TL;DR

Dublin Airport

• Eat/Drink
  • Fallow Kitchen and Bar, Terminal 2, Dublin Airport
    • Airport bar and restaurant with less than great service, but great views! Check out this video to see.
• See/Do
  • T2 Lounge, Terminal 2, Dublin Airport
    • Use your Priority Pass to get in for free (otherwise it’s €30 p/p online or from €35 p/p payable at reception) – nothing to write home about here, but we found a small private room at the far end away from reception which was great for the kids to hang out in.

Carvoeiro, Algarve

• Stay
  • Villa with Swimming pool and Tennis court, 14-20 Rua de Vale do Milho 2 8, Carvoeiro, Faro 8400-564, Portugal
    • A beautiful and large home, excellent for hosting a large family gathering. The tennis court is old and cracked, but the pool is lovely.
• Eat/Drink
  • Sal & Tal, Pestana Palm Gardens, 8400-525 Carvoeiro, Portugal
    • Found this place on Google (a 10-15 minute downhill walk from our place) – and it sits inside a resort called Pestana Palm Gardens. They accommodate our large group at an outdoors table and food was decent!
  • Nosolo Italia, Praça Manuel Teixeira Gomes, 8500-542 Portimão, Portugal
    • This place hit the spot after a long day on the water, and was a short 10-15 minute walk from where we disembarked after the pirate ship cruise.
  • Recanto Dos Mouros, Estr. do Monte Branco, 8300-034 Silves, Portugal
    • A bit outside of the Carvoeiro area sits Silves, a charming little town with a couple of castles and nearby attractions. We found this gem of a restaurant and enjoyed a lovely meal of fish, stews, rice, and of course we tried the iconic sardines for which Portugal is famous.

• See/Do
  • Rock&Reel Land Based Fishing Adventures
    • If you come to the Algarve and don’t go out on the water to do a little fishing, you are missing out on something that will leave memories for a lifetime. We spent a few hours out on a smallish boat, the staff was super helpful in setting everything up (I had never fished before), and you can keep everything you catch (or give it to the fishermen). They depart from the Marina de Albufeira.
  • Portimão: Pirate Ship Cave Cruise, 8500-702 Portimão, Portugal
    • Board this ship in Portimão and prepare for a lovely experience on a decently sized ship. You’ll sail out past lighthouses and islands, eventually passing cute beaches that you may want to spend more time at later on. At one point, they ask if you want to explore the water caves (I highly recommend it) and will transfer you to smaller motor-powered boats to take you into the caves. Make sure you bring your hat, sunglasses, water, and snacks!
  • Castelo de Silves (the Castle of Silves), R. do Castelo, 8300-135 Silves, Portugal
    • I didn’t join the family while they ascended the castle steps, opting to chill out in the car and read. But from what they shared, this is definitely worth seeing!  There’s also an Aldi grocery store nearby so if you need to reload on groceries, that’s your best bet!

Sintra

• Stay
  • Villa das Oliveiras, Estrada de Janas 1223, 2710-265 Sintra, Portugal
    • Our lovely vacation home, affectionately called “Casa das Oliveiras” on the outside, was great for a big family. Lots of bedrooms, a big pool, long hallways for kids to run down, and a decently sized kitchen. It even had a formal dining room which we didn’t really use – but could have!
• Eat/Drink
  • Café Central de Janas, Largo Visc. da Asseca 4, 2710-253 Sintra
    • Charming little shop for pastries!
  • Aldea Coop, Largo Visc. da Asseca 6A, 2710-277 Sintra
    • Stop here and load up on groceries.
  • Padaria da Carlota, R. da Ponte N 4, 2710-277 Sintra
    • Bread. Bread. And more bread.
  • O Melhor Croissant da Minha Rua,  Largo Afonso de Albuquerque n15c, 2710-568 Sintra
    • Grab a snack (ideally a croissant) here if the weather is warm!
  • Pinga Doce Sintra
    • A convenient grocery store right in the middle of Sintra.
  • Barmacia, R. Fernão Magalhães 8, 2705-315 Colares, Portugal
    • We did not actually get to eat here as we had a big group with strollers and this place is narrow and tiny. But it smelled fantastic and the menu looked amazing – with spectacular sea views looking down onto the ocean.
  • Restaurante Neptuno, R. Bartolomeu Dias, Colares, Portugal
    • This restaurant feels touristy but you cannot beat the beachside location.
  • Kebabish, Largo Afonso de Albuquerque 9, 2710-572 Sintra, Portugal
    • Our stop amidst a particularly warm day – and I just wanted a simple snack. Thankfully this place delivered!
  • Gelato Della Linea, Av. Heliodoro Salgado 19, 2710-575 Sintra, Portugal
    • Need a mid-afternoon ice cream pick-me-up? Then here you go!
• See/Do
  • Vasco da Gama Bridge
    • You’ll cross this bridge coming back from the Algarve and pass Lisbon, en route to Sintra. Enjoy the view!
  • Parque Infantil Portela De Sintra (Portlea de Sintra Children’s Park)
    • Great place to let the kids play!
  • Parque infantil da Praia das Maçãs (Children’s playground at Praia das Maçãs)
    • We let the kids run around here before dinner at Restaurante Neptuno.
  • National Palace of Pena
    • MUST. SEE. PERIOD.
  • The Moorish Castle
    • ALSO MUST SEE.

Lisbon

• Stay
  • Hyatt Regency Lisbon, Rua da Junqueira 65, 1300-343, Lisboa, Portugal,
    • Where we stayed the first night before driving down to the Algarve. A standard guest room with a couch and king sized bed can easily fit a family of four. We errantly thought it wouldn’t and booked two rooms with our Hyatt Cat-1-4 free night certs, and basically wasted one of them. This hotel was LOVELY. Modern, spacious, with kitchen and fridge for each room. Views are stunning (although our rooms looked into the courtyard). Breakfast was EPIC – service was excellent. Although finding the front entrance of the hotel was oddly difficult.
  • Marriott Homes and Villas – STUNNING 2BR APT W/GARDEN, BY THE AVENIDA SUBWAY & BOTANICAL GARDEN OF LISBON, R. do Salitre 1111250-198 Lisboa, Portugal
    • Our first time booking on Marriott Homes and Villas. Nice location and proximity to the botanical gardens, walkable to a lot of things, and very quaint. Backyard in theory was nice but was overgrown and nothing like the pictures. The company that manages the property (Altido) set us up with groceries (we had to pay) and welcomed us warmly, but when we communicated problems (water damage and mold in unit, no garbage bags or paper towels, and an ant infestation), they went radio silent on us. They eventually offered a 20% refund, which we accepted, but very unfortunate way to experience both Marriott Homes and Villas and Altido for the first time
• Eat/Drink
  • Instant Crunch, R. da Mãe de Água 9, 1250-154 Lisboa, Portugal
    • LOVELY outdoor back patio dining area with excellent food and wine.
  • Gin Lovers Bar and Restaurant, Praça do Príncipe Real 26, 1250-184 Lisboa, Portugal
    • Do you love gin? Then you come here after dinner at Instant Crunch or just come here in general.
  • Pasteis de Belem, R. de Belém 84 92, 1300-085 Lisboa, Portugal
    • There’s a takeaway only side on the left – otherwise you can enter the right side for table service.
  • Ni Michi Cocina Latina, LX Factory – R. Rodrigues de Faria, 103 Edifício I, Espaço 0.01, 1300-501 Lisboa, Portugal
    • Latin Cuisine with a subtle Asian flare. We got chips and guac as a snack, and their happy hour Aperol Spritz and Margarita are €5 each! We also had their tasty tuna tartare.
  • Chickinho Lx Factory, R. Rodrigues de Faria 103, 1300-501 Lisboa, Portugal
    • Kind of a fast casual place with fried chicken
  • Le Petit Café, Largo São Martinho, 1100-537 Lisboa, Portugal
    • We sat down here for a light lunch on the way to one of the viewpoints and were blown away by the quality of the food. Cooper and Clemmie both ate my arroz de polvo (octopus rice), which was excellent, and Caitlin had a tasty sliced salmon + crème fraiche meal.
  • NoNo HK, R. da Vitória 69 71, 1100-618 Lisboa, Portugal
    • If I find a Chinese restaurant slinging beef chow fun in any city I go to, I am stopping there. The noodles could have been cooked a bit longer (they were a bit too chewy) but this was tasty – and if I lived here, I’d eat this often!
  • A Ginjinha, Largo São Domingos 8, 1100-201 Lisboa, Portugal
    • We’d heard about this place and randomly stumbled upon it. Get in line, order one shot of the famous cherry liqueur per person (€1.5 per shot), and watch it get poured into a small shot glass with the brandied cherries. Sip it or shoot it. Eat the cherries. Take the sting of the alcohol or the sugar (or both). And continue on your merry way.
  • Flores de Pampas, Praça das Flores 18, 1200-332 Lisboa, Portugal
    • Couve Flor Braseada – roasted cauliflower, watercress and goat cheese, oyster mushroom, and cured egg yolk. Damnit it was good.
    • Bochechas de Porco Preto – Pork cheeks. the pomegranates and he gravy shouldn’t work together. But they do. 
    • Escabeche de Carapau Frito – imagine a fish sauce-like broth. Slightly sour. Slightly sweet. Perfectly cooked fried horse mackerel Japanese style escabeche with pickle, mushroom, and vermicelli. The light breading is perfect. Get this.
    • Tartare & Tarascon – Raw beef, herbs, raw egg yolk, toast. Tasty.
    • Pair these with a couple glasses of wine (really any wine) or the rosemary negroni and you’ll be in a good place.
  • Jamie’s Italian Lisboa, Praça do Príncipe Real 28A, 1250-184 Lisboa, Portugal
    • Jamie Oliver’s Lisbon outpost was a welcome treat especially after I lost my sunglasses at the Botanical Gardens 😭
  • Betania Restaurante, R. Camilo Castelo Branco 4, 1150-084 Lisboa, Portugal
    • First impressions: not good. Tookus a half hour of walking to try to get into this place as it both sits inside a building plaza that is NOT accessible to strollers or wheelchairs (once we found the entrance, we had to lift the stroller up and down a couple flights of stairs). Once inside, it was empty – literally.
    • But once we started ordering, we got to experience some good food and wine. And the service – it turns out the team that runs this place left Afghanistan years ago and set up shop in Lisbon. We didn’t eat anything Afghan but I loved meeting the folks who worked here. Also super generous wine pours haha.
  • Royal Donuts Portugal, R. Alexandre Herculano 7B, 1150-005 Lisboa, Portugal
    • Last night in Lisbon meant grab some desserts for the kids that would double as breakfast for our early flight out the next day. Yum!
• See/Do
  • 25 de Abril Bridge
    • This is the stunner that evokes memories of the Golden Gate Bridge in my hometown of San Francisco, CA. Both of these bridges use the same color (international orange) and along with the Bay Bridge in San Francisco were all built by the same company (the United States Steel Export Company) – all of this info courtesy of the bridge’s wikipedia page!
  • Jerónimos Monastery, Praça do Império 1400-206 Lisboa, Portugal
    • Stunning building and great location to explore nearby
  • Belem Tower, Av. Brasília, 1400-038 Lisboa, Portugal
    • Definitely a tourist trap but the views of the bridge and the water are outstanding
  • Jardim da Torre de Belem (Park across from the Belem Tower), Av. Brasília, 1400-038 Lisboa, Portugal
    • If it’s a hot day, head across the street from the Belem Tower and just rest in the grass. There are vendors nearby selling bottled drinks, and this could be a really cute spot to picnic!
  • LX Factory, R. Rodrigues de Faria 103, 1300-501 Lisboa, Portugal
    • This is a MUST SEE destination – an old factory refurbished with charming restaurants, bars, boutiques will have something for everyone. Check out Ler Devagar for books!
  • Ler Devagar, R. Rodrigues de Faria 103 – G 0.3, 1300-501 Lisboa, Portugal
    • Two levels with a super industrial feel and metal steps/ladders to ascend. A coffee shop. A record section. Lots of awesome stuff to be found here.
  • Miradouro de Santa Luzia, Largo Santa Luzia, 1100-487 Lisboa, Portugal
    • One of the many viewpoints of the city – not as great as I was hoping, but it’s right near the Lisbon Cathedral and the Castelo de Sao Jorge, so if you’re already in the Alfama neighborhood, check it out. The vines have grown (compared to this pic) so you get some shade from the oppressive heat and sunshine.
  • Lisboa Story Centre, Praça do Comércio 78, 1100-148 Lisboa, Portugal
    • If you’re in Lisbon when it’s hot, this is a worthwhile destination if only to get out of the sun and heat. But it’s also a very interesting look into the history of Lisbon – and the exhibit on the famous earthquake of 1755 that flattened the city is super interesting (especially being from San Francisco myself). 
  • Praça do Comercio
    • This is the image you’ll see in a lot of guidebooks or in travel show videos focused on Lisbon. The gorgeous Rua Augusta Arch anchors the plaza and welcomes you to either head north into the charming shopping areas or head south toward the water.
  • National Museum of Contemporary Art
    • We stopped in here since it was included in our Lisboa Card benefits and wound up stepping into a really intriguing exhibit on Veloso Salgado, a Portuguese artist who lived from 1864-1945 and whose ability to capture detail is striking.
  • Soma Ideas Gift Store, R. dos Fanqueiros 98 100, 1100-232 Lisboa, Portugal
    • A nice contrast from all the crappy wares being sold at every tourist site, this charming shop features local artists and craftspeople’s’ work. We bought several souvenirs here!
  • STRÓ Flagship Store, R. Nova de São Mamede 66, 1250-173 Lisboa, Portugal
    • Portuguese apparel store that specializes in linens and wool. Definitely not cheap, and you get what you pay for. I bought a lovely linen shirt for the summer season. There’s also two other STRO shops around the corner from here.
  • Botanical Garden of Lisbon, R. da Escola Politécnica 58, 1250-102 Lisboa, Portugal
    • Right behind our house (literally), this was a wonderful natural respite from the urban jungle. Lots of places to walk, to take in nature – and sadly for me to lose my sunglasses. 😦

Trip Background

I remember where I was when we bought these tickets – we were sitting in the Kona airport back in 2022, awaiting our flight back to the American mainland and we pulled the trigger on what is probably the most expensive tickets we’ve ever bought. And these were just coach tickets! We happened to settle on the end of June in Portugal, which apparently is the high season when all of Europe goes there on holiday.

This was a trip Caitlin and I had wanted to take for awhile but it was actually Caitlin’s sister (Casey) whose family committed first. Therein followed discussion around the whole of Caitlin’s family going – her parents committed next, as did we, and we did not know whether or not CJ (Caitlin’s brother) and his fiancée Daosamay would join us until a few weeks before we all were scheduled to fly.

The months lead up to this trip to Portugal were honestly some of the most stressful ones I’ve ever had. I was a new manager, working through a lot of work problems that culminated in a late night trip to the ER a few weeks before this trip. Most of the family expected me to weigh in more on planning but I was so burned out that I had minimal input relative to how I normally plan for trips.

When the time came for this trip, I was just relieved to be not working for a couple weeks! And thankfully this trip gave me several opportunities to not think about work.

Day 0 (June 16, 2023): Transit

Our day 0 began with our nanny Lauren giving us a ride to airport – which worked out super well for all of us. We put the money in her pocket instead of some random driver and it made it easier to leave the car seats in our car until we arrived at O’Hare.

The experience of getting through security was substantially more difficult than all of our previous flights. It took us nearly thirty minutes to get checked in because Precheck closed the moment we got there. We were definitely not used to the non-precheck experience (removing shoes, laptops, etc.) while also dealing with the kids.

From there we settled in at the Admirals Club before boarding our flight to Dublin. Now I don’t remember very much from the night because having little kids fly across an ocean on a redeye flight usually means you don’t sleep much. And this was definitely the case for us.

Day 1 (June 17, 2023): Dublin and Flight to Lisbon

We landed in Dublin at 11:15 AM and got through customs easily. Knowing we had a long layover, we went to the T2 Lounge through (Priority Pass). This is one of those situations in which I am so thankful to have lounge access. We got in, grabbed ourselves a coffee and a snack, and at one point a private room opened up at the far end. We rushed in, set ourselves up, and I even managed a half hour nap which I desperately needed.

We explored Dublin Airport (the last time we were in Ireland was in 2015!). As the kids were getting a bit peckish, we decided to sit down at Fallow Kitchen and Bar, which oddly has no website that I could find but has this video on their Instagram page.

After a leisurely meal in which both kids passed out, we boarded our flight to Lisbon where Cooper and Clemmie both struggled mightily to be comfortable. Upon landing in Lisbon, everyone was so friendly that it momentarily shocked me. An agent directed us to the service line reserved for workers, we got our (many) bags quickly, and then we went to the rental car desk where Tiago at National Can Rental was super helpful. It took us a bit to find the car itself (we made the mistake of taking the wrong elevator). After righting ourselves and going to the second floor of next building, we loaded the car like movers packing a big truck and thank goodness everything barely fit.

Here is an important lesson for parents traveling to Europe with small kids: buy a lighter, travel car seat for your kids, if that is an option.

We brought Cooper’s heavy Diono car seat which is normally anchored in the minivan and it was both huge and heavy. Add that to Clemmie’s car seat (which is slightly smaller and lighter but neither small nor light), and all the gear we needed for two weeks, and you have the makings of a car absolutely packed to the gills.

We drove to the Hyatt Regency Lisbon to spend the night before driving down to the Algarve, and I am so glad we did. I made the mistake of booking two rooms when one would have been more than enough for all four of us. The rooms at the Hyatt Regency Lisbon are VERY spacious, and I didn’t need to use two room certificates, but I did enjoy having a bed all to myself. Also we ordered some late night room service as we were starving – so we had a burger, an omelette, some fries, and a bottle of Beaujolais.

Day 2 (June 18, 2023): Drive to the Algarve

Upon awaking in the Portuguese capital, we experienced what will go down as one of the best hotel breakfasts I’ve ever had. Let’s start with the stunning view from the ground level (when you step outside of the restaurant) – seeing the 25 de Abril Bridge in full daylight really can’t be beat.

We had a sumptuous breakfast with excellent service and then packed up and drove to the Algarve.

The journey by car is a relatively easy two and a half to three hour journey and upon our arrival at our shared house, I was very pleasantly surprised by how big the house was. My sister-in-law found the Villa with Swimming pool and Tennis court on Airbnb, and while the tennis courts were in run down shape, the house itself was lovely for a big family trip.

As we settled in and got unpacked in our room (Caitlin and I shared two double beds with the kids), we started to discuss how to get something for dinner. We first opted for some afternoon swimming before venturing from the house and exploring the area around the house. We headed nearby to Sal & Tal, a restaurant that I found on Google (which was a 10-15 minute downhill walk from our place). It sits inside a resort called Pestana Palm Gardens, and to my surprise they accommodated our large group on virtually no notice, seated us at an outdoor table and food was decent!

Day 3 (June 19, 2023) – Life on the Sea

Our first full day separated a few of us from the rest of the family. My mother-in-law Tina, father-in-law Craig, my sister-in-law’s husband Jack, Jack’s son Cedar and I decided to head out on the water and do some fishing with Rock & Reel Land Based Fishing Adventures. I hadn’t really had a proper fishing experience since my childhood (if you count my wonderful dad trying to show me how to fish en route to Reno, and getting the fishing line stuck in branches that hung over a small river, then abandoning said effort). We drove from our Airbnb to the port of Albufeira, grabbing some pastel di nata near the loading area while we waited for our fishing cruise to begin.

I wound up catching a decent number of fish but nowhere near as many as my nephew who had the time of his life. I’m not actually sure but this company might also have been called Fishandwish but regardless of who took us out, we caught white sea bream and enjoyed a lovely morning on the water!

We returned home for lunch and the family had put together a cheeseboard for snacks, followed by some light tennis on the house court. I wish the court had been in better condition but it was still cool to have our own private court!

After some time to rest, we drove to Portimão to board the Portimão: Pirate Ship Cave Cruise that Casey had reserved for us. While we waited to board the ship, a wildly drunken women was stumbling around the dock waiting to board. We all collectively rolled our eyes as she staggered to keep her balance. The Santa Bernarda pirate ship was super comfortable, with a bar/snack shop on board, and the water was calm all afternoon. We sailed out past lighthouses and islands, eventually passing cute beaches that I would love to have spent more time at.

At one point, they asked us if we wanted to explore the water caves (I highly recommend it) and transferred us to smaller motor-powered boats to take us into the caves. Make sure you bring your hat, sunglasses, water, and snacks!

Upon disembarking, we ate a light dinner at Nosolo Italia, which included my future sister in law bringing over ginjinha, the infamous Portuguese cherry liqueur drink – which was terribly sweet and strong. Thankfully in Lisbon later in this trip, we would confirm what good ginjinha would taste like!

That night after most of the kids had gone to bed, Jack grilled up the fish we had caught on the fishing cruise and it was so delightfully flaky and delicious.

Day 4 (June 20, 2023) – Transition from Algarve to Silves then onward to Sintra

In the morning, we packed the cars and started our day by driving to the Castelo de Silves (the Castle of Silves). If you’re looking for a good place to park, check out this ping I dropped: https://maps.apple.com/?ll=37.193458,-8.436747&q=Dropped%20Pin&t=m

I got super introspective as I hung out in the car while the kids, Caitlin, and her sister went up to the castle, and wrote this passage:

“What does it mean to be fully present? To do only one thing? To be in the moment, aware of your surroundings, grateful for your surroundings? While my family decided to go to the castle, I chose to sit in the car because I didn’t feel comfortable leaving a car full of our stuff in a parking lot. But the silence and tranquility of being by myself, the ability to read at my own leisure, and a fresh hot cup of coffee made me incredibly appreciative of and aware of the moment I was in.”

When the fam returned, I made a quick dash over to a nearby Aldi grocery store, buying Trader Joe brand hot dogs and very nearly buying this ice cream sign before we departed. We stopped for lunch at Recanto Dos Mouros in Silves, which I consider to be on of the finds of this trip. Grilled sardines amongst other fish, stews, and rice made for an outstanding meal, all served in a charming outdoor courtyard.

After our meal, we drove three hours to Sintra, crossing the Vasco da Gama Bridge (we’ll come back to this in the Lisbon section), before finally arriving at Villa das Oliveiras.

Now finding this place was a bit of a challenge, as the street address the hosts sent us didn’t bring us where we needed to go. Once they helped us navigate and came to welcome us in, we had our first “Holy shit” moment of the trip.

The vastness of this property, the splendid views of the National Palace and the Moorish Castle (admittedly from a distance), the presence of old olive trees that had been on the property for over a hundred years – it all made the place seem surreal. The hosts even left us a nice welcome basket with wine, snacks, and fruit. Because we arrived before everyone else, we got settled in the basement to make it easier for everyone else to figure out which rooms they wanted. I heated up some frozen pizzas I’d bought at Aldi to feed the kids and us, and the rest of the family arrived a few hours later.

Day 5 (June 21, 2023) – Initial Exploration of Sintra and sunset dining on the Atlantic

The first morning in Sintra was decidedly relaxed. A few adults, awake relatively early, took on the responsibility of going into town to pick up pastries and snacks from  Café Central de Janas, Aldea Coop, and Padaria da Carlota. Because I didn’t go with them, I can’t attest to the smells and wonderful sights of the food available, but I did get to eat a bunch of them when they were brought back to the house. The kids seemed to be quite satisfied with their choice of pastries as well.

(brief digression: if you only have one day in Sintra, have a look at this article which served to provide some inspiration for our plan: https://embracesomeplace.com/one-day-sintra-itinerary/)

We drove into Sintra, where it became quickly obvious how much of a cluster parking is. We hoped we could uber but we didn’t know how to handle the car seat situation and didn’t want to be lugging them around with us all afternoon. In retrospect, driving was the right call and we got lucky in finding two spaces next to the Parque Infantil Portela De Sintra (Portela de Sintra Children’s Park). It was actually great for the kids to get some energy out and once they’d played for awhile, we decided to take a walk through Old Town Sintra (before the castle day the following morning). The walk revealed the beautiful architecture of the area, a plethora of souvenir vendors, and no shortage of snacks and those gorgeous Portuguese tiles. We made sure to get an ice cream to cool us all down in the heat and then as the day was winding down, we made two stops: the first at O Melhor Croissant da Minha Rua for a croissant and a coffee, then at Pinga Doce Sintra for groceries.

From Sintra we drove out to Praia das Maçãs, a charming beach down northwest of Sintra. While we waited for the others to arrive, we let Cooper and Clemmie play at the Parque infantil da Praia das Maçãs (Children’s playground at Praia das Maçãs), where a large set of play structures served to entertain the kids of many families while also providing a stunning sunset view of the Atlantic Ocean.

We had originally hoped to eat dinner at Barmacia but after waiting for a table, it became obvious that we wouldn’t be able to fit our strollers into this place. Deeply disappointed and hungry (the smells here were absolutely lovely). We thus retreated before deciding to descend down the beach to eat at Restaurante Neptuno. This place gives off touristy vibes but you really cannot beat the location within a rock’s throw of the sandy beach. The sand served to occupy the kids while the food was being prepared. As for the foot, it wasn’t bad – but I think you can do better in this area!

Day 6 (June 22, 2023) – Sintra Castle Days

(if you want a dedicated article on the Sintra bus 434, read this article)

So this was the big day. We got up later than I would have liked and drove to Sintra, finding parking a healthy distance from where we needed to get to. We hiked up to the train station, alternating who pushed the stroller while the other one carried a backpack that one of the kids could have stood in (in retrospect that was a silly thing to do but we weren’t sure what we needed). We bought bus tickets for €15 each to get us up the the palaces and castles and decided to let two regular sized buses pass, then a small one, and then got onto the fourth one where the station attendant helped us nab the handicap seat (as we had the stroller).

Here is where we our faith in humanity was restored (first of several instances on this trip!) by Portuguese thoughtfulness. We get off the bus and inside the main gate of the National Palace of Pena before realizing we have to either ride one more bus (we weren’t going to be able to fit the double stroller on) or hike up the hill on foot. So we start huffing it up on foot, worried we weren’t going to make our entrance time of 10:30 AM. As we start getting closer to the start of the main line to get in, we show our ticket to one of the attendants and they direct us to the middle (in between one long ass line to go up and one line of people descending). They tell us because we have the stroller and kids that we can cut the main line. So like VIP’s we bypass the long line, showing our tickets, and get inside!

We had to park the stroller and take the kids in on foot because there are a lot of steps, but we were just fine with that arrangement! At one point, Cooper randomly took the hand of a woman in front of us who we thought might have been a princess or celebrity (she was super glamorous looking). She smiled and laughed as Cooper held her hand, then once we could persuade him to let go, she wished us well. I think Cooper is just practicing his flirting skills – he won her heart over quite easily.

The palace is simply gorgeous from the outside with its gray stone and yellow painted exteriors juxtaposed against red walls and purple paint elsewhere. The inside provides some lovely historical context, a reminder of the luxuries the royal family must have had at the time, and much needed shelter from the hot Portuguese summer sun. We explored the grounds of the area for a couple hours before heading toward the The Moorish Castle.

Now whomever told us you could do the Moorish Castle with a stroller was a complete idiot.

Or maybe no one told us that and I just made it up – making me the idiot.

But clearly this is a place not meant for little kids. Caitlin took a quick glance inside the gates, then decided she would stay back with the kids while I explored the Moorish Castle. I scrambled in, racing through and up to the top of one of the peaks and back to the front gate in 40 minutes.

At this point, it was nearly 3 PM and the kids were getting tired, so we started descending from the Moorish Castle on the bus back down into Sintra. We passed by Kebabish and I asked to stop for a snack, getting a doner kebab and fries before we stopped at Gelato Della Linea to get Caitlin and the kids some ice cream.

At 4:50 we returned to the house where we discovered we had been locked out of the house. We could get into the compound, but there was only one key to the house and one of the other family members took it (and had locked a door they shouldn’t have). Caitlin and the kids swam while we waited for either the family member with the key to return or for the host to bring a backup key – the latter happened first, thank god. While the kids splashed their way to happiness, we discovered snails everywhere in the yard and I ate my kebab before leaving it on my bag (while the door was being opened). I returned to my kebab under siege from a bunch of ants…no more kebab 😦

Day 7 (June 23, 2023) – drive to Lisbon

The time came to finally split up – for Caitlin, the kids and I to break off and head into Lisbon while the rest of the family stayed in Sintra for a couple more days. We gassed up the car and spent the morning at Praia da Adraga, which was a lovely beach. I was very pleasnaltly surprise by how nice the beach was.

Our drive to Lisbon was relatively quick and easy. This was our first time using Marriott’s home rental platform, which which subcontracted out to Altido, a company that has seemingly merged with another platform called Joivy. Having this not be run my Marriott was a little awkward, especially when Altido was less than responsive around some customer service elements. But getting into our home, rented through Marriott Homes and Villas, was super easy as a staff member welcomed us and helped us move the luggage into the apartment.

After we unloaded the car, Caitlin and the kids got settled while I returned the rental car to the Lisbon airport. If you do this, know that the garage is a pretty tight fit and hard to navigate. We had a BMW stationwagon and I felt like I was going to scrape the doors on the walls on more than a few occasions.

Once that was done, I picked up our Lisbon cards at the airport before taking an Uber (tesla) back to our house (which cost me an astounding €11.65 and might be the cheapest airport ride I’ve ever taken).

After returning to the house, we decided to explore the area around our apartment and wound up perusing a charming set of local vendors selling art and wares. I bought a cool piece with a quote from the famed Portuguese poet Fernando Pessoa: “para viajar basta existir,” which means “To travel, you just need to exist.”

Brief digression: the quote is part of a longer piece, which is worth reading:

Our wandering took us from street to street and eventually to a restaurant called Instant Crunch. Now if that name doesn’t conjure up images of a romantic or charming Lisbon restaurant in your mind, I wouldn’t blame you. But this place was so incredibly lovely that I cannot convey the charm even with the photos and food descriptions. First off, we wheeled the stroller in through a narrow restaurant and into the back courtyard area, covered with a lovely pergola and anchored by a pair of trees. Each of the dishes we ordered was sublime, from the sardines to the meatballs, stuffed peppers and stuffed mushrooms we ate. The kids enjoyed the food too!

Our post-meal ambling led us to Gin Lovers Bar and Restaurant and turned into a mini date night as both kids passed out – so mom and dad got gin cocktails and a nice view to end our first full day in Lisbon!

We returned to the apartment with both kids crashing hard and noticed the first major issue with our home away from home: water damage on the walls of the bathroom. There will be more issues the rest of this trip, but we’ll save those for the next few days. Now, time for sleep.

Day 8 (June 24, 2023): Exploring Lisbon

We began our morning by boarding Bus 727 and heading for Pasteis de Belem, the famed bakery serving their eponymous pastries. Hint: there’s a takeaway only side which will save you a lot of time. We bought a sleeve of tarts and I immediately inhaled one before handing them out to Caitlin and the kids.

We stopped for coffee before heading into the Jerónimos Monastery for a tour of this gorgeous structure. This place is known for holding the tomb of the famous explorer Vasco de Gama, but the design of this structure is what makes this place worth visiting.

From there we walked toward the Belem Tower, another iconic place to check out. We did make one pit stop at Nosolo Italia (same chain as the one we stopped at in the Algarve) for a gelato to cool the kids down. But thew Belem Tower served as another example of Portuguese hospitality for visitors who clearly are handling tiny kids. Once we got inside, one of the staff told us we could cut the line to go up the tower, which we gratefully accepted. You don’t need to go up the tower to get great views of the 25 de Abril bridge, but they get better and better the higher you go!

We took a few minutes for an impromptu rest in the Jardim da Torre de Belem (the park across from the Belem Tower) under the shade of a large tree before using a walkway to walk over the main road and to get on the light rail toward the LX Factory. While we waited, I bought the kids a cup of sliced fruit (which they annihilated) and the sunshine was particularly rough on this day.

Caitlin and I agreed that the LX Factory remains one of the highlights of this trip. An old industrial facility repurposed with 50+ shops and restaurants, this place is ABSOLUTELY worth visiting for a meal, to buy books, or to purchase a classy Portuguese outfit.

The bookstore I mentioned was Ler Devagar – a two story shop with a super industrial feel and metal steps/ladders to ascend. There’s also a coffee shop inside, along with a record section and lots of awesome stuff to be found here.

We also stopped at a sticker store, ate lunch at Ni Michi Cocina Latina (Asian fusion – including chips and guac, tuna tartare, and beverages), and picked up some snacks from Chickinho Lx Factory. Honestly if you don’t at least come here to check it out, you’re missing out!

We took the bus back to our apartment, where another issue with the space came up: the outside. Take a look at the listing (which is not on Marriott anymore, but instead is on Altido’s site). The backyard looks well kept and clean – but when we arrived, the grass was all dead and the trees overgrown. Sigh. The interior space (minus the water damage) was lovely but I think places need to just ensure their photos match the spaces – and that includes the outside spaces!

Day 9 (June 25, 2023)

Note to self (and to all of you): Pasteis de Belem should not be eaten after the first day. That perfect texture is gone. This was our morning breakfast lesson, learned personally.

Our morning continued with a lovely walk and culminated with Caitlin buying a hat she loved (and still wears often). Our intended destination was a placed called Dear Breakfast, recommended by several friends. Sadly the line to get in was too long and there was no takeaway section for us to even get a coffee. There was also a little attitude from the staff so we elected to go elsewhere.

We came upon a place called Le Petit Café and not knowing anything about the place, we decided to stop as it was lunchtime and we were all getting hungry. This was yet another BRILLIANT discovery that we lucked into. We peruse the menu and Caitlin gets this salmon, toast, and salad combination which looks great. The kids naturally don’t love the salmon and they crush a plate of fruit. Then to my surprise, Cooper starts motioning to try my arroz de polvo (octopus rice). It’s this subtle, beautiful dish that I can still taste if I concentrate hard enough on the memory. And Cooper doesn’t often deviate from what he knows or is familiar with, but seeing as we can’t have American bacon for every meal, he’s willing to try something else.

He takes a bite. Then another. Then another. It makes me so happy to see him try something new. All while there’s a guitar player in the background serenading us with lovely music. If you come to Lisbon, this needs to be on your list of places to dine.

Following lunch, we started walking up to the Miradouro de Santa Luzia, one of several gorgeous places to view the water from in the Alfama section of Lisbon.

If you’re in Lisbon when it’s hot, taking an hour or two to visit the Lisboa Story Centre is a worthwhile way to get out of the sun and heat and also learn more about the history of Lisbon. The exhibit on the famous earthquake of 1755 that flattened the city is super interesting (especially being from San Francisco myself).

The Praça do Comercio is the image you’ll see in a lot of guidebooks or in travel show videos focused on Lisbon. The gorgeous Rua Augusta Arch anchors the plaza and welcomes you to either head north into the charming shopping areas or head south toward the water. But like some tourist destinations, once you see it – that’s it.

We stopped at the National Museum of Contemporary Art since it was included in our Lisboa Card benefits and we wound up stepping into a really intriguing exhibit on Veloso Salgado, a Portuguese artist who lived from 1864-1945 and whose ability to capture detail is striking.

I think contemporary art isn’t my bag, but I am still glad we came here. You learn so much about the culture and history from the museums in the places you visit – and this is something I try to honor in every place I go.

I asked Caitlin if we could stop at NoNo HK for some beef chow fun – which is one of my traditions when we travel. I have to find the local Chinese restaurant, if they serve Cantonese food, and find the staple beef chow fun dish which is my favorite food in the world. I also use it as a measure of comparison – how is the chow fun in Ireland vs. in Portugal vs. what I can get at home in San Francisco or in Hong Kong?

Nearby, we discovered Soma Ideas Gift Store, a charming artisan marketplace with cute souvenirs and designed items. We bought some cups, magnets, and then decided it was good to head home. As we started walking back to our apartment, we came across a plaza and a small shop called A Ginjinha, and it finally struck me. This is the iconic place for a shot of that cherry liqueur we’d had on the beach in the Algarve. I knew it was a bit of a tourist trap, but I had to at least try it. You wait in line, and for €3, you get two shots of ginjinha, served in small glasses. Each comes with several ginja berries (cherries) that have been steeping in alcohol, water, sugar and cinnamon, and this having this drink here was like having a proper scotch compared to a rail bottle of shabbily made whiskey. It was sweet and flavorful, and eating the cherries with the drink made it feel less mass produced (even if it was).

We took a brief rest at home before deciding to get some dinner at Flores de Pampas, which was a recommendation from my friend Marlo. Our first impressions of this place were very positive – you walk in and descend into effectively a garden level restaurant with tall ceilings, gorgeous lights, clean stone floors, an array of plants which make the space feel more alive, and herringbone tiles lining the underside of the bar. The server brought Clemmie some paper and a bunch of pens/markers so she could color, which was super thoughtful of her. The kids were pacified with a screen, freeing Caitlin and I up to have a nice meal and drinks, which included:

-Started with four oysters with their homemade slaw (yesss)

-Couve flor braseada (roasted cauliflower) – damnit it was good

-Rosemary Negroni

-Bochechas de porco Preto – the pomegranates and the gravy shouldn’t work together. But they do. 

-Escabeche – imagine a fish sauce-like broth. Slightly sour. Slightly sweet. Perfectly cooked horse mackerel with a light breading. Vermicelli.

-And ended with beef tartare.

We hiked ourselves uphill back to the apartment and set up for a lovely slumber.

Day 10 (June 26, 2023)

Our last full day began with breakfast at the house. I had passed by this boutique called STRÓ Flagship Store, a Portuguese apparel store that specializes in linens and wool. Definitely not cheap, but you get what you pay for. I bought a lovely linen shirt for the summer season.

We then walked to the Botanical Garden of Lisbon, which sat literally behind our apartment (the wall behind the yard is on the side of the garden). This is a great place to escape to, or to be in nature for a bit after spending a lot of time in touristy areas. Somewhere inside or around the garden, I lost my ray ban sunglasses and proceeded to spend a half hour retracing my steps and looking at every sidewalk, every shop entrance, and every store I’d been to that morning.

Defeated, the fam and I stopped at Jamie’s Italian Lisboa (Jamie Oliver’s outpost) for some Italian comfort food. After some pizza and pasta plus some cheese and meat, we returned to the apartment to get some packing done and rest from the heat.

That evening, Caitlin found a place called Betania Restaurante, whose website features a lot of self-aggrandizing promotion. I’m glad a restaurant believes in their product (“serving the most delicious and exceptional Portuguese food in the heart of Portugal”) but in retrospect seeing this description is a funny contrast. It took us a long time to find this place, as it sits inside an office building courtyard that is not accessible (we had to carry the stroller up a few flights of steps), and when we did find it, half of the place was dark and it was completely empty.

When the staff finally emerged, we had our doubts if this was going to be the right place to dine, but we decided to give it a chance. The food wasn’t bad but the service was outstanding. Our servers were very friendly and welcoming despite our inability to speak good Portuguese. After we finished our meal and started walking back, we passed Royal Donuts Portugal and decided to pick up some breakfast since we were leaving really early the next morning. Now given it was 7:45 PM, they didn’t have as much variety as we would have liked, but we got enough to placate the kids and grown ups in the morning.

Day 11 (June 27, 2023)

The end is nigh. We woke up at 3 AM to get ready for the car, which was due to arrive at 4 AM. Our Uber van arrived at 4 AM and we packed the van to the gills with our car seats and gear.

We got to Lisbon airport in short order and checked our bags. I will definitely appreciate having the kids not need car seats and diapers as they get older. I mean, look at the cart I pushed with all of our gear while Caitlin pushed the stroller with both kids?

Oh – remember how I told you Portugal is incredibly welcoming to families? Well, everywhere we went, we got treated well or passed to the front of a line. Again, this is a small thing but it really does make our journey easier. We proceeded to the ANZ lounge for waters and coffee and then had the unfortunate issue of having to check our stroller at the gate (and being told we couldn’t get it back til Chicago). This led to a tough transition at Heathrow, where connection was/is/always will be a huge pain. I lost my Fellow coffee mug (heard it clang when it fell and couldn’t spare the time to look for it) as we hustled through terminal. We got to gate with a few minutes to spare before boarding. The flight home from London was decent, but here is where the end of our trip sours.

We land at O’Hare and it turns out that our car seats and one of our bags were left behind at Heathrow. I could even see it on my FindMy app 😦 We submitted a report to American and the roughest thing was imagining how we would get the kids home without the car seats. Thankfully our nanny was picking us up and was able to get us a backup car seat, but we didn’t have use those two car seats for several days. In the end, American refused to compensate us for losing our bags and car seats, which irritated me to no end – but sadly I didn’t have any power to mandate compensation.

Final Thoughts

And so ended what was otherwise an incredible journey to Portugal. The kids’ first trip out of the United States. Our first international trip as a family of four. The first time Caitlin and I had been out of the country since before the pandemic.

Portugal is a magical place, and I only wish I’d been able to see Porto. Lisbon is a must visit for everyone, as is Sintra. I liked the Algarve but I think it merits more time if you plan to go, given the driving time from Lisbon down south.

Perhaps it’s a tenet of Portuguese culture to be so relaxed and to have proper work-life balance. But for whatever reason, I found myself deeply attracted to Portugal and what it represents. Part of me wishes I could apply for that Golden Visa program that just underwent major changes last fall, but sadly I didn’t have the required funds to invest in Portuguese real estate projects. But what I know is that this will not be the last time I go to Portugal.

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Unrelated final thoughts:

I realized I should have brought a number of items which would have made the trip better:

• Dash cam: Some folks tell me this is overkill but so is insurance…until you need it.
• Ice backpack: We went to the beach or the pool so often and keeping drinks and food cool is so critical under the scorching summer sun.
• Freeze-able ice packs: See the item above.
• Bottle sleeves: If you want to bring vino verde back, you need to be able to protect those bottles from breaking.
• Small flask: Sometimes you just want a drink.
• Beach shoes: Helps to navigate the beach and rocks!
• Camelback (at least the water reservoir): Hydration in Portugal in summer is not joke.
• Chip clip: If your kids eat chips (and let’s face it, whose kids don’t?), bring a chip clip. Helps avoid bugs and stale chips.
• Stasher bags: We love these silicon bags for holding food, whether it’s chips, a sandwich, candy, or leftovers in the fridge.
• Power strip: Helps when charging gadgets.
• Alexa device: If you have a home base for even a few days, you can use a small Echo device. The trip made us realize how often we turn to gadgets for time, weather, directions, etc. Of course now that I write this I realize how ridiculous this sounds.

There were also some critical lessons learned on this trip:

• Just use Uber instead of Welcome Pickups – someone recommended we use this local service, and I’m sure it works well – but if you already use Uber, why wouldn’t you keep using it?
• Don’t go through Heathrow if you can help it – pretty self explanatory. Transferring from arrivals through customs and to the international departures area is a huge pain.
• If you are part of a group trip, and someone asks you what you want to do (for dinner, as an activity, that evening, the next day), don’t say “I’ll do whatever everyone else wants to do.” When you have a group, this kind of response doesn’t help. Say what you want, otherwise whomever wants to do something will get his/her/their way.