The SA Airlink plane left Johannesburg on a six-hour journey to the British-ruled territory, which hopes to draw more tourists to the deposed French emperor's final abode, Longwood House, as well as rugged landscapes, marine life and the novelty of visiting a spot far off the beaten track.
The new weekly air service brings an end to what had been the only regular way to reach the island. The royal mail ship St Helena, which takes nearly a week to arrive from Cape Town, will stop its voyages in February.
Phillips' social media posts have highlighted some of the volcanic island's quirkier fixtures, including a giant tortoise named Jonathan that is said to be 185 years old and Jacob's Ladder, a 699-step outdoor staircase leading from a valley to a hilltop in Jamestown, the capital.
The story of how air travel to St Helena came about is also, well, unusual.
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The official opening of the St Helena airport, built on the island's Prosperous Bay Plain for about USD 380 million of British taxpayers' money, was supposed to happen in May 2016.
Larger aircraft can land at the airport but with weight restrictions, meaning fewer passengers. SA Airlink's smaller Embraer E190 is carrying nearly 80 passengers, including "Saints", the nickname for people from St Helena, tour operators from South Africa and journalists. The flight from Johannesburg includes a stop in Windhoek, the Namibian capital.
Tourism would bring a much-needed boost to St Helena, which lies about 1,930 kilometers (1,200 miles) west of the border between Angola and Namibia, the nearest mainland.
The island's biggest industry was once growing flax for the manufacture of rope, but St Helena's population of more than 4,000 people is now heavily dependent on British government support.
Published in December, the British parliamentary report that criticised the handling of the airport said significant tourism growth is needed for the island to become economically self-sufficient and that a local entity promoting development "has some way to go to improve the marketing for the island's location and attractions".
First exiled to the Mediterranean island of Elba, he escaped, met defeat at the battle of Waterloo and was sent to far more remote St Helena in 1815. He died there in 1821 and his body was later exhumed and entombed at Les Invalides in Paris.
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