In 1958 the BBC World Service shut down Caribbean Voices, a programme that had provided a nurturing platform for fledgling West Indian authors, a handful of whom went on to become luminaries of the region. Explaining the reasons for its closure, a BBC official announced that inevitably “the children had outgrown the patronage of the parent”. Four years later Jamaica and Trinidad gained independence from the UK, with a rush of jubilation and anxiety. It is particularly this theme – the fallout from change – that travel writer Joshua Jelly-Schapiro explores cogently in Island People.

It takes courage to venture into a territory already inhabited by Anthony Trollope, Patrick Leigh Fermor and VS Naipaul. A writer is bound to ask himself whether he has anything to say – to match their wit and arrogance. The Trinidadian-born Naipaul was most disparaging about the void created by the departing British, which he claimed left his compatriots (of African and Indian descent) squabbling like “monkeys pleading for evolution”. Notwithstanding the dyspeptic tone of Naipaul’s 1962 non-fiction work The Middle Passage, the Nobel prize-winning writer set a high bar for reflections on life in the Caribbean from then onwards. Jelly-Schapiro proves equal to the task, and eschews the temptation to lampoon.

He writes more obviously in the shadow of Leigh Fermor, who published The Traveller’s Tree: A Journey Through the Caribbean Islands in 1950. The gap between the gentleman explorer/traveller and his native subjects appears to have narrowed. Jelly-Schapiro forgoes the white linen suit for T-shirt and shorts. Informality and greater familiarity (he is a frequent visitor to the region) invests his book with a deeper understanding of the corrupted human transactions and brutal history just beneath the surface of the sanitised, all-inclusive-holiday branded, sun‑kissed islands.

Facebook Twitter Pinterest Woman adjust their headdresses before the Carnival in Port of Spain, Trinidad. Photograph: Lynne Sladky/AP

It is more in the spirit of a critical friend than participating observer that Jelly-Schapiro records the degraded resentments of the louche Rasta pimp offering “nice girls. Nice and clean”, and the monetising model in “royal-blue dress and zebra-print heels” propping up the bar who, having invited him not to buy her a drink but to pay for her rent, settles for a glass of Chablis. At times, though, his familiarity seems to inure him to events that a novice would find shocking: when held up at gunpoint in Trinidad he dispatches the incident in a few lines as if it were no more troubling than a persistently buzzing mosquito.

When held up at gunpoint in Trinidad he dispatches the incident as if it were no more troubling than a mosquito

The contrasts in tone between Island People and The Traveller’s Tree are telling. Leigh Fermor talks of “Negroes” on dozens of occasions, and Jelly-Schapiro’s tongue would cleave to his palate before uttering such a word. But while Fermor respectfully admires a “room full of sable Venuses”, Jelly-Schapiro favours the company of the dancehall queen, Lady Saw, and celebrates the riotously shameless “slackness” of the lyricist behind “let me fuck you with my heels on”.

A century ago in The West Indies and the Spanish Main, Trollope wrote, “If we could, we would fain forget Jamaica altogether.” But Jelly-Schapiro is drawn to the exuberance of a country (as Island Records founder Chris Blackwell reminds him) “with its own frigging soundtrack. Imagine that!” Island People offsets the dominance of Jamaican reggae with reflections on the culture of other countries with their own soundtracks, notably Cuba and Trinidad, whose siren songs (salsa and calypso/soca) prove equally alluring.

The book manages a difficult balancing act. There are over a thousand islands in the Caribbean, 28 countries and numerous languages including French, English, Spanish, Dutch, Hindi, Mandarin and Creole/Patois. In attempting to straddle this wealth of cultures and histories, Jelly-Schapiro can offer no more than sketches. When our guide excels – as he does in Grenada, capturing the heady excitement of 1970s revolution (“Utopian dreams on a lush small Antille with weed and waterfalls from Eden”), quickly followed by tragedy (culminating in the execution of the charismatic leader Maurice Bishop) – you wish he had made fewer stops and dallied a while longer.

The final chapter homes in on Trinidad, an island that bears disturbing similarities to Jamaica with its corrupt politicians, gangsters and pervading sense of wildness: “this still-young nation retains the ambience of the OK Corral”. Jelly-Schapiro begins with unsparing reportage of the escalating violence on the island – the sign above the emergency wing of the Mt Hope hospital, outside the capital, Port of Spain, announces “Gun Shot and Chop Wounds this way”. He then moves on to write a homage of sorts to two of Trinidad’s most famous sons, the socialist writer CLR James and VS Naipaul. The chapter’s title, “Return to El Dorado”, is a nod to Naipaul’s history book The Loss of El Dorado.

Facebook Twitter Pinterest A fresh fruit stand in Scarborough on Tobago. Photograph: Alamy

The ghosts of other writers haunt the pages of Jelly-Schapiro’s book, in particular the idiosyncratic and ungenerous Naipaul, whose fresh and stinging insights were born both of titanic certainty and the confidence of belonging to the story. You can take issue with Naipaul’s odium in The Middle Passage but you can’t deny the guilty pleasure of reading its pompous, brutal, piquant and despairingly dark humour. Indeed the devilish Naipaul has the best lines in Island People, and in frequently reminding us of his predecessor’s bons and not so bons mots, the latest chronicler of the Caribbean cedes too much ground and advantage to them.

Close to the book’s end, Jelly-Schapiro quotes a wise and elderly mentor who advises: “Do not speak untruth, no matter how pleasing. Do not speak truth that is displeasing. Only speak the truth that is pleasing.” Ultimately, Island People, written by a careful and compassionate author, is a worthy travel and history book, a fresh study of these economically hamstrung islands and their failing attempts at rebranding. But in elegantly recycling the tales told by Naipaul and others, Jelly-Schapiro puts himself overly in their authors’ shadow. He might have been better advised to be more arrogant, and a little less considerate.

• Colin Grant’s books include Negro With a Hat and A Smell of Burning: The Story of Epilepsy. Island People: The Caribbean and the World is published by Canongate. To order a copy for £17 (RRP £22) go to bookshop.theguardian.com or call 0330 333 6846. Free UK p&p over £10, online orders only. Phone orders min p&p of £1.99.