Dwindling margins saw Cutty Sark's owners take the decision to sell her off to a Portuguese firm.

After being bought by J. Ferreira & Co., Cutty Sark was renamed the Ferreira. Reminiscent of her days in the late 1870s and early 1880s, Ferreira tramped various cargoes mainly between Portugal and her empire, and was a regular visitor to Rio, New Orleans, Mozambique, Angola and the UK. In the 20th century she traded regularly between Oporto, Rio, New Orleans and Lisbon, and her crew claimed she was still capable of doing 16 knots.

In October 1915 Portugal declared war on Germany, which meant that the ship was in constant danger of being sunk by enemy naval activity. She survived unscathed until May 1916, when the rolling of the ship in bad weather led to the dismasting of the main mast and everything above the fore lowermast and the mizzen top-masts. Badly damaged, Ferreira was towed into port, arriving at Table Bay, South Africa.

Due to the war, the cost and rarity of adequate masts and yards meant that she was converted into a barquentine (fore and aft rig) over an 18-month period at Cape Town.

By January 1922 Ferreira ran into a Channel gale, and the captain put into Falmouth harbour to repair the damage. Wilfred Dowman, a retired windjammer skipper and owner of the training ship Lady of Avenel, saw the ship and set out to buy her.

However, she returned to Lisbon without further mishap and was sold to a new Portuguese owner who changed her name to Maria do Amparo.

Dowman was determined to rescue her. He offered a price of £3750 – more than what she was worth even in 1895 – and finally Ferreira was brought back to Falmouth.

In 1923 her old name and nationality was restored – Cutty Sark had returned to British ownership.