The ultimate trip planning BLOG

Plan & book your dream trip

The 7 Most Charming Small Towns for your Portugal Road Trip

Print Friendly, PDF & Email

Welcome to Portugal! This small country is big on character, with stunning views, fabulous beaches, fantastic local vineyards, charming villages and amazing food. Time to check out the 7 most charming small towns for the perfect Portugal road trip!

So, what are you waiting for? Start planning your perfect trip to Portugal!

Popular itinerary in Portugal:


An impressive hilltop castle, a massive wall surrounding the town, cobbled streets and bright vivid colors, Obidos is the quintessential Portuguese small town. Wander the medieval streets and you will fall in love with its small town charm!

Obidos, Portugal
Panoramic aerial view of medieval town Obidos in a beautiful summer day, Portugal


Sintra is an exquisite Portuguese town that is located west of Lisbon. This UNESCO World Heritage Site is known for its stunning 19th century romantic architecture. Set against green hills, Sintra’s awe inspiring palaces, castles and manors will make you feel like royalty straight out of a fairy tale on your Portugal road trip map.

Palace of Pena in Sintra. Lisbon, Portugal. Famous landmark. Summer morning landscape with blue sky.
Sintra, Portugal
Sintra, Portugal at the Initiation Well


In 1938, Monsanto was named the most “Portuguese town in Portugal.”  Monsanto is located on a mountaintop, overlooking some stunning scenery. With red roofed houses that are carved from rocky cliffs and granite boulders and little narrow streets, this small town is as unique as it is beautiful.

Monsanto, Portugal
Monsanto, Portugal
Aerial view of the beutiful historical village of Monsaraz, in Alentejo, Portugal; Concept for travel in Portugal


A tiny and charming village which boasts white washed houses, an impressive castle, and feels like you’ve traveled back in time.

Monsaraz, Portugal
Aerial view of the beutiful historical village of Monsaraz, in Alentejo, Portugal; Concept for travel in Portugal


Aveiro is a charming little town that has hidden gems around every turn. Known as “Portuguese Venice” this picturesque town has beautiful canals, small bridges and colorful houses.

Aveiro, Portugal
Aveiro, Portugal


This historical small town is home to a spectacular attraction: The Capela Dos Ossos (Bone Chapel). The walls and pillars of this church are actually made of skulls and bones. This stunning and shocking chapel was built by Franciscan monks out of a need. the cemeteries were over populated and taking up valuable space in Evora, so the bones were moved to the chapel.

The Capela Dos Ossos (Bone Chapel), Portugal
View of the Giraldo square located on Evora, Portugal.

Porto Moniz

The tiny little gem boasts hidden natural swimming pools that were created by volcanic lava, with crystal-clear water.

Porto Moniz, Portugal
Lava pools in Porto Moniz town in Madeira island, Portugal

Did we miss anything? Let us know in the comments!

You might also like Undiscovered Paradise – The Best Things To Do In Portugal!

Print Friendly, PDF & Email



Routeperfect Blog Worldwide

Routeperfect is the ultimate trip-planning tool. We help you create your dream trip based on your travel preferences, budget and style.

Recent Posts



subscribe to our newsletter