nobody's optioned this as a film. It's not all that different than a Jules Verne novel, only it's actual history.
7 reviews
July 12, 2013
Sea of Gray is an excellent recounting of the operations of the Confederate commerce raider Shenandoah during the last part of the American Civil War.

This is the history of a commerce raider; a ship whose purpose was to find and capture or destroy the merchant ships of its enemy; and whose intent was to avoid all enemy warships. It is not a tale of rousing derring-do at sea; nor an exciting account of heroic sailors in gray swinging onto the decks of enemy warships in deadly and exciting hand-to-hand combat.

As a history, the book looks at what is important to such a vessel; the ship, the captain, the officers, the crew, and their orders. The reader learns that the captain and officers were not the pick-of-the-litter, but were drawn from the small number of Confederate naval personnel available in England when the ship was acquired. The captain was not the best suited individual for his role, nor were many of the officers, and certainly not the almost entirely foreign crew. What the author shows, is how these individuals worked to accomplish, or sometimes not accomplish, their mission.

Following the Shenandoah as it cruises around the world, the reader is presented with all of the problems facing such a ship. Purchased covertly, to avoid entanglement with the British government, the ship had to be fitted out at sea, and completed arming itself plus even finding a full crew while underway. This was a ship which had no friends or allies. All other vessels were either neutral (and sure to report the raider’s position), warships (whether U.S. Navy or others, something to be avoided at all costs), or U.S. merchant ships, which had to be captured and then dealt with. Once captured, there were the problems of what to do with a ship, its cargo, and its crew. On top of this were the dangers of chasing the U.S. whaling fleet in the poorly charted and ice filled waters of the far North Pacific. Then, there was the final issue; what to do when it became clear that the war was over.

If what you want is an exciting tale of adventure on the high seas, go read a Rafael Sabatini novel. If instead what you want is to learn what it was like to be the last Confederate commerce raider during the Civil War, then it is highly recommended that you get this book.
497 reviews2 followers
July 9, 2018
Nice narrative history of the outfitting and cruise of the CSS Shenandoah. Chaffin offers a good, thorough history of the Shenandoah and her circumnavigation - there are good discussions about some of the challenges faced - dealing with neutral ports, remaining supplied, and having adequate crew. I think when Chaffin tries to discuss the legal aspects of commerce raiding v. privateers v. piracy, it feels like he's trying to overdramatize and muddy waters that I think were fairly clear in the Shenandoah's case (or he didn't provide a compelling argument, in my view on why they should be muddy.) Chaffin also looks to discuss the challenges of the crew dynamic, particularly vis-a-vis the captain and officers - it's interesting, but it feels incomplete.
All in all, a solid, good read.
Profile Image for Eric.
465 reviews11 followers
February 26, 2014
Dem rebs are good soldiers AND sailors! The depradations of the Shenandoah were insignificant compared to the wider war, but impressive, nonetheless!
Good read, kept me riveted!
Profile Image for Randall Harrison.
213 reviews
October 19, 2023
This is a detailed and fascinating book about a little-know chapter of Civil War history. The Shenandoah was a CSA commerce raider that continued sinking ships in the Pacific Ocean long after the Civil War officially ended.

Chaffin does a great job describing how the ship was built, outfitted, crewed, and sailed around the world during the last months of the war. Launched in England, she was the only CSA ship to circumnavigate the world, crossing the Equator four times in a journey that took them to Australia, the Bering Straits and several islands in and around the Pacific, while hunting for commercial ships and whalers to seize and plunder.

The details about the officers and crew are extensive. Chaffin was able to access their diaries, ship logs and later accounts of the cruise, written mostly long after the war ended.

Chaffin gives us a good sense of the type of men who manned the ship; the details about ship construction, outfitting, crewing, and operating were interesting for one like me without extensive knowledge about these topics.

Even though you know how this story ends, it is still a great tale, well told that keeps the narrative flowing smoothly, providing great detail that never overwhelmed me. The last few chapters about what the captain decided to do with the ship after learning the war was over I found particularly interesting. While not a huge Civil War fan, I nonetheless found this a fascinating tale.

Oddly, there was another book on the same subject, written about the same time. The Last Shot by Lynn Schooler. Not sure if I'll read that one too, although Sea of Gray certainly piqued my interest.

I enjoyed Chaffin's biography of John C. Fremont; highly recommend that book too, although I didn't realize Chaffin was the author of that volume I enjoyed until I read his bio on the dustjacket of Sea of Gray.

Recommend this book for those interested in Civil War, naval, and 19th century American history. Might be too detailed for the casual reader but I'd encourage everybody to give it a try before dismissing it if they are not originally drawn to its specific focus.
Profile Image for Jacob.
497 reviews7 followers
February 23, 2024
Wow. This was a slog. I like nautical stories usually. And I always am fascinated by soldiers/sailors, laboring on, even when defeat is certain. So there were elements here to make this a potentially interesting read for me.

However, this was an unimaginative recounting of a relatively boring raider voyage. The CSS Shenandoah leaves London and then sails to Australia...for 150 pages. Most of this is about the petty squabbling between the captain and his executive officer and the author's evaluation of each. Talk about a yawner. Things pick up in Australia with some repairs and some evening balls. Yeah, I know, not super exciting, but after the previous 150 pages its practically riveting.

As we get into the meat of the raiding, we get a relatively uninspired listing of events and loot taken. Partly, I think it's uninspiring as there is little seamanship or audacity at display here. The ship rolls up, fires a gun or two, the raiders go on board and take what they want and then burn the ships. The unimaginative, clerk-like writing is not helpful either, making for a rather droll recounting.

Taking loot and burning ships, of course begs the question of what happens to the unfortunate crews? Prisoners are either left on inhabited islands near where their ships are captured, impressed into service (sometimes via tricing), or released on a ship the confederates elect not to burn. The fate of the early prisoners (most of whom were impressed) is actually some of the most interesting writing in the book.

At any rate, after basically 4 big days of boarding (1 in the South Pacific and 3 in the whaling grounds of the Arctic), the captain and crew of the Shenandoah come to realize that the war is over and their legal predicament is shaky at best. This happens on page 300. It takes 70 more pages to sail back to England, with more Real Housewives of the CSS Shenandoah on display until they reach their destination and the voyage ends.

If you are looking for a good raider book, consider The Wolf, which is a well-wrought tale about a German raider in WWI. Much more interesting. This one? Hard to recommend, unless you have a strong niche interest here.
Profile Image for Jon  Bradley.
340 reviews4 followers
January 27, 2023
I bought my copy of this book used for two and a half bucks at a "Friends of the LSU Library" book sale last spring. This book tells the incredible story of the CSS Shenandoh, a Confederate commerce raider sent to sea from Britain in late 1864 to travel to the Bering Strait and destroy the Yankee arctic whaling fleet. The ship started its voyage with a too-small crew and inadequte supplies, but it somehow carried out its mission, making stops in Australia and Ascension Island along the way. By the time it reached the far northern Pacific and began sinking whalers, the Civil War had been over for two months. On finally learning about the end of the war, the Shenandoah sailed back to Britain, thereby completing a circumnavigation of the globe. This is one of the stranger tales from the Civil War and I found the book fascinating. Four out of five stars.
Profile Image for William Edmund Wilkin.
26 reviews2 followers
September 29, 2022
This book would make a great movie! True story of a Confederate navy ship in 1864-65. The crew took the vessel from UK south around Africa, across to Australia, then north to the Arctic to attack Yankee whaling ships. Author Tom Chaffin uses the diaries and letters of the ship officers to develop a view of personalities and interactions, useful for a screenwriter. Also interesting to understand the actions of Yankee consular officials who were trying to prevent the Confederates from purchasing vessels in UK. The book has fine illustrations: portraits of the participants as well as useful maps and a fine chart of the ship for non-sailors.
Profile Image for Brendan (History Nerds United).
814 reviews736 followers
November 6, 2022
Truth is stranger than fiction.

The CSS Shenandoah was sent out by the Confederate States of America (otherwise known as “losers”) to wreak havoc on Union shipping and they were actually quite good at it. Ultimately, the ship and crew would capture 38 vessels. The ship would ultimately go around the globe and do a lot of damage in a lot of different places.

In war, these actions are perfectly legal and not frowned upon. However, when you continue to do it after the way is over (unbeknownst to them) then you become something else: pirates.

This book covers the whole strange odyssey and the fate of the crew after. It’s a good read.
Profile Image for Diane Depew.
75 reviews1 follower
February 15, 2024
Fascinating read on the Confederacy’s attempts to disrupt the Union’s merchant vessels, especially the arctic whaling fleet, by utilizing a modern (for the time period),and outfitted for war, steamship to raid the high seas. The raiding outlasted the war as the Confederate Raider, named the C.S.S. Shenandoah, usually received news that was months old and the crew doubted initial reports of Southern losses. Consequently, some claim the last shots of the war fired by the Confederacy were from the C.S.S. Shenandoah.
239 reviews5 followers
February 8, 2017
This was a look into a part of the Civil War you don't get to hear much about. It's thoroughly researched by the author and comes across as a labor of love. The writing is not dry in any sense and the author paints a pretty vivid picture of life at sea for the Confederate naval men. If you like tales of the sea or reading about the civil war you should do yourself a favor and pick this up.
Profile Image for Megan Miller.
374 reviews
December 22, 2024
Finished 👌🏼

It's well researched, and an interesting story - but not engagingly written. I also left not knowing how exactly to feel about the people, but that's rather reflective of life. 🤷🏼‍♀️

Three stars seems fair. It isn't /bad/ but it's not super fun lol.
Profile Image for Shaun.
159 reviews2 followers
November 10, 2017
I think 372 pages to tell this story was a bit much. Great tale, but I was bogged down in seeming endless details when the ongoing oddysee was the main focus. Maybe I read the description wrong.
Profile Image for Hank Stone.
10 reviews3 followers
November 29, 2018
Excellent research, presented in a novelistic narrative. Little-known not-so-trivial civil war incident sheds light on many other subjects.
7 reviews
October 17, 2021
The is a pretty slow burn. It definitely made for some peaceful reading. Readers looking for action or something provocative probably shouldn’t look here. I liked the story though.
212 reviews2 followers
November 5, 2021
Thorough telling of the Shenandoah's voyage, but probably could have been edited to read more tightly.
Profile Image for Alan Hosch.
53 reviews
January 12, 2024
It's a fascinating account of naval derring-do in the face of insurmountable odds.
Profile Image for Brian .
976 reviews3 followers
January 8, 2012

There have been many great books written on the confederates commerce raiding and its impact on the civil war. Tom Chaffin adds another excellent book to this growing collection of literature. Tracking the CSS Shenandoah as it was surreptitiously bought, armed at a secluded island and put to see with the intent to raid whaling ships in the artic. The ship was a last ditch effort in the dying days of the confederacy as Richmond was being surrounded to strike back at the Yankees. Overall they were very successful as they captured ships along their trip to Australia where they refitted before heading to the Artic. One of the things this book covers better than some of the other was the legal and diplomatic battles waged by Union European Counsels against their shadowy Confederate counterparts as they tried to prevent these ships form going to sea or leaving a neutral port. The Shenandoah continued fighting after the war was over and continued its plundering cruise until confirming that the South had surrendered. They became one of the most hunted ships in the history of the world and managed to elude capture until sailing back into Great Britain where they surrendered to the British. Overall just an intriguing story and one that will hold the readers attention in this little covered topic of confederate sea raiders.
Profile Image for Gerald.
277 reviews12 followers
June 21, 2015
This non-fiction account of the 1864-1865 voyage of the Confederate States commerce raider CSS Shenandoah tells the tale of her 13-month, 58,000-mile circumnavigation of the globe to carry out her assigned duty of the disruption of the commerce of the North, most particularly the significant income for New England derived from their whaling ships' journeys into the Bering Sea. The Shenandoah crossed the equator 4 times and during their incredible voyage covering points from its Liverpool, England departure, around South Africa's Cape of Good Hope, into Antarctic waters, an extended stopover for repair and provisioning at Sydney, Australia, from the South Pacific into Arctic waters above the Aleutian Islands, south around South America's Cape Horn, then back to Liverpool to surrender their ship to the English after learning of the defeat of the Confederate States, ending Shenandoah's its adventures and misadventures.

Shenandoah was said to have "destroyed 32 vessels, ransomed 6 others, and taken 1,053 prisoners. In all the value of the vessels and cargoes destroyed by the raider, according to her officers' calculations, came to $1.4 million." It was also said by her Captain that "the last gun in defense of the South was fired from her deck."

I most thoroughly enjoyed this amazing story and very highly recommend it to interested readers.
Profile Image for Patrick.
1,045 reviews27 followers
March 13, 2008
This is a story I never would have heard of if not for the trusty non-fiction kiosk at Provo Library. This raider is commissioned by the South near the end of the Civil War to mess with American trade in an attempt to hurt the North economically. The guy sails off and starts looting American vessels all over the world months after the war is over because they hadn't received word yet. And then, the captain continues some plunder even after they find out the war is over and that they have been labeled criminals rather than combatants.

There is a lot of interesting commentary about the complicated politics between the North and South and other nations around the world. Also, the personalities on the boat mesh and conflict. Great story. That said, the writing is not as enthralling as some other contemporary history and the author could be more succinct sometimes. Highly recommended if you are interested in obscure Civil War history and politics. (Having read the Patrick O'Brian Master and Commander series helps understand some of the culture and background as well.)
Profile Image for K.M. Weiland.
Author 29 books2,529 followers
June 23, 2012
I picked this one up thanks to its relatively unique subject matter. Aside from the Monitor and the Merrimac, you don't hear too much about naval warfare during the Civil War, and you certainly don't hear much of anything about the Confederate Navy abroad. So I dived in, thinking I would get a rousing sea yarn and learn a few new things along the way. Unfortunately, the story itself, focused around the CSS Shenandoah, is a tale in which not much happens. The ship's feats are interesting enough, but they had no noticeable impact on the war itself, which lowers the story's excitement and tension considerable. Even worse, the ship's officers are a collection of invariably unlikable gents, who aren't helped any by the author's obvious distaste for them. So, ultimately, what we have is a rather dull tale about unsympathetic people who do nothing important.
Profile Image for Dustin Lonero.
23 reviews4 followers
August 5, 2012
This book covered a topic I'd always been interested in: the voyage of the CSS SHENNANDOAH from England to the Bering Sea and back Amazingly, the Confederate Raider took the Civil War to the Arctic and at one point even considered a raid on San Francisco. As exciting as the summary sounds, the details of the voyage are far-less intriguing. The book was tedious and reminded me of being on a long stretch of underway while on deployment. You hear of all the annoying in-fighting among wardroom; the depradations of food, women, and entertainment; and the general disapointment of a deployment that didn't quite live-up to its expectations. The author did a great deal of research and wrote in a fairly easy-to-read manner, but I'd recommend getting a quick summary of the SHENNANDOAH from WIKIPEDIA vice trudging through 478 pages.
Profile Image for Matt.
197 reviews9 followers
August 15, 2010
Sea of Gray is a good look into the history of the CSS Shenandoah. Chaffin does a good job of integrating sea going terms and their definitions into the text which makes understanding what he discussing for first time maritime readers easier. The narrative moves along at an quick an steady pace however I never became to involved with the figures involved. After I was finished I knew more about the ship and crew but never felt like I cared about them. Chaffin could have spent more time discussing the consequences of continuing the Shenandoah's mission after Lee had surrendered would mean to the crew. Over all it was a good quick read that was informative but not Earth shattering in the conclusion or narrative.
Profile Image for SJ.
185 reviews3 followers
November 12, 2011
For me this book was an awfully hard slog. I think part of it was simply the total lack of sympathetic characters involved. It was interesting to read about a piece of history I was not aware of--that the Shenandoah kept fighting after the war was declared over--and to read about naval history in a later period than I have done previously. I had pretty much no familiarity with the era of steam-augmented sailing ships and so that was interesting.

But in summary, definitely a hard one to finish, and if I had not borrowed this from a friend who was eager to discuss it, I probably would have abandoned it.
Profile Image for Michael.
308 reviews31 followers
February 3, 2016
This was a pretty good book and right to the point. This book is the story of the Shenandoah. With very little sidetracking. I personally felt like it was well written and a great story. It seemed longer than I expected but it wasn't a boring read. If I was a fan of Civil War history I probably would have given it 5 stars. Honestly. I purchased this book because I found it dirt cheap and had a mild interest in it. Now I'm glad I did. Good book and great account of the adventures of the Confederate raider Shenandoah.
108 reviews22 followers
July 17, 2012
A good historical read about a part of the civil war which I was completely unfamiliar with. The descriptions come directly from the participants' memoirs and are very believable and well done. I liked the way the historical citations f these memoirs was mixed with the fictional prose. While some of the longer sea journeys seemed interminable for the sailors, they unfortuantely also translated that way to the reader and I had to skip some sections which were wordy and irrelevant.
Profile Image for S.M. Johnson.
Author 4 books9 followers
September 30, 2013
Wow. I assumed that this would be an interesting read but it went further and left me not only unable to put the book down, but also invested in the lives of the players involved. Case in point, I found myself hunting for more information on the subject after I'd finished the title because I was hungry for more. Even the "layman" who doesn't read many history books will likely find this an enjoyable and very readable little adventure. I only wish there was more to read!
Profile Image for Shan.
38 reviews1 follower
February 3, 2013
Like everyone else who rated 2 stars, I think this book was kind of dull. It would be more appropriate in a history class than in the hands of someone searching for exciting maritime. The purpose isn't to excite but, nonetheless, Chaffin could have used at least some imagery to capture his reader's attention a little bit.
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