Lisbon, Alentejo or Both? Planning Where to Sleep

The neighbourhood question

Lisbon's neighbourhoods have very different personalities and choosing where to stay shapes the whole experience. We looked at three serious candidates:

Alfama — the oldest part of the city, hilly, atmospheric, full of fado houses and narrow staircases. Beautiful to walk through. Less practical as a base: the streets are hard on luggage, restaurant density is lower, and the hills catch up with you by day three.

Chiado / Bairro Alto — central, flat enough, excellent eating and drinking, easy access to everything. Also the most tourist-concentrated area. We'd stay here on a shorter trip without hesitation.

Príncipe Real — slightly quieter, still very walkable, sits above Bairro Alto. Independent shops, good coffee, a mix of locals and travellers. This is where we landed.

Hotel or apartment?

For two weeks, the apartment case is strong. You gain a kitchen (useful for breakfast and the occasional low-key dinner), more storage, and more space to decompress. You lose daily room cleaning and the ease of just handing off your bag at a hotel.

We found an apartment in Príncipe Real through a property management company rather than the usual platform — slightly less convenient to book but the communication has been excellent and the pricing was noticeably better for a 10-night stay.

The Alentejo leg

This took longer to figure out than Lisbon. The Alentejo is rural — in a good way — but rural means the accommodation landscape is different. Options fall into a few categories:

• Quintas — farmhouse-style properties, often beautiful, often priced high and designed for romantic getaways or wine retreats
• Small hotels in Évora — more practical, central, easier to use as a base for day trips
• Agriturismo-style stays in the countryside, away from Évora entirely

We almost booked a quinta about 20km outside Évora. It was genuinely stunning. We talked ourselves out of it because without a car it becomes logistically awkward, and we weren't sure yet whether we were hiring one. We ended up booking a small hotel in Évora's historic centre for four nights — decision pending on the car.

What we still haven't sorted

• Car hire for the Alentejo (this will determine a lot)
• Whether four nights in Évora is the right call or whether we should split between Évora and somewhere else in the region
• Backup plan if the Príncipe Real apartment falls through

Next episode: activities — and whether you can over-plan what you do in a city like Lisbon.