This was an ambitious driving vacation that we loved – starting in Madrid and then skirting the coastline down to Lisbon. Very diverse, packed with history, great food!

Days 1 and 2: Madrid

We hit the ground running – thankfully the city is organized, easy to explore (really good public transportation system), and full of interesting people. 

​​We stayed at the *ME Madrid Reina Victoria, and didn’t like it much. Good location, overly hip and not particularly clean.

Favorite Sites

  • ***Sargadelos Gallery (ceramics you can buy) – LOVE this. There are other locations, and it’s worth seeking them out.
  • **Lazarro Museum (open 10-4:30): charming and odd. The guy was a major collector of all sorts of interesting things, from guns to jewelry to fabric.
  • **Biblioteca National – quite grand, free exhibits. Content is hit and miss, but really worth it if you like the subject matter. 
  • **Catedral de la Almudena: the new Cathedral, don’t miss it. The building itself is fairly traditional in style, with clean lines and white stone. The ceiling and apse are an explosion of color – all primaries, very modern design.
  • **Ermita de San Antonio de la Florida (Goya’s grave, church) – open 8:30-1 and 4-8:30: mildly interesting, worthwhile if you’re in the area. 
  • ***Thyssen-Bornemisza Museum – so good! Really worth it, very digestible and a wonderful collection. Worth traveling for. It covers art from about 1600 to the present (earlier work from the collection is at the MNAC in Barcelona) and includes more than 800 paintings. The collection is arranged in such a way that it’s possible to see the development of numerous art styles. The audio guide explains why changes occurred, and also goes into considerable depth about the contributions and talents of individual artists.
  • ***The Reina Sofia Museum: I really enjoyed it, despite the fact that I only liked 2 sculptures and 3 paintings out of the entire collection. Odd. I can’t quite put my finger on why it was still a good experience – maybe the setting? The lighting was great, and the crowds were minimal. 
  • **The Palacio Real: If you’re into palaces, it’s a painless one to visit, and is quite attractive (claims to be the third best in Europe, after Versailles and the Schonbrunn in Vienna). The crowds were nothing like those I battled at Versailles. 
  • ***The Prado: overwhelming in size (here’s a staggering fact for you: the Prado only has room to display about 1,700 of the 19,000 plus works in its collection. Plans are underway to make a space large enough for it all). The Prado is much more specific in scope and artists (I think there were 8 rooms devoted to El Greco, for example), and much more crowded. If forced to choose, I’d definitely say that the Thyssen collection is better.


  • Tapas crawl for dinner (late) – ***Cava Baja Street. This was fun!
  • ***El Club Allard – Excellent meal, very elegant one-Michelin-star setting, pleasant service, creative and delicious food. 10 course tasting menu.
  • **Taberna Angel Sierra: one of the oldest surviving pubs, on a lovely little square that’s perfect for lunch.

Madrid is a great city that feels just right when you visit. This wasn’t our first visit, so we were able to focus on new sites. I’d recommend spending at least 3-4 days in the city if it’s your first time, and doing one museum a day, rather than packing them all in and risking brain overload. 

Full Madrid notes here.

Day 3: El Escorial, Valley of the Fallen, Segovia

After a very difficult and time consuming process of picking up our rental car at the airport, we toured all three of these sites. It was doable, the distances are short.

***San Lorenzo de El Escorial (45km north-west of Madrid) is very grand and impressive, on the world’s best libraries list. Avoid weekends if you can and allow 2-3 hours for your visit. The library is spectacular, as is the huge cathedral. There are numerous rooms of art, including multiple El Grecos. Everything is labeled in English. If your time is limited, this is a better choice than visiting the royal palace in Madrid.

The controversial but astonishing ***Valle de los Caídos basilica is at the end of a peaceful valley in the San Lorenzo de El Escorial municipality. Conceived as a memorial to those who died in the civil war, it houses General Franco’s remains (or did). Built with the labor of political prisoners, it is an uncomfortable but awe-inspiring experience. We found it creepy, almost empty, and extremely impressive.

Segovia is a wonderful overnight. It’s crowded during the day, but if you arrive in the late afternoon you’ll have a wonderful time exploring. Check out the aquaduct, the church, and the Alcazar. One night is plenty, a full day would be too much.

We stayed at ***Hotel Infanta Isabel, which we really liked. Classic and a great location. Old fashioned. Dinner was at ***El Bernardino, Cervantes No. 2. Very good, with outdoor seating.

Full posts for El Escorial, Valley of the Fallen, and Segovia.


Day 4: Segovia > Pedraza > Burgos > Bilbao

Pedraza is tiny and charming, a historic walled town – not worth spending the night, but a worthwhile lunch break if you’re passing by. It’s about 40 minutes from Segovia. We peeked in La Taberna de Don Mariano (the oldest bar in Spain, why this was on our radar), and had an excellent, rather formal lunch at ***La Olma de Pedraza.

Stop 2 was Burgos, a big town with a historically important, huge church. We were underwhelmed, not a must-see. 

Bilbao is probably worth seeing. I didn’t love it, it felt very unsafe and grungy, and for that reason this was a perfectly long enough stop. Food was fairly bad. The **Bilbao museum (the architecture at least) is wonderful. We stayed at the unremarkable *Miro Hotel.

This was a classic case of having a long-ish drive to do and trying to invent interesting stops along the way. Nothing was particularly standout, though our lunch in Pedraza was quite good. If I was to do it again, I’d consider making the central stop in Valladolid to see the Museo Nacional de Escultura.

More pictures of Pedraza here.

Days 5-6: San Sebastián, Day Trip to Saint-Jean-de-Luz

San Sebastián is really charming – spend at least two days. Rent bikes, eat a lot, go to the beach. We stayed at **Hotel Villa Soro, which was nice, but I’d select somewhere more central to stay (by the beach).


  • ***Bar Egosari, one of our favorite pintxos bars.
  • ***Restaurante Arzak: remains one of the best meals I’ve ever had. Not super “fancy”, retains a homey feel, but perfectly executed.

We drove north on the second day to see Saint-Jean-de-Luz, a pretty little town (where Galen studied abroad).

We did this by accident – *Le Petit Train de la Rhune, a historic railway line. There’s also a Petit Train de St. Jean, which we originally set out to do. Not particularly worthwhile unless you’re into traveling by train and want to see the mountains. It’s similar to other areas we saw by car.

Saint-Jean-de-Luz felt like an afterthought – I’d recommend exploring it in more depth as part of a different, more France-oriented trip, and allow more time to enjoy San Sebastián.

Day 7: Basque Country Small Towns

This was one of my favorite days of the trip – if you like dramatic views and winding roads, this is exceptional country.

We stuck to the coast from San Sebastián, through Getaria, and on to Gaztelugatxe.

Getaria has some of the world’s great seafood restaurants. The turbot at ***Elkano, caught in the bay, grilled outdoors and served whole, may be the best we’ve tasted. *** The Cristóbal Balenciaga Museum was truly excellent. Go out of your way to visit. I’d definitely spend a night next time.

The island of **San Juan de Gaztelugatxe is dramatic – many will recognize it as the island fortress of “Dragonstone” from season 7 of Game of Thrones. The island is connected to the mainland by a man-made stone bridge and a very long staircase that I remember being fairly punishing on a 100 degree day. It’s worth a stop if you’re in the area.

After a detour to Santander (a family-friendly beach destination, didn’t seem worth the effort and I wouldn’t recommend as a stop), we made it to Santillana del Mar for the night. It claims to be “one of the most picturesque villages in Spain”. It’s cute, easy to explore on foot. Difficult to drive in. We didn’t find it particularly differentiated from many other locations.

It’s next to the (real) Altamira caves, which we didn’t make it to. After learning that you tour the fake version, we decided to skip the whole experience. In town, there were a variety of sites we checked out (the unremarkable Museum of Torture being one), but nothing seemed like a real must-do.

We stayed at **La Casa del Organista Santillana. It was nice enough, friendly owners. Dinner was at **Los Blasones, which was quite good. Eat on the patio and order beef (what they’re known for).

Spend a night in Getaria! It was gorgeous, and it’s turned into quite the foodie destination. Also see Day 8 – Comillas could be a good alternate overnight stay.

More on the history of Gaztelugatxe here.

Day 8: A Long Driving Day

The roads of Spain in the North are generally lovely, scenic, and well maintained. A few highlights as we drove towards Santiago de Compostela (about 6 hours in total driving):

Comillas: another beach town, with a large pretty beach within walking distance of the town centre, a Friday morning market of fresh produce in the main square, trendy night-time bars and some beautiful historical buildings, including the impressive neo-gothic Sobrellano Palace and Gaudí’s’ El Capricho. It was bigger and more dynamic, probably a better choice than Santillana del Mar for an overnight stop.

Oviedo: The palaces and churches in the surroundings of Oviedo have a unique architectural style, neither palaeo-Christian art nor a feature of Carolingian art. These churches, which are basilical in layout and entirely vaulted, and which make use of columns instead of piers, have very rich decors which contain Visigothic references, Arabic elements, and shapes that associate them with the great sanctuaries of Asia Minor. We visited **Santa María del Naranco (converted from an older house around 1000 AD) and the Jesus statue on Mont Naranco, and had a great lunch with apple cider sangria and pork from furry pigs at **Ristorante Vista Alegre. The town below was large and not the most attractive, covered in a thick layer of smog.

Oviedo deserved more time, it’s interesting, but we felt a bit rushed. (more pictures here). Not sure I’d recommend it on a repeat of this itinerary.

Day 9: Santiago de Compostela

A major destination, and not one that we particularly loved. Two nights was too much. Gritty and a bit chaotic. I think you need the weight of a long journey to appreciate it, rather than just driving there. We did really enjoy sitting in the central square and watching the pilgrims arrive at the cathedral, navigating the pickpockets was less entertaining.

The **Parador de SANTIAGO DE COMPOSTELA (aka the Hostal dos Reis Católicos) was worthwhile, and including a not-great meal with lots of lovely company, hearing about the journeys most of the other people had been on. The Hostal first saw life as a Royal Hospital in 1499 to house the many pilgrims arriving in Santiago. Considered the oldest hotel in the world.

I wouldn’t go so far as to skip this entirely, but just one night is more than enough.

Day 10: Guimaraes > Duoro Valley > Porto

The historic town of Guimarães is associated with the emergence of the Portuguese national identity in the 12th century, “an exceptionally well-preserved and authentic example of the evolution of a medieval settlement into a modern town.”

The shell of the **castle of Countess Mumadona Dias, considered to have been the most powerful woman in Portugal in the 10th century, is about a five-minute walk above the center of Guimarães. Next door is the far better preserved 15th-century palace of the **Dukes of Bragança, now a museum.

We enjoyed lunch and a few hours exploring the town. It’s a good stop on the way to somewhere else.

The rest of our day involved navigating the Duoro Valley, and trying to find wine tasting. It’s not California (or wasn’t), and tasting rooms just didn’t seem to exist. Pretty, but exhausting day. Next time stay at one of the Duoro “wine hotels” to make it work.

Further notes on Guimaraes here. Other options we considered, but didn’t make it to, included Ourense (“one of the finest bridges in the whole of Spain,” Cathedral which dates back to 572) and Baiona (where the Pinta landed, bring news of the new world).

Days 11-12: Porto

We loved Porto, and its zombie apocalypse vibe. It was nearly empty, with buildings crumbling and a nearly dark skyline. The tile is amazing, food was okay (not much open), and it’s a great manageable city to walk around. Two days was leisurely.

We stayed at *Castelo Santa Catarina, a B&B-style place, walking distance to town, in a 200-year old castle. It was fine, though in a neighborhood filled with prostitution – mostly men. I would stay on the east side of the river.

The port houses of Porto aren’t actually in Porto. They’re across the river (a 5-10 minute walk) in Vila Nova de Gaia. Just over the iron-trellised Ponte Luís I bridge (which may look familiar in style, as it was made by a partner of Eiffel) there are over a dozen port houses that open their doors for free or low-cost tasting.

We went to Sandeman’s (quite interesting) and Graham’s, and discovered we prefer Ruby Port.

This trip was over 10 years ago, and I’d really like to return – Porto appears to have made a major turnaround, as a major tech center and destination for younger worker (expats and Portuguese).

More Porto notes here.

Day 13 – Alcobaça, Óbidos

Another rather pleasant driving day, as we made our way south towards Lisbon. The **Cistercian Monastery of Santa Maria d’Alcobaça is a masterpiece of Gothic Cistercian art, famous for its funeral sculptures. It is quite lovely, and surrounded by a huge open square lined with cafes. A great lunch stop.

We’re not convinced our stop for the night (Óbidos) was entirely worth it. This town is the most perfectly preserved 13th-century village in central Portugal. For 600 years, Óbidos was the personal property of Portuguese queens, a symbolic love offering from their adoring husbands.

It’s very pretty, fun to walk the walls, and specializes in historical costume events. Had a very family friendly focus, and without kids we felt rather out of place. We ate at the “fancy” restaurant in the castle (**Posada do Castelo), not amazing but a good experience.

Stay in the old town. We opted for *Casa d’Obidos just outside, and it was too country for our taste, lots and lots of bugs that made being outside difficult.

Notes on Alcobaça here, Obidos here.

Day 14 – Sintra

Sintra was a highlight of our time in Portugal – not only because of the wonderful B&B we stayed at, the ***Villa Mira Longa. Wonderful hosts!

We could have used more time, but loved the modern castle scene.

**Castelo dos Mouros: In the 19th century, the monarchs ordered that this castle, evocative of the Moorish occupation of Portugal, remain as a ruined ornament to embellish their sprawling parks and gardens. Set near the much larger, much more ornate Pena palace, the squat, thick-walled fortress was begun around A.D. 750 by the Moors and captured with the help of Scandinavian Crusaders in 1147. It retains its jagged battlements, a quartet of eroded towers, and a ruined Romanesque chapel erected by the Portuguese as a symbol of their domination of former Moorish territories. There was a lot of excavation during our visit (restoration related), but we liked this for the views regardless.

***Palácio Nacional de Pena: Only a cosmopolitan 19th-century courtier could have produced this eclectic, expensive mélange of architectural styles. Set in a 200-hectare (495-acre) walled park, it was commissioned by the German-born consort of the Portuguese queen; it reminds some visitors of the Bavarian castles of Mad King Ludwig. Appointed with heavy furnishings and rich ornamentation, it’s a symbol of the Portuguese monarchs in their most aesthetically decadent stages. This was Wonderful too – grand, elegant, great crowds, amazing views. It’s packed with people – go early and don’t try to walk from town, it’s a big hike.

The ***Quintada Regaleira was Galen’s favorite. The house in cool, but the grounds themselves are unreal – groats, hidden passages, sculptures, you name it. We could have stayed all day. Far less crowded than the other sites, and right be our hotel.

***Tacho Real was the best meal of the trip (leaving aside Michelin star destinations). It’s tiny, easy to overlook, but seek it out.

Sintra deserves 2 days, this was too rushed.

Days 15-16: Lisbon

Lisbon wasn’t our favorite destination. It felt more complicated than necessary, with transportation consistently frustrating (the city streets were under a lot of construction). Ditch the car as soon as you arrive, this is not a good driving city. I hoped for more of a view, but it’s not the most attractive city.

We stayed at the **International Design Hotel: a perfectly fine option, actually better than expected. Central, clean, large room, with parking (though getting to the parking wasn’t easy).


  • Both the **Mosteiro dos Jeronimos and **Torre de Belem, though worth a stop, are underwhelming and crawling with tourists. The Mosteiro library was closed for renovations (a multi-year process). We did enjoy the bus ride to Belem however – a good way to see the waterfront.
  • Near to both, the **Monument to the Discoveries is very cool, and overlooks the (fake, unimpressive) Golden Gate Bridge. The shade of red is wrong and the proportions are all odd.
  • The ***National Carriage Museum stands out, we had low expectations and loved it.
  • The funicular to the higher parts of town was entertaining
  • The Aflama isn’t particularly picturesque (especially after Porto).
  • Skip the *Castelo de Sao Jorge – it’s expensive, and the view isn’t great.

We should give Lisbon another try. I think it suffered from my usual “big cities just don’t work at the end of a long trip” problem.

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