I recently returned from an 10 day road trip around Alentejo, Portugal. I drove 1500km around Portugal’s largest region in search of hidden villages, stunning views and unforgettable experiences. I found all of the above in abundance all thanks to curating this epic itinerary. By spending so much time on the road I was able to explore deeply and find the very best experiences the region has to offer.

On this particular Alentejo trip I stuck to the interior so you won’t see any coastal areas such as Porto Covo and Vila Nova de Milfontes in this itinerary. You can find a guide on the whole Alentejo region here (coming soon).

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The main reason I was attracted to Alentejo is that it still feels relatively undiscovered in comparison to many other places in Portugal. There are still a huge amount of sleepy villages, rolling swathes of countryside and (for me at least) the region offers an honest insight into Portuguese culture and lifestyle. I have always loved living in Portugal but perhaps in a somewhat superficial way (hot weather, cheap beer etc) but it was only when I returned from Alentejo that I started to understand more about the country and I feel so proud to call Portugal my adoptive home.

I’m not sure why Alentejo slips under most people’s radar when they visit Portugal but If it is somewhere you haven’t really thought of before then hopefully I’m about to change your mind.

If you want to find out more in-depth information about the Alentejo region don’t forget to visit the Visit Alentejo website.


The Alentejo is the largest region in Portugal which is located on the Iberian peninsula. It is bordered by the Algarve, Lisbon and Central regions and despite being the largest region in the country it attracts the lowest number of visitors in mainland Portugal. 


The region is easily accessible from all of Portugal’s major airports (Lisbon, Porto and Faro). Which one you choose will depend on how long you have in the region and what itinerary you are planning to take.

Although most towns and villages are accessible by train or (more likely) bus the best way to ensure you get the most out of Alentejo is by hiring a car. Having a car ill give you more freedom and flexibility with your itinerary but cruising around in your own four wheels (in my humble opinion) is the best way to experience Alentejo.


I spent 10 days exploring Alentejo and I there is still plenty more I still want to see but I do believe this 10 day itinerary will show you the absolute best of the region. I spent weeks of research making sure my itinerary included the perfect mix of medieval hilltop towns, quiet villages and true experiences. I also made sure I had gaps in my original itinerary so I that I could talk with the locals en route and squeeze more memorable moments into the trip. There will always be more to discover but I feel the this 10 day itinerary will allow you to really get beneath the surface of the Alentejo.

This itinerary is the exact route I took around the Alentejo and includes both places i stayed and spots I visited for just a few hours. I have included links for accommodation options in each place – these are places I stayed during my trip and can personally recommend.

Make sure you check out these 5 Unique Places to Stay in Alentejo.

I drove from Algarve and returned to Algarve. If you are driving from Lisbon or Porto you can switch the itinerary up and/or create a different loop easily enough. If you only have a short amount of time I recommend basing yourself in central Alentejo and making day trips from Ėvora.


This gem of a medieval village sits proudly on the Guadiana river just a whisper into the region. It is small enough to wander around in a day but if you have the time stay for a few nights and enjoy the picturesque streets without rushing. If you have extra time take a drive to one of the river beaches nearby.

STAY | Mértola Studios or for something more upmarket try Hotel Museu

EAT/ DRINK | Espaco Casa Amarela

EXPERIENCE | Dinner, wine and sunset at Espaco Casa Amarela on the other side of the river.


I spent a few hours walking the beautiful streets of Vila Viçosa and loved the spotting the pretty tiles, choosing an alfresco cafe and browsing typical artisan products from the region. This would be a great stay over too! Check out Bookingcom for Vila Viçosa accommodation options.


I didn’t even know this natural park existed until I stayed at a beautiful Quinta (Quinta da Dourada) just outside Portalegre. The natural park is a dream to drive around; quiet, winding (but not too winding) roads with seriously gorgeous views. You can also visit one of Alentejo’s highest points in São Mamede, this summit gets snow in the winter which is unimaginable when you visit in July! I highly recommend the drive from Quinta da Dourada to Castelo de Vide.

STAY | Quinta da Dourada

EAT/DRINK | At the Quinta. Contact the owner Nuno in advance and you’ll be able to enjoy delicious Portuguese home cooking during your stay.

EXPERIENCE | Driving through the Mamede Natural Park.


I only spent a matter of hours here but I can confidently tell you it as one of my favourite places I visited in Alentejo. Castelo de Vide feels lived in yet looks beautiful from top to bottom. People shout from windows and Fado music drifts in and out of houses. It is also the most ‘flowery’ place I saw on my trip. Every house was a piece of wild art!

I didn’t stay the night here but I absolutely will next time. Find Castelo de Vide accommodation using the Bookingcom search function!EMBEDDED SCRIPTSThis block contains embedded scripts. Embedded scripts are disabled while you’re logged in and editing your site.PREVIEW IN SAFE


Another big favourite for me was experiencing Marvão. This hilltop village is picture perfect, so much so that it kind of feels like you are in a medieval theme park. It may look like it is geared up solely for tourists but there is still authenticity to be found when you peek around the corners. Don’t leave until you have walked the circumference of the castle walls

STAY | Maruan Heaven

EAT/DRINK | O Castelo

EXPERIENCE | Sunset from Marvão castle.marvao


The cutest village in central Alentejo you ever did see. White houses beam in the afternoon sunshine, olive groves stretch out from it’s borders and locals remain curious but friendly towards newcomers. Rendondo is also a DOC wine region and pottery centre. The town has a good selection of restaurants and bars and is well worth a stop overnight.

STAY | Casa Porfirios

EAT/DRINK | Choose a lively one in the main square.

EXPERIENCE | Drinking with the locals at an authentic snack bar. There is also a wine museum and plenty of vineyards close by!


The capital of Alentejo and its most well-known asset. Évora is probably the busiest you’re going to get when it comes to Alentejo but with good reason. The city is steeped in history, full of authentic Alentejan cuisine and surrounded by some of the region’s best vineyards. I have to admit I didn’t get a chance to make the most of Évora but I will certainly be back to spend a few days enjoying the city buzz.

STAY | Quinta da Espada

EAT/DRINK | Quiosque Jardim Diana

EXPERIENCE | Capela dos Ossos (Chaple of bones). Enjoying tapas and cocktails with a view!


I’m mentioning this as a must-stop experience on your Alentejo itinerary because Monte da Ravasqueira is one of the most alluring vineyards I have visited in Portugal to date. The experience also introduced me to my new go-to bottle of vinho branco. I have several chilling in my fridge as I write this. Book a tour, tasting or experience and you will be welcomed warmly, invited to sip on some award-winning wines and enjoy time soaking up sun-drenched vineyard views and the real beauty of Alentejo. Of course, Alentejo is not short on wine experiences and I fully encourage you to squeeze in a few if you can; but, if you only have time for one vineyard during your trip make it this one! Located only 5km from Arraiolos and 25km from Évora.

You can read more about my wine travels in Portugal here (coming soon).


Estremoz sits nicely between Évora and Elvas and has an attractive buzz about it. It is obvious that this isn’t a tourist town but there are lots of cute streets and a pretty epic castle view to top it off. Estremoz also has plenty of vineyards within a short distance.

STAY | Find a great apartment in Estremoz on Bookingcom.

EAT/DRINK | Alcrim

Take a stroll up to the old castle wall and take in the vineyard views.


Most people who already know about Alentejo will direct you to Monsaraz as a place to add to your itinerary and with good reason too. Monsaraz is pocket-sized and picturesque (almost to a fault) and a magical introduction to Alentejo. Tiny streets boast restaurants with panoramic views and little nooks host artisan shops filled with ceramics and honey.

STAY | Casa Tia Anica

EAT/DRINK | I ate in my apartment during my stay but I had several recommendations for Taverna Os Templários and Restaurante Bar Sem-Fim.

EXPERIENCE | Wandering the cobbled streets early morning.


This town usually doesn’t make it on a typical Alentejo itinerary which is exactly why i wanted to visit. Vidigueira is actually a really important town for the history of wine in Portugal and its also delightful to explore by foot.

STAY | Casa Grainha

EAT/DRINK | Enjoy a cold beer at Casao Da Praça.

EXPERIENCE | Adega Cooperativa Vidigueira for a wine tour and unique Talha wine tasting.

So here ends my Alentejo itinerary! I hope this helps you capture at least a small picture of how wonderful this region is to explore. Stay tuned for a complete ‘’Alentejo travel guide’ and ‘unique places to stay guide’.

Don’t forget to check out my other Portugal experience based travel guides.




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