Music, Monasteries And Miradouros – The Ultimate Lisbon Itinerary (2024)

Portugal’s radiant capital boasts a history of over two millennia, reflected in a colourful medley of Moorish architecture and Baroque splendour. Lisbon is a wanderer’s delight, from cobbled alleys lined with azeulejo tiles to the patterned pathways of its promenades and the gold-laden churches to the ancient fortification of São Jorge Castle. The city’s iconic yellow trams rattle through the steep streets overflowing with cafes and tavernas. The nightlife of Bairro Alto vies for attention with the cultural venues of Chiado and the maritime legacy of Belém, creating a unique vibe of its own. Whether it’s the joy of savouring a creamy pastel de nata in a bustling bakery or cheering a street musician at a busy square, Lisbon is a city that promises to enchant and inspire at every turn. Let us pique your curiosity with this thoughtfully crafted five-day Lisbon itinerary, peppered with just the right mix of history, culture, art and cuisine.

From hilltop castles to beach towns and time-worn villages, get started with this selection of the most beautiful places in Portugal.

Best time to visit Lisbon

Lisbon is a city for every season. The pleasant weather of spring (March to May) and fall (September to November) is ideal for exploring the city’s historic sites and enjoying outdoor activities. Beachgoers can take advantage of warm temperatures to enjoy the spectacular coastline. Even during winter, the weather remains mild enough to explore Lisbon comfortably, with fewer crowds at popular attractions. Festivals, concerts, and art exhibitions run through the year. Create a Lisbon itinerary that suits your individual style and preference.

For a detailed breakdown, check out this guide to the best time to visit Portugal for good weather, lower prices and more, according to a local.

Itinerary days 1-2: Olá Lisbon!

For a perfect introduction to your Lisbon itinerary, take a yellow tram to Belém, a neighbourhood emblematic of the city’s maritime heritage and architectural brilliance. One of the notable landmarks here is the UNESCO World Heritage tagged Jerónimos Monastery, a masterpiece of Manueline architecture, housing the tomb of Portuguese explorer Vasco da Gama. Explore the cloisters and vaulted ceilings and decode the religious symbolism. The iconic Pastéis de Belém bakery nearby is the best place to sample the famous pastéis de nata, delicate custard tarts dusted with cinnamon. The long queue-up is well worth it.

A short stroll will take you to the riverside Belém Tower, where battlements offer sweeping views of sailboats and the 25 de Abril Bridge astride the Tagus River. Stop at The Monument to the Discoveries, a striking structure designed to resemble the prow of a ship. Take a minute to salute the original explorers who took to the high seas searching for unknown worlds.

Also, find out about the coastal city known as the ‘Venice of Portugal’.

On day 2, head to Lisbon’s oldest neighbourhood, Alfama, to gawp at a panorama of the red-roofed city from Miradouro das Portas do Sol. Hours flit by in the jumble of cobblestone streets filled with whitewashed houses, azulejo-decked walls and hanging laundry. One of the must-see landmarks of the area is the Lisbon Cathedral (Sé de Lisboa), notable for its mixture of architectural styles, including Romanesque, Gothic, and Baroque elements. The best way to spend the evening is to treat yourself to an authentic Portuguese meal at a local Fado house. Try the bacalhau à brás, a flavourful cod dish with velvety Portuguese wine, while Fado singers serenade with soulful tunes.

Book your stay at Four Seasons Hotel Ritz Lisbon via Booking.com

Book your stay at Four Seasons Hotel Ritz Lisbon via Agoda.com

Lisbon itinerary day 3: Sintra

On day 3, leave the city behind for a trip to Sintra, a fairytale town in the Sintra Mountains. The area’s highlight is the colourful and whimsical Pena Palace, a Romanticist castle that seamlessly blends Gothic, Renaissance, and Moorish architectural styles. Roam the castle, then fan your love for nature in the extensive forest-like gardens filled with exotic plants and intricate pathways. The Lisbon itinerary continues to Quinta da Regaleira, an estate with lush gardens, mysterious underground tunnels, and symbolic architecture. Delve into the symbolism of the initiation well, a deep, spiral staircase representing spiritual rebirth. On your way back to Lisbon, you can stop at the coastal town of Cascais to stroll along the waterfront promenade lined with cafes and shops or visit the historic Cascais Citadel overlooking the vast Atlantic Ocean. Those who prefer a relaxing evening can unwind at beaches like Praia da Rainha or Praia do Guincho, swim, or try surfing.

Lisbon itinerary day 4: Óbidos and Nazaré

On day 4of your Lisbon itinerary, drive to Óbidos, a hilltop medieval town with stunning views of the rolling hills of the surrounding countryside. You will feel like a character in a storybook while traversing the narrow cobblestone streets bordered by whitewashed houses and decked with bright bunches of bougainvillaea. Pick up pretty artisanal souvenirs and try the local cherry liqueur known as”Ginja de Óbidos” or simply “Ginjinha” served in a small chocolate cup. Those with a taste of history can explore the 12th-century Óbidos Castle, a majestic fortress with imposing walls.

On the way back, stop at the fishing village famous for Nazaré, known for its giant waves and deep maritime traditions. Join locals and pilgrims to admire the Sanctuary of Our Lady of Nazaré, perched dramatically on a cliff overlooking the crashing waves of the Atlantic Ocean. You may notice local women in seven skirts as part of their traditional attire. The colourful, embroidered layers, ranging from deep blues to bright reds, protect against coastal winds and symbolise a deep connection to the sea and fishing traditions. Before you leave, how about some freshly grilled seafood at a cosy restaurant in a quaint street? This simple culinary experience will be one of the high points of your Lisbon itinerary.

Explore more with this guide to the must-visit countries in Southern Europe.

Book your stay at Memmo Alfama - Design Hotels via Booking.com

Book your stay at Memmo Alfama - Design Hotels via Agoda.com

Lisbon itinerary day 5: Shopping and more!

On the last day of your Lisbon itinerary, dive into a shopping spree at Rua Augusta in Baixa, where you’ll find a mix of international brands and local crafts. Head to Príncipe Real, a favourite among fashion enthusiasts and design aficionados, for its exclusive boutiques and concept stores. Avenida da Liberdade offers a grand boulevard lined with high-end luxury brands and designer shops, while Bairro Alto’sAlto’s quirky boutiques and vintage stores cater to those with a bohemian spirit.

In the afternoon, unleash your creativity with a hands-on azulejo tile-making workshop, delving into an ancient craft synonymous with Portuguese artistry. Learn traditional techniques from skilled artisans, creating your own tile masterpiece to take home as a souvenir. For further artistic inspiration, visit LX Factory, a vibrant hub of creativity housed in a converted industrial complex. Explore galleries showcasing local artists and vintage shops nestled in repurposed warehouses. Conclude your Lisbon itinerary with a sumptuous feast at a waterfront restaurant, reflecting on the city’s blend of old-world charm and modern flair. Tchau-tchau Lisbon!

Things to remember when travelling to Lisbon

• Respect local customs by dressing modestly in religious sites.
• Learn a few basic Portuguese phrases for a richer experience.
• Stay hydrated and protect yourself from the sun, especially during summer.
• Utilise public transportation like trams, buses, and the metro for easy city navigation.
• Be cautious of your belongings in crowded tourist areas, and consider using hotel safes for valuables.

Book your stay at TURIM Boulevard Hotel via Booking.com

Book your stay at TURIM Boulevard Hotel via Agoda.com

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(Feature Image Credit: ajay_suresh/Flickr)

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