We’ve always wanted to visit Portugal but amazingly have never been. We have even sent clients there, but somehow never managed to make it ourselves. I have no explanation, and now that we finally went…I can’t believe we waited this long.

Portugal is beautiful, the people are kind and thoughtful, and the culture is fascinating. More specifically in Lisbon, we loved the architecture, the friendly markets, the many narrow cobblestoned streets filled with shops, restaurants, churches, bakeries, and so much more.

While I could write a book on all there is to see and do in Lisbon, there is enough research and numerous blogs easily accessible on the Internet to help you get a feel for this beautiful country. Instead I’d love to share our photos of some of the most beautiful or interesting places we discovered. I will create additional posts later, but I’ve already waited too long to share these.

Just a few practical tips before I stop. First, we are located in Chicago. Normally, we prefer to fly nonstop, if at all possible. The only airline that allowed us to do this was TAP Airlines. Looking back now, maybe we should have been more flexible, and accepted a stop along the way. The booking process with TAP was incredibly difficult. We had trouble getting the flights we needed, were not able to book our “free” stopover in Lisbon on our way to Madeira, and then could not get through to anyone on the phone for customer assistance.

It took a period of two weeks, and many long wait times (thank you, Ryan, for your patience in doing this!), and many hang ups by the airline staff to finally find someone who could assist us. Even the day of our flight was a bit stressful, because according to the TAP app – our departing flight looked like it had been canceled. But no, it was just a glitch on their app. (Thank you, Steve, for your last minute assistance on this issue!!!).

Once we boarded our flight, everything went well. The staff was pleasant, seating comfortable. We even got our luggage when we arrived into Lisbon – a huge positive, as we were flying during a period when many airlines were losing luggage due to staff shortages. That said, I’m not sure it was worth the hassle of everything we went through prior to our departure. Next time, we may consider flying a more user-friendly airline, even if that means a layover. For full transparency sake, we did talk to fellow travel colleagues (and friends) that had no issues whatsoever with TAP, as they booked a few weeks earlier than we did – so maybe our experience was a one off. I can’t know for sure.

Other helpful tips:

Carry On: We brought an extra carry on bag with a few clothing items and dress shoes we did not want to lose, in case our luggage disappeared for a while. Since we were also attending a conference in Madeira later in the week, we couldn’t really afford to show up without our business attire. I normally prefer traveling light, but not this time.

Apple Air Tags: We invested in four Apple Air Tags with leather cases, and attached each tag to our luggage and carry on. I loved having the ability to see exactly where our bags were at any given time.

Saying Hello and Thank You: The language in Portugal is very different than its neighboring country, Spain. While I have studied Spanish over the years, it is actually easier to pick up Italian with my Spanish knowledge than it is to understand Portuguese. That said, we always try to learn a few of the basics.

• Hello: Ola
• Thank You: If you are a male, you would say “Obrigado” and if you are a female, you would say “Obrigada“. This literally means you feel gratitude, hence the change in gender endings.
• Good Morning: Bom Dia

Wear Comfortable Shoes. While in many European Countries, it is fashionable and preferable to dress up and wear nice shoes, in Lisbon, you’ll be thankful to have on a comfortable pair of walking shoes. Those things that make the city so pretty (the narrow, steep streets and uneven cobblestone walkways) are what also make the streets difficult to navigate on foot, especially if wearing heels. Trust me – you’ll thank me later.

Tickets and Guides: Book tickets in advance, use “Skip the Line” if available, and for special places like Sintra and Peña Palace, do yourself a favor and hire a knowledgeable tour guide. So often we like to explore on our own, but this time around, we were so thankful to have had a tour guide walk us through the Peña Palace. We would have missed out on so many little but important details, had we been on our own.

So…that’s it for now. More later.