Off the Clock
← The Travel JournalThis 12-day Spain and Portugal itinerary starts in Madrid, heads north by train to Santiago de Compostela and Vigo in Galicia, crosses into Portugal by private car with a stop in Guimarães, then finishes in Porto, the Douro Valley, and Lisbon. Here's exactly how we did it in late May 2026: where we stayed, how we got between cities, the tours worth booking, and the places we'd go back to.
The Route
Twelve Days in Spain & Portugal
Fly into Madrid, take the train up to Santiago de Compostela, drop south to Vigo, cross the border by private car to Porto, then ride the train down to Lisbon. Six cities, two countries, one very full trip.
We landed at 9:55 AM and checked into the Catalonia Las Cortes on Calle del Prado, a quiet, well-located hotel in Barrio de las Letras, within walking distance of the Prado Museum and Retiro Park. We LOVED this hotel and neighborhood and would gladly stay here again! May 24 was a long travel day, so we kept it simple: walk, find lunch, get oriented.
May 25 was a full museum day at the Reina Sofía, and Picasso's Guernica did not disappoint. If you haven't stood in front of his work in person, add it to the list.
On the morning of May 26, before catching the afternoon train to Santiago, we took a highlights tour of the Prado. We highly recommend it: the museum is HUGE, and the tour got us oriented and shared the stories behind key works before we explored on our own. Two major museums in two days is a lot, but Madrid's collections are genuinely world-class, and the Prado tour kept it focused. Worth it.
The train from Chamartín takes about three hours. We departed at 2:40 PM and arrived in Santiago just before 6 — enough time to drop our bags at the Hotel Palacio del Carmen and walk straight into the Old Town.
If you do one thing in Santiago, go to the Praza do Obradoiro first. The cathedral at dusk, with the square nearly empty, is the kind of moment you don't plan; it just happens. From there, drift down Rúa do Vilar into Praza da Quintana and let yourself get a little lost — the side streets are the point.
On day two we took the 7-stop Costa da Morte tour with Galicia Travels (booked via TripAdvisor). Pickup was at 9 AM at the Chapel of the Pillar on Avenida de Xoán Carlos I, and we were back by 6 PM. The coastline is dramatic and remote in a way that's hard to find in Western Europe anymore: historic villages, coastal towns, and miles of wild, rugged shoreline. Worth every minute.
We spent the next morning at the Cathedral itself (go inside — the interior is stunning), wandered the three main squares (Obradoiro, Quintana, Praterías), and made a pass through the Mercado de Abastos before catching the bus for the quick trip to Vigo.
The MonBus from Santiago to Vigo runs about 1.5 hours. We departed around 2 PM and took a taxi from the station to the AC Hotel Vigo — a solid, well-located business hotel right in the city.
Vigo doesn't get much press, and that's part of why it's great. It's a real working port city with a lively waterfront, a proper old town (Casco Vello), and a dinner scene that punches well above its tourist profile.
A military festival was in town for the weekend, with the King scheduled to arrive the next day. We wandered through the festival along the waterfront, hiked up to the castle (Castelo do Castro) for beautiful views over the city, then made our way into the old town around Praza da Constituição. We had drinks in the square while a military band played a concert. Festive, fun, and VERY Spanish.
The next morning a private car picked us up for the drive to Porto, with a stop of a few hours in Guimarães, the birthplace of Portugal. It's a charming town, crowned by the hilltop castle where Portugal's first king is said to have been born. We wandered through the old town, had lunch, then continued on to Porto.
Porto lived up to expectations! We checked into our Airbnb in the heart of the Ribeira district. The apartment was small, central, and well stocked, but it sat on a VERY loud street, so earplugs were a requirement for sleep.
We started by walking up the hill (every day is leg day in Portugal, LOL) and kicked off the evening with a cocktail on the lawn at Base. Then we did a fantastic wine tasting at Dogma Wine Bar, with light snacks for dinner.
The next day we were up early for a full-day tour of the Douro Valley. If you're a wine lover, I highly recommend it. We booked a small-group tour through TripAdvisor that included a stop in a small village for pastry and coffee, a river boat ride, then two tastings: one at a small independent winery and one at a larger winery with a fabulous late lunch. Lunch was so big we didn't need dinner!
The next day was all Porto, on foot. Highlights were Igreja do Carmo, a pork bifana for lunch, a port tasting at A Copo Wine e Tapas, a small wine bar in Gaia, and then sunset on the hillside at Jardim do Morro. Two strong recommendations: do your port tasting at a small wine bar rather than a big port house (it's far more personal), and don't miss sunset at Jardim do Morro, with live music and drinks. It was a highlight of the week! Pizza at La Salumeria afterward was the perfect way to end the night (and amazing pizza).
The next morning we headed to the train station for our final destination: Lisbon.
Lisbon closes the loop. It's a stunning city, highly reminiscent of San Francisco. We checked into our fabulous Airbnb in Mouraria, the old Moorish quarter, and immediately headed down the hill for a tuk-tuk tour of the city to get our bearings. Lisbon is just as hilly as Porto, if not more so, so be ready to use those legs! We had a light dinner at an Asian food court and went to bed early to prepare for a big day exploring the city.
The next day started in Alfama, where we visited the castle (Castelo de São Jorge): fabulous views, history, and peacocks! We wandered the streets of Alfama, browsed the Feira da Ladra flea market (mostly junk, but fun to see), and then stumbled upon a hidden restaurant in an alleyway, O Beco – A Tradição do Bacalhau, where you have to knock to be let in. It was a highly memorable lunch!
We saw a short, informative fado show at Lisboa Em Fado, learned the history of the city at the Lisboa Story Centre, and walked for miles through Alfama, Baixa, Chiado, and Bairro Alto.
The best port tonic (among other great cocktails) in ALL of Portugal is at Bar 1868 in Chiado. And the best ice cream is definitely Santini (look for the red-and-white stripes). Lisbon is a world-class city, and we only scratched the surface, so we're hoping for many more visits.
Take the Renfe high-speed train from Madrid's Chamartín station. The trip takes about three hours, and you can book through Renfe directly or through a reseller like Railclick.
Yes. Vigo is an underrated working port city with a lively waterfront, a walkable old town (Casco Vello), a great dinner scene, and big views from Castelo do Castro. Even one night gives you a good feel for it, and it's a natural jumping-off point for crossing into Portugal.
We hired a private car, which let us stop for a few hours in Guimarães, the birthplace of Portugal, along the way. It turned a transfer day into a sightseeing day.
If you love wine, absolutely. Our full-day, small-group tour included a village stop for pastry and coffee, a river boat ride, and tastings at both a small independent winery and a larger winery with a long late lunch.
Skip the big port houses and book a small, personal tasting at a wine bar. We loved A Copo Wine e Tapas in Vila Nova de Gaia, just across the river from Porto's Ribeira district.
The Alfa Pendular high-speed train connects the two cities in just under three hours.
We covered six cities in 12 days (11 nights), which was full but very doable by train and car. If you can, add an extra day or two in Lisbon. We only scratched the surface.
Six cities, two countries, twelve days — and a long list of places we'd go back to.
And the best port tonic in Portugal? Bar 1868, Chiado.