Road Trip In Southern Portugal – Cascais to the Algarve

Road Trip In Southern Portugal – Cascais to the Algarve

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Boca Do InfernoHow I wish we had more time to enjoy Cascais. Though I could appreciate the beauty of the area the night before, waking up to a bright sunny Saturday morning just made it that much better. However we had a three night stay waiting for us in the Algarve, and we couldn’t keep it waiting (I know, poor me, have to go to the Algarve). The Algarve is about a 3-hour drive south of Cascais and our check in was for late afternoon, so we decided to stroll the streets of Cascais for most of the morning before hitting the road.

Boca Do Inferno

We drove to town and then took about a 15-minute walk along the coast to see the Boca Do Inferno (Mouth of Hell). The Boca Do Inferno is a chasm in the sea cliffs along the coast. The waves are quite spectacular when they hit it just right. It’s a pretty cool thing to see, but the ocean kind of stinks here for some reason. We only stayed about twenty minutes. If you’re in Cascais, it’s worth your time to check and and snag a few pictures.

On our stroll back to the city center from the Boca Do Inferno, we stumbled upon a car show. Kendra and I aren’t too into cars, but it was fun to check out what they had there. It was getting close to noon so we figured we’d get Kendra in Cascaissome lunch. We walked up and down the streets looking for a spot to eat and finally decided on a burger booth that was set up next to the beach. We were also able to find a pastel de nata, a Portuguese bundle of goodness recommended to me by my friend who grew up in the area. We sat next to some pretty artful sand sculptures while we ate (see above).

Ponte 25 de Abril

After lunch, we decided we should start our trek down to the Algarve. Not many people know this, but there are actually two Golden Gate Bridges in the world. One of them happens to be in Lisbon. Okay, that’s not true, but it looks like it could be the Golden Gate’s sister. Oddly enough, it was built by the same company that built the Oakland Bay Bridge, but not the Golden Gate Bridge. People often compare the two because they have a similar structure and color. It’s called the Ponte 25 de Abril (April 25th Bridge). The name commemorates the date of a military coup that occurred in the 1970s to overthrow an authoritarian regime. It connects Lisbon to the city of Almada to the south. And we had the privilege of driving over it on our way to the Algarve.Ponte 25 de Abril

The Algarve

We arrived at our hotel in the Algarve around 4 or 5 in the afternoon. We booked a stay for 3 nights at the Hilton Conrad for 210,000 HHonors points that we acquired using various American Express co-branded Hilton cards. This hotel was pretty fancy. Kendra really enjoyed the wood monkey sculptures in the lobby. We got to the room and quickly started looking up places to go eat; we were pretty sure anything cooked in this establishment would be way overpriced. We found a place online called Julia’s Restaurant and Bar. It was right on the beach and we were able to watch the sunset as we ate.

So I have a confession to make. Kendra and I typically don’t go out of our way to interact with strangers. So when the guy sitting alone next to us started asking us questions about where we were from, I wasn’t too excited about doing small talk with him. Little did I know that Roger the Brit (as we now refer to him) would turn out to be one of the highlights of our whole trip. We ended up talking with him for a few hours and thoroughly enjoyed it. We spoke about all the forbidden topics: religion, politics, etc. Keep in mind, this is when Hillary Clinton and Donald Monkeys in the Conrad LobbyTrump were neck and neck for the US Presidential election. So both candidates were pretty easy to poke fun of. But it was nice to know that he was as worried about our country as we were. We discussed his views on Brexit, and the turmoils his country was facing as well. He told us that he has kids who live on both coasts of the United States and he visits often. He has a vacation home in the Algarve and spends a lot of time there. The job that he had retired from took him many places around the world and he told us about a lot of his exciting experiences.

We never asked, but we suspect he’s a widower. After we finished the main course, I got up to go use the restroom, and later Kendra mentioned to me that when I stood up he looked like he was sad that we were leaving. So my sweet wife decided that we would get some dessert to keep him company a little longer. I wish we would have got a picture to remember him, but nonetheless it was an evening and a conversation I will never forget. It was a great reminder to both Kendra and I of another aspect of traveling that we enjoy; seeing the world from other perspectives. We may not always agree on those “forbidden subjects”, but it was delightful to learn from and laugh with Roger the Brit.

Not only was it nice to visit with him, but being a connoisseur of the area, he gave us some excellent recommendations. He told us of a great beach that was pretty much empty if you got up early enough for a good walk. He also told us of the Sao Lorenzo, a church with traditional Portuguese blue and white tile throughout the whole interior. He also gave us some good restaurant recommendations while we were in the area. We took up all three recommendations, which will be posted about later.

Kendra at DinnerNot to get all kumbaya, but I’m glad Rodger initiated the conversation that broke Kendra and I out of our “stick to who you know” attitude. Our journey in the Algarve would not have been as remarkable. We still struggle with this, but that evening at Julia’s makes me want to branch out a little more. I would recommend if you have the opportunity to get to know the local people or other travelers to take it.  You may be lucky enough to spend the evening with someone as remarkable as Roger the Brit.

I’d love to hear any experiences you’ve had connecting with locals or other travelers. Please feel free to leave any in the comments.

10 Replies to “Road Trip In Southern Portugal – Cascais to the Algarve”

  1. Hey Dustin!

    My wife and I love roadtripping! There’s nothing better than just hit the road and see where it takes you 😉

    I’ve been hearing a lot of good things about the Algarve, and that’s a place where I’ll surely will go soon. It looks beautiful!

    Love your travel posts! Thanks for sharing!

  2. Great article and nice photos. After reading your article I feel like I want to go to Algarve and other places in Portugal too.

    Although my dream is to travel all over Spain, now after reading your article, I think that I should also add Portugal to my plan. Thanks again for the great read!

    1. I’ve been wanting to go to Spain as well; it’s definitely somewhere in my 5-year plan.

      Luckily, they’re right by each other so it makes total sense to hit them both in one trip. I’d love to hear about your trip.  Thanks for the comment.

  3. Ahh, the Algarve, I remember it well but have yet to return to this wonderful part of the world. The last time I was there was in 1999 when me and my late husband went to look at the amazing meteor shower the leonids which were particularly spectacular that year. The skies were so dark then, I suspect there may be more light pollution now.
    Thanks for sharing all your adventures in this best part of Portugal. A little bit of politics in the mix was probably a break from the normal holiday highlights. Being British, we too are worried about Brexit. We voted to get out because we want to be in charge of our own destiny and not controlled by Europe/Germany.
    Portugal will always hold special memories for me and I enjoyed my reminiscing.

    1. A meteor shower in the Algarve. That would have been a cool thing to see. Thanks for sharing your experience.

  4. Thanks for sharing this great post Dustin. I know the Atlantic coast in Spain south of Portugal very well from Cadiz down to Tarifa which I love but I have never got further north into Portugal or the Algarve. You have certainly made me curious and another one onto the bucket list!! Thanks again for sharing. Positively, Keith

    1. Hi Keith,

      When I make it back to the Algarve, I’d like to take a road trip down the coast to Gibraltar, and all the way up to Barcelona along the Mediterranean coast. It looks like it would be a wonderful trip. If you’ve got any suggestions for me in the Cadiz area, I’d love to hear them.

      Thanks for the post.


  5. How cool that you and your wife were able to do this road trip! I thoroughly enjoy the open road and getting lost on occasion. I’ve been dreaming of exploring Portugal and possible getting married there. What were your favorite beaches and small towns along the way? What is the food like there and were you able to check out any of the local entertainment?

    1. Thanks for the comment Courtney. There are dozens of picturesque beaches in the Algarve would be a great destination for a wedding. We really enjoyed Praia do Garrao, Praia de Vale do Lobo, Praia do Trafal, and Praia de Loule Velho. Though there’s four names, it’s really just one long interconnected beach. We woke up early and went for a jog and had it all to ourselves.

      Praia de Benagil was great as well. A little more crowded since it’s right next to the famous Benagil cave. But it was a lot of fun and really cool to swim over to the cave. 

      The town of Lagos was pretty cool. And it’s where Ponta de Piedade is located. There are really cool golden like rock formations along the coast with grottos that can be visited by boat tour.

      The food was great. We were able to find anything from typical Portuguese cuisine to Argentine steak houses. It’s a pretty diverse area as there are a lot of tourists from all over the world. English is heavily spoken here as a large portion of tourism comes from the UK.

      I hope you make it there. I’d love to hear about it if you do.

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