Our TAP Portugal flight from Chicago to Lisbon was smooth, far better than last year’s forgettable experience on ultra-cheap Norwegian Air. The kids enjoyed the big screens, free headphones, and ample selection of movies, along with the small goody bags they received at the start of the flight. Noah and Emmie slept the most on the flight, but we all managed at least a little sleep on the 7-plus hour flight.

Dinner on our TAP flight included a very mild pasta, chicken, salad with vinegar and olive oil, chocolate mousse cake, roll, and a drink.

We landed in Lisbon just after our scheduled 8:00 a.m. arrival time. After a shuttle bus from the plane’s parking spot to the main terminal, we breezed through customs, collected our passport stamps, and worked our way through the airport to catch a ride to Cascais, the coastal town near Lisbon where we were spending the night.

The first time we arrived in Lisbon, we took a terrifying taxi van into the city. Last year, we used public transportation via the Metro, which was extremely economical but at times a hassle given we were traveling with kids and luggage. This year, we ordered an UberXL, which was probably the smoothest of the three but still not perfect: We had to walk a long way and follow vague app instructions to find the specific Uber pickup spot, and the “non-smoking” van had a pretty heavy smoking smell.

After about an hour on the road, we arrived at the hotel, where our room had been cleaned but was still finishing its inspection. We ended up waiting about 30 minutes in the lobby, but the kids entertained themselves with coloring and writing, and we were still fortunate overall to be settled into our room several hours before the stated check-in time.

Eilidh colored in the hotel lobby while we waited for our room. The colored pencils and small coloring book were courtesy of the TAP goodie bags given to the kids on our Chicago-to-Lisbon flight.

The Sheraton Resort in Cascais felt slightly dated, but we had the perfect space to spread out for our daytime naps. Even the older kids, who absolutely did not want to sleep, managed solid naps in their beds. We wanted to take advantage of the opportunity for much-needed rest to look as sharp as possible for our lone activity of the day: photos with our favorite overseas photographer Rita.

Post-nap and pre-photos, Emmie posed for a photo on our room’s balcony.

Rita had taken our photos in 2017 and 2018, so we were excited she was available to do so again for our 2019 international vacation. We’d planned to have photos taken in Cascais, to stay close to our resort, but a questionable weather forecast led Rita to suggest we take photos in Lisbon instead. We agreed to this suggestion, though it did make our stay at the Cascais “resort” a little less relaxing: a second round-trip into the city of Lisbon added an extra two hours of Uber rides during our 24-hour Portugal stopover.

A collection of stacked and painted rocks made for a fun photo backdrop, on our walk between the Uber drop-off point and Lisbon’s central downtown square.

We started photos in the familiar central square, where Rita surprised the kids with colorful balloons. The balloons yielded some big smiles, and we worked our way down the Tagus River, stopping every few minutes for photos in front of a different backdrop. We ended our journey near Lisbon’s Time Out Market, a place we’d really enjoyed on our previous Lisbon trips.

The older kids were all smiles with Rita and their balloons, at the end of the photoshoot.

We appreciated the smaller crowd at the market than we’ve seen in past visits, as Lisbon is presumably a little less tourist-filled on Monday nights in late October. Eilidh was fixated on ice cream, so we started at Gelados Santini for two scoops of chocolate ice cream and two pieces of O Mehlor Do Mundo Bolo De Chocolate, which translates to “Best Chocolate Cake in the World.”

Amanda and I each ordered fish and chips, while Noah requested a cheese pizza from the Zero Zero stand. He set a new record for pizza consumption, eating six pieces of the Margherita pie. We rounded out our meal with an order of delicious custard tarts from Manteigaria. We ordered another UberXL for the return ride to Cascais, where we tried to get some sleep before another day of travel on Tuesday.

Eilidh started her meal with chocolate ice cream, and finished with fish sticks!

Noah, pre-pizza record.

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