This trip is built around opportunities to walk through beautiful and authentic places, dramatic scenery, good food and wine, and cool discoveries along the way. It moves from Porto north to a peaceful riverside pause on the Douro, into the Douro Valley's vineyards, across to one of Portugal's strangest and most wonderful villages, down into the sun-baked Alentejo, out to the wild Atlantic coast, and finally into Lisbon for a relaxed close before we fly home.
Below is the full day-by-day, along with confirmed lodging details and ideas for what to see and do at each stop.
| Dates | Where | Highlights |
|---|---|---|
| Sep 29–30 | Depart & Arrive Porto | Overnight flight, arrival mid-morning |
| Sep 30–Oct 2 | Porto | Livraria Lello, Ribeira, port wine cellars, neighborhoods |
| Oct 3–4 | Marco de Canaveses | A relaxed riverside spot on the Douro — bikes, kayaks |
| Oct 4–6 | Douro Valley | Quinta de la Rosa, the Casal de Loivos ridge hike |
| Oct 6–8 | Monsanto | A village built into massive granite boulders |
| Oct 8–9 | Évora | Roman ruins, the Chapel of Bones, charming town |
| Oct 9–10 | Cabo da Roca to Sintra | Atlantic cliffs, then Pena Palace and Quinta da Regaleira |
| Oct 10–12 | Lisbon | Alfama, Belém, neighborhoods |
| Oct 12 | Depart Lisbon | 12:45 PM flight home |
September 30 – October 2
Porto
Three nights, arriving mid-morning on September 30
Possible things to do
- Wander the Ribeira riverfront and cross partway onto the Dom Luís I Bridge for the classic view back at the colorful houses.
- Livraria Lello — the 1906 Art Nouveau bookshop with its famous red staircase and stained-glass skylight. Go at opening to beat the crowds.
- Mercado do Bolhão — Porto's beautifully renovated food market. Great for browsing and a casual lunch.
- Clérigos Tower for a climb and a view over the city; São Bento Station for its tiled hall.
- Vila Nova de Gaia, across the river: port wine cellar tours (Taylor's, Graham's, or quieter options like Quinta do Noval), and the walk up to Jardim do Morro for the best skyline view back at Porto.
- A different neighborhood: Cedofeita for contemporary art and vintage shops, or Miragaia for better food at better prices than the touristy riverfront.
- Restaurants worth seeking out: Taberna Santo António (Ribeira), Cantina 32 (Rua das Flores), Zé Bota or Calhambeque (Cordoaria), and if we want one real splurge, Euskalduna Studio (one Michelin star).
- Perhaps try a francesinha, Porto's famous sandwich, and a roast-pork sandwich from Casa Guedes.
October 3 – 4
Marco de Canaveses
A riverside pause on the Douro
A riverside stay directly on the Douro, with bikes and kayaks available at the property.
October 4
On to the Douro Valley
- Drive toward Peso da Régua, then take the N222 for the final scenic stretch into Pinhão — internationally recognized as one of the most beautiful roads in the world, winding through terraced vineyards with river views most of the way.
The Paiva Walkways (a hike through a river gorge near Arouca) were considered for this day but set aside in favor of the river house. Still an idea worth keeping in mind for a future trip.
October 4 – 6
Douro Valley
Two nights among the vineyards
Two nights at a family-run wine estate on the Douro since 1906, with vineyard walks and dinner available at Cozinha da Clara, the estate's own restaurant.
Possible things to do
- Settle in, walk the vineyard, dinner at the Quinta.
- October 5: the Casal de Loivos ridge hike, roughly 6km round trip and 3 hours with stops, climbing through terraced vineyards to a viewpoint the BBC has called one of the best views in the world. Quinta de la Rosa itself is visible from the top, and there's a small bar at the viewpoint for a glass of local wine.
- More vineyard walking, a wine tasting, dinner.
October 6 – 8
Monsanto
Two nights in a village built into the boulders
Two nights in Monsanto in a village built into and around massive granite boulders.
Possible things to do
- Drive from Pinhão to Monsanto (roughly 3+ hours) through central Portugal's interior.
- The PR5 Rota dos Barrocais trail: medieval pigsties built into boulders (furdas), the Penedos Juntos natural rock tunnel, the Laje das 13 Tigelas rock formation, and the 11th-century Templar castle ruins with views toward Spain.
- Wander the village itself — narrow stone streets, houses tucked beneath and between granite slabs the size of small buildings.
Parking note: cars are banned from the upper village. Park at the Miradouro de Monsanto lot or in Relva at the base, and carry bags up steep cobbled streets — worth asking our hosts for their specific guidance on arrival.
October 8 – 9
Évora
One night in the walled city
One night in Évora, a walled city in the Alentejo with a working town center alongside its ancient core.
Possible things to do
- The Roman Temple of Évora, standing in the middle of the city since antiquity.
- The Chapel of Bones — a 16th-century chapel lined with the bones of thousands of monks.
- A meal and a wander through the whitewashed old town.
October 9 – 10
Cabo da Roca & Sintra
Atlantic cliffs, then palaces and gardens
October 9
Évora to Cabo da Roca to Sintra
A plan for the day: an Atlantic clifftop hike on the way to Sintra, then Quinta da Regaleira in the afternoon.
- Depart Évora around 8:00–8:30 AM.
- Drive to Cabo da Roca (about 1h47m) — the westernmost point of mainland Europe.
- A roughly two-hour hike along the clifftop trail.
- Drive to Sintra (about 28 minutes).
- Lunch in Sintra — Tascantiga, a tapas spot near Quinta da Regaleira (cod fritters, grilled octopus, cheese with port-soaked dates).
- Quinta da Regaleira in the afternoon — the Initiation Well, hidden tunnels, and gardens; worth at least two hours.
Lodging
Eighteen21 Houses — Quinta Velha
A property near Quinta da Regaleira with its own private trail access. Following up with our hosts about parking on arrival and, if available, a home-cooked dinner served outside.
View booking
October 10
Pena Palace and the Moorish Castle
Exteriors and grounds only — no interior tours
- Pena Palace — exterior terraces and gardens only, a colorful Romanticist palace.
- Walk to the Moorish Castle (roughly 30–40 minutes) — 8th-century walls with sweeping views.
- Walk into Sintra town for lunch.
- Walk back to our car, then drive to the airport to return the rental.
Estimated arrival in Lisbon: between 3:00 and 4:00 PM, depending on pace.
October 10 – 12
Lisbon
Two nights to close the trip, car-free
Possible things to do
- Alfama — Lisbon's oldest, hilliest neighborhood, best explored on foot.
- Belém — Jerónimos Monastery, Belém Tower, and pastéis de nata at Pastéis de Belém.
- Baixa and Chiado — wandering, shopping, a final dinner.