I'd been itching to get back across an ocean since the pandemic, so last winter we decided to finally make it happen and hired a travel agent to plan a trip to the Mediterranean. She suggested Croatia, we provided rough parameters and waited for a plan.

After months of no response, we gave a nudge, and I'm pretty sure she just copied and pasted someone else's Game of Thrones themed itinerary and sent it over. wtf? I mean, we've seen the show, but we're not super fans and don't really need GoT tours or private drivers every day of the trip. So, we gave her some feedback, didn't hear back for weeks, and eventually just let her know it wasn't gonna work out.

It was a bummer, but not wanting to give up on a trip, we spontaneously switched it up Portugal, booked flights and hotels in 3 regions, and wound up doing almost no planning beyond that because of our busy schedules. We literally winged the entire trip.

Planes, trains, and automobiles... but mostly, on foot.

Here's how it went.

Porto

Beautiful, romantic, slightly chaotic, old with a rich history, a bit touristy, very walkable, and definitely hilly.

Day 1

We landed around 10am after some smooth flights, but we both slept like shit on the plane, which is never a good way to start a trip with 6+ hours of time change.

Once through customs, we grabbed a Bolt (a European rideshare service) to Vila Nova de Gaia to check in to the Yeatman hotel and were immediately handed glasses of rosé port. Then, we grabbed lunch on the patio, hopped in the pool, and enjoyed the perfect view of downtown Porto.

That afternoon we went exploring on foot, grabbed some snacks, hung in a park, and took the light rail across the Luis bridge to try our first Francesinha - a wild regional "sandwich." Then we walked off the dinner a bit, watched the sunset from the park, and crashed hard.

Day 2

I woke up, slammed my smuggled dewski and then we went to check out the Livraria Lello bookstore. Afterwards, we stopped by a corner cafe to taste our first Pastel de Nata, which is like a little egg custard crème brûlée tart in a flaky pastry. Incredible - especially with cinnamon sprinkled on top.

We then spent most of the day moseying around town, checking out cathedrals, towers, souvenir shops and grabbed a port tonic before cooling off in the hotel pool. After that, we toured Taylor's (Taylor Fladgate) port cellars, which happened to be right next to our hotel and had an incredible dinner at a nearby steakhouse that had another amazing view.

To finish the night, we watched the Portugal v Croatia World Cup game... which was kind of a funny match since we'd originally planned to travel to Croatia with the travel agent, but then spontaneously switched to Portugal after she dropped the ball. The soccer game was effectively us vs our travel agent... so it felt redeeming that Portugal won, haha.

Day 3

We slept in a bit, grabbed a light lunch at this fancy palace turned hotel and took a yacht up the Douro River. Spending the afternoon on a boat, sipping on Vinho Verde, eating snacks, and taking in the beautiful city was very nice. After that, we cooled off in the pool again then walked down to the river for an incredible Minhota style Cod dinner.

Our last night in Porto was topped off with a white port + grapefruit cocktail on a rooftop while watching more of the World Cup.

More photos of Porto ›

Lisbon

Bigger, less touristy, a little grimier, but still beautiful with incredible culture. It felt a little like smashing New York and San Francisco together... in a place with much more history. It was very cool, and I'm wishing we had more time there. I hope to return.

Day 4

After a nice breakfast at the hotel in Porto, we took a train down to Lisbon and checked into Memmo Príncipe Real, which had a wild entrance through a small alley. Once there, we were handed some sparkling wine and once again, cooled off in the pool before heading into town.

The first half of our vacation was unseasonably hot, which put a damper on some things... but thankfully, we had easy access to pools.

That evening we grabbed a cocktail at a neighborhood bar then had an incredible dinner at a little spot called Da Noi. After that, our waiter pointed us to another neighborhood bar, where we hung with the locals, watched more World Cup, and had a blast.

Day 5

We slept in a bit, went to a brunch spot and then spent most of the day just moseying around, shopping, snacking, riding a Tuk Tuk, etc. Later, we grabbed some incredible pizza and then popped into a little spot to hear some Fado music. It was awesome.

Day 6

We'd planned to check out the palaces and castles of Sintra, but due to the heat, the entire forest was closed. So, we just ubered to an incredible beach where we walked, swam, chilled, and enjoyed some mussels for lunch. After that, we swung by a shopping district and headed back to the hotel to get ready for dinner and Portugal's next World Cup game.

That evening we popped into a conservas bar on pink street to have a bunch of tinned seafood served to us while we watched Portugal play from temporary street side TVs. It was a really, really fun evening, despite Portugal losing to Spain.

More photos of Lisbon ›

Algarve

The last stop of our trip. The goal was to take a scenic drive there and spend most of our time chilling on beaches and we nailed it. The coastlines were absolutely stunning, but a bit packed with European families on summer vacation. We did our best to evade them.

Day 7

We woke up, rented a Mini Cooper convertible and took a scenic road trip South. To start, we drove under a wild aqueduct, across their clone of the Golden Gate bridge, past Kung Fu Jesus, along the coast, and took in the incredible views of Setúbal.

One of the incredible views was from this old military fort that was graffiti'd up with some giant turrets and a little eerie. It was pretty damned cool, but Kari didn't like it very much, haha. After that, we popped into a giant local market to check out the wild fish, produce, treats, and grab some lunch and sweets. Then we continued down the A2 highway, taking in the beautifully groomed + pruned countrysides of orchards and cork oak savannas. The drive was very nice. I loved not having slow pokes in the fast lane or billboards crammed down my throat like they are in the US. I also loved how few stop signs and traffic lights there were. Driving in Portugal was a treat in itself.

Once in Algarve, we checked into our hotel (which had an OK view), swam in the pool for a bit, and walked into town for an incredible tiger prawn risotto.

Day 8

We had brekkie and then took the Mini back out to explore the southern coastline and find a beach. The first stop was Praia da Marinha, which was absolutely beautiful with some incredible rock formations... but it was also small, busy and largely covered with seaweed. Kari didn't love it and they wouldn't rent us a kayak unless we had a guide, so we left. This honestly felt like the first big miss of the trip, which isn't bad for having winged it the entire time.

So, we went for another cruise and wound up at a huge beach in Luz, which didn't quite have the same views, but had plenty of space and beautifully clear water.

That night, we walked into town for some Indian food and a sunset before crashing.

Day 9

Our last full day in Portugal. We drove to a giant beach in Portimão and spent the day walking, swimming, snacking, and chilling.

For dinner, we walked to a local Italian spot and had a pretty hilarious American lesson. We noticed that the cocktail menu said Tanqueray, and when gin is listed on a cocktail menu in Portugal, it's often just served as a gin and tonic. However, Kari and I both love a good Tanqueray martini, so we figured we'd try to order one. Kari ordered hers dirty and the guy just looked at her... so she said, “you know. With olives and olive juice.” He was like, “ah! Ok!” ... so I just ordered the same to keep it simple. A couple minutes later, they came out with 2 big glasses of ice and a shot of gin in the bottom. Alongside that was a dish of olives (with pits) and 2 bottles of tonic, haha. We decided to just make it work, so Kari started pulling some of the ice out of her glass and the guy asks if everything was ok. She explained that she wanted, “you know. Like a martini. With olive juice. You shake it up in a shaker with ice.” He was like, “olive JUICE??? Like olive OIL???” Hahah. After trying to explain, he just said, "we do not do that here." and so we just threw our olives into the drink and sipped on iced Tanqueray, hahaha.

To finish the final night, we went back to our hotel's rooftop bar to have a nightcap and watch the sunset over the ocean. They knew how to make a martini there. A vesper, even.

Day 10

We woke up early to enjoy a nice, brisk sunrise cruise back to Lisbon, saw some storks, and flew home.

Hilariously, on the plane they served us Portuguese food and I got another Francesinha. We were also randomly greeted by Dylan and Harper at ORD.

More photos of Algarve ›

Overall...

Portugal's history, culture, landscape, and infrastructure are all awesome
The cobblestone roads and sidewalks are incredible, but can bite ya if you're not careful
Actually, it's not very friendly to folks with disabilities, injuries, or other mobility issues at all
They're much better and more efficient drivers than we are, despite having fewer street signs and less traffic control
The metric system is much more logical, especially when driving
They had many more interesting EV (and fuel) vehicle options that we don't
Restaurants and bars are much more relaxed without the tipping culture
Their nightlife is much richer. Folks eat later and hang out later
Their wine culture is strong, but their beer and cocktail game is weak. Tonic is overrated
Their food is amazing, and a lot of the ingredients make it so.
Their eggs, breads, and baked beans were much better than ours
The way they kept their trees so well pruned, even in the countryside baffled me

It was an incredibly refreshing change of pace and scenery and exactly what I was looking for. We accidentally planned the trip during America's 250th birthday, and I'm glad it worked out that way. I've not been feeling the direction of the US for years and would've been forcing any kind of celebration of it. As such, the timing turned out to be a really nice reminder that we Americans need to get over ourselves. There's so much more to appreciate about this earth and its people.

While there, I kept thinking about Mark Twain's quote, "Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime." It's such a nice way to approach travel and use it as an opportunity to grow...

I want more.