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

Back Roads Alentejo Tour (Spring 2022)
11 Days
Cycling

This tour takes place in Alentejo, the Central Region of Portugal, a largely agricultural place where we will see expanses…

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Schist Villages Walking Tour in Central Portugal (Spring 2022)
10 Days
Walking

Finding the hidden treasures of Central Portugal is the goal of this fantastic trip. Starting from Lisbon, we will first…

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Culture and Wine Country Tour in Northern Portugal (Spring 2022)
10 Days
Walking

Northern Portugal is a region rich in old traditions and idyllic natural and man-made landscapes. It is full of village…

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Southern Coast Cycling Tour (Fall 2022)
12 Days
Cycling

This tour takes place within two protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing villages…

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Southern Coast Cycling Tour (Spring 2022)
12 Days
Cycling

This tour takes place within two protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing villages…

Explore
Back Roads Alentejo Tour (Fall 2022)
11 Days
Cycling

This tour takes place in Alentejo, the Central Region of Portugal, a largely agricultural place where we will see expanses…

Explore
Schist Villages Walking Tour in Central Portugal (Fall 2022)
10 Days
Walking

Finding the hidden treasures of Central Portugal is the goal of this fantastic trip. Starting from Lisbon, we will first…

Explore
Culture and Wine Country Tour in Northern Portugal (Fall 2022)
10 Days
Walking

Northern Portugal is a region rich in old traditions and idyllic natural and man-made landscapes. It is full of village…

Explore
Cape St. Vincent (Rota Vicentina) and Southern Coast Walking Tour (Fall 2022)
10 Days
Walking

This tour takes place almost exclusively within protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing…

Explore
Cape St. Vincent (Rota Vicentina) and Southern Coast Walking Tour (Spring 2022)
10 Days
Walking

This tour takes place almost exclusively within protected areas along the coast from Alentejo to Algarve, meandering through authentic fishing…

Explore

Our Amazing Reviews

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!

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