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A new name for an old timer, Oliph Blossom is given on the 50c stamp. She appeared on a Barbados Id. issued in 1905 as the Olive Blossom. The Dictionary of National Biography states that "Charles Leigh, merchant and voyager brother of Sir Oliph Leigh, sailed from Woolwich for the West Indies on March 21, 1604 in the Olive Plant, described as a barque of 50 tons, with 46 men and boys all told."
The West Indies Year Book. however has other names for the vessel: "An English ship, variously named the Olive, Olive Branch, and Olive Blossom is stated to have nominally taken possession of the island (Barbados) in 1608 in the name of King James I.
That the ship Olive Branch sailed from London on April 12, 1605, having on board 67 English passengers intended as a reinforcement for the Colony planted by Charles Leigh in the preceding year on the River Wiapoco, in Guiana, is true. There is however no evidence that this vessel touched at any other island than that of St. Lucia. To say the least, historians seem to be a little uncertain about the ship's name. All pictures of the ship are obviously artists' impressions. SG354 Sea Breezes Sept 1973

The British ship Olive Blossom is given that she is depict on the stamp issued in 1905, supposedly to mark the 300th Anniversary of the discovery of Barbados by the English.
The stamp is designed by Lady Gilbert-Carter, who produced her stamp picture from a study of vessels of the period, no picture of the OLIVE BLOSSOM being known to exist
The OLIVE BLOSSOM or OLIPH BLOSSOME or OLIPH BLOSSOM a small ship of 50 ton was fitted out for a voyage to Guyana by Sir Olive Leigh Knight.
She sailed from Woolwich on 14 April 1605 (other source gives 12 April) under command of Captain Catalina with colonists and stores for “Master Charles Leigh” his brother, who had founded a colony on the River Wiapoco (now Oyapock River), Guyana.
The sailing master was Richard Chambers and as consequence of his unskilfulness the OLIVE BLOSSOM made a call at Barbados.
After landing the crew found the island uninhabited, they took possession of the island by erecting a cross upon the spot where Jamestown (no Holetown) was afterwards built.
They cut in the bark of a tree which stood nearby, “James K(ing) of E(ngland) and this island.
They then followed the shore until she arrived at a river which afterwards received the name Indian River.
When she left Barbados she sailed to St Lucia instead to the settlement in Guyana, where on 23 August 1606 sixty-seven colonists left the vessel.
Then the OLIVE BLOSSOM proceeded to Guyana, on her return trip she called again at Barbados.
When she returned in the U.K is unknown and also afterwards is she not more mentioned in officially papers.
Her fate unknown

Other sources give that the OLIVE BLOSSOM never made a call a Barbados.

A vessel under the name OLIVE BLOSSOM given in other sources captained by John Powell arriving in Barbados in 1625 does not exist, Wikipedia gives only a “ship” under command of John Powell arrived in Barbados, and then it gives she was the first English ship which had arrived in Barbados.

Barbados 1906 1d sg, scott109. 1996 55c sg1067, scott910.
St Lucia 1973 50c sg354, scott339.

Source: Ships on stamps by E.W. Argyle. The History of Barbados by R.H. Schomburg.