Trip highlights
- 1Second Home Lisboa co-working in a conservatory
- 2NHR tax regime overview for potential movers
- 3Weekend trip to Sintra's fairy-tale palaces
- 4Surf lessons at Cascais or Costa da Caparica
- 5Alfama neighbourhood sunset and fado
Daily spend
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Day-by-day plan
Settle & Orientation
Friday, October 1
Est. spend
$80
per person
🌅 Morning
Arrive and check into monthly apartment
Central Lisbon, Portugal
For a 14-day stay, rent a furnished apartment (Uniplaces, Idealista, Airbnb monthly): €800–1,200/month in Mouraria, Intendente, or Anjos is the sweet spot — central, affordable, non-touristy. The green Arroios neighbourhood has the most authentic neighbourhood feel close to the centre.
Avoid Bairro Alto and Príncipe Real for long stays — too touristy and expensive. Arroios (around Rua Morais Soares) is where young Lisbonites live and the neighbourhood restaurants cost a quarter of tourist-area prices.
☀️ Afternoon
Neighbourhood walk and grocery setup
Arroios / Intendente, Lisbon
Walk the immediate neighbourhood, find the local supermarket (Pingo Doce or Minipreço), the nearest café, and the best tascas (cheap traditional restaurants). The local market in Intendente (Praça do Intendente) has vegetables and fish directly from Portuguese farms.
The Feira da Ladra flea market (Tuesday and Saturday mornings at Campo de Santa Clara) has the best vintage finds in Lisbon — furniture, clothes, books, and ceramics from Lisbon's houses.
🍽️ Meals
Local tasca dinner
Portuguese · $15 · The neighbourhood tasca (small traditional restaurant) serves a daily set lunch and dinner — €7–10 for soup, main, dessert, and wine. Find yours by following the lunch queue.
First Work Day — Co-working Scouting
Saturday, October 2
Est. spend
$80
per person
🌅 Morning
Second Home Lisboa
Second Home Lisboa, Rua Rodrigues de Faria 103, Alcântara, Lisbon
The most beautiful co-working space in Europe — a 19th-century conservatory filled with 1,000 plants, standing desks, phone booths, and excellent espresso at Café Janis. Day pass €25, monthly membership €350. Located in LX Factory (Alcântara).
Second Home has meeting rooms, event space, and a community of Lisbon's most interesting founders, designers, and writers. The Thursday evening community events are free for members.
☀️ Afternoon
Copenhagen Coffee Lab — afternoon work
Copenhagen Coffee Lab, Rua Nova do Carvalho 31, Lisbon
Lisbon's best specialty coffee café (Rua Nova do Carvalho, Cais do Sodré) — Speciality beans, laptop-friendly, and open until 6pm. Alternative: Fauna & Flora (Rua do Prior 18) or Hello, Kristof (Rua Actor Tasso 18) in Arroios.
Lisbon café culture is laptop-tolerant but not laptop-dedicated — order a coffee every 90 minutes or use a dedicated co-working for long sessions.
🍽️ Meals
Time Out Market, Cais do Sodré
Portuguese · $20 · The original Time Out Market (2014, before the chain expanded globally) has 35 excellent food stalls in a covered market. Go for the bacalhau à Brás and the bifanas.
Alfama Deep Dive
Sunday, October 3
Est. spend
$110
per person
🌅 Morning
Alfama morning — castle and miradouros
Alfama, Lisbon
The medieval Moorish quarter — the São Jorge Castle above it (entry €15, skip if budget-conscious), the Miradouro da Graça (best free view in Lisbon), and the tram 28 route through the narrowest streets. Morning light on the terracotta rooftops is extraordinary.
The Miradouro das Portas do Sol and Miradouro da Graça are both free and have better coffee than Miradouro de Santa Luzia (the overcrowded tourist one). Go to Graça early morning.
☀️ Afternoon
Work from Tasca do Chico — fado restaurant
Museu do Fado, Largo do Chafariz de Dentro, Alfama
After a morning off exploring, afternoon work from one of Alfama's neighbourhood cafés before the evening fado shows begin. The Museu do Fado (€5) near the Alfama tram stop tells the story of fado's UNESCO recognition.
🌙 Evening
Fado dinner at Tasca do Chico
Tasca do Chico, Rua dos Remédios 83, Alfama, Lisbon
The best intimate fado experience in Lisbon — 20-person restaurant, professional fadistas, two sets per evening. Entry included in dinner price (€35–45 per person). Book 2 weeks ahead.
The fado is performed acoustically — no microphones, no amplification. The traditional 'shh' when a good fado begins is universal. Don't talk during the music.
🍽️ Meals
Cantinho do Aziz, Mouraria
Mozambican-Portuguese · $18 · The most interesting restaurant in Mouraria — Mozambican food in a Lisbon neighbourhood from the African diaspora. The piri-piri camarão is extraordinary.
Sintra Weekend Trip
Thursday, October 7
Est. spend
$90
per person
🌅 Morning
Sintra day trip — Pena Palace and Moorish Castle
Sintra, Sintra Municipality
40 minutes from Lisbon by train (€4.50 return from Rossio station) — the fairy-tale hilltop UNESCO town with Pena Palace (neo-Romantic 19th-century palace painted yellow, red, and blue), the Moorish Castle, and the magical Quinta da Regaleira (entry €10, park with initiatic wells and tunnels).
Go on a Tuesday or Wednesday — the town is overwhelmed on weekends. Pena Palace: €17.50 adult. Moorish Castle: €10. Get both with a combined ticket. The walk from Sintra town centre to Pena Palace (2km uphill) is more scenic than the crowded tuk-tuks.
🍽️ Meals
Casa Piriquita, Sintra
Portuguese · $12 · The original travesseiros (egg and almond puff pastries) and queijadas (cheese tarts) since 1862. The most important pastry shop in Sintra.
Surfing at Cascais or Costa da Caparica
Sunday, October 10
Est. spend
$80
per person
🌅 Morning
Surfing lesson at Costa da Caparica
Costa da Caparica, Almada, Setúbal
Costa da Caparica is 30km south of Lisbon by bus — 30km of Atlantic beach breaks, the largest concentration of surf schools in the Lisbon area, and generally uncrowded on weekdays. 2-hour beginner lesson: €35–45.
Caparica is a proper surfing community, not a tourist beach — the surf is consistent and the local instruction quality is high. Casca de Noz and the RipCurl school are the most reliable operators.
🍽️ Meals
Snack bar on the beach, Caparica
Portuguese · $10 · Fresh grilled fish, cold Super Bock beer, and a view of the Atlantic. Simple and perfect.
Final Day & NHR Research
Thursday, October 14
Est. spend
$80
per person
🌅 Morning
Research the NHR tax regime and expat community
Online research or at a co-working
If considering a longer move: the Non-Habitual Resident (NHR) tax regime offers 20% flat tax on Portuguese-source income for 10 years. The Digital Nomad Visa (€760 application fee) allows non-EU citizens to live and work remotely. The Lisbon expat community meets at events organised by internations.org and at Second Home Lisboa.
Book a consultation with a Portuguese tax advisor before applying for NHR — the rules changed in 2024 and specific income streams have different treatments. Cost: €200–500 for a full consultation.
☀️ Afternoon
Farewell Bairro Alto walk and departure
Bairro Alto, Lisbon
The Bairro Alto neighbourhood for a final afternoon — the independent wine shops, antique dealers, and the classic A Cevicheria restaurant. Airport transfer by Metro Red Line.
🍽️ Meals
A Cevicheria, Bairro Alto
Modern Portuguese/Peruvian · $40 · Chef Kiko Martins's Peruvian-Portuguese restaurant. The ceviche with Portuguese sardines is the signature. Book ahead.
Before you go
📅 Best time to visit
September–November is the best nomad season — summer crowds gone, warm weather (22–26°C), and Lisbon at its most liveable. May–July is also excellent. February–March is the quietest and cheapest — mild (15–18°C) but grey.
🛂 Visas
Portugal is Schengen — EU citizens can live and work freely. Non-EU citizens with remote income can apply for the Digital Nomad Visa (from €760, requires proof of income >€3,280/month). UK citizens get 90 days Schengen-free.
💱 Currency
Euro. Portugal is the most affordable country in Western Europe — monthly apartment rent from €900–1,400 in central Lisbon, restaurant set lunch €7–10, co-working from €15/day.
🆘 Emergency numbers
police: 112
ambulance: 112
💬 Things you won't find in a guidebook
- The Lisboa Card (€6.75/day unlimited transport) covers all Metro, buses, trams, and some museum entries. Worth it for the first week.
- Portuguese hospitality: walk into any pastelaria (pastry café) at 8am, order a bica (espresso) and a pastel de nata, eat standing at the counter, pay €1.30 total. This is the correct Portuguese morning. Eating at a table costs 20–30% more.
- The Lisbon hills: the city is built on 7 hills — the hills are steep and the cobblestones (calçadas) are slippery when wet. Wear good shoes. The Miradouros (viewpoints) at the top of each hill are the social hubs of the respective neighbourhoods.
One thing worth not skipping
A 14-day trip to Lisbon, Portugal without insurance is a gamble. Medical emergencies, cancelled flights, lost luggage — cover yourself before you leave.
Comprehensive cover for 150+ adventure activities, medical evacuation, trip cancellation, and baggage. Recommended for most travellers.
Subscription-based travel medical insurance. Best for longer trips, digital nomads, or frequent travellers. Renews weekly or monthly.
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