Santiago de Cuba: A 'steaming, breathing, rhythmic city' of revolution, rum and perseverance

I caught my first glimpse of the Sierra Maestra mountain range from a plane window during a flight into Santiago de Cuba last January for a family vacation. I was like a child seeing mountains for the first time; I pressed my face against the glass. These were more than just mountains: I could see that from the sky. I watched them rise abruptly from the sea – no small talk, no gentle transition, no messing around here. And I was so entranced by these undulating mounds of mossy green and sunburnt brown with their plumes of smoke, their secret caves, their stories of battles and hardships, of national treasures and bloody murders, that I took out my notebook and started outlining a novel. (Could the so-called cradle of a revolution inspire anything less?)

I returned to Santiago, Cuba's second largest city next to Havana, this past September. I came on my own to hunt the story I was trying to write because I'd moved well past the outline, but the novel still felt like it had no flesh. Where better to find what I was looking for than here, in this coastal city edged by these mythical mountains and as far away from the standard all-inclusive Cuban experience as possible? Santiago de Cuba is currently celebrating the 500th anniversary of its founding, and is home to a fabled carnival that brings flocks of intrepid tourists every July. The city has a history that includes burning to the ground and rising from the ashes, being plundered by both the French and the British, and a besiegement by the Americans during the Spanish-American War. The ill-fated 1953 attack on the Moncada Barracks happened here, and although things didn't go exactly according to Fidel Castro et al's plan that time, a revolution was still born and grew up on these streets. Later, Castro proclaimed the revolution's victory from a balcony on city hall.

I started my week staying in the gloriously faded Casa Granda, which is the opulent former guesthouse of a Spaniard named Don Manuel de Granda but opened as a hotel in 1914. The hotel sits proudly in the heart of the city's old town, facing the Parque Cespedes and the Metropolitan Cathedral – which at the time I was there was being made ready for the arrival of Pope Francis; he was stopping over in Cuba on his way to the United States the following week, a move that highlighted the immediacy of the thaw between the two adversarial countries: Even the Pope was trying to broker peace.

I checked into my room knowing my story lurked on the streets of this steaming, breathing, rhythmic city – but at first, I rarely went outside. I wasn't nervous about being a woman travelling alone in a city filled with dark mystery at night and raw heat during the day: It was just that I was away from my children for a week. Writers who are also parents know how closely uninterrupted writing time must be guarded. I holed up in my high-ceilinged room-with-a-view and tried to channel Hemingway (there were a few bottles of rum in the hotel room fridge, at least). I stared out the window at the angels that looked like they were about to take flight from the cathedral's roof and tried to picture the Pope here. I admired the view while I ate dinner at the hotel's rooftop restaurant. And finally, one morning, I wandered away from the hotel and ended up at the Museo del Ron, where I learned that Bacardi was Cuban before it was anything else, and that the rum was produced in Cuba for 100 years before the factories were abandoned in favour of less politically challenging places to do business. No matter: The Cubans took over the factories and learned to make rum without anyone's help, as they've learned to do most other things for some time.

I drank a shot of rum at 10 o'clock in the morning, and decided I wasn't going to do any more writing that day. Instead, I went to the Cementerio Santa Ifigenia. Here lie the so-called martyrs of the 1953 Moncada Barracks attack, but also Compay Segundo, the musician made famous by the Buena Vista Social Club. Here, I watched the hourly change of the guard at the tomb of Jose Marti, poet and revolutionary philosopher. And here, I realized that my story's final scene needed to happen in a cemetery. It was probably the rum talking, but I thanked Hemingway no less. Because when you have an end, you also have a beginning.

On my last night in Santiago, I watched a local band with so much talent they could have played anywhere in the world light up the night at the Casa de la Tradiciones. The next morning, I left the city behind for a few days at a beachside resort. I felt freedom from everything, but especially my obsessive hunt for a muse, as I rode on the back of a motorcycle alongside the mountains that had haunted my dreams for months. I didn't know where to look first: at my beloved mountain ranges or at the rough majesty of the coast, with its lonely beaches, distant fishing boats and blue-green water dashing itself against jagged, unwelcoming cliffs. My Cuban guide performed a death-defying pass of a Soviet-era lorry, its bed filled with early morning travellers on their way to work who gazed at us impassively as we hurtled by, and I focused for a moment on not dying horribly before relaxing my grip. And suddenly, I felt like I could really see this place.

Everywhere, there were pro-revolution slogans, painted on rocks and fence posts and walls, painted even on the mountains themselves: Patria o muerte; Viva Fidel; Patria es Humanidad, Viva Raul. And everywhere was the radically legendary face of Che Guevara, which means so much more here than it does at home. It's supposed to feel to these people like it's still happening, I thought. Like there's still something to rail against, like this island still stands – as a whole that is greater than the sum of its parts – for the uncompromising ideals of the ruling party. But this is what it really feels like: It feels like an island run by the Lost Boys from Peter Pan. It feels like a place forgotten by time. And it felt unfair here, on a pitted and potholed coastal road that progress hadn't touched yet. The villages I passed only had electricity during certain hours of the day, if at all. The people who lived in them had just enough – but just enough never feels like enough. (Westerners know this; it's why we're always striving for more.)

Like many Canadians, I fear, with a certain smugness, what the thaw in Cuban-American relations will mean for an island we have long considered a little bit ours. But just because we vacation here – and mostly on the temperate white sand beaches that are like the refined cousin of the relentlessly hot and rebelliously rugged south side of the island – does not mean this place belongs to us at all. In fact, Cuba technically belongs to no one: But it might, soon enough. And all we can do is pray that the hopeful and hard-working people who have always been the greatest asset of the revolution, who have made this an unforgettable island to vacation on, who have made this feel like home, will benefit and prevail.

A little further down the road and we were forced to take a detour because a bridge had been washed out – two years ago; they were still waiting for the right machine to fix it. And I found the end of my story in a lonely cemetery facing the ocean. The cemetery was simple, ordered, plain. It possessed none of the glory of the one I had seen in the city. There were no changing guards, no huge granite stones, no statues, no flower beds, no pathways. Instead, there was the hard ground, and the sea, and a beach covered with pebbles and larger rocks that looked as if they had been strewn about by an angry spirit. The graves were only white crosses atop rough concrete boxes. These graves, my guide told me, are dug by groups of families and friends who put their money together to buy the concrete, who join together to dig and mourn and pour. "When someone in your family dies, you call everyone you know to come and help," he told me. "And they come." Of course they do. Because that's how it's done here, on this island where people live and die and grieve as a single entity, since they know no other way to be. It's a beautiful ending.

Marissa Stapley is the bestselling author of Mating for Life. Her second novel, Things To Do When It's Raining, will be released by Simon & Schuster in 2016.

IF YOU GO

If you're veering off the all-inclusive path, it helps to plan your trip through Cuba Travel Network (cubatravelnetwork.com; cubahotelreservation.com); they make it easier to customize your trip with a few nights in Santiago and in the coastal village of Chivirico. And they have local specialists in Santiago – and other locations across Cuba – who are friendly, efficient, and available by phone and email to help you with things like finding a travel guide and booking side trips. Chivirico is about an hour by bus or taxi from the Antonio Maceo airport.

WHERE TO STAY

In Santiago, stay at the Hotel Casa Granda (gran-caribe.com; rooms from $110) or the Hotel San Basilio (rooms from $100). Both are centrally located historic buildings, but the San Basilio is in a quieter neighbourhood than the Casa Granda.

Brisas has two hotels in Chivirico: Sierra Mar and Los Galeones. Both have their charms, but are somewhat clunky – at Sierra Mar (rooms from $105), the elevators almost never work, so don't go if you can't do stairs; Los Galeones (rooms from $110) is perched on a cliff and there is no elevator down to the beach, so same goes for the stair issue. But the stunning views of the oceans and mountains make up for the climb. (And stairs mean an excuse to indulge more while on vacation, right?) Both hotels are filled with regulars during the high season, and the vibe is a little bit "summer camp for adults." Staff are friendly and the local musicians who play at the restaurants, in the lobby bar and on the beach make every meal and cocktail hour feel like an event, especially when they break into a haunting Spanish version of Leonard Cohen's Hallelujah, just for the Canadians who feel like they own the place.

WHERE TO EAT

Go to the Restaurante el Palenquito. This paladar – a private restaurant, not state-run; and a great way to enjoy local Cuban fare and avoid feeling like a tourist – is not located in the city proper but is worth the cab fare to the outskirts of Santiago. Atmosphere is tropical backyard barbecue. The service is slow-ish, the mojitos are great and the lobster is fantastic – none of which are a surprise for Cuba. What is a surprise is how good the beef is. (Avenida del Rio 28 entre calle 6 y Carretera del Caney)

Next, forget what you think you know about food in Cuba: Café Rumba does everything right, from coffee to breakfast to tapas. Highlights are 5 p.m. happy hour and the Rumba Beauty Centre, where you can get your nails done and have a cocktail at the same time. The terrace is perfect for people watching. (San Felix 455 A)

WHAT TO DO

Spend a day exploring Santiago on foot, with a map, or with a local guide. Ask your tour operator, or the staff at your hotel, or trust your instincts. Common sense must prevail but the city is generally a safe place for intrepid travellers to set out looking for adventure, and there is almost always someone around willing to help you with this. Some city highlights are San Pedro de la Roca del Morro Castle, Cementerio Santa Ifigenia and the Moncada Barracks.

Ask around about the best place to hear live music and you'll likely be told to go to Casa de la Trova. It's fine, with good bands, lively salsa dancing and several balconies from which to enjoy both the music and city atmosphere. (Bartolome Maso) But Casa de las Tradiciones feels more like the genuine live Cuban music deal. (Calle General Lacret 651)

There are also bands almost every night – and good food, and a captivating view of the city at night – at the Hotel Casa Granda's terrace bar.