Bear's Best Bets — Lisbon, Portugal
Bear's Best Bets is our series of personal destination guides — the places we've been, the spots we love, and the recommendations we actually give our clients.
Lisbon has been one of the great travel stories of the last decade — a city that went from underappreciated to unmissable while somehow managing to hold onto the qualities that made it special in the first place. The light is extraordinary. The food is exceptional. The people are warm without being performative about it. And the hills — yes, the hills are real, but they're worth every step.
Where to stay
For a luxury experience, the Bairro Alto Hotel is our consistent recommendation — a beautifully restored 18th century palace in the heart of the city with a rooftop terrace that has arguably the best view in Lisbon. The service is impeccable and the location puts you within walking distance of almost everything.
For something more intimate and city center, Convent Square Lisbon gives you the experience of staying in the walls of a historical convent that has been turned into a beautiful hotel. Ask them about their daily tea service where you can hear about the history of the convent while tasting various teas.
What to eat
Start every morning with a pastel de nata — the custard tarts — from Pasteis de Belem, the original, which has been making them since 1837. Order at least two. For dinner, Taberna da Rua das Flores is a small, perpetually full restaurant serving traditional Portuguese food at its most honest and delicious. No reservations — arrive early or wait at the bar with a glass of Vinho Verde. For a special occasion dinner, Alma by chef Henrique Sa Pessoa is one of the finest restaurants in the country — modern Portuguese cuisine in a stunning space in Chiado. Book well in advance.
What to do
Walk Alfama in the morning before the crowds arrive. The neighborhood — the oldest in Lisbon, built on the hillside above the river — is genuinely beautiful in the early light, and the viewpoints (miradouros) offer sweeping views over the red rooftops to the Tagus.
The palaces and castles of Sintra sit just 40 minutes from the city — the fairytale Pena Palace, the mysterious Quinta da Regaleira with its initiation wells and secret tunnels, the medieval ramparts of the Castle of the Moors — and a private guided tour through them is one of the most memorable days you can spend in Portugal.
Don't miss the Museu Nacional do Azulejo — an entire museum dedicated to the decorative blue tiles that define Portuguese culture. It sounds niche. It is completely transporting.
For literary travelers, make time for Livraria Bertrand in the Chiado district — the oldest operating bookstore in the world, open since 1732. It survived the great earthquake of 1755, outlasted empires, and still sells books today in a series of beautiful interconnected rooms. It's the kind of place that makes you understand why Lisbon has always attracted writers and romantics.
How to get around
Tram 28 is famous for a reason — it winds through the oldest neighborhoods in a way that no other transport does. Take it once for the experience. After that, use the metro and your feet. Lisbon is very walkable once you accept the hills.
How we can help
Lisbon works beautifully as a standalone destination and equally well as part of a wider Portugal itinerary — paired with Porto and the Douro Valley for a wine-focused trip, or combined with a Douro river cruise for something truly memorable. We plan both regularly and know the operators and hotels inside out.
Ready to go? Get in touch and we'll design your perfect Portugal itinerary.