Stop 1: Lisbon
7 days · 7 nights
An easy first base with day trips to Sintra and the coast.
Where to stay: Baixa or Chiado to walk everywhere; Alfama for views and fado.
Illustrative example. A sample Multi-Country Journey trip made to show what Trouble builds — not live availability, prices or bookings. Route: Portugal → Spain → Italy → Greece.
Portugal · Spain · Italy · Greece
Lisbonthen Sevillethen Romethen Athens
4 stops
7 days · 7 nights
An easy first base with day trips to Sintra and the coast.
Where to stay: Baixa or Chiado to walk everywhere; Alfama for views and fado.
6 days · 6 nights
A walkable old town, with Córdoba 45 minutes away by train.
Where to stay: Santa Cruz or the Arenal, close to the Alcázar and cathedral.
9 days · 9 nights
Enough days for the big sights plus Tivoli, Ostia and Orvieto.
Where to stay: Monti or the Centro Storico; Trastevere for evenings.
8 days · 7 nights
A base for Delphi, Cape Sounion and an island day on Aegina.
Where to stay: Plaka or Koukaki, walking distance to the Acropolis.
Numbered stops are joined in route order. Map data © OpenStreetMap contributors.
Days 1–7
Morning
The riverside square where the city opens onto the Tagus.
Noon
A food hall of Lisbon favourites for an easy first lunch.
Evening
Tiled terrace over Alfama's rooftops at golden hour.
Morning
Moorish castle walls with the widest view of the city.
Noon
The fortress-like Sé, Lisbon's oldest church.
Evening
An intimate fado house in the lanes of Alfama.
Morning
Manueline cloisters carved with ropes, shells and sea creatures.
Noon
Warm custard tarts from the original 1837 recipe.
Evening
The riverside tower that saw the explorers off, best at sunset.
Morning
A romantic hilltop palace painted yellow and red.
Noon
Gardens, grottoes and the famous initiation well.
Evening
Cliffs at mainland Europe's westernmost point.
Morning
A small sheltered beach in the heart of Cascais.
Noon
Sea cliffs and a roaring rock arch just outside town.
Evening
Old printing works turned into shops, bars and bookshops.
Morning
A superb private collection set in quiet gardens.
Noon
Five centuries of azulejos in a former convent.
Evening
A lively seafood hall famous for garlic prawns.
Morning
One of Europe's great aquariums, built around a vast central tank.
Noon
A neighbourhood market with small food counters.
Evening
A garden viewpoint at the top of Bairro Alto.
Days 8–13
Morning
Corinthian columns in the centre of a walled Alentejo town.
Noon
A small, striking chapel inside the Church of St Francis.
Evening
Seville's old Jewish quarter of whitewashed lanes and patios.
Morning
Mudéjar palaces and gardens still used by the royal family.
Noon
The largest Gothic cathedral, with the Giralda bell tower.
Evening
An intimate flamenco show in a historic courtyard.
Morning
A sweeping tiled plaza built for the 1929 expo.
Noon
Tapas counters inside the market by the Triana bridge.
Evening
Riverside Triana at dusk, looking back across to the old town.
Morning
A forest of red-and-white arches around a Renaissance nave.
Noon
Fortress gardens of pools, fountains and orange trees.
Evening
The old bridge over the Guadalquivir, lit up after dark.
Morning
A noble palace mixing Mudéjar tiles and Renaissance courtyards.
Noon
Seville's oldest tapas bar, open since 1670.
Evening
The giant wooden "mushrooms" with a walkway on top.
Morning
Ruins of the Roman city where Emperor Trajan was born.
Noon
A quiet palace of patios, bougainvillea and art.
Evening
A long square of tapas bars where locals meet at night.
Days 14–22
Morning
Free time
Noon
A village-like square in the Monti neighbourhood.
Evening
Coin toss at the baroque fountain, quieter late in the evening.
Morning
The great amphitheatre, best right at opening time.
Noon
The ruins of Rome's ancient civic heart, below the Palatine.
Evening
Michelangelo's square, with sunset views over the Forum.
Morning
Raphael's rooms and the Sistine Chapel.
Noon
Michelangelo's dome and Bernini's colonnade.
Evening
Hadrian's tomb turned fortress, beside the Tiber.
Morning
Noon
A deli-restaurant famous for carbonara and cured meats.
Evening
Bernini's fountains in a square shaped like a stadium.
Morning
Terraced Renaissance gardens with hundreds of fountains.
Noon
An emperor's vast country retreat of pools and ruins.
Evening
Back in Rome for an evening in the busy square.
Morning
Bernini sculptures and Caravaggio paintings in a villa.
Noon
The famous staircase below Trinità dei Monti.
Evening
Golden mosaics in the heart of Trastevere's lanes.
Morning
Rome's ancient port, with streets, baths and a theatre.
Noon
Street-food stalls in a neighbourhood market.
Evening
The orange-tree garden on the Aventine at sunset.
Morning
Early Christian tunnels along the ancient road.
Noon
Towering ruins of Rome's grandest public baths.
Evening
A small Roman trattoria in Trastevere.
Morning
A gleaming striped façade on a hilltop town.
Noon
A deep Renaissance well with a double spiral stair.
Evening
Back in Rome for dinner in the old Jewish Ghetto.
Days 23–30
Morning
Free time
Noon
The old quarter of neoclassical houses below the Acropolis.
Evening
A lively square with rooftop views of the lit Acropolis.
Morning
The Parthenon and its temples, best at opening time.
Noon
The original sculptures, with a view back to the Parthenon.
Evening
A pine-covered hill facing the Acropolis at sunset.
Morning
The marketplace of Socrates, with the intact Temple of Hephaestus.
Noon
The bustling central market with small tavernas.
Evening
The city's highest viewpoint, reached by funicular.
Morning
Greece's great collection, from Mycenaean gold to bronzes.
Noon
A deli-meze house of cured meats and cheeses.
Evening
A clifftop temple at Cape Sounion, famous for sunsets.
Morning
The sanctuary of Apollo on the slopes of Mount Parnassus.
Noon
Home of the bronze Charioteer of Delphi.
Evening
A stone mountain village for dinner before the drive back.
Morning
A harbour town of fishing boats and pistachio stalls.
Noon
A well-preserved temple on a pine-covered hilltop.
Evening
A little harbour in Piraeus lined with seafood tavernas.
Morning
The towering columns of Athens' largest temple.
Noon
The marble stadium of the first modern Olympics.
Evening
A park, canal and rooftop by the sea.
Morning
The changing of the guard in front of Parliament.
Noon
Greek art and crafts from antiquity to today.
Evening
Free time
21 activities
Day 1 · Morning
The riverside square where the city opens onto the Tagus.
Day 1 · Noon
A food hall of Lisbon favourites for an easy first lunch.
Day 1 · Evening
Tiled terrace over Alfama's rooftops at golden hour.
Day 2 · Morning
Moorish castle walls with the widest view of the city.
Day 2 · Noon
The fortress-like Sé, Lisbon's oldest church.
Day 2 · Evening
An intimate fado house in the lanes of Alfama.
Day 3 · Morning
Manueline cloisters carved with ropes, shells and sea creatures.
Day 3 · Noon
Warm custard tarts from the original 1837 recipe.
Day 3 · Evening
The riverside tower that saw the explorers off, best at sunset.
Day 4 · Morning
A romantic hilltop palace painted yellow and red.
Day 4 · Noon
Gardens, grottoes and the famous initiation well.
Day 4 · Evening
Cliffs at mainland Europe's westernmost point.
Day 5 · Morning
A small sheltered beach in the heart of Cascais.
Day 5 · Noon
Sea cliffs and a roaring rock arch just outside town.
Day 5 · Evening
Old printing works turned into shops, bars and bookshops.
Day 6 · Morning
A superb private collection set in quiet gardens.
Day 6 · Noon
Five centuries of azulejos in a former convent.
Day 6 · Evening
A lively seafood hall famous for garlic prawns.
Day 7 · Morning
One of Europe's great aquariums, built around a vast central tank.
Day 7 · Noon
A neighbourhood market with small food counters.
Day 7 · Evening
A garden viewpoint at the top of Bairro Alto.
18 activities
Day 8 · Morning
Corinthian columns in the centre of a walled Alentejo town.
Day 8 · Noon
A small, striking chapel inside the Church of St Francis.
Day 8 · Evening
Seville's old Jewish quarter of whitewashed lanes and patios.
Day 9 · Morning
Mudéjar palaces and gardens still used by the royal family.
Day 9 · Noon
The largest Gothic cathedral, with the Giralda bell tower.
Day 9 · Evening
An intimate flamenco show in a historic courtyard.
Day 10 · Morning
A sweeping tiled plaza built for the 1929 expo.
Day 10 · Noon
Tapas counters inside the market by the Triana bridge.
Day 10 · Evening
Riverside Triana at dusk, looking back across to the old town.
Day 11 · Morning
A forest of red-and-white arches around a Renaissance nave.
Day 11 · Noon
Fortress gardens of pools, fountains and orange trees.
Day 11 · Evening
The old bridge over the Guadalquivir, lit up after dark.
Day 12 · Morning
A noble palace mixing Mudéjar tiles and Renaissance courtyards.
Day 12 · Noon
Seville's oldest tapas bar, open since 1670.
Day 12 · Evening
The giant wooden "mushrooms" with a walkway on top.
Day 13 · Morning
Ruins of the Roman city where Emperor Trajan was born.
Day 13 · Noon
A quiet palace of patios, bougainvillea and art.
Day 13 · Evening
A long square of tapas bars where locals meet at night.
26 activities
Day 14 · Noon
A village-like square in the Monti neighbourhood.
Day 14 · Evening
Coin toss at the baroque fountain, quieter late in the evening.
Day 15 · Morning
The great amphitheatre, best right at opening time.
Day 15 · Noon
The ruins of Rome's ancient civic heart, below the Palatine.
Day 15 · Evening
Michelangelo's square, with sunset views over the Forum.
Day 16 · Morning
Raphael's rooms and the Sistine Chapel.
Day 16 · Noon
Michelangelo's dome and Bernini's colonnade.
Day 16 · Evening
Hadrian's tomb turned fortress, beside the Tiber.
Day 17 · Morning
A 2,000-year-old dome with an open oculus.
Day 17 · Noon
A deli-restaurant famous for carbonara and cured meats.
Day 17 · Evening
Bernini's fountains in a square shaped like a stadium.
Day 18 · Morning
Terraced Renaissance gardens with hundreds of fountains.
Day 18 · Noon
An emperor's vast country retreat of pools and ruins.
Day 18 · Evening
Back in Rome for an evening in the busy square.
Day 19 · Morning
Bernini sculptures and Caravaggio paintings in a villa.
Day 19 · Noon
The famous staircase below Trinità dei Monti.
Day 19 · Evening
Golden mosaics in the heart of Trastevere's lanes.
Day 20 · Morning
Rome's ancient port, with streets, baths and a theatre.
Day 20 · Noon
Street-food stalls in a neighbourhood market.
Day 20 · Evening
The orange-tree garden on the Aventine at sunset.
Day 21 · Morning
Early Christian tunnels along the ancient road.
Day 21 · Noon
Towering ruins of Rome's grandest public baths.
Day 21 · Evening
A small Roman trattoria in Trastevere.
Day 22 · Morning
A gleaming striped façade on a hilltop town.
Day 22 · Noon
A deep Renaissance well with a double spiral stair.
Day 22 · Evening
Back in Rome for dinner in the old Jewish Ghetto.
22 activities
Day 23 · Noon
The old quarter of neoclassical houses below the Acropolis.
Day 23 · Evening
A lively square with rooftop views of the lit Acropolis.
Day 24 · Morning
The Parthenon and its temples, best at opening time.
Day 24 · Noon
The original sculptures, with a view back to the Parthenon.
Day 24 · Evening
A pine-covered hill facing the Acropolis at sunset.
Day 25 · Morning
The marketplace of Socrates, with the intact Temple of Hephaestus.
Day 25 · Noon
The bustling central market with small tavernas.
Day 25 · Evening
The city's highest viewpoint, reached by funicular.
Day 26 · Morning
Greece's great collection, from Mycenaean gold to bronzes.
Day 26 · Noon
A deli-meze house of cured meats and cheeses.
Day 26 · Evening
A clifftop temple at Cape Sounion, famous for sunsets.
Day 27 · Morning
The sanctuary of Apollo on the slopes of Mount Parnassus.
Day 27 · Noon
Home of the bronze Charioteer of Delphi.
Day 27 · Evening
A stone mountain village for dinner before the drive back.
Day 28 · Morning
A harbour town of fishing boats and pistachio stalls.
Day 28 · Noon
A well-preserved temple on a pine-covered hilltop.
Day 28 · Evening
A little harbour in Piraeus lined with seafood tavernas.
Day 29 · Morning
The towering columns of Athens' largest temple.
Day 29 · Noon
The marble stadium of the first modern Olympics.
Day 29 · Evening
A park, canal and rooftop by the sea.
Day 30 · Morning
The changing of the guard in front of Parliament.
Day 30 · Noon
Greek art and crafts from antiquity to today.
Places saved to this trip, grouped by stop.
mid-range
Walk to the castle, the cathedral and the fado houses.
luxury
A classic stay a few minutes from the old town.
luxury
Central for walking the historic centre.
luxury
Metro at the door and an Acropolis view from the roof.
Seafood · mid-range
Lisbon's best-loved seafood hall.
Tapas · budget
Seville's oldest tapas bar.
Roman · mid-range
A Roman classic; book ahead.
Greek meze · budget
Great value in the centre.
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