I met America at the bar; she was black, beautiful, and wrote for Empower magazine. ‘One last trip before <they> get here,’ she told me. Diplomatic ties had only just been reopened between Cuba and the US, but America hadn’t quite reversed the flow of passage yet. Our homestay host Roberto* told us every day hundreds of Cubans were still clambering into fishing vessels and sailing out of the Havana harbour to a ‘freer’ life in Miami.

Direct flights from America were still exclusively via charter at that point. It would be six months before mega cruise ships deposited scores of flag-wearing holidaymakers into Old Havana; or <Fast & Furious> re-commandeered a fleet of classic Yank tanks; and Chanel clogged up the Paseo de Marti with a string of fashionistas in socialist military-inspired berets and straw fedoras.

There we were at El Floridita, the spirit-filled home of American writer and drunkard, Ernest Hemingway, where they only know how to make one drink. Order anything other than a daiquiri here — even Cuban stalwarts like mojitos — and it’ll be treated as an off-menu ‘give it a go’ suggestion.

The great American drunk had led America here on a sacred pilgrimage of Americanised Cuba, and she had already consumed too much rum. Cuba didn’t like her, it taxed her 10% on every dollar she exchanged, but it didn’t stop her slurring on about the impending wave of US tourists who would ‘ruin Cuba’. I was fascinated. I thought America had already done its fair share; there are bookstores full of locally-produced tomes railing against Americanised history, especially the occupation of Guantanamo Bay by its ‘unwanted neighbour’.

America’s influence on Cuba is mixed in like a Cuba Libre; the cola adds enough sweetness to the Cuban rum that you can’t decide if it’d be better off drinking it straight.

I asked Roberto about the new American ties. Would it be better or worse for people like him? ‘Who knows?’ He said. He couldn’t see any changes to the government’s noose coming within the next five to 10 years, he explained, raising his hands to his neck. After that…? ‘Who knows?’

Homestay hospitality is one of the few state-sanctioned small businesses available to cash-controlled Cubans. That and driving a cab; most everything else is state-owned or run. Every day you’d talk to someone who’d previously worked as a doctor, or a chef who’d studied in France, or a mechanical engineer designing bridges, all taking the same monthly wage of 20-30 CUC (one-to-one with the US dollar) as everyone else across the nation. Now, they’re taxi drivers or have put everything into a homestay.

Even if you have the opportunity to start a homestay, it doesn’t guarantee success. The regulations are tight and spaces limited. The state puts caps on the number of homestay licenses it grants in any one region, and you must have two spare rooms to be considered. In a country where houses and apartments are largely inherited not bought (the property market only reopened in 2012), it’s a pre-Revolution lottery for homestay eligibility. One quaint place we booked in Santa Clara was years in the making. The host had sold his square single-room family home to help fund his homestay dream. His father had agreed to let his son build on top of his existing house, but the money from the house sale only covered two thirds of the main structure; our host had to borrow the remainder for bathrooms, kitchen and the rest. Over a year later, he opened his homestay, heavily in debt, but holding a key to one of few truly optimistic futures in Cuba.

Once you’ve got a license, keeping occupancy rates up is as crucial as for any CBD hotel. The state taxes a flat rate for the license of 180CUC/month, cutting deep into off-season margins. There’s also a black market for homestays. Daring residents will occasionally hang out their official-looking shingles hoping to sway an ill-planned tourist into staying the night.

Privately-owned restaurants, paladares, have been a feature of Cuba long before they became legal in the ’90s. Small, mostly in-home restaurants, are a good way of sampling local cuisine. However, food isn’t Cuba’s strongest point. The limited amount of ingredients available (even though lobster comes relatively cheaply) and low incentive to be truly great, means you’ll have more average meals than good ones.

It really shows what low accessibility to the internet does to the marketability of truly good, off-the-beaten track joints. Our taxi driver, Chocolate, stopped for homemade ham roll at an indistinct point on the side of the highway, and it was one of the best things we ate. If only you could drop a pin and review it on Yelp.

It’s hard to see much American money filtering down to the average Cuban when tourists are still relying on Lonely Planet hard copies to navigate around. Most won’t get much further than El Floridita.

*Names changed.