The Classic Travel Quandary: Checklist in Lisbon? or Linger by the Sea?

On our recent trip to Portugal we chose to stay in the lovely seaside town of Cascais, 40 minutes outside of Lisbon.  We had a pretty swish HomeAway overlooking the hills and sea of our quaint fishing town.  My favorite part of the home was that we could depart on foot and hike for hours in the hills in front of our house exploring the various trails that criss crossed the cliffs.  At every free moment I had, I set out on those paths.

Those beckoning hills in front of our home.

BUT we were in Portugal and you can’t go to Portugal without seeing Lisbon, right?  Even if you are super comfy in your seaside perch?  “Right, I guess…” I say reluctantly, but sometimes I wonder about the benefits of traveling by a checklist of things to see vs. just traveling to be part of the landscape.

I totally get and frequently succumb to the siren song of that “must see” destination, but what do I remember more fondly?  My tour through the Church of Jerome and it’s “most magnificent cloister in all of Europe”

Church of Jerome

 – OR –

The oysters by the sea at a barefoot beach side eatery that was serendipitously discovered after a three hour one way hike?


Hands down the latter wins the lodged in my memory prize, but I still climbed on the former train the very next day.

Maybe it shouldn’t be an either/or?  Maybe the key to traveling, my travel anyway, is some combination of the two.  Lingering and discovering one day, learning about history, culture and checking things off the list the next day?  Or merging the two in one day?  Or does one scrap tourist stops all together and just strive to live as a local??  This option is blaring in my brain as the way to go, but I don’t think I have the discipline to turn my back on the – “well I am here so I should see these specific sites” mentality!!!???


Perhaps a worthy exercise for us as a family or group is to mentally go back on our various journeys and write down our most favorite and memorable parts of each trip.  Here we could discover patterns about what makes a trip a success or not.  Then, when planning future travels, find the discipline to hold dear to what our memories will most treasure!??

I do know that as we careened through the hills of Lisbon in the comfortable mini van of our tour guide there were many a street and many an outdoor cafe that caught my eye and demanded closer attention.  Lisbon, though sprawling and super hilly, appears to be a town best explored on foot, neighborhood by neighborhood.  It definitely is a town that seems to have mastered the art of the sidewalk cafe and one could spend days trolling for the perfect outdoor perch to sip cafe or some rose.

In our minivan I was more observer than participant, but I was grateful to be zipped around from viewpoint (Cristo Rei) to church (Church of Jerome) to viewpoint (Santa Justa Elevator) to church (Se Cathedral) and again to a view point (Portas do Sol) by our knowledgeable and passionate about all things Portugal driver Pedro.


Maybe the point of our whirlwind tour was to see if we wanted more of Lisbon?  Should we come back?  One person in our group mentioned adding it to her potential places to move to she loved it so much.  I definitely want to go back and log some time on foot and at those aforementioned cafes.  I will most certainly return to Pasteis de Belem for one of it’s delicious sweet cakes as they call it (was more like a custard to me).


I may pop into a church or two for their swooning magnificence. But only if I stumble on by and it catches my eye, not because it is on my list of things to grab my group and go to.    Grab Your Group and GO, but think carefully about how you are going to allocate your time when on the next adventure.  I sure will.


3 Responses

  1. Great point. Great photos too! I’m right now doing mini stops in Asheville Nashville and Memphis and have to decide between stops like Graceland or Civil rights Museum, I think we are going with the latter.

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