The folks at Winding Road Tours have been very responsive to our needs. They have clearly explained what to expect regarding the tours we are interested in and we look forward to planning this adventure with them!
Authentic Journeys Across Portugal
Small group cycling and Hiking tours in Portugal
Authentic Journeys Across Portugal
Small group cycling and Hiking tours in Portugal
Authentic Journeys Across Portugal
Small group cycling and Hiking tours in Portugal
Our Mission
We are committed to serving our diverse clientele with experiences that reveal the best of Portugal’s natural, cultural, historical, and folkways heritage; providing back roads destinations that many travelers do not commonly visit and selecting top-quality accommodations in small, authentic venues.

Featured Tours

Southern Coast Cycling Tour (Spring 2022)
This tour takes place within two protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing villages…



Back Roads Alentejo Tour (Spring 2022)
This tour takes place in Alentejo, the Central Region of Portugal, a largely agricultural place where we will see expanses…



Schist Villages Walking Tour in Central Portugal (Spring 2022)
Finding the hidden treasures of Central Portugal is the goal of this fantastic trip. Starting from Lisbon, we will first…



Culture and Wine Country Tour in Northern Portugal (Spring 2022)
Northern Portugal is a region rich in old traditions and idyllic natural and man-made landscapes. It is full of village…



Cape St. Vincent (Rota Vicentina) and Southern Coast Walking Tour (Spring 2022)
This tour takes place almost exclusively within protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing…



Culture and Wine Country Tour in Northern Portugal (Fall 2022)
Northern Portugal is a region rich in old traditions and idyllic natural and man-made landscapes. It is full of village…



Cape St. Vincent (Rota Vicentina) and Southern Coast Walking Tour (Fall 2022)
This tour takes place almost exclusively within protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing…



Schist Villages Walking Tour in Central Portugal (Fall 2022)
Finding the hidden treasures of Central Portugal is the goal of this fantastic trip. Starting from Lisbon, we will first…



Back Roads Alentejo Tour (Fall 2022)
This tour takes place in Alentejo, the Central Region of Portugal, a largely agricultural place where we will see expanses…



Southern Coast Cycling Tour (Fall 2022)
This tour takes place within two protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing villages…
Our Amazing Reviews
Dave L., Orlando, FL
“What a great experience! Want to turn around and do this visit all over again. I recommend a trip through Winding Road Tours 100%!”
Sandra C., Washington DC
“I was captivated by the Portuguese landscape and the relaxed Portuguese people. Winding Road Tours has done a good job introducing me to the “real” Portugal through its authentic tour offerings”
Leah O., Missoula, MT

