Great tours are often born from the most unexpected moments…

… Like that one time I found myself climbing Montejunto, those last two kilometres that feel like a mountain’s way of challenging you, with a 14% grade. It’s as if the mountain decided the previous 40 minutes of climbing were just a warm-up. That’s where the idea for the 1000km Coast to Coast adventure was born.

As I neared the summit, the edge of the road seemed to drop off into the valley below, revealing a breathtaking horizon adorned with vineyards, apple orchards, and cornfields stretching all the way to the Atlantic Ocean. The sheer beauty made my vision blur.

I glanced down at my heart rate monitor, realizing I had pushed myself to the limit for too long. Above me, my friends waited at the summit, cheering me on as I conquered the last hairpin turn. Legs screaming, sweat pouring, heart pounding—it was an October day, but the Portuguese sun showed no mercy.

At the summit of Montejunto, a peculiar charm enveloped the place. Ancient ruins of a 12th-century convent stood amidst modern radio pylons and military radar dishes. An eerie silence hung in the gentle breeze—a silence rarely found down in the valley.

While my friends debated the descent route and the journey back, I regained my composure. I grabbed an energy bar and drained the last drops of water from my bidon. My body was suffering, but my mind was already racing with thoughts.

“I have an idea,” I blurted out in my rudimentary Portuguese, earning puzzled looks from my companions. They often struggled to understand me, regardless of the language. “Let’s cycle to Santander in Spain. It’s only 1000kms, and I know some fantastic restaurants along the way.”

The word ‘restaurant’ transcends language barriers, especially in the Romance languages, and it soon caught their attention. Dining on exquisite food and sipping fine wine was their passion (aside from cycling, of course).

“Quando?” they inquired.

“Next May?” I suggested. They exchanged murmurs among themselves. I wasn’t sure if they were taking me seriously or still debating the best way down.

“Okay,” they finally chimed in.

I couldn’t believe it. I hadn’t expected anyone to agree!


No tour truly begins on Day 1, especially one like the 1000k Coast to Coast.

It starts the day before, with a grand banquet. This time, it was hosted at Gentil’s house. Gentil and his wife were known for their elaborate, convivial meals. You couldn’t help but notice their oversized saucepans—evidence of their culinary enthusiasm. Carlos arrived with delicacies from his countryside smallholding, followed by other members of our cycling group, each bearing something delicious for the table.

The conversation during lunch was lively and filled with excitement. This tour was unlike any of our previous ones; it was an endurance challenge, covering 1000 kilometres in just six days. It wouldn’t be easy. It’s not like climbing a mountain where every ascent is followed by a descent.

But we couldn’t linger; we had to pick up the other riders from England, who were due at the airport in an hour.

Lisbon welcomed us with sweltering heat, and my friend Carlos decided to take us on what he called the ‘scenic route.’ We suspected he was just terrible with directions. Regardless, the shouting, gesticulations, and even some heated arguments with other drivers had worked up our appetite. With new faces on board, we set our sights on our next destination—dinner.


The heat persisted through the night, and we woke up to glorious sunshine, a promising sign. Today was going to be a long day as we headed east out of Lisbon, crossing the stunningly beautiful Alentejo.

May had transformed the Alentejo into a colourful tapestry of flowering pasturelands. The rolling hills made for easy cycling, and while there were climbs, our route was designed to keep them manageable on the first day. We paused for lunch under the shade of olive trees, feasting on cured meats, quail eggs, goat’s cheese, omelette, and cake.

After a brief siesta, the final 70 kilometres of the day’s ride passed by as we pedalled deeper into the countryside, reaching our first night’s stop.

The farmhouse owner welcomed us like family and had prepared a table on the terrace overflowing with local delicacies and regional dishes. With a few bottles of wine from the nearby vineyard, we watched the sun set on the first day.

Our slumber was interrupted by the sound of rain, but we knew the tour had to go on. The Spanish border awaited, and a short recovery ride would take us to our next stop in Caceres—an extraordinary medieval town in the heart of Extremadura.

Navigating the narrow, winding cobbled streets that meandered among ancient stone walls of palaces, mansions, and churches, we found our way to our hotel in the middle of the town’s 16th-century splendour.

Caceres was a gastronomic delight and a capital of Spanish cuisine. Dining in the historic Plaza Mayor was an experience worth repeating.

DAY 3 – to be continued

Adriano Placidi

Team Director at Volta Pro Tours