How to choose a hotel in Lisbon
Lisbon is a hill city, and that decides your hotel more than the star rating does. The distance between two addresses on a map means nothing here. Alfama and Bairro Alto are separated by a valley, and the climb back up from the Baixa after dinner is real. If you want to walk the whole trip, stay on the upper ridge at Bairro Alto Hotel or Verride and let gravity work for you. If you have luggage, mobility limits or small children, stay flat on the Avenida or in the Baixa at The One Palácio da Anunciada or Pousada de Lisboa.
Terraces are the local currency. Lisbon's skyline is low and stepped, so a hotel with a rooftop is selling something the city itself is famous for. The three that matter are BAHR at Bairro Alto Hotel, the terrace at Memmo Alfama, and the whole roof of Verride. Check whether the terrace is open to non-guests before booking. The ones that are get very loud from about six in the evening.
Pools are rarer than the photographs suggest. Most historic-centre buildings are protected and cannot dig. If a pool matters, your genuine options are The One Palácio da Anunciada with a heated walled garden pool, Olissippo Lapa Palace with indoor and outdoor pools in the biggest gardens in the city, Torel Palace, Tivoli Avenida Liberdade and EPIC SANA Marquês. Everything else is a plunge pool.
Peak season is sharper than most guides admit. Mid June to mid September is peak, but the real spike is 12 and 13 June for Santo António, when Alfama becomes one long sardine grill and rooms in that quarter double in price and sell out months ahead. August is the crowd peak. The second half of September is the best trade in the calendar: the same weather with two thirds of the people.
Weather rewards the shoulders. Lisbon averages around 2,800 hours of sun a year, more than any other European capital. Highs sit at 20 to 23 degrees in April and May, 28 to 30 in July and August with a reliable Atlantic breeze in the afternoon, and 23 to 28 in September when the sea is at its warmest for a Cascais or Costa da Caparica day. November is the wettest month by a wide margin. Winter is mild at 15 degrees and rarely stops you doing anything.
Cheap flights follow a predictable pattern. The two lowest-fare windows into Lisbon are late January to early March, and the first three weeks of November. Midweek departures, Tuesday and Wednesday, are consistently cheaper than weekend ones, and the sweet spot for booking is six to ten weeks out. Fares to avoid: the second week of June, Easter week and the final week of August. Lisbon's airport is seven kilometres from the centre, so a cheap fare is not undone by an expensive transfer.
Room size is where the money goes. Lisbon's protected buildings mean five star does not guarantee space. Twenty four square metres is normal in Chiado and Alfama even at USD$540. If space matters, Four Seasons Ritz, EPIC SANA Marquês and Hotel Britania are the three that consistently deliver it, the last of those at around half the price of the first.
Build in Sintra, but sleep in Lisbon. Sintra is forty minutes by train from Rossio and it is worth a full day. It is not worth relocating for. Every hotel in this guide can arrange a driver, and going early, before ten, is the difference between Pena Palace being magical and being a queue.