Portugal Private Journey

Hiking the Hidden Towns of Alentejo

Trip Level

This trip is rated 2-3, easy to moderate, depending on your choice of hiking options. Hikes range from 3 to 7 miles with some elevation gain and descent. There are more challenging options on most days (5-10 miles). This trip is suitable for anyone in relatively good physical condition. For your own enjoyment, we recommend you make a special effort to get in shape for the trip. Daily brisk walking and/or regular hiking are excellent preparatory exercises. You should wear sturdy, well-broken in hiking boots for maximum comfort on the trail.


The trails are fairly well maintained but can be primitive in spots with loose rocks and soft sand and dirt. The hikes will bring you on historic trails from village to village, through pastures where sheep graze, and along a coastal trail in the Serra Arrábida.


You can expect comfortable temperatures for sightseeing year-round, from temperatures in the mid to high 60s in March and April to the 70s in May and October. Portugal’s rainy season begins in November, with temperatures in the mid-60s. The summer sun in the Alentejo can get very hot, up to the mid-80s, and we don’t recommend traveling here from June to September


Many of the accommodations are in pousadas, traditional or historic properties that help tell the story of Portugal’s past, from former convents and monasteries to medieval castles or historical government buildings. Other lodgings are in small hotels with limited rooms and some are more luxurious. All have private facilities.


Foodies will enjoy this trip because the Alentejo region probably has the most distinctive (and different) regional food in Portugal with dishes you won’t find anywhere else. The gastronomy is famous for its meat (lots of lamb and pork, including the famous local Iberian black pig), bread, and cheeses. The dishes are often bread-based, flavored with coriander, pennyroyal, and other local herbs (both wild and cultivated), and high quality olive oil.

Choosing the Right Trip

We work hard to help you choose the right trip for you, paying attention to your individual interests, abilities, and needs. If you have questions about the level of comfort or any of the activities described in this itinerary, please contact us.


We are proud to have an exceptionally high rate of repeat travelers. For more information, we would be happy to put you in touch with a client who has traveled with us.