CSS Alabama ' s Eastern Atlantic Expeditionary Raid The CSS " Alabama " s Eastern Atlantic Expeditionary Raid commenced shortly after the ship left Liverpool and was commissioned as the CSS " Alabama " , a Confederate commerce raider , lasting from August 24 , 1862 to about September 30 , 1862 . The primary area of operation during this expeditionary raid , was the Azores west of the African and European continent . Raid overview . On its maiden voyage , the CSS " Alabama " , newly commissioned on August 24 , 1862 , set sail for the eastern Atlantic Ocean in the area of the Azores , reaching the Western Azores along Pico Island and Faial Island by September 4 . The following day , " Alabama " sighted the " Ocmulgee " , and came in close under the pretense of the United States colors . The " Ocmulgee " , with whales still beside her , was taken with no resistance , and Captain Raphael Semmes waited until the following morning to burn her , not wanting to alert other whalers in the area . On September 7 , slowly making its way around Flores Island , Sunday muster was held , and Capt . Semmes read to the crew the Articles of War . The " Ocmulgee " s prisoners were let off at Lagens on Flores Island , and soon sighted another sail on the horizon . This time , it was the British colors hoisted as the " Alabama " gave chase , and shoots a 32 - pounder just over the heads of the crew of the " Starlight " out of Boston , a fast schooner . The " Starlight " heaves to , and the crew is captured . The following morning , " Starlight " s crew are paroled at Santa Cruz on Flores Island . Spotting another sail , CSS " Alabama " quickly overtakes a Portuguese whaling brig , letting her go . But luck returns , and on the afternoon of September 8 the ruse of the U . S . colors is used once again , successfully , to overtake the large whaler " Ocean Rover " , out of New Bedford , Massachusetts . The " Ocean Rover " is surprised to find that the CSS " Alabama " is merely a " rebel " ship , and not a protecting U . S . privateer , such as Gideon Welles , Secretary of the Navy , had promised the industry . The captain and crew are let off in their lifeboats to row the short distance to Flores , for which the " Ocean Rover " s captain later claimed that Captain Semmes was nothing short of a barbarous rouge . That night yet another whaler is sighted , and as dawn breaks , Semmes uses the British colors again , giving equal time for both sets of false colors . The " Alert " ( the ship made famous by the American author Richard Henry Dana , Jr . in his memoir Two Years Before the Mast ) , out of New London , shows no colors , and Semmes orders her to heave to , after demonstrating yet again the Alabama ' s 32 - pounder . The crew are paroled at Flores , and then Semmes proceeds to light the Atlantic sky with a three - ship torching . Later the same day , September 9 , while the blaze is still going , the crew spot yet another whaler . This time both hoist the U . S . colors . However , spotting the burning show afar behind the CSS " Alabama " , the Captain of the " Weathergauge " out of Provincetown , Massachusetts figures that all is not right , and suddenly comes about , only to witness the CSS " Alabama " change colors and fire a blank cartridge . The crew of the CSS " Alabama " realize that wasting actual ammunition is not always necessary , given the ease of the Yankee surrenders . This time the prisoners are put off at Corvo Island , and the CSS " Alabama " is off yet again , another sail having been spotted . After a thrilling all night chase , the new sail is found merely to be a Danish ship , and having no bones to pick with any of the world but Yankee vessels , Semmes lays off . The CSS " Alabama " returns to Corvo Island for the usual prisoner debarking , and the " Weathergauge " is put to the torch on September 10 . A three - day break is now had by Semmes , ample time to ensure that enough torching materials have been provisioned . Breaking the short lull , September 13 brings another sail sighted , and it ' s up with the U . S . colors again as the " Altamaha " out of New Bedford , another whaler , heaves to without chase . The now traditional blaze is made , and CSS " Alabama " overtakes yet another foreign ship in the evening , a Spaniard vessel . The following night , September 14 , shows the wise move in having targeted the Azores as chase is given yet again . This time two blank shots are required for the usual scare , and the final prize of this expedition is pulled over , the " Benjamin Tucker " , also out of New Bedford . In keeping with his tradition of not alerting the entire whaling industry , the match is put to the " Tucker " by mid - morning on the 15th . His crew needing rest from such enlightening activities , Captain Semmes sets course to the west , on a two - week cruise toward the New England coast , with hopes to increase the burning pace , thus ending the CSS Alabama ' s expeditionary raid of the eastern Atlantic and Azores area . During this raid , the capture of any ships was both unnecessary and unfeasible . Most of the targets were whalers . With a total of ten prizes burned in the eastern Atlantic , the CSS " Alabama " had destroyed $ 230 , 000 worth of property , almost equating to the original cost to purchase the " Alabama " . From this raiding area in the eastern Atlantic Ocean , the CSS " Alabama " departed and sailed west toward the northeastern seaboard of Newfoundland and New England along the North American coastline . Along the way , she experienced a long succession of gales and bad weather for almost two weeks while en route to the coast off North America .