There’s a cowboy waiting outside my room. Kitted out in a checked shirt, jeans and a Stetson, he introduces himself as Miguel, and soon we’re clip-clopping away in a horse-drawn cart.
Trinidad, in southern Cuba, is more than just a photogenic, Unesco-listed town (though it is that, too). It’s surrounded by natural attractions; within just a few kilometres are some of the country’s best beaches, with sweeping hills and valleys ripe for exploring.
We’re dropped off near the edge of town, and Miguel gets our group of wannabe cowboys saddled up. “Only one hand,” he says, as I reach for the reins; the other holds on to a metal handle on the saddle — something I’m thankful for once I realise I have no control over my horse’s speed.
We ride along a dusty trail, through scrubby meadows and palm-dotted woodland, stopping en route at a grass-roofed open-air bar serving refreshing cups of sugar-cane juice. We ride a little further before dismounting again, and making the short walk to El Pilón. It’s dry season, so this normally impressive waterfall isn’t much more than a trickle, but it flows into a pair of beautiful natural rock pools, framed by caves and forest. I clamber into the cool, dark water, with cigar smoke and the sound of acoustic guitar drifting over from the makeshift bar nearby.
Arriving back in Trinidad in the late afternoon, the sun is starting to slip down behind the colourful Spanish colonial houses, and I walk slowly back to my homestay, slightly bruised from a day in the saddle.
It’s two decades since Cuba’s casas particulares (“private homes”) scheme was introduced, allowing locals to rent out their spare rooms to tourists. They offer a sharp contrast to the state-run hotels, which, while often grand, tend to come with rather indifferent service (“They know they will always have a job, so they have no reason to try,” one Cuban tells me). Until last year, when rules were relaxed, it was illegal to own a private business, but as running a casa particular is considered self-employment, the scheme has been a great way for Cubans to boost their incomes, which, according to official figures, average about £20 a month.
Casas, meanwhile, are a cross between a B&B and a family home: you get your own key but you might also hang out with your hosts. On practically every street in Trinidad or Old Havana you’ll spot at least one of the scheme’s blue signs, and with so much competition, owners often come up with a USP. At “Casa El Ceramista” (The Potter’s House), where I’m staying, host Alexey will show you how to throw a pot on his wheel — the walls are decorated with his clay creations.
The next day I take a tour of the town’s historic centre with Roxy, whose parents run another casa. Having grown up in Trinidad, she’s full of local insight, like where to find the best views (the top of the tower at Museo Lucha Contra Bandidos) and the most unusual night out (Disco Ayala, a club in a spectacular natural cave).
Tourism is booming in Cuba, thanks in part to the US easing its rules for visiting — a move that may be reversed by President Trump. For now, though, new businesses are springing up to cater to the growing number of travellers, and among them is Bar Café El Mago. With its white-washed walls and quirky reclaimed furniture, it wouldn’t look out of place in Hackney or Brooklyn, though like the casas particulares, it’s also someone’s home; the delicious coffee is made in the family kitchen.
Soon it’s time for me to move on to Havana, and a five-hour cab ride in a gorgeous, if somewhat rickety, Fifties Buick leads me to my next casa. Marisela’s apartment, part of a grand old townhouse in the capital’s Vedado neighbourhood, is decorated in every colour of the rainbow, and Marisela chooses her clothes to match.
I can’t leave Cuba without a stroll around Habana Vieja (Old Havana), whose pristine streets are the city’s most photographed, so the next day I head over in another old taxi. Winding between a series of pretty squares, I take in the imposing baroque cathedral and moated fort before finding myself outside Hotel Ambos Mundos.
Most Havana establishments trumpet even the most tenuous connection to Ernest Hemingway, who lived here in the 1930s, but Ambos Mundos is bona fide — the writer rented a room in the hotel for seven years. So I decide to stop for a drink in the Art Deco lobby bar. Unsure of what “Papa” would have ordered, I opt for a coffee spiked with rum. It’s a potent, not entirely pleasant, concoction, but as I sit back in my chair, the sound of jazz piano drifting over me, it feels like little has changed since Hemingway drank here — even if he preferred a mojito.
Nicola Trup travelled with Homestay.com, which offers doubles at Alexey’s in Trinidad (bit.ly/ThePotter) from £24, B&B, and doubles at Marisela’s in Havana (bit.ly/MariselaColores) from £31, B&B. Virgin Atlantic (virgin-atlantic.com) flies from Gatwick to Havana.