When my wife Jody and I were at home researching our trip to Jibacoa, we checked out a variety of travel advisory websites for tour guide recommendations, and wrote down the contact info for a man whose name kept recurring: Humberto Mesa. Once we were at our resort and had hooked up with the lovely Aurora and expert traveller Lorraine, we had to laugh when Lorraine whipped out her cell phone and speed-dialed the same Humberto, arranging our day trip to Havana for us in the blink of an eye.

Humberto picked us up at our resort in a small Renault that had seen better days, and he laughed as we ogled some of the beautifully restored, colourful American cars waiting for other guests. “From the outside they look good. From the inside, no good.”

He went on to explain that most of the cars had no shocks, no air conditioning, and were prone to breaking down – understandable given their mechanical history and availability of parts. Sure enough, we saw several overheated cars with overheated tourists on the side of the road awaiting tow trucks. We sailed past in our boring but reliable car, excited to see what Havana held in store for us.

We arrived in the city just after 10 a.m., and the scorching hot sun meant our walking tour around Old Havana would be taken at a leisurely pace.

Humberto led us through the cobblestone streets to Plaza de Armas, where vendors hawk mainly political books in their stalls (Che and Fidel always on display), and we could admire sights like stone columns flanking giant bells on the sidewalk.

There were plenty of locals trying to get any tourist’s attention as we passed, including women in brightly coloured dresses who jumped in front of me while chomping on their obligatory cigars. I avoided them and instead tried to catch some quiet portraits of the more interesting faces we encountered, always with their permission.

Anxious to show us a stunning landmark, Humberto led us to the Plaza de San Francisco, in which stands the Basilica Menor de San Francisco de Asis, built during the late sixteenth century. He encouraged us to hike the bell tower for the spectacular view, but said he felt no need to join us for the climb, since he’d done it before. I’m sure the oppressive heat had nothing to do with it!

Inside, it thrilled us to stumble upon a small orchestra holding a rehearsal on this Tuesday morning. The space is apparently used for concerts instead of worship, due to its glorious acoustics that aren’t done justice in this brief clip:

As with so many of the buildings in Cuban cities, the church had a courtyard open to the sky and filled with greenery.

Several claustrophobic, perspiration-inducing flights of stairs later, we had earned the views Humberto promised us of the city, the plaza, and the Terminal Sierra Maestra, where cruise ships come to dock.

Fading a little from the heat and exertion, Humberto suggested that some classic Cuban refreshments were now in order. Who were we to argue? Next stop: the rooftop bar at the bright pink Hotel Ambos Mundos, where Ernest Hemingway stayed for extended periods throughout the 1930s. The lobby has an entire wall dedicated to photos of him (as do several bars in Havana), and his former room 511 is now a museum with a tour fee.

The 1924 Otis cage elevator we stepped into was the same one that lifted Hemingway himself, which I confess ignited my imagination on the ride up.

In the blessed shade, we enjoyed a cold mojito and the views while listening to a live Cuban band.

We continued walking the maze of streets in Havana, and Humberto pointed out the many building facades with unsightly and uneven wooden struts which we’d thought were signs of construction in progress. Sadly not – the awkward wooden arms spanning various balconies and stretching above doorways were literally holding the buildings upright. Restorations throughout the old city were underway ten years ago, when Hurricane Ivan blew through with other plans. Many residents are living in buildings that most would consider uninhabitable, relying on their own makeshift supports for their safety.

Humberto explained that these buildings on interior streets were the “real” Havana, and occasional coats of colourful paint are only applied to the buildings lining the main roads for appearance’s sake.

Other trivia offered by Humberto on our walk included the number of monuments erected in Cuba for people who have no connection to the country. A garden dedicated to Princess Diana? “Never been here,” he said. A statue in a park for John Lennon? “Nope, never came to Havana. But Cuba gets many British tourists, and the government wants to impress.” Aha.

After meeting some more interesting characters, enjoying another cocktail at Hemingway’s favourite watering hole El Floridita (where a life-sized statue of him sits at the end of the bar), and grabbing an authentic Cuban lunch, we wrapped up the walking portion of our tour and headed by car to the waterfront to explore Morro Castle. The stone fortress dates back to the late sixteenth century, is visible from all around the bay, and offers beautiful sight lines to the Old Havana skyline.

Ominous clouds began to gather when we left the castle, and the weather changed dramatically on our way to Colon Cemetery. I realized my good luck with photo ops was about to run out. We paid an entry fee of $5 CUC per person to drive through the cemetery in the light rain, while Humberto explained to us the Cuban custom regarding death and burial.

Each family has a crypt, and when a person dies they are buried in the tomb for two years. After that time, a member of the family is responsible for removing the bones, washing them, and placing them back in a smaller box within the crypt. This way you can fit several generations of family members’ remains in a single plot. Humberto said after his father passed away he had nightmares for days ahead of this duty, and the day he had to come to the cemetery to wash his father’s bones was one of the worst in his life.

Photography and even sightseeing became impossible as the rain pelted down, so after driving past Revolution Square, we turned and headed back for the hotel. Humberto’s fee for the private tour was just $70 CUC total, as opposed to some of the hotel/Sunwing options at $100 CUC per person for group tours. We added a generous tip and covered his food and drinks for the day, and still felt we got a great deal. We had the freedom to stay at each place he took us to for as long as we liked, and to change the itinerary as the day wore on. We were so happy with our experience that we promptly booked him again for our last day, to take us through Matanzas and Varadero on the way to the airport.

In between, we had a couple of final days of relaxation at the resort, which included putting our new snorkelling gear (and waterproof iPhone case) to use. It was surprising to find that the coral reef actually reaches nearly to the shoreline of our own beach, but it’s nearly all dead from people trampling it. There are notices in the hotel brochures and on the website asking people to not step on the living coral, but no signage at the actual beach. Not only were people standing on the coral, walking over it, and pulling chunks of it out of the water…but two locals were throwing large nets out into the water to catch the fish the tourists were snorkelling to see! They walked over the coral, dragged in the nets, and dumped the multicoloured fish into a bucket on the shore. As I wrestled with whether to ask them to please fish elsewhere with a miles-long beach to choose from, other people went over and raised a ruckus. A man who I think was a hotel employee eventually came over and asked the fisherman to leave, thankfully.

Since so much of the reef was dead and brown near the resort (you could see people standing up on it a hundred feet out in the water), we hired a catamaran from the hotel’s activity centre on the beach to take us much further out. Our professional diver/guide was Pedro, the man whose house we’d been at just a few days before with our new friend Lorraine (whom we’d taken to calling Don Lorraine, since she seemed to know everyone and always received the royal treatment).

It took about twenty minutes to get to the area he had in mind, given that there wasn’t much of a breeze. He anchored the boat, we jumped in the water, and found ourselves surrounded by marine life that seemed almost as curious about us as we were about them.

Aside from the nagging fear of having something scarier than Jody creep up behind me in the water, the only thing that freaked me out was the presence of small jellyfish. They were completely transparent and easy to miss until they pulsed, but would suddenly come into focus right next to my face.

I panicked when I found myself surrounded by them in the water, but Pedro swam over and grabbed one with his hand. We surfaced and he explained that these small ones don’t sting, showing me what looked like a puddle of mucus in his palm. From then on I couldn’t help reaching out to touch them as they floated past me!

Pedro also led us to an area with coral-encrusted cannons, and incredibly beautiful mollusks that he dove to retrieve, and then carefully replaced.

As we turned to swim back to the catamaran and call it a day, a school of bright blue fish arrived and performed a beautiful ballet amongst the coral right in front of us.

It was the perfect end to our excursion, and we found ourselves wishing we had more time at the resort to do this again.

Our last day on the island arrived all too soon, and Humberto picked us up again to tour Matanzas and Varadero. Unfortunately it was one of the only days where the weather was not cooperating, but we made the best of it.

The town of Matanzas had a very different feel than Havana. It felt much poorer, the people did not seem as happy, and we were the only tourists in sight. My camera attracted more than a few stares, and had we not had Humberto with us I would have felt unsafe for the first time on our entire trip. Humberto walked us through the streets, past the struggling businesses, and into a few of the stores to see the lack of goods and high prices. Our education continued.

Humberto had tried to explain Cuban economics to us on our Havana tour, but it was much clearer to us in Matanzas. Simplified, the idea is to eliminate social classes and wealth – no one should have more than their neighbour. If you start your own business, the government must approve it and will then watch that you don’t become “too successful”. They can shut you down at any time.

Instead of ensuring equality it encourages a secretive, underground economy where you must hide your earnings from the government and from those around you. Money earned cannot be deposited in the bank, nor can you buy luxury items (should they be available) that would create jealousy in friends and family, who might turn you in. Life appears incredibly hard.

And still the dogs. Always breaking my heart.

I was actually glad to wrap up our walk and head on to Varadero.

The tourist town was much as I expected, with enormous resorts and Westernized stores. It was oddly deserted, however, I guess since it was low season and a rainy day. Humberto showed us a few points of interest on the drive, then took us to the enormous Xanadu estate, constructed in 1930 for the recently retired head of the Dupont chemical empire. Within a few years a golf course was built on the grounds, and the mansion is now used as a hotel, restaurant, and bar as part of the Varadero Golf Club.

For our final stop, Humberto drove us to what looked like a sprawling stone house on the main drag. Called “La Casa de Al”, it is neither stone nor a house. It’s a restaurant that the famous gangster Al Capone once used to store weapons, and the entire structure is made of coral.

Humberto told us the seafood is quite good, but it would have to wait for another visit.

We walked around the back for our last view of the ocean before leaving, where Humberto gave us his thumbs up.

When we booked our trip to Cuba, we’d envisioned days of lying by the water, just reading books and enjoying a few drinks. Somehow our best laid plans to simply rest and relax never pan out; we itch to see new things and meet new people.

But don’t get me wrong – I still managed to devour three books and a sufficient quantity of local rum.

It was perfect.