About Us

Winding Road Tours

For me, Portugal is a bit magical and always a mysterious place. In the over twenty years that I have traveled this country, I am always surprised that there are more remarkable places to discover. And I have traveled Portugal a lot! Not just the castles of old that you commonly see or the monasteries that dot the landscape everywhere but to discover a town living quite literally under huge boulders or a field of a hundred standing stones just 30 minutes from where we stay or a community festival that decorates its entire town in walkways of handmade flowers is truly breath-taking!

My love affair with Portugal began in 2002. I had just left the U.S. National Park Service, where I had served as a landscape architect and park manager, among other duties and now I was free to travel – for as long as I wanted! I landed in Lisbon for a month. And I was captivated!

I had studied Brazilian Portuguese and lived with Brazilians in graduate school but the Portuguese of this country was nothing like that! My adventure to learn European Portuguese and dive into the culture began! I was no stranger to the outdoors and enjoyed the historical context of this rather unknown part of Europe. It had the castles, landscapes, wine and folk culture that I admired.

And everyone I met was patient and helpful. I learned that the Portuguese motto of “If I can help you, I will” to be true and regularly exercised. The population here was more diverse than I expected. The flavors and rhythms of people from Brazil, Portuguese-speaking Africa and the historical influence of the Moors from northern Africa permeate the culture here. What you find is that Portugal has variety you did not expect.

Because of all the aforementioned, I have created my tour company, Winding Road Tours. I have chosen to share with you the personal spaces that I have found in Portugal to be enticing and unexpected. I love this country and want you to discover it, too!

We are working intensely to provide organized and custom-designed trips that are affordable, intriguing and low impact on the landscape.

Take a look at our culture, history, wine-tasting and Nature walk itineraries and join us in 2024 and 2025, won’t you?

Waiting for you in Alentejo, Portugal,

Lynn Pilgrim-Little