If you want to experience Portugal in five days without stress, without rushing, and without the “I took photos but didn’t feel the place” feeling, this itinerary is for you.

This is a complete, ready-to-use 5-day itinerary plan built around the private tours I run from Lisbon. It’s designed for travellers who want the perfect balance of iconic highlights, real history, beautiful scenery, and a pace that still leaves room for good food, small moments, and spontaneity. Additionally, you'll also find hotel recommendations in Lisbon.

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Base: Lisbon Tour style: private, comfortable, flexible.

Perfect for: First-timers, return visitors, couples, families, small groups

Quick overview: your 5-day itinerary

Day 1: Lisbon Half-Day Tour — Santa Luzia & Baixa → Cristo Rei → Belém - A perfect introduction to Lisbon, combining historic viewpoints, elegant downtown streets, a panoramic river crossing, and the city’s Age of Discoveries landmarks.

Day 2: Sintra & Cascais Tour — palaces, mountains, Atlantic cliffs - A UNESCO World Heritage landscape of fairy-tale palaces and lush hills, paired with dramatic Atlantic coastline and coastal elegance.

Day 3: Évora Tour — Roman heritage and the soul of Alentejo - A UNESCO-listed city where Roman ruins, medieval history, and Alentejo’s slow rhythm come together.

Day 4: Fátima – Nazaré – Óbidos Tour — pilgrimage, ocean power, medieval charm - A day of contrasts, from Portugal’s most important pilgrimage site to the Atlantic’s raw force and a beautifully preserved medieval town.

Day 5: Setúbal – Arrábida – Palmela Tour — markets, beaches, castles, and wine views - An authentic coastal journey combining local market life, one of Portugal’s most stunning natural parks, and a hilltop castle overlooking sea and vineyards.

Day 1 — Lisbon Half-Day Tour

Santa Luzia & Baixa → Cristo Rei → Belém

This half-day itinerary is the perfect first taste of Lisbon.

You’ll start inside the city’s historic heart, climb up to one of its most photogenic viewpoints, walk through the elegant downtown rebuilt after the 1755 earthquake, cross the river for a panoramic moment at Cristo Rei, and finish in Belém, where Portugal’s Age of Discoveries shaped world history.

It’s Lisbon’s story, told in the right order: the city, the view, the river, and the global legacy.

1) Miradouro de Santa Luzia: Lisbon’s postcard moment

If Lisbon has a “classic postcard scene,” it’s here.

Santa Luzia sits above the Alfama area and delivers one of the most iconic views in the city:

• terracotta rooftops rolling down toward the river

• historic church domes in the foreground

• The Tagus shining in the distance

It also has one of the most charming details in Lisbon: the blue-and-white tile panels (azulejos), telling stories of Portuguese history and traditional life.

Why it matters: This viewpoint helps you understand Lisbon’s geography instantly — the hills, the layers, and the city’s relationship with the river. It’s the perfect “first wow” moment.

Peppe’s local tip: This is the best place to slow down for five minutes and take it in properly. Lisbon is not a city you rush — it’s a city you absorb.

2) Baixa: the elegant Lisbon rebuilt after the disaster

After the viewpoint, we go down into Baixa, Lisbon’s grand and structured downtown.

Baixa looks orderly for a reason: it was rebuilt almost from scratch after the 1755 earthquake, followed by a tsunami and fires that devastated the city. What came next was one of Europe’s most impressive reconstruction projects — a new “modern” Lisbon with wider streets, safer buildings, and an urban layout that was revolutionary at the time.

What we explore in Baixa

• Praça do ComércioLisbon’s monumental riverfront square — once the entry point for kings, diplomats, and merchants arriving by boat.

• Rua AugustaThe main pedestrian street, is full of life, architecture, and classic Lisbon energy.

• Rossio Square (Praça Dom Pedro IV) is one of the city’s most historic squares — a stage for centuries of Lisbon’s public life.

  
  

Why it matters: Baixa represents Lisbon’s resilience. This is the city that rebuilt itself and decided to come back stronger, brighter, and more open to the world.

3) Cristo Rei: the panoramic Lisbon moment across the river

Now we cross the Tagus to the south bank for one of the most striking viewpoints in the Lisbon area.

Cristo Rei was built in the mid-20th century as a symbol of faith and gratitude, inspired by Rio de Janeiro’s famous statue — but the real reason this stop is unforgettable is the view.

From here you’ll see:

• The 25 de Abril Bridge stretches across the river

• The full skyline of Lisbon from a cinematic angle

• The Tagus opens toward the Atlantic

Why it matters: This is the best “big picture” perspective you’ll get of Lisbon. It connects everything: hills, river, history, and scale.

Peppe’s local tip: Even travellers who think they’re “not into viewpoints” end up loving this stop. It’s a Lisbon moment that stays with you.

4) Belém: where Portugal became global

We finish the half-day in Belém, one of the most historically significant areas in Portugal.

During the 15th and 16th centuries, Lisbon became one of the world’s most powerful ports — and Belém was its gateway. Ships left this stretch of river to cross oceans, reach India, and reshape world trade routes. This isn’t “just history.” It’s Portugal’s global identity.

What you’ll see in Belém ( from the outside, as it's a half-day tour)

• Jerónimos Monastery (Mosteiro dos Jerónimos) —A UNESCO World Heritage masterpiece and the ultimate example of Manueline architecture — a uniquely Portuguese style filled with maritime symbolism. Built to honour Vasco da Gama’s voyage to India, it represents Portugal’s golden age.

• Belém Tower (Torre de Belém) — originally a defensive fortress guarding the harbour — today is one of the most iconic monuments in Portugal, elegant, military, and poetic all at once.

• Monument to the Discoveries (Padrão dos Descobrimentos) — A dramatic memorial shaped like a ship’s prow, honouring the explorers, navigators, and visionaries behind Portugal’s Age of Discoveries.

• And of course…

• A pastel stop (because this is non-negotiable). You can’t do Belém without tasting the famous pastries. It’s not just a sweet — it’s part of Lisbon’s tradition.

Day 2 — Sintra & Cascais Tour

Palaces • lush hills • Atlantic cliffs • coastal charm

Sintra feels like a fairytale, but it’s very real — and it has fascinated people for centuries.

Once a summer retreat for Portuguese royalty and aristocrats, Sintra became the setting for romantic architecture, gardens, and palaces built to impress, protect, and escape the heat of Lisbon.

This tour combines Sintra’s magic with Cascais’ coastal beauty, making it one of the most spectacular day trips you can do from Lisbon.

1) Sintra: a UNESCO dream in the mountains

Sintra is cooler, greener, and more mysterious than Lisbon — a landscape of misty forests and dramatic hills.

Key landmarks (chosen based on your preferences)

• Pena Palace (Palácio da Pena): The most famous palace in Sintra and a symbol of 19th-century Romanticism. It’s colourful, theatrical, and sits at the top of the mountain like a dream.

• Quinta da Regaleira: A magical estate filled with symbolism, secret tunnels, hidden gardens, and the famous Initiation Well — one of the most intriguing places in Portugal.

• Monserrate Palace: A 19th-century Romantic palace blending Gothic, Moorish, and Indian influences, surrounded by one of the most extraordinary botanical gardens in Europe.

• Moorish Castle: A 9th-century Moorish fortress set along Sintra’s mountain ridge, offering sweeping views over the forested hills and all the way to the Atlantic Ocean.

• The historic centre of Sintra: Charming streets, local pastry shops, and the kind of atmosphere that makes people slow down without even noticing.

• Peppe’s local highlight: Try a travesseiro pastry in Sintra — light, sweet, and dangerously addictive.

2) Cabo da Roca: the edge of Europe

Cabo da Roca is the westernmost point of mainland Europe.

It’s not a place you visit for monuments — you visit for the feeling:

• cliffs dropping into the Atlantic

• wind, sea spray, and open horizon

• the sense of standing at the edge of the continent

Why it matters: This stop delivers a different Portugal: wild, dramatic, and powerful.

3) Cascais: relaxed coastal elegance

Cascais is where Lisbon goes to breathe. Once a fishing village, it became a stylish seaside escape for the royal family in the late 19th century — and that blend of tradition and elegance is still there.

What you’ll experience

• ocean views and beachfront streets

• the charming old town

• a relaxed, end-of-day coastal vibe

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If you want to end the day with a sunset by the sea, Cascais is the perfect place to do it.

Day 3 — Fátima, Nazaré & Óbidos Tour

Pilgrimage • waves • medieval walls

This is one of Portugal’s most powerful contrast days: spiritual history, raw Atlantic beauty, and a medieval village that feels straight out of a storybook.

1) Fátima: Portugal’s most important pilgrimage site

Fátima became world-famous after the reported Marian apparitions of 1917, witnessed by three young shepherd children. Today, it’s one of the most visited pilgrimage destinations in the world.

Key places

• Sanctuary of Our Lady of Fátima: A vast religious complex with two major basilicas and a powerful atmosphere — even for non-religious travellers.

• The main square and pilgrimage path. This is where you feel the scale of what Fátima represents: faith, devotion, tradition, and human emotion.

• Why it matters: Fátima is not about ticking a box. It’s about understanding a piece of modern Portugal that still shapes identity and culture.

2) Nazaré: the ocean’s wild theatre

Nazaré is famous for two things: tradition and waves. This is a fishing town with deep roots — but it also became a global phenomenon because of the giant waves formed by the underwater Nazaré Canyon.

What you’ll experience

• Sítio da Nazaré viewpoint: The best panoramic view over the town and coastline.

• Praia do Norte (seasonal) If the conditions are right (especially in autumn and winter), you may see the Atlantic at its most dramatic.

• Why it matters: Nazaré reminds you that Portugal is shaped by the ocean — not just geographically, but emotionally.

3) Óbidos: medieval Portugal in one walk

Óbidos is one of Portugal’s most beautiful walled towns. It was historically gifted to Portuguese queens, earning the nickname “The Wedding Gift Town.” And when you walk its narrow streets, you understand why it feels romantic.

What you’ll do

• wander the cobbled streets and whitewashed houses

• explore artisan shops

• walk the castle walls (weather and comfort permitting)

Peppe’s local highlight: Try the famous ginjinha (cherry liqueur) served in a chocolate cup. It’s a classic Óbidos ritual.

Day 4 — Évora Tour

Roman heritage • UNESCO charm • Alentejo soul

Évora is one of the most important historic cities in Portugal, and the perfect introduction to the Alentejo region — a place of wide landscapes, slow rhythm, and deep tradition.

What makes Évora special

Évora has layers: Roman, medieval, religious, and academic. It’s a city that feels beautifully preserved, but still lived-in.

Key landmarks

• Cork Factory Visit An insightful stop to understand how Portugal became the world’s leading cork producer, from raw material to finished product — and why cork remains such a sustainable and iconic Portuguese industry.

• Roman Temple (Templo Romano de Évora): Often (incorrectly) called the Temple of Diana, this is one of the best-preserved Roman monuments in Portugal.

• Évora Cathedral (Sé de Évora): A monumental cathedral blending Romanesque and Gothic styles, with incredible views from the roof.

• Chapel of Bones (Capela dos Ossos): A haunting, unforgettable space lined with human bones and skulls — created as a reminder of mortality.

• Alentejo Wine Tasting (optional)An opportunity to taste local Alentejo wines, known for their warmth, depth, and character, and to understand why this region is one of Portugal’s most respected wine-producing areas.

• Why it matters: Évora is a history lover’s dream, but it also delivers atmosphere — the quiet beauty of Alentejo is very different from Lisbon’s energy.

Day 5 — Setúbal, Arrábida & Palmela Tour

Market culture • coastal beauty • castle views

This is one of the most underrated and rewarding day trips from Lisbon, combining authentic local life, breathtaking natural scenery, and one of the region’s most important wine traditions.

You’ll experience the working character of Setúbal, the dramatic landscapes of the Arrábida Natural Park, and a historic hilltop castle with panoramic views over vineyards and the Atlantic.

1) Setúbal: local flavour and real Portugal

Setúbal is a coastal city with a strong, genuine character — less polished, more authentic, and deeply connected to the sea. A stop at the Mercado do Livramento is a perfect introduction to local life, with its colourful stalls of seafood, fresh produce, and regional products.

Local highlight: Setúbal is famous for its fresh fish and seafood, especially cuttlefish (choco frito), one of the region’s most traditional dishes.

2) Arrábida: Portugal’s hidden coastline near Lisbon

The Arrábida Natural Park offers some of the most beautiful landscapes in Portugal:

• green mountains dropping into turquoise water

• winding scenic coastal roads

• small, secluded beaches with an almost Mediterranean feel

• Despite its proximity to Lisbon, Arrábida still feels like a well-kept secret.

3) Palmela: castles, vineyards, and wine traditions

Palmela Castle sits high above the peninsula, with sweeping views over:

• the Setúbal coastline

• the surrounding vineyards

• and, on clear days, all the way to Lisbon

The castle has a long strategic history, shaped by the Reconquista and the military orders that once defended this territory.

Wine tasting experience (after lunch)After lunch, there is the opportunity to visit one of the local winemakers for a wine tasting session, where you can try the famous Moscatel de Setúbal, alongside other regional wines. This experience offers insight into one of Portugal’s most distinctive fortified wines and the winemaking traditions that define the region.

Optional alternative landmarks (depending on pace and interests)

This tour is flexible and can include alternative or additional stops such as:

• Cabo Espichel, a dramatic headland with sheer cliffs, pilgrimage history, and vast Atlantic views

• Sesimbra, a traditional fishing town known for its castle, beaches, and relaxed seaside atmosphere

• Portinho da Arrábida, one of the most picturesque beaches in the region, with crystal-clear waters and sheltered coves

Why it matters

This day brings together landscape, tradition, and flavour. From local markets to wild coastline, historic fortresses, and iconic wines, it’s a perfect closing chapter — where Portugal’s natural beauty and cultural depth meet in one unforgettable journey.

Why this itinerary works

This 5-day plan gives you a complete Portugal experience:

• Lisbon’s history and viewpoints

• Sintra’s magic + coastal cliffs

• Sacred tradition + ocean power + medieval charm

• UNESCO heritage in Alentejo

• A stunning hidden coastline near Lisbon

It’s the kind of itinerary that feels varied, complete, and memorable — without exhausting you.

Want to do this as a private, seamless journey?

If you’d like to experience Portugal with everything taken care of — comfortable transport, local insight, flexible pacing, and the best stops along the way — I’d love to tailor these days to your travel style.

FOR FURTHER INFO OR TO MAKE A RESERVATION, CLICK BELOW TO SEND AN EMAIL

mailto:bookings@portugaljourneyswithpeppe.co

Portugal isn’t a place you rush through. It’s a place you return to — even if it’s your first time.