DAY 1-2

The first thing I like to do when I arrive in a new city is a bike tour. There’s something about the feel of the wind on my face, the sounds of local people on the streets going about their day, the smells (and yes, not all of them are good and that’s ok), and the backroads not accessible by car that makes the city come to life for me…. Which is how we found ourselves on e-bikes a mere 4 hours after our overnight flight landed in Lisbon at 9am yesterday.

We biked the narrow, labyrinth-like streets of the Alfama neighborhood passing old men on stoops smoking cigars, laundry billowing from clotheslines outside second-story windows, and old churches every few blocks. Our guide introduced us to local cuisine at tiny hole-in-the-wall places we never would have found ourselves. And to top it all off? We finished the tour at a small juice shop doubling as a bar and celebrated our arrival with Portuguese cocktails, including shots of Ginjinha….essentially cherry syrup liqueur served in a chocolate shot glass (which unfortunately triggered our jet lag sending us to bed, without dinner, at 8pm!)

A good 12 hours of sleep later, we were off for another tour of Lisbon, this time on foot. At the slower pace, we could really appreciate the old architecture and bright colors of the city and unique things like elevators that take you from the bottom of the hill to the top (I could have used one of these as I climbed the two blocks of stairs to high school in San Francisco every day!!!!)

Have you ever eaten a barnacle? No? Neither had I until tonight! The verdict? It’s like eating rubbery seawater. Not great. Now the langoustines? Those were delicious! Portugal is known for its fresh seafood and tonight did not disappoint.

We even got to meet up with our Bay Area friends, Rachel and Carnet, who are now living in Portugal, this morning over breakfast 🙂

Tomorrow, we are off to see the castles of Sintra!


I learned today that there are castles and then THERE ARE CASTLES! Just a mere 45 minutes outside of Lisbon, in the small town of Sintra, the Palacio de Pena definitely falls into the second category with its bright reds and yellows, accented by brilliant blue mosaics and gray stone. It’s something you might find at Disneyland, except in this case, real life kings and queens used to lived there!

What makes Sintra so special is that everywhere you turn, there is another castle/palace, each in its own style. I’m not really an architecture buff, but even I was impressed! None are as spectacular as Pena, but Quinta da Regaleira had a cool well we climbed down which is a first for me!

Did you know that the Western-most point on continental Europe is found in Portugal? I didn’t, but now I do! And I can officially say that I have stood at said point, Cabo Da Roca, and admired the view. It’s pretty crazy to think that hundreds of years ago, people thought that it was the end of the world!

As we wrap up Lisbon, I wanted to give a huge shout-out to our guide Gui. A guide can make or break a trip and he was awesome. I’d highly recommend him to anybody planning a trip to Portugal!

What’s next? Tomorrow we pick up our rental car and head North to the Douro Valley, a wine region known for its spectacular scenery and good wines.

DAY 4-5

I think we can all agree that I prefer off-the-beaten-path experiences. Today was no exception as we bumped along in our 4×4 jeep down steep, rocky, dirt roads winding through “quintas” (wine estates) and small villages in the Douro Valley region in the North. Not another tourist in sight. My kind of day!

We arrived at our B & B quinta last night having driven from Lisbon, with stops in the medieval walled city of Obidos and the surfing town of Nazarre, famous for its huge waves (though there aren’t any this time of year 🙁). Fresh seafood abounds in Nazarre, so we found a place and ate one of their specialties, fresh sardines. The jury is still out on whether we really liked them or not!

As most of you know, I’m not a huge drinker… But I’m certainly discerning enough to know a good wine from bad…. I live 45 minutes from Napa Valley after all! But I had no idea wine production was so big in Portugal or that its wine region was so spectacularly beautiful. Whereas Napa is mostly flat with some rolling hills, Douro Valley is characterized by 2000+ foot mountains with rows of vines crisscrossing steep slopes and the Douro River winding through the middle.

We spent an underwhelming hour on a boat going up and down the river, followed by a delicious lunch at a local spot where one of the dishes was cod, which is a staple in any Portuguese diet. The irony? In Portugal, cod is not only imported, but it is salted and preserved, then reconstituted by soaking in water for a few days before cooking it up. Suffice it to say, we much prefer the fresh seafood we’ve enjoyed so far!

A visit here wouldn’t be complete without some wine tasting which we did at a small local winery in our guide’s the village. Now I have to figure out how to pack the two bottles of wine I bought to bring home 🙂

Tomorrow, we leave this region and go off the grid in the medieval village of Talasnal, one of many “Schist” villages in the Lousã mountains. Along the way, we will stop for a few hours in the town of Porto.

DAY 6-7

Fortunately, we only had one accidental crash into a ditch yesterday (and no, it wasn’t me…haha). How did we get there?

Well, if you really want to do the road less traveled when visiting Portugal, a visit to the 13th century villages on the slopes of the Lousã mountains in the middle of the country is an absolute must on your itinerary. There are 27 tiny villages, the simple homes built into the hillside using schist, a slate-like stone. Each home has been handed down from generation to generation, many restored and turned into Airbnbs, which is how we got to stay in the village of Talasnal (pronounced TalaSHnal).

Our Airbnb was at the end of a narrow alley. It was rustic and quaint and totally my kind of place….narrow stairs winding down to the kitchen from the small living room…and another set going up to the bedroom. Low ceilings and small windows with shutters look out onto the village. It’s truly mind-boggling to think that people have lived here for over 800 years! I’ll admit, we were grateful for the updated plumbing and electricity!

You can hike from village to village, but why hike when you can bike, right? So, off we went on cool mountain bikes to visit 6 of the 27 villages, each with its own personality, but all characterized by narrow alleys and lots of stairs leading this way and that. And that’s how Krysten found herself in a ditch. To be fair, it was a steep and very rocky road… tough conditions for even the most experienced bikers. Fortunately, she was totally fine and a total trooper for doing an activity that was not really in her comfort zone (though I think she has seen the light and might actually bike while on vacation in the future!)

As you know, I love my plan B and they seem to happen a lot in my travels. Because it started to rain in Talasnal and wasn’t forecasted to end, we decided to cut our losses and left a day early for our last stop, the Algarve on Southern coast of Portugal. We arrived late last night and are looking forward to exploring the area known for its beautiful coastline.

DAY 8-9

When my alarm went off at 4:55am this morning, I seriously questioned my sanity in booking a sunrise paddleboard activity. Krysten passed on the idea, so it was just me. But, I’m certainly not questioning my sanity anymore after having a truly magical experience.

The coastline between Praia da Dona Ana and Ponta da Piedade is characterized by towering, orange sandstone cliffs with large pinnacles jutting dramatically out of the water. Natural arches and caves are abundant and totally accessible by paddleboard.

Most people do this activity later in the day and what they miss out on is the quiet beauty of the place…. The sun slowly rising over the horizon casting an orange hue on the rocks, the birds calling to each other as they fish, the quiet of the ocean without the tourist motorboats to disrupt things. With the exception of one other paddle group and a fisherman collecting his crab pots, we didn’t see a soul. The icing on the cake? Three dolphins at the very end! If you find yourself visiting the Algarve region, I highly recommend this activity whether you are an experienced paddle boarder or not!

Yesterday, we visited the most famous site in this region, Benagil Cave. It is huge with two arched entrances, a good sized beach inside, and an enormous hole in the top. The problem with a place being so beautiful is that it brings in the hordes. That’s why I decided to padddleboard elsewhere this morning. But we still couldn’t miss seeing this cave. So yesterday, we hopped on one of the many speedboats, and spent the next 45 minutes driving into and out of caves along the shore, including Benagil (which is indeed impressive).

Since tonight is our last night, we decided to celebrate it by enjoying the sunset “at the end of the earth”, the southernmost point in Portugal. The setting was beautiful with more dramatic cliffs. The clouds and actual sunset? Pretty underwhelming…. But the potential is definitely there!

It’s been a whirlwind 9 days of travel and Portugal did not disappoint. It’s such a diverse country and easily accessible by renting a car. Without a doubt, I’d love to return and for those wanting to go, I’d love to help you plan your trip!

Check out my travel video from Portugal!