The Tallahassee, under the command Captain John Taylor Wood, a grandson of Zachary Taylor, 12th President of the United States, evaded the blockade of her home port of Wilmington, North Carolina on August 6, 1864. Her first day out, four Union cruisers chased the Tallahassee without incident.

She made a spectacular 19-day raid off the Atlantic coast as far north as Halifax, Nova Scotia. The Tallahassee destroyed 26 vessels and captured 7 others that were bonded or released. Wood sailed the Tallahassee into Halifax Harbour on August 18 to take on bunker coal and water. Neutrality laws limited her stay in Halifax to 24 hours. Two Federal war ships had chased her north and were believed to be waiting for the Tallahassee at the harbour entrance.

Captain Wood hired a legendary Halifax pilot John "Jock" Flemming, who is believed to have guided the warship through the narrow and shallow Eastern Passage between Dartmouth and McNabs Island, a route only suited for small fishing vessels. Tallahassee succeeded in negotiating the passage out of the harbour, although no Northern warships were in fact waiting. The first Northern warship, the gunboat USS Pontoosuc, arrived at the harbour entrance several hours after the Confederate cruiser departed.

Being unable to procure enough coal to continue, Wood was forced to return to Wilmington where he arrived safely on August 26.