 Connecticut left the New York Naval Yard on 5 December 1907 and arrived the next day in Hampton Roads , where the Great White Fleet would assemble with her as their flagship . After an eight @-@ day period known as " Navy Farewell Week " during which festivities were held for the departing sailors , and all 16 battleships took on full loads of coal , stores , and ammunition , the ships were ready to depart . The battleship captains paid their respects to President Theodore Roosevelt on the presidential yacht Mayflower , and all the ships weighed anchor and departed at 1000 . They passed in review before the President , and then began traveling south . After steaming past Cape Hatteras , the fleet headed for the Caribbean . They approached Puerto Rico on the 20th , caught sight of Venezuela on the 22nd , and later dropped anchor in Port of Spain , the capital of Trinidad , making the first port visit of the Great White Fleet . With the torpedo boat flotilla that had left Hampton Roads two weeks previously , and five colliers to fill the coal bunkers of the fleet , Port of Spain had a total of 32 US Navy ships in the harbor , making it " [ resemble ] a U.S. Navy base " . 
