A shorter version of this piece about was first published in The Times in July 2018, before the trip detailed below.  

One of the hardest things about being a sole parent, I keep telling anyone who will listen, is that you have to make all the major life decisions alone. “I can’t imagine how difficult that must be,” friends consistently remark.

The truth is that I still rely on conversations I had with my wife, Desreen, in the years before she died suddenly in November 2012. Five and a half years on, I still find myself going back over all of the things we said in the hope that I might be able to do the right thing by my now two-person family

That’s because she and I kind of had a plan. Our little boy, Jackson, was just two when Desreen was struck and killed by a speeding car that mounted the curb we walked home from friends in north London. Desreen had recently turned 33, her fashion business was on the point of flourishing, as was my career in PR. There was nothing holding us back. Desreen believed in the power of positive thinking. The back page of her diary listed all of the things we would do and achieve as a family.

Shortly after Desreen’s death I found in an Amazon locker in my local Co-op store The New York Times, 36 Hours, 125 Weekends in Europe. It was the last gift she ever bought me. The travel guide featured dozens of itineraries for destinations across the continent. I unwrapped it, rolled my teary eyes, and thought, Well I won’t be doing any travelling any time soon. Now I was single dad, lost in grief.

Gradually, though, I began to see things differently. Perhaps this last present from her could become the foundations of a pilgrimage of sorts, when Jackson was say, ten or fifteen. But the truth is I had no real concept of what we would able to achieve together back then; any sense of bravery or confidence seemed to die with Desreen.

Then my outlook began to change one day in a work meeting in Paris. After my wife died, I gave up my big PR job to care for Jackson while somewhat emotionally abusing myself through the act of writing a book about grief. The day after I submitted the final draft, I went back to my old life. I promised myself that I would work part-time, control my hours, and use the perspective life had taught me never to allow professional stresses to get on top of me again. It worked for a while. That was, of course, until it didn’t.

In that meeting in Paris I looked at my watch and realised I had missed the Eurostar back to London. An hour passed, and I had missed another. My opportunity to see Jackson that day had gone. And for what? I can’t remember achieving anything in that meeting room, but I can remember how disappointed in myself I felt.

I was well-paid and successful, but I felt like I was messing things up. I leaned on my mother-in-law too much to look after Jackson. Schools holidays involved shipping him off to his grandparents. When I was around, Jackson spent too much time playing Minecraft on his iPad and I spent too much time asking him to be quiet while I joined conference calls on my phone. Our days just seemed to have become repetitive episodes of school, work, meals, baths and bed.

When I eventually took my seat on the Eurostar that night, I took a hard look at my life. I realised that I needed my own plan. Like Shakespeare’s tragic Danish prince, I was still effectively looking to a ghost for answers. My career, I decided, needed rethinking. With graveside monologues doing nothing to help me reach the conclusions I needed, I turned to my seven-year-old son for his input.

Do you know what New Year’s resolutions are, Jackson?” I asked him. He said he didn’t, so I tried to explain.

“What do you want to happen this year?” I asked him. “It can be something good.”

“I want you to give up your job and spend more time with me,” he responded without hesitation.

In the weeks running up to Christmas, I had noticed how frequently he told me he missed his mum. After years of learning how to handle such a young grieving infant when he spoke about the loss of his mum, these days all I can really do is tell him that I understand; that I miss her deeply, too; keep her alive in daily conversation; keep the pictures of her on the wall; mark as many anniversaries as I can think of; and allow him to open up about his feelings as much as he does or doesn’t wish at any specific moment when he choses to talk about her. But, in all honesty, I suspected that he was missing his dad, too. And he had finally just confirmed it.

“Good idea!” I replied, “Then that’s what I’ll do.”

I had a little money set aside for a rainy day, but it actually felt like what we really needed in our lives was some sunshine. “I’m taking the whole of the summer off,” I told my boss who has always been very understanding. “I had some time off when Desreen died but it was, of course, the worst time of my life. Now I feel like it’s time for a happy break.”

I felt brave for the first time in years. I booked the cheapest flights I could find to Italy for the day he finished school and started to map a six-week route around the country that Desreen and I had planned to visit on a belated honeymoon (we got married when Jackson was ten months old and were waiting for the right time to travel together as a family). This trip, however, would be just me, my son.

Not that I didn’t have a few anxieties.

“What am I doing?” I panicked to a colleague. “Do you think he’s too young for the two of us to actually have fun together?”

Then a couple of weeks later, I was sitting at my computer with Jackson.

“Dad, have you seen my new horse in Minecraft?” he asked.

“Neigh!” I replied with a smile.

“Did you just say, ‘Neigh’?” he asked.

“Yes, I did,” I smirked.

His little fist slammed down on the desk as he threw his head back with laughter. He was still chuckling about this almost unforgiveable ‘dad joke’ as I gave him his evening bath. We’re going to be just fine, I told myself.

And he seems to agree. Jackson has been telling everyone from his teachers to his grandparents about our adventure. He has even announced that he won’t need his iPad because the two of us will be so busy enjoying ourselves. We are still making plans. We have studied the book Desreen left us and Jackson has already decided that he wants to see Rome and Venice. The rest he has left up me.

“So, what’s your plan when you get there?” asked a dad I (barely) know the other day.

I explained that all I had done was book a flight and plotted the roughest of routes from north to south.

“That’s brave!” he exclaimed.

Having felt timid, indecisive and scared of life for so long, his words really buoyed me. It was like being told I had finally qualified to become the thing that I wanted to be the most. Not a writer, not a PR director, not anything remotely professional. Just a dad who dares to start again.