Updated 2026
Welcome to one of my original travel guides. This is one of the best Portugal road trips of all time. Written after (and I’m not exaggerating) a life changing trip to interior Alentejo – Portugal’s most undiscovered region, in 2020. I drove 1500km through the region over the space of 10 days in search of hidden villages, stunning views and unforgettable experiences. Alentejo delivered. I found all of the above and so, so much more. Alentejo turned out to be one of the best trips I have ever experienced and so I had to share my epic 10 day itinerary with you.
Planning a trip to Portugal? You’re in the right place! Welcome to Travel Planning and Itinerary design by Candy. Olá! I’m an independent travel advisor living in Portugal (since 2016). I help people plan their dream trip to Portugal, Spain and Italy. You’re currently reading a post from my collection of travel guides. I also offer personal travel consultation and a bespoke itinerary service.
Notes from this trip:
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.
This is my original Alentejo Itinerary which I created and followed in 2020. I have since explored the region in much more depth. If you’re focus is on Baixo Alentejo (Évora and south) hop over to my latest Baixo Alentejo Travel Guide for more ideas.
I may well have written this road trip guide in 2020 but I pop in and update it every year so you can guarantee it is still relevant for planning a road trip in Alentejo.
Planning a Road Trip in Portugal
Being on the road is all about freedom and we love that about it, but being able to fully embrace that freedom involves doing some pre-planning first. The more prepared you are before you go, the more time you have to enjoy the experience of being on the road trip.
One of the biggest joys of a road trip is going off-route and making new discoveries, but sometimes it helps to have some places or points of interest already in mind that can help shape your route. When you already have a list or map of options to choose, you’re not left scrambling last minute. This is exactly why I created the Portugal Travel Map.
Portugal Travel Planning Map
The best way to plan your Portugal itinerary is by having all of the options in one place. I’ve created a trip planning map for Portugal with hundreds of pins to help you plan your trip. Need trip inspiration or itinerary ideas? You’ll find everything you need on the map.
WHY VISIT ALENTEJO?
Alentejo is Portugal’s largest yet most undiscovered region. Ever since my first visit I felt Alentejo represents the ‘real’ Portugal and the region where culture and tradition is best celebrated. The region is vast and the landscape changes constantly from north to south. Travel from top to bottom and you can expect mountains and valleys, vineyards and sunflower fields, medieval castles and a wild coastline.
I first moved to Portugal in 2016 but it wasn’t until 2020 I embarked on my first adventure to Alentejo. The 10 day road trip took me deeper into the country and it was this trip allowed me to get beneath the surface of what it means to live in Portugal. It was the trip that launched me into travel planning in a more meaningful way.
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WHERE IS ALENTEJO?
Alentejo is the largest region in Portugal, it spans 31,000 km stretching East from Lisbon to the Spanish border and south to border with Algarve.
The landscape changes from dry, arid rolling plains in the south and into greener and more mountainous areas in the north-east.
HOW TO GET TO ALENTEJO?
One of the frustrating things about this region is the lack of quality public transport. Its inaccessibility, I realise, is also one of the reasons it is still somewhat undiscovered.
To explore here and get beneath the surface of Alentejo you need a car. Either that or a private driver and tour guide. Évora is the exception and is easily reachable in 1h30 from Lisbon by bus or train.
You can hire a car from Lisbon, Faro or Porto (and in some cases Évora) for a very reasonable price. For those of you concerned about driving in Portugal – it is easy, I promise. Outside of Lisbon and Porto the roads are quiet. In Alentejo it is even quieter.
BEST 10 DAY ITINERARY FOR ALENTEJO
This was my first trip to Alentejo. I spent 10 days exploring both Baixo and Alto, moving between the two. Of course, there is still plenty more you can see and do outside of this itinerary, but after almost 5 years of travel in Alentejo I still feel this 10 day itinerary will give you a varied and full experience. As always, I spend weeks of research when planning itineraries for my guests or for myself. I did everything to ensure this itinerary included the perfect mix of medieval hilltop towns, castles, vineyards, cute villages and unforgettable experiences.
Want Beaches? Since I was focused on the interior of the region, there is no coastal stops here. You can easily add on a few days to the itinerary to explore the Costa Vicentina and Fisherman’s trail.
This itinerary is the exact route I took around the Alentejo and includes overnight stays and day trips but you may choose to switch the days around to make it make sense to you. I wasn’t in any rush and hopped back and forth between Baixo and Alto. I drove from Algarve and returned to Algarve. If you are driving from Lisbon or Porto you can switch the itinerary around easily enough. If you only have a short amount of time I recommend basing yourself in central Alentejo and making day trips from Ėvora/ Vidigueira.
You don’t need to follow this route exactly. In fact I recommend you don’t. Use the places and points of interest to build your own itinerary or get a a full map route on the Portugal Travel Map.
MÉRTOLA
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.
VILA VIÇOSA
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.
SERRA DE SÃO MAMEDE NATURAL PARK
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.
CASTELO DE VIDE
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!
MARVÃO
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
REDONDO
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!
ÉVORA
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!
MONTE DA RAVESQUEIRA
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. Located only 5km from Arraiolos and 25km from Évora.
ESTREMOZ
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 | Alecrim
EXPERIENCE | Take a stroll up to the old castle wall and take in the vineyard views.
MONSARAZ
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.
VIDIGUEIRA
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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