Ever since I joined inGamba, I have been intrigued by our trips to Alentejo. Now, I’ll be the first to admit that I didn’t know much about this part of the country, situated just south and east of Lisbon. But the more I learned about this region, filled with vineyards, olive groves, and, among other things, cork trees, the more attracted I became. And the idea of spending a week riding along quiet, rolling country roads? Well, what’s not to like?
I had to wait more than a year, but I finally caught up with a group, joining our last Alentejo trip of 2026. And as the dust settles, the many superlatives that describe this trip only continue to grow.
Like most of the guests, my trip began with a night in Lisbon, a city that enchants me more with each visit. There is something about walking through the streets of Alfama or Bairro Alto as they come alive at nightfall that offers a touch of both magic and mystery. Lisbon is a wonderful walking city, and it’s easy to get lost, if only for a moment.
Meeting up with the rest of the group on Sunday morning, we drove east to our first hotel, where I was greeted with a true wow factor. Torre de Palma is a family-run estate at the heart of a sprawling property with roots dating back to ancient Rome. A long gravel road led us to the estate itself, and the wow factor was instant. The cypress trees, the chapel, and the many low-lying buildings called to mind a Western movie setting as much as a Giorgio de Chirico painting. The location would have been the perfect setting for a fashion shoot, but on this day, it proved to be the perfect home for an inGamba trip.
After suiting up, we headed out for our first ride, rolling over a steady succession of gentle hills. But what struck me most about the landscape was the pervasive sense of stillness in the air. This combination of location and landscape would set the tone for the rest of the week.
All of the hotels, from Torre de Palma to Herdade do Sobroso—one of Forbes’ 50 Best Wineries in 2025—were unique in their own special way, linked together by the warm autumn sun and the quietly beautiful countryside that is Alentejo.
Along the way, there were plenty of surprises, like the Roman Temple in Évora and the sinuous corridors of Convento do Espinheiro. Friendships were formed, great food was enjoyed courtesy of the region’s countless specialties, and wine was savored from the many wineries found here.
In short, my week in Alentejo had all the ingredients of a classic inGamba trip. The roads and the tables brought us all together, from the first day to the last. As is often the case, conversation flowed freely throughout the week, and when it finally came to an end, we all shared the same desire: to simply hit rewind and do it all over again.
