Vitor Oliveira · CC BY-SA 2.0Stop 1: Lisbon
2 days · 2 nights
An easy first base: trams, viewpoints and the river all within walking distance.
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.
Illustrative example · Multi-Country Journey
Europe in 21 Days
Portugal · Spain · Italy · Greece
- Duration: 21 days · 20 nights
- 4 countries · 8 stops
- 2 travelers
Lisbon then Porto then Madrid then Barcelona then Rome then Florence then Athens then Santorini
Countries & cities
4 countries · 8 stops
- Portugal· 4 nights
- Spain· 5 nights
- Italy· 6 nights
- Greece· 5 nights
Portugal
2 stops · 4 nights
Lisbon then Porto
- Vitor Oliveira · CC BY-SA 2.0Porto · By train · ~3h
Diego Delso · CC BY-SA 3.0Stop 2: Porto
2 days · 2 nights
Compact and hilly, with the Douro and the port lodges just across the bridge.
Where to stay: Ribeira or around Aliados; Vila Nova de Gaia for river views.
Porto → Madrid · By plane · ~1h 20m
Spain
2 stops · 5 nights
Madrid then Barcelona
Jorge Franganillo · CC BY 2.0Stop 3: Madrid
2 days · 2 nights
Two days for the Prado, the Retiro and a long Spanish dinner.
Where to stay: Sol, Huertas or the Literary Quarter, between the plazas and the museums.
Barcelona · By train · ~2h 30m
essetefano · CC BY 3.0Stop 4: Barcelona
3 days · 3 nights
Gaudí, the Gothic Quarter and the beach, each a short metro ride apart.
Where to stay: The Eixample for Gaudí; the Gothic Quarter or El Born for old-town lanes.
Barcelona → Rome · By plane · ~2h
Italy
2 stops · 6 nights
Rome then Florence
FeaturedPics · CC BY-SA 4.0Stop 5: Rome
3 days · 3 nights
Three days for ancient Rome, the Vatican and long evenings in the piazzas.
Where to stay: Monti or the Centro Storico; Trastevere for evenings.
Florence · By train · ~1h 35m
Gary Campbell-Hall · CC BY 2.0Stop 6: Florence
3 days · 3 nights
A small, walkable city packed with Renaissance art.
Where to stay: Around the Duomo, or across the river in the quieter Oltrarno.
Florence → Athens · By plane · ~2h
Greece
2 stops · 5 nights
Athens then Santorini
Giles Laurent · CC BY-SA 4.0Stop 7: Athens
2 days · 2 nights
The Acropolis above a lively modern city, and the gateway to the islands.
Where to stay: Plaka or Koukaki, walking distance to the Acropolis.
Santorini · By plane · ~45mGerd Giesinger
Stop 8: Santorini
4 days · 3 nights
Caldera sunsets, volcanic beaches and wine — a slow ending to the journey.
Where to stay: Caldera-edge lanes between Fira and Firostefani for the view without Oia prices.
Trip map
- Stops (numbered)
- Activities (circles)
- Hotels (squares)
- Restaurants (diamonds)
8 numbered stops, joined in route order: 1 Lisbon, 2 Porto, 3 Madrid, 4 Barcelona, 5 Rome, 6 Florence, 7 Athens, 8 Santorini. Pins show 51 activities (circles), 5 hotels (squares), 14 restaurants (diamonds) — all listed in the Days, Activities and Services tabs. Use the arrow keys to move the map and plus or minus to zoom. Map data © OpenStreetMap contributors.
Lisbon
Days 1–2
Day 1:Arrive in Lisbon
Morning
Praça do Comércio
The riverside square where the city opens onto the Tagus.
Noon
Time Out Market Lisboa
RestaurantA food hall of Lisbon favourites for an easy first lunch.
Evening
Miradouro de Santa Luzia
Tiled terrace over Alfama’s rooftops at golden hour.
Day 2:Castle hill and fado
Morning
Castelo de São Jorge
Moorish castle walls with the widest view of the city.
Noon
Lisbon Cathedral
The fortress-like Sé, Lisbon’s oldest church.
Evening
Clube de Fado
An intimate fado house in the lanes of Alfama.
Porto
Days 3–4
Day 3:Train to Porto and the Ribeira
Travel day: Lisbon → Porto · By train · ~3h
Morning
São Bento Railway Station
Arrive under twenty thousand blue-and-white tiles telling Portugal’s history.
Noon
Clérigos Tower
Climb the baroque tower for the best view over the old town’s rooftops.
Evening
Diego Delso · CC BY-SA 3.0Cais da Ribeira
The riverside quay under the Dom Luís I bridge — dinner facing the lit-up Gaia cellars.
Day 4:Books, markets and port wine
Morning
Livraria Lello
The neo-Gothic bookshop with the crimson staircase; a timed ticket beats the queue.
Noon
Mercado do Bolhão
RestaurantThe restored market hall for sardines, cheese and a petiscos lunch.
Evening
Port lodges of Vila Nova de Gaia
Walk the bridge’s upper deck to Gaia for a tasting in the old port cellars.
Madrid
Days 5–6
Day 5:Fly to Madrid: plazas and tapas
Travel day: Porto → Madrid · By plane · ~1h 20m
Morning
Travel from Porto
Noon
Mercado de San Miguel
RestaurantAn iron-and-glass market hall for croquetas, oysters and vermouth.
Evening
Jorge Franganillo · CC BY 2.0Plaza Mayor
The arcaded 17th-century square, at its best as the lamps come on.
Day 6:The Prado and the Retiro
Morning
Museo del Prado
Velázquez, Goya and Bosch; go at opening time and choose a few rooms.
Noon
El Retiro Park
Row a boat on the great pond, then a slow lunch in the shade.
Evening
Templo de Debod
A real Egyptian temple on a hill — Madrid’s favourite sunset spot.
Barcelona
Days 7–9
Day 7:Train to Barcelona and the Gothic Quarter
Travel day: Madrid → Barcelona · By train · ~2h 30m
Morning
Travel from Madrid
Noon
La Boqueria
RestaurantThe famous market off La Rambla — find a counter bar for lunch.
Evening
Barcelona Cathedral
Gothic lanes and quiet squares around the cathedral as the day cools.
Day 8:Gaudí day
Morning
Bernard Gagnon · CC BY-SA 3.0Sagrada Família
Gaudí’s basilica, still being built — the stained-glass light is best in the morning.
Noon
Casa Batlló
Gaudí’s rippling “house of bones” on the Passeig de Gràcia.
Evening
Bunkers del Carmel
Old anti-aircraft bunkers with a 360° view over the city at sunset.
Day 9:Park Güell and the beach
Morning
essetefano · CC BY 3.0Park Güell
Gaudí’s mosaic terrace and pavilions above the city; book a morning slot.
Noon
Santa Maria del Mar
El Born’s soaring Gothic church, then tapas in the lanes around it.
Evening
Barceloneta Beach
A last swim, then seafood by the sea.
Rome
Days 10–12
Day 10:Fly to Rome
Travel day: Barcelona → Rome · By plane · ~2h
Morning
Travel from Barcelona
Noon
Piazza della Madonna dei Monti
A village-like square in the Monti neighbourhood.
Evening
Diliff · CC BY 3.0Trevi Fountain
Coin toss at the baroque fountain, quieter late in the evening.
Day 11:Ancient Rome
Morning
FeaturedPics · CC BY-SA 4.0Colosseum
The great amphitheatre, best right at opening time.
Noon
Roman Forum
The ruins of Rome’s ancient civic heart, below the Palatine.
Evening
Piazza del Campidoglio
Michelangelo’s square, with sunset views over the Forum.
Day 12:The Vatican
Morning
Vatican Museums
Raphael’s rooms and the Sistine Chapel.
Noon
St. Peter’s Basilica
Michelangelo’s dome and Bernini’s colonnade.
Evening
Castel Sant’Angelo
Hadrian’s tomb turned fortress, beside the Tiber.
Florence
Days 13–15
Day 13:Train to Florence and the Duomo
Travel day: Rome → Florence · By train · ~1h 35m
Morning
Travel from Rome
Noon
Gary Campbell-Hall · CC BY 2.0Florence Cathedral
Brunelleschi’s dome — climb it, or the bell tower beside it for a view of the dome.
Evening
Korinta · CC BY-SA 4.0Ponte Vecchio
The medieval bridge of goldsmiths’ shops, golden at sunset.
Day 14:The Uffizi and the view
Morning
Uffizi Gallery
Botticelli’s Venus and Primavera; book the first entry of the day.
Noon
Mercato Centrale
RestaurantThe upstairs food hall for fresh pasta, lampredotto and pizza.
Evening
Piazzale Michelangelo
The whole city at your feet as the sun goes down.
Day 15:David, gardens and Santo Spirito
Morning
Galleria dell’Accademia
Michelangelo’s David, best seen early before the tour groups.
Noon
Boboli Gardens
Terraced Medici gardens behind the Pitti Palace.
Evening
Piazza Santo Spirito
The Oltrarno’s lively square for an aperitivo and dinner.
Athens
Days 16–17
Day 16:Fly to Athens
Travel day: Florence → Athens · By plane · ~2h
Morning
Travel from Florence
Noon
Plaka
The old quarter of neoclassical houses below the Acropolis.
Evening
Monastiraki Square
A lively square with rooftop views of the lit Acropolis.
Day 17:The Acropolis
Morning
Giles Laurent · CC BY-SA 4.0Acropolis of Athens
The Parthenon and its temples, best at opening time.
Noon
Acropolis Museum
The original sculptures, with a view back to the Parthenon.
Evening
Philopappos Hill
A pine-covered hill facing the Acropolis at sunset.
Santorini
Days 18–21
Day 18:Arrival and first caldera views
Travel day: Athens → Santorini · By plane · ~45m
Morning
Fira Caldera Viewpoint
Get your bearings on the cliff-edge promenade, the volcano floating on the horizon.
Noon
PitoGyros Traditional Grill Fira
RestaurantA local favourite for souvlaki and grilled meats a few steps back from the caldera.
Evening
Franco’s Bar Santorini
A cocktail on a terrace hanging over the caldera as the cliffs turn gold.
Day 19:Akrotiri, the Red Beach and volcanic wine
Morning
Akrotiri Archaeological Site
The astonishingly preserved Bronze-Age town buried by the eruption that shaped the island.
Noon
Red Beach
Dramatic crimson cliffs plunging into clear water, best admired from the viewpoint path.
Evening
Santo Wines Winery
Assyrtiko flights on a terrace above the caldera — the classic Santorini sunset tasting.
Day 20:The caldera hike to Oia
Morning
Fira to Oia Hiking Trail
The island’s classic clifftop walk through Firostefani and Imerovigli with nonstop views.
Noon
Skaros Rock
A short detour to the ruined headland castle jutting out into the caldera.
Evening
Oia Castle
The Byzantine castle ruins at the village tip — the front-row seat for the Oia sunset.
Day 21:Ammoudi Bay and a slow goodbye
Morning
Ammoudi Bay
The red-cliff fishing port below Oia — swim off the rocks before the boats come in.
Noon
Ammoudi Fish Tavern
RestaurantSun-dried octopus and the catch of the day at a table almost in the Aegean.
Evening
Atlantis Books Oia
A tiny, much-loved cave bookshop in the lanes for a last unhurried hour.
Lisbon
6 activities
Day 1 · Morning
Praça do Comércio
The riverside square where the city opens onto the Tagus.
Day 1 · Noon
Time Out Market Lisboa
RestaurantA food hall of Lisbon favourites for an easy first lunch.
Day 1 · Evening
Miradouro de Santa Luzia
Tiled terrace over Alfama’s rooftops at golden hour.
Day 2 · Morning
Castelo de São Jorge
Moorish castle walls with the widest view of the city.
Day 2 · Noon
Lisbon Cathedral
The fortress-like Sé, Lisbon’s oldest church.
Day 2 · Evening
Clube de Fado
An intimate fado house in the lanes of Alfama.
Porto
6 activities
Day 3 · Morning
São Bento Railway Station
Arrive under twenty thousand blue-and-white tiles telling Portugal’s history.
Day 3 · Noon
Clérigos Tower
Climb the baroque tower for the best view over the old town’s rooftops.
- Diego Delso · CC BY-SA 3.0
Day 3 · Evening
Cais da Ribeira
The riverside quay under the Dom Luís I bridge — dinner facing the lit-up Gaia cellars.
Day 4 · Morning
Livraria Lello
The neo-Gothic bookshop with the crimson staircase; a timed ticket beats the queue.
Day 4 · Noon
Mercado do Bolhão
RestaurantThe restored market hall for sardines, cheese and a petiscos lunch.
Day 4 · Evening
Port lodges of Vila Nova de Gaia
Walk the bridge’s upper deck to Gaia for a tasting in the old port cellars.
Madrid
5 activities
Day 5 · Noon
Mercado de San Miguel
RestaurantAn iron-and-glass market hall for croquetas, oysters and vermouth.
- Jorge Franganillo · CC BY 2.0
Day 5 · Evening
Plaza Mayor
The arcaded 17th-century square, at its best as the lamps come on.
Day 6 · Morning
Museo del Prado
Velázquez, Goya and Bosch; go at opening time and choose a few rooms.
Day 6 · Noon
El Retiro Park
Row a boat on the great pond, then a slow lunch in the shade.
Day 6 · Evening
Templo de Debod
A real Egyptian temple on a hill — Madrid’s favourite sunset spot.
Barcelona
8 activities
Day 7 · Noon
La Boqueria
RestaurantThe famous market off La Rambla — find a counter bar for lunch.
Day 7 · Evening
Barcelona Cathedral
Gothic lanes and quiet squares around the cathedral as the day cools.
- Bernard Gagnon · CC BY-SA 3.0
Day 8 · Morning
Sagrada Família
Gaudí’s basilica, still being built — the stained-glass light is best in the morning.
Day 8 · Noon
Casa Batlló
Gaudí’s rippling “house of bones” on the Passeig de Gràcia.
Day 8 · Evening
Bunkers del Carmel
Old anti-aircraft bunkers with a 360° view over the city at sunset.
- essetefano · CC BY 3.0
Day 9 · Morning
Park Güell
Gaudí’s mosaic terrace and pavilions above the city; book a morning slot.
Day 9 · Noon
Santa Maria del Mar
El Born’s soaring Gothic church, then tapas in the lanes around it.
Day 9 · Evening
Barceloneta Beach
A last swim, then seafood by the sea.
Rome
8 activities
Day 10 · Noon
Piazza della Madonna dei Monti
A village-like square in the Monti neighbourhood.
- Diliff · CC BY 3.0
Day 10 · Evening
Trevi Fountain
Coin toss at the baroque fountain, quieter late in the evening.
- FeaturedPics · CC BY-SA 4.0
Day 11 · Morning
Colosseum
The great amphitheatre, best right at opening time.
Day 11 · Noon
Roman Forum
The ruins of Rome’s ancient civic heart, below the Palatine.
Day 11 · Evening
Piazza del Campidoglio
Michelangelo’s square, with sunset views over the Forum.
Day 12 · Morning
Vatican Museums
Raphael’s rooms and the Sistine Chapel.
Day 12 · Noon
St. Peter’s Basilica
Michelangelo’s dome and Bernini’s colonnade.
Day 12 · Evening
Castel Sant’Angelo
Hadrian’s tomb turned fortress, beside the Tiber.
Florence
8 activities
- Gary Campbell-Hall · CC BY 2.0
Day 13 · Noon
Florence Cathedral
Brunelleschi’s dome — climb it, or the bell tower beside it for a view of the dome.
- Korinta · CC BY-SA 4.0
Day 13 · Evening
Ponte Vecchio
The medieval bridge of goldsmiths’ shops, golden at sunset.
Day 14 · Morning
Uffizi Gallery
Botticelli’s Venus and Primavera; book the first entry of the day.
Day 14 · Noon
Mercato Centrale
RestaurantThe upstairs food hall for fresh pasta, lampredotto and pizza.
Day 14 · Evening
Piazzale Michelangelo
The whole city at your feet as the sun goes down.
Day 15 · Morning
Galleria dell’Accademia
Michelangelo’s David, best seen early before the tour groups.
Day 15 · Noon
Boboli Gardens
Terraced Medici gardens behind the Pitti Palace.
Day 15 · Evening
Piazza Santo Spirito
The Oltrarno’s lively square for an aperitivo and dinner.
Athens
5 activities
Day 16 · Noon
Plaka
The old quarter of neoclassical houses below the Acropolis.
Day 16 · Evening
Monastiraki Square
A lively square with rooftop views of the lit Acropolis.
- Giles Laurent · CC BY-SA 4.0
Day 17 · Morning
Acropolis of Athens
The Parthenon and its temples, best at opening time.
Day 17 · Noon
Acropolis Museum
The original sculptures, with a view back to the Parthenon.
Day 17 · Evening
Philopappos Hill
A pine-covered hill facing the Acropolis at sunset.
Santorini
12 activities
Day 18 · Morning
Fira Caldera Viewpoint
Get your bearings on the cliff-edge promenade, the volcano floating on the horizon.
Day 18 · Noon
PitoGyros Traditional Grill Fira
RestaurantA local favourite for souvlaki and grilled meats a few steps back from the caldera.
Ted Chen
Day 18 · Evening
Franco’s Bar Santorini
A cocktail on a terrace hanging over the caldera as the cliffs turn gold.
Day 19 · Morning
Akrotiri Archaeological Site
The astonishingly preserved Bronze-Age town buried by the eruption that shaped the island.
Jakub Budzyński
Day 19 · Noon
Red Beach
Dramatic crimson cliffs plunging into clear water, best admired from the viewpoint path.
Helena
Day 19 · Evening
Santo Wines Winery
Assyrtiko flights on a terrace above the caldera — the classic Santorini sunset tasting.
Macy
Day 20 · Morning
Fira to Oia Hiking Trail
The island’s classic clifftop walk through Firostefani and Imerovigli with nonstop views.
Anastasios Papaioannou
Day 20 · Noon
Skaros Rock
A short detour to the ruined headland castle jutting out into the caldera.
Romano Conte
Day 20 · Evening
Oia Castle
The Byzantine castle ruins at the village tip — the front-row seat for the Oia sunset.
Ammoudi Bay
Day 21 · Morning
Ammoudi Bay
The red-cliff fishing port below Oia — swim off the rocks before the boats come in.
Ammoudi Fish Tavern
Day 21 · Noon
Ammoudi Fish Tavern
RestaurantSun-dried octopus and the catch of the day at a table almost in the Aegean.
Day 21 · Evening
Atlantis Books Oia
A tiny, much-loved cave bookshop in the lanes for a last unhurried hour.
Places saved to this trip, grouped by stop.
Hotels
Lisbon
Memmo Alfama
mid-range
Walk to the castle, the cathedral and the fado houses.
Porto
The Yeatman
luxury
Port-lodge country on the doorstep and the classic view of Porto.
Rome
Hotel Raphael
luxury
Central for walking the historic centre.
Athens
Hotel Grande Bretagne
luxury
The metro at the door and an Acropolis view from the roof.
Santorini
Cosmopolitan Suites Santorini
luxury
Sunset views and a central Fira base without the Oia crush.
Restaurants
Lisbon
Cervejaria Ramiro
Seafood · mid-range
Lisbon’s best-loved seafood hall.
Madrid
Sobrino de Botín
Castilian · mid-range
One of the world’s oldest restaurants; book ahead for dinner.
Barcelona
El Xampanyet
Tapas · budget
A standing-room El Born classic; go early.
Rome
Roscioli Salumeria con Cucina
Roman · mid-range
A Roman classic; book ahead.
Florence
All’Antico Vinaio
Sandwiches · budget
The queue moves quickly; eat on the steps of a nearby piazza.
Athens
Ta Karamanlidika tou Fani
Greek meze · budget
Great value in the centre.
Santorini
Metaxi Mas Restaurant
Greek · mid-range
The island favourite locals book days ahead — worth the short drive.
Image credits
- Vitor Oliveira — Wikimedia Commons (opens in a new tab) (CC BY-SA 2.0)
- Diego Delso — Wikimedia Commons (opens in a new tab) (CC BY-SA 3.0)
- Jorge Franganillo — Wikimedia Commons (opens in a new tab) (CC BY 2.0)
- essetefano — Wikimedia Commons (opens in a new tab) (CC BY 3.0)
- FeaturedPics — Wikimedia Commons (opens in a new tab) (CC BY-SA 4.0)
- Gary Campbell-Hall — Wikimedia Commons (opens in a new tab) (CC BY 2.0)
- Giles Laurent — Wikimedia Commons (opens in a new tab) (CC BY-SA 4.0)
- Bernard Gagnon — Wikimedia Commons (opens in a new tab) (CC BY-SA 3.0)
- Diliff — Wikimedia Commons (opens in a new tab) (CC BY 3.0)
- Korinta — Wikimedia Commons (opens in a new tab) (CC BY-SA 4.0)
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