Spain & Portugal – December 2025/January 2026
December 27, 2025 – January 4, 2026
Nine days, two countries, and two proposals – separately timed and perfectly understated. I road-tripped through Spain and Portugal with my cousin and his now-fiancée, looping through castle towns, seafood capitals, and some very strong rain systems in Galicia. It was just after Christmas, which meant Spain was still decked out for the holidays and easing into the Three Kings Parade. We made it through six UNESCO sites, several medieval walls, a few foggy lookouts, and one New Year’s Eve race. We never missed a siesta. We did miss the parade. Fair trade!










Day 1 – Madrid & Toledo, Spain
- Madrid Arrival – Landed early morning after an overnight flight from CHA through ATL and powered through jetlag with a walk and caffeine
- Plaza Mayor – Still lit up with Christmas lights and packed with market stalls selling crafts, and seasonal snacks
- Mirador del Valle (Toledo) – Scenic overlook with a panoramic view of Toledo’s old town
- Historic City of Toledo (UNESCO Site) – Former capital of Spain with a rich blend of Christian, Jewish, and Muslim history preserved in the architecture
- Food/Drink:
- El Horno de Miguel (Toledo) – Traditional restaurant near Old Town with jamón, croquettes, and Spanish red wine that hit the reset button after a long travel day
Day 2 – Toledo, Spain
- Old Town Toledo – Explored the winding streets with Maria’s dad as our personal tour guide.
- Toledo Cathedral – Massive Gothic cathedral with golden altars, and detailed chapels.
- Siesta – Fully committed to the Spanish sleep schedule!
- Food/Drink:
- La Abadía del Buen Jamón (Local Cafe) – Quick breakfast with more jamón, cafe co leche, and criossants
- Grocery Store – We love exploring local grocery stores to see all the unique foods.
- Dinner at Maria’s Family Home – Homemade paella and jamón for dinner, followed by her abuela’s lemon flan that might have ruined flan anywhere else for me!
Day 3 & 4 – Toledo, León, & Santiago de Compostela, Spain
- León Cathedral – Gothic cathedral known for its stained glass.
- Casa Botines (House of the Dragon) – Early Gaudí building that looks part-castle, part-fortress.
- Drive to Galicia – Long but scenic drive into the rainy, green northwest of Spain
- Santiago de Compostela and the Camino (UNESCO Site) – Final destination of the famous pilgrimage route, filled with history and we saw several pilgrims finishing their trek
- Cathedral of Santiago – One of the most iconic pilgrimage sites in Europe. Baroque front, Romanesque interior, and Saint James’ tomb underneath
- Old Town & Main Square – Stone streets and live bagpipe music added some Celtic flair in the middle of the city.
- San Silvestre Race – New Year’s Eve tradition in many Spanish cities. We planned to walk but Maria & I switched to spectating once we realized no one else was walking! Peter finished the race and we saw lots of fun costumes!
- Food/Drink:
- Churros & Porras (Breakfast) – Dipped in thick hot chocolate at Maria’s before hitting the road
- Vermutería Cervantes (Lunch) – Stopped in León for a quick glass of vermouth and a bite before sightseeing
- Codex (Dinner) – Octopus, garlic shrimp, peppers, and local cheese. Galicia knows how to feed people
- Monastery Bakery – Bought cookies from cloistered nuns through a silent rotating window. No talking, just excellent shortbread
- New Year’s Eve Dinner – Multi-course meal that started at 8:30 and ran until midnight. Pacing was key. A tradition here is one grape for each bell chime at midnight. More stressful than expected!
Day 5 – Pontevedra, Spain
- Drive to Pontevedra – Rainy and green drive along the Galician coast
- Parador de Pontevedra – 16th-century noble estate turned hotel with thick stone walls and plush decor
- New Year’s Day Concert at Pazo da Cultura de Pontevedra – Mix of Galician music, classical selections, and a ballet act. Local families turned out in full holiday mode
- Food/Drink:
- Pizzería Rebusca 46 (Dinner) – After the long day and rich meals, pizza hit the spot. No notes
Day 6 – Braga & Guimarães, Portugal
- Historic Centre of Guimarães (UNESCO Site) – Compact old town with cobbled lanes, tiled buildings, and a claim to being the birthplace of Portugal
- Guimarães Castle – Hilltop medieval fortress with foggy views and a very climbable tower
- Food/Drink:
- aTipica – Modern restaurant in Braga with a glass floor showing preserved Roman ruins underneath.
- Norma – Michelin Bib Gourmand restaurant with creative small plates and cool decor
Day 7 – Guimarães to Porto, Portugal to Salamanca Region, Spain
- Porto Riverside – Short walk along the Douro River with views of tiled rooftops and iconic iron bridges
- Castillo del Buen Amor – Stayed in a castle hotel near Salamanca with vaulted ceilings and candlelit dinner. Felt appropriately regal after the sandwich
- Food/Drink:
- Local Café – Quick stop for espresso and a Nata – a custard-based Portuguese pastry
- Francesinha – Stopped at a cafe on the river to try Porto’s famous sandwich layered with meats, melted cheese, fried egg, and a beer-based gravy. Served in a bowl.
Day 8 & 9 – Segovia & Madrid, Spain
- Segovia Aqueduct and Old Town (UNESCO Site) – Roman aqueduct still standing with no mortar. Old Town has that pastel medieval vibe Spain does so well
- Alcázar of Segovia – Fairytale-style castle with turrets, armor collections, and panoramic views.
- Museo del Prado – Arrived for the free last hour. Saw Velázquez, Goya, and a greatest-hits tour of Spanish art
- Departure – Left Spain with full bellies, heavier bags, and two new engagement stories
- Food/Drink:
- La Filomena – A small local place tucked on a side street. Early dinner by local standards at 7:30, but we were hungry.
Trip Stats:
Countries: 2 (Spain & Portugal