Tailor-Made Lisbon City Breaks

Lisbon at a glance

Lisbon is often called the “City of Seven Hills” with each offering impressive views over the city’s terracotta roofs and whitewashed buildings to the River Tagus and beyond.

This striking capital is the perfect starting point for a Portuguese adventure, blending culture, coastal beauty and unforgettable experiences that easily fit into a well-paced itinerary.

Begin by exploring the heart of the city in Baixa and Chiado, Lisbon’s elegant downtown districts. Stroll through grand plazas, browse local boutiques and enjoy a bica (espresso) with a pastel de nata. Then wander up to Alfama, the city’s oldest neighbourhood, filled with medieval alleys and the impressive St George’s Castle.

As evening falls, head to Bairro Alto, Lisbon’s lively nightlife hub, known for vibrant bars, rooftop terraces, and authentic Fado venues.

The riverside district of Belém is home to iconic landmarks like Jerónimos Monastery and Belém Tower, as well as museums and waterfront walks.

For a special day trip, explore the magical Pena Palace in Sintra and the charming former fishing village of Cascais. Food lovers can add a Small Group Food and Wine Tour, tasting traditional Portuguese delights, perfectly paired with wines from the Alentejo region.

Finally, consider a twin-centre break by pairing Lisbon with Porto, known for its historic riverside and famous wine, or the Algarve, offering stunning beaches and charming coastal villages. And with direct train transfers included in the itinerary, it allows for a hassle-free experience.

Things to do in Lisbon

• St George’s Castle: On the top of the highest hill in Lisbon sits this ancient Moorish castle.
• Alfama District: Particularly charming and historic area of the city, with its maze of cobbled streets, churches and pretty squares.
• Monastery of St Jerome: 16th century monastery housing the tomb of explorer Vasco de Gama.
• Oceanarium: Beautifully laid out and modern aquarium, with fascinating displays of aquatic life.
• Feria da Ladra: Lisbon’s flea market is held beside the impressive Santa Engracia church and boasts a great variety of clothes and trinket stalls.

We can book many tours to make your trip to Lisbon truly memroable, visit our Osprey Experiences page for more information or contact on our our team.