Will Boris Johnson have to declare his latest Caribbean holiday?

Boris Johnson looks set to launch an improbable second tilt at the Conservative Party leadership, less than two months after being replaced as prime minister by Liz Truss.

With her absurdly short-lived premiership already up in flames, many Tories are keen to see Mr Johnson reinstalled in Downing Street, none more so than lovestruck loyalists Nadine Dorries and Jacob Rees-Mogg.

However, it should not be forgotten that Mr Johnson’s first term was riddled with scandal, from Wallpapergate to the PPE contracts controversy, the Owen Paterson affair, Partygate and Chris Pincher, or that, less than three months ago, almost 60 MPs resigned in protest at his desperate efforts to cling to power.

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Sir Roger Gale, a senior Tory backbencher, has been at pains to remind voters this week that Mr Johnson remains under investigation by the House of Commons’ privileges committee for potentially misleading Parliament over Partygate.

If found guilty, Mr Johnson could face recall proceedings or risk losing his Uxbridge and South Ruislip seat in a by-election in the event that he receives a suspension of 10 days or more.

Sir Roger, among others, has also said that, if Mr Johnson were to be brought back as PM, he would give up the whip and stand as an independent.

But who would write off that eventuality coming to pass? Certainly not Boris Johnson.

Boosted by the news that popular defence secretary Ben Wallace is not planning to join the race and is instead “leaning towards” supporting him, as he has in the past, Mr Johnson is reportedly jetting back from a family holiday in the Caribbean to resume scheming in Westminster.

Mr Johnson is understood to have been in the Dominican Republic for the last two weeks, basking in the sun with his wife Carrie Johnson and their two young children, Wilfred and Romy, stoically fighting back the urge to comment on Ms Truss’s disastrous run.

However, holidays have undone Mr Johnson several times before so he might be well advised to tread carefully in his handling of this one.

It was only in August (admittedly a lifetime ago now) that he endured a storm of scorn when he was pictured at a supermarket in Nea Makri, Greece, just weeks after spending time at a luxury mountain spa in Slovenia, as his rudderless government failed to address the cost of living crisis and the prolonged Tory leadership contest to choose his successor dragged hopelessly on.

More seriously, Mr Johnson came under fire almost immediately after winning the December 2019 general election when he decided to take up a generous offer from Tory donor and Carphone Warehouse co-founder David Ross to stay at a luxury villa in Mustique, also in the Caribbean.

Mr Johnson’s 10-day trip was subsequently made the subject of a Parliamentary Standards Committee probe in May 2021 over who precisely paid for it and the possibility that the PM might have broken the ministerial code.

The committee ultimately found that his register entries regarding the jaunt had been “accurate and complete” but said the funding arrangements had been “ad hoc and informal” and expressed frustration that the then-PM had not been more proactive in helping to dispel the confusion.

“Given that Mr Johnson was twice reprimanded by our predecessor committee in the last Parliament in the space of four months for an over-casual attitude towards obeying the rules of the House, we would have expected him to have gone the extra mile to ensure there was no uncertainty about the arrangements,” the committee said in July 2021.

Whether this latest Caribbean jolly has the potential to land him in hot water again depends on who paid for it and how he goes on to register it.

If the Johnsons shelled out for their holiday entirely by themselves, all well and good, because, under the the MPs’ Code of Conduct detailing the rules for registering overseas visits, trips abroad do not need to be declared so long as they are undertaken “wholly unconnected with membership of the house or with the member’s parliamentary or political activities (e.g. family holidays).”

But if the stay was in any way a gift from a friend or Conservative Party donor, which he has never been shy about accepting in the past, the same guidelines state: “Members must register… any visits to destinations outside the UK where the cost is over £300 if that cost is not wholly borne by the member or by UK public funds.”

During his time as PM in summer 2021, Mr Johnson attracted controversy after he accepted a vacation at Tory peer Zac Goldsmith’s 13-room mansion on the Costa del Sol in Marbella and then subsequently declared it only on the ministerial register of interest, which does not require monetary details, rather than the MPs’ register, which does, on the grounds that the trip had been a freebie from Mr Goldsmith.

“In line with transparency requirements, he has declared the arrangement in his ministerial capacity, given the hospitality was provided by another minister,” a Downing Street spokesman said at the time.

“Ministerial code declarations fall outside the remit of the Commons register.”

Whether Mr Johnson has learned from his past mistakes will be a key question if he is to return to Downing Street, an occurrence he effectively predicted in his farewell address outside of No 10 on the morning of Tuesday 6 September when he drew a parallel with a famous hero of Ancient Rome who saved the empire from defeat and ignominy before retiring to obscurity.

“Like Cincinnatus, I am returning to my plough and I will be offering this government nothing but the most fervent support,” he declared, tongue firmly in cheek.

Lucius Quinctius Cincinnatus (519–430BC) was, however, called back from the fields by the Roman senate to win the day for a second time, as Mr Johnson no doubt knew full well when he invoked his memory.

But even a character as knowing as Mr Johnson cannot have believed in his wildest dreams that a summons from his fellow Tories might have come quite so soon as it has.

He will be thinking of emulating another personal hero, Sir Winston Churchill, as he contemplates a fresh grab for power but perhaps Italian comeback king Silvio Berlusconi is closer to the mark.