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As the first English colony to have a post office, Jamaica is of great import to the history of stamps.

It was as early as 1663, when Jamaica's Governor, one Thomas Lynch, made arrangements for a post office upon request of the Postmaster General in London, with twos structures following eight years later – one in St. Jago de la Vega and another at Rio Cobre in St. Catherine. It was a short-lived venture. The service was not up to scratch and the islanders returned to the older method of asking sea captains to carry mail while the authorities worked out the wrinkles of the organised service. In fact, the iconic 18th century café the Jamaican Coffee House, in St. Michael's Alley, Cornhill, England, received its name for being a regular haunt for captains arriving in London bearing letters to merchants with investments in the Caribbean.

It wasn’t until 1720 that Jamaica's post office was re-established and throughout the century, due to the island's burgeoning sugar cane industry, a further 34 post offices were added from Bailles’ Town to Buff Bay. By 1924, there was a post office every 17 square miles; many of which remain active post offices even to this day.

In 1860, the island began to produce its own stamps with a distinctive pineapple watermark; a pictorial stamp of Llandovery Falls in St. Ann, followed in 1900, though with its unappealing all-red casement it was nicknamed the ‘bedspread with the Welsh name’; four stamps featuring historic locations were issued to commemorate the 300th anniversary of British rule in 1955; and in 1962, when Jamaica gained independence, all stamps were fittingly overprinted with the word ‘Independence.’

The region is also known for two political specimens. Firstly, the 1921 Abolition of Slavery stamp of which only one exists – because the stamp was never actually issued. And one to commemorate the island’s most famous son: Bob Marley issued in 1982, a year after the legendary reggae musician and Rastafari activist passed away aged only 36.