Lisbon and the Algarve pair naturally into one coastal week — three unhurried days in the capital’s tiled hills and river light, then three more along the Algarve’s cave-pocked cliffs near Portimão and Lagos. No day here tries to cram in more than one real thing, on purpose.
Day 1
Arrive in Lisbon
Land at Humberto Delgado Airport and settle into Baixa/Chiado — Lisbon rewards an unhurried first evening spent wandering the grid streets more than a packed arrival-day itinerary.
🚕 Private Transfer — Lisbon Airport (LIS) to City Center
~25 minutes · Fixed rate from €25–35 (~$27–38 USD) per vehicle, up to 4 people
A pre-booked, flat-rate transfer meets you in arrivals with a name sign and tracks your flight — no queuing for a taxi after a long overnight flight.
Welcome Pickups · welcomepickups.com
🛎️ Overnight — Hotel Avenida Palace
From $300–360 USD / night, for 2 people
A Belle Époque 5-star hotel dating to 1892 on Rua 1.º de Dezembro, steps from Rossio and Restauradores squares — an easy walking base for all three Lisbon nights.
Hotel Avenida Palace · +351 213 218 100 · hotelavenidapalace.pt
🍽️ Dinner in Chiado
Est. $25–40 USD / person
On your own — Chiado’s café terraces and tiled façades make for an easy first-night wander before dinner at one of the neighborhood’s tascas.
Day 2
Alfama, Belém & a Night of Fado
Ride the rattling Tram 28 through Alfama’s oldest lanes in the morning, then head west to Belém’s monastery and tower before an evening of Fado in the old quarter.
🚋 Tram 28 & Alfama Self-Guided Walk
~2–3 hours · Self-guided, tram fare ~€3.40 (~$3.70 USD) with a Viva Viagem card
Lisbon’s most famous tram climbs through Alfama’s steep, tile-covered lanes past São Jorge Castle — ride it end to end, then double back on foot through the neighborhood’s miradouros (viewpoints).
🏛️ Jerónimos Monastery & Belém Tower
~3 hours · Entry from €10 (~$11 USD) each, UNESCO World Heritage sites
Portugal’s Age of Discoveries is written into the limestone of these two Manueline-style landmarks, a 10-minute walk apart along the Belém riverfront — pair the visit with a pastel de nata at the original Pastéis de Belém bakery nearby.
Direção-Geral do Património Cultural · patrimoniocultural.gov.pt
🎶 Fado Dinner at Clube de Fado
~2.5 hours · Dinner menu from €78 (~$84 USD) / person, live Fado nightly from 8:30pm
A working fado house in a 300-year-old building steps from Lisbon Cathedral, founded by guitarist Mário Pacheco in 1995 — Fado is woven into the meal here rather than staged as a separate ticketed show. Book ahead; tables fill on weekends.
Clube de Fado · Rua de São João da Praça 94, Alfama · +351 218 852 704 · clubedefado.pt
🛎️ Overnight — Hotel Avenida Palace
From $300–360 USD / night, for 2 people
Second night at the same hotel — no need to pack up.
Hotel Avenida Palace · +351 213 218 100 · hotelavenidapalace.pt
Day 3
Sintra Day Trip
A UNESCO fairytale in the hills above Lisbon — a full day among the pastel palaces and forested gardens of Sintra, back in the city by evening.
🏰 Small-Group Sintra Tour — Pena Palace & Quinta da Regaleira
~8 hours · From $142.84 USD / person, round-trip from central Lisbon
Departing Praça da Figueira at 7:40am in an air-conditioned vehicle capped at 8 travelers, the guide handles transport and entry logistics for the two unmissable sites — the candy-colored Pena Palace crowning its hilltop, and the mystical, tunnel-riddled gardens of Quinta da Regaleira — with time built in to wander Sintra’s historic center.
Portuguese For a Day Tours, via Viator · viator.com
🍽️ Dinner in Bairro Alto
Est. $25–40 USD / person
On your own — Lisbon’s nightlife district is quiet by day and easy to explore; by dinner hour its narrow streets fill with small plates and fado bars.
🛎️ Overnight — Hotel Avenida Palace
From $300–360 USD / night, for 2 people
Third and final night at the same hotel.
Hotel Avenida Palace · +351 213 218 100 · hotelavenidapalace.pt
Day 4
Lisbon to the Algarve
Trade the capital for the coast — a scenic train south to Portimão, which becomes your Algarve base for the next three nights, an easy reach of both Lagos and Benagil.
🚆 Train — Lisboa (Oriente) to Portimão
~3–3.5 hours, direct Intercidades service · From €22–28 (~$24–30 USD) / person, second class
CP’s Intercidades line runs south along the coast direct to Portimão station — reserve seats a few weeks ahead in summer, when the route fills up with beachgoers heading to the Algarve.
CP – Comboios de Portugal · cp.pt
🛎️ Overnight — Bela Vista Hotel & Spa
From $350–450 USD / night, for 2 people
A Relais & Châteaux clifftop hotel above Praia da Rocha in Portimão, built around a restored 1892 seaside villa — most rooms open onto sea-facing balconies, and it sits a short walk from the marina where the next day’s boat tour departs.
Bela Vista Hotel & Spa · +351 282 460 280 · hotelbelavista.net
🍽️ Dinner in Praia da Rocha
Est. $30–50 USD / person
On your own — the clifftop promenade above the beach holds a dense cluster of seafood grills and marisqueiras, most with ocean-view terraces.
Day 5
Algarve Coastline by Boat
The Algarve’s limestone caves and cliffs are best seen from the water — a short walk to the marina for a boat tour past Benagil, then an afternoon in Lagos.
⛵ Benagil & Marinha Boat Tour
~2 hours · From €35 (~$38 USD) / person
A small boat threads through sea caves and past Praia da Marinha’s cliffs, with a stop inside the famous open-roofed Benagil cave when swell allows. Departs from Clube Naval de Portimão, an easy walk from the hotel — book the early departure, the cave gets crowded by midday.
Benagil Express · +351 932 300 600 · benagilexpress.com
🏖️ Ponta da Piedade & Praia Dona Ana, Lagos
~2–3 hours · Self-guided, taxi/drive from Portimão ~20 minutes, no admission cost
In the afternoon, head to Lagos to walk the clifftop path out to Ponta da Piedade’s golden rock arches and grottoes, then cool off at Praia Dona Ana below — one of the Algarve’s most photographed beaches.
🛎️ Overnight — Bela Vista Hotel & Spa
From $350–450 USD / night, for 2 people
Second night at the same hotel.
Bela Vista Hotel & Spa · +351 282 460 280 · hotelbelavista.net
Day 6
West Coast to Sagres
The Algarve turns wild and windswept at its southwestern tip — a half-day out to the cliffs of Cabo de São Vicente and Sagres, then a slow final evening on the coast.
🚗 Self-Drive — Portimão to Sagres & Cabo de São Vicente
~40 minutes each way · Rental car from €25–45 (~$27–49 USD) / day
Europe’s southwesternmost point once marked the edge of the known world — the fortress at Sagres and the lighthouse at Cabo de São Vicente sit a short, easy drive from Portimão along the N125 and the Costa Vicentina.
Europcar – Faro Airport & Portimão · europcar.pt
🍽️ Farewell Dinner in Portimão Marina
Est. $35–55 USD / person
On your own — a fitting last night on the coast; the marina’s restaurant row looks back toward Praia da Rocha’s cliffs at sunset.
🛎️ Overnight — Bela Vista Hotel & Spa
From $350–450 USD / night, for 2 people
Third and final night at the same hotel.
Bela Vista Hotel & Spa · +351 282 460 280 · hotelbelavista.net
Day 7
Depart from the Algarve
Last stretch of the trip — a private transfer over to Faro for your flight home.
🚕 Private Transfer — Portimão to Faro Airport (FAO)
~45 minutes · From €55–70 (~$60–76 USD) per vehicle, one-way
Build in buffer time for the drive along the A22 — it can add 15–20 minutes in summer traffic, and you’ll want margin before an international flight.
Welcome Pickups · welcomepickups.com
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