“If someone has to go to prison, I volunteer,” said new first mate, Neal, with a grin as we sat on Hummingbird in Cancun discussing our upcoming Cuba expedition. “Really?” I asked incredulously.

“It’s a life experience, isn’t it? I’ve never been to prison,” he replied. Neal is not short on life experience: from being headmaster of a school in Tanzania to summiting unclimbed mountains in east Greenland, he is quite the adventurer. A little brush with the Cuban authorities wasn’t going to cause him too much anxiety. I, on the other hand, was having last minute misgivings.

We’d been planning the Cuba trip for months: I’d joined every forum and Facebook group and dug up every contact I could find to research the current situation, but there was little information available. “Just don’t fall foul of any local rules or regulations,” was the scant advice we got.

I tried for the umpteenth time to get through to the Cuban authorities to triple check the arrival procedures, but to no avail. There appeared to be no requirement for pre-registration and everyone had their tourist cards already, so that was all we could do.

It’s an upwind slog from the lovely marina on Isla Mujeres, Cancun, to Cuba with the easterly trades blowing consistently. After filling the boat with food we watched the weather for some northing in the wind and set off. On port tack with the Gulf Stream on the leeward bow shunting us northwards, we made due east for 120 miles across the Yucatán Channel.

We abandoned our original plan of making landfall at Los Morros, the Customs point on the western tip of Cuba, as the open roadstead needs settled weather, which meant sailing on to the next port of entry at Cayo Largo, 200 miles further east.

It was a shame to have to bypass much of the south coast, but I wasn’t going to make landfall somewhere other than a port of entry, even for a rest in an anchorage. I’m sure Neal is a man of his word, but I didn’t fancy testing his gaol offer. Cayo Largo turned out to be a good place to check in. An easy approach through a large gap in the reef and well-marked channel led to a decent marina.

Never smile at a crocodile

The azure water and white sandy beaches were a welcome sight after the upwind passage and I had a struggle keeping the crew from jumping into the bay. The deputy marina manager Embellio met us on the pontoon. “Don’t go swimming”, he said with a smile. “There are crocodiles in the marina.” We weren’t sure if he was joking.

Soon the authorities arrived. The Guarda Frontera (Border control) checked our despacho from Mexico, issued us with an internal despacho for Cuba and stamped our tourist cards. You need permission to move from one port to another in Cuba, so over the next few weeks we’d become very familiar with their green uniforms.

The customs officer had a less conventional outfit: short skirt, fishnet tights and heels. She had a spaniel by her side, which jumped aboard. After various questions including how many mobile phones we carried and what type, our satellite phone was sealed in a bin bag with Cuban Customs tape around it. The spaniel took a good look around, decided we were smelly but innocent and departed. Finally the health officer took our temperatures while the agriculture officer inspected our provisions, sifting through our rice for weevils. We were given a clean bill of health and welcomed into the country. Phew!

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That night we ate at the marina bar, which served grilled fish, chicken and lobster while a local band serenaded us. The band was superb and it was very much the taste of things to come. As budding revolutionaries, we sang along and soon knew the lyrics off by heart.

Afterwards the waitress scraped the plates over the decking, straight into the open jaws of enormous tarpon fish below. They swallowed the chicken carcasses whole. We all stood transfixed when suddenly a scream went up: a crocodile had appeared on the scene. Embellio hadn’t been joking.

‘What’s the crocodile policy?’ Michelle, veteran of many Rubicon 3 expeditions, asked. I had to confess that although we have a procedure for everything from polar bear attack to man overboard, we didn’t have a crocodile policy. All I could offer was some advice from a friend who grew up in Zimbabwe: “You’ve got to stick your arm all the way into its throat. If you get your fist far enough down you’ll lock its jaws open and it won’t be able to swallow.”

In my professional opinion, things have probably gone a little too far by that stage. However I did discover that crocodiles are endangered and unlikely to be found in the places where you might swim, so I didn’t begrudge it the remains of my lobster.

Freedom to roam

Once checked in we had a little more freedom to roam. We were given permission to cruise the Jardines de la Reine, an extensive coral reef system further east. There are no permanent settlements, just coral, mangroves and perfect white beaches. The nearest town is 80 miles away so self-sufficiency is essential and we became heavily reliant on our watermaker. In four days’ cruising we saw only three yachts and a fleet of identical, grey fishing boats, which looked straight out of the USSR. We were all sheltering from a strong north easterly in Cayo Cuervo, a huge circular island with excellent shelter inside.

As soon as the wind dropped we set off for Cayo Algodon Grande. It was poorly charted so the dinghy went ahead and found a deep water channel into a mangrove-fringed lagoon. Once inside we had perfect solitude and set about exploring. The pilot guide mentioned a mile long dinghy channel to an abandoned holiday camp. Neal returned after an hour. “It’s more of a ditch than a channel,” he reported. It had clearly silted up since Nigel Calder was writing 20 years ago. There wasn’t much left of the resort, just a few lumps of concrete, but there was a beautiful windswept coral beach.

We made it ashore for sundowners and started ferrying everyone back to Hummingbird a little before sunset. It was a weird and wonderful spot, magical because there aren’t many places in the Caribbean that are getting wilder. The mosquitos were glad to see us according to Matt, Rod and Nick, who were in the last dinghy ride home.

From wilderness to civilisation

After five days cruising this desert island paradise we made for civilisation. The UNESCO world heritage site of Trinidad is just inshore of an approved yacht port, Casilda. The small marina couldn’t be raised on the VHF so we made straight for the commercial port. I employed my usual berthing tactic – seek forgiveness not permission – and tied alongside an official looking wharf.

It didn’t go down very well: “You’re in a military zone!” Barked an irate security guard, “Leave, now!” Juan, our Spanish speaker, tactfully apologised and with incredible charm asked how to proceed. We had to anchor in the bay and take the dinghy in to the shallow marina two miles away, where the Guarda would meet us.

Three hours later we were checked in and two taxis arrived to take us into town: an immaculate pink Chevy and a red Cadillac. Trinidad is a much-loved time warp with a well preserved old town, ochre-coloured buildings and cobbled streets.

We were hoping to pick up some supplies but our first taste of Cuban supermarkets lacked promise. Long shelves were stacked one row deep with a single brand of tinned tuna.

The next aisle was devoted entirely to bags of rice and beans. “Cornflakes?” I enquired, “No.” “Fruit?”. “No.” “Eggs?” “No”. I asked where to buy vegetables. “I just saw the guy with the tomatoes go past the window,” the shop assistant replied.

I hurried out after him, and so began a long day hunting barrow loads of vegetables in a warren of streets, not helped by the fact that Cuban streets all have two names: pre- and post-revolution.

Cienfuegos, our next stop, was a short sail further west, where we’d make a crew change. It is another colonial town with grand pastel-coloured buildings arranged around neat central squares. By sea it is accessed through a narrow entrance but the harbour opens up into a vast inland waterway, although much of it is off limits.

We were allowed alongside briefly at the marina to re-fuel and check in before anchoring off with the rest of the ‘transients’. The nightlife was fantastic – there were rooftop bars and an open dance school where salsa students (who ranged from 18 to 80) were dancing the night away.

Disaster struck the next day when the rubber flexi-coupling between our Perkins Perama M30 generator and the PTO shaft for the watermaker pump failed. I couldn’t find the spare on board. Cursing myself for being so stupid we ran through the options. “Life without the watermaker will be miserable,” pointed out Neal.

“Yeah,” I agreed, “there’s only one marina with a hosepipe between here and Havana.” In any other country you could probably ship a part from the UK but the embargoes would have made that very difficult. Our only hope was that there might be one here – but it was a long shot.

Engineering ingenuity

We explained the situation to a friendly engineer on one of the tourist boats. He took one look at the coupling and shook his head. “The last time I saw one of these was on an old Soviet water pump in a 1960s apartment block. It failed and we couldn’t get another one.” My heart sank.

“But I did fix it with some rubber strips, and it’s still working. I’ll try to get some of that special rubber for you.”

“We’re planning to leave tomorrow morning…” I said. “Oh, I don’t think I can get it in time, not by tomorrow,” he said apologetically.

Reluctantly we decided to move on – the new crew were keen to escape the city heat and explore the islands. Besides, there was no guarantee we’d fix the coupling if we stayed. So we limited fresh water use to drinking and set off on the second leg of our trip: westwards to Havana.

Knowing the scarcity of supplies in Cuba, Neal offered the marina manager some of our old alternator belts and asked if they’d like them for their boats. “For the boats?” she exclaimed. “No, no, no, I’ll take them home, my husband might finally be able to fix our washing machine!”

After checking in to Cayo Largo again we continued to Cayo Rosario, an uninhabited island with fine white sand and a sheltered anchorage through a gap in the reef. It was quite windy and although the echosounder gave some indication of the isolated coral heads below we couldn’t see them clearly due to the disturbed water.

We dropped the anchor in what looked like a clear patch, but when the chain abruptly pulled tight we knew we’d hooked one. Yorkshireman Ian jumped in with a snorkel: “You’ve got to unwind the chain by circling around it clockwise,” he said pointing to its position. To our relief it worked first time and he scouted out a clear patch of sand for take two.

While the crew explored ashore I thought about our predicament. We had a perfectly functioning watermaker and a perfectly functioning generator. Cubans wouldn’t wait for a supply ship; there probably wouldn’t be one.

They’d find a way around the problem with what they had to hand. I ransacked the repair box, eventually bolting some webbing to the flanges, realising that the webbing needed to be taut in the direction the shaft turns in order to minimise the shock-load as it started spinning. On the third attempt it worked! The webbing withstood an hour of running and looked like it would take more. With any luck we’d have enough webbing left to replace it every few days and make it to Havana without water rationing.

Out-of-the-way places

We continued westwards, exploring some of the coastline we’d bypassed on the way from Mexico. We had some fantastic downwind sailing in flat water in the lee of the islands underway to the Isla de la Juventud. Despite being Cuba’s biggest island it is also one of the least explored. The ‘marina’ is really just a shallow harbour that acts as a base for a dive centre.

It is 40 miles from the main town of Nuevo Gerona, but well worth the trip. We arrived on a Sunday when the town was in full party mode, with every variety of rum you could think of, a hog roast on every corner and families socialising in the streets. It was a very happy affair.

On leaving Juventud we’d hoped to visit the Cayos to the west before rounding Cabo de San Antonio and heading up to Havana. Unfortunately it was too windy and with no all-weather anchorages we pulled in to Maria La Gorda instead. The bottom was irregular and we were relieved to pick out one of the moorings in the moonlight. Ashore we discovered a small resort, a sandy beach (with pizzeria), dive school and great snorkelling.

For the final beat to Havana we had a choice: stay inshore for flat water but battle a one knot counter current, or head offshore to make use of the Gulf Stream but contend with the short seas of wind against tide conditions. There were a few longing glances at the Club Med cruise ship which floated past serenely, but there were also squeals of exhilaration as the boat rocketed on into the night.

At Hemingway Marina we were reintroduced to luxuries such as shore power, a walk ashore pontoon and showers with hot and cold running water (although you have to use a bucket to flush the loo). It is a vast, largely empty marina complex ten miles from the city.

Havana itself was a fitting place to end a remarkable month: it is a majestic, crumbling edifice to the rejection of capitalism. Cuba isn’t just another Caribbean island; it’s a completely different world where money can’t buy everything. In fact, it can’t buy very much but, as the Cubans are so quick to point out, everyone’s essential needs are cared for: despite the terrible condition of some of the housing, no-one is homeless, and although food supplies are basic, everyone is fed.

It left us wondering if we’d give up our material world for a simpler life, but in a way that’s why we go sailing. We have many things in common: self-sufficiency and an ability to live simply, taking care of what you’ve got and working with the environment rather than against it. And an appreciation of good rum. Perhaps the spirit of the revolution runs in sailors more strongly than most.