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Explore Spanish fortresses and pirate history

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Uncover a bloodthirsty history of conquistadors and pirates in the former Spanish stronghold of Portobelo.

We’ll drive you right across the Panamanian isthmus to the Caribbean province of Colón to visit the sleepy town of Portobelo, a UNESCO World Heritage Site that was once the stage for many dramatic historical events.

During the colonial era, heavily fortified Portobelo was one of the most important strongholds on the Spanish Main, protecting the northern extreme of the Camino Real. It was along this ‘Royal Road’ that the conquistadors hauled their looted gold, silver and gemstones from the Inca Empire to ship them off to Spain.

However, the glittering stream of treasure flowing across the isthmus soon caught the attention of the real-life pirates of the Caribbean, including famous figures like Sir Francis Drake and Henry Morgan. Portobelo was attacked, overwhelmed and captured four times – in fact, Portobello Road in London, the Portobello area of Edinburgh and Dublin’s Portobello Barracks all owe their names to British victories here.

You’ll learn about Spanish treasure, pirate raids and violent sieges as you explore Portobelo’s most important fortresses and encounter remnants of the area’s volatile history. Return via the Panama Canal Railway, the first railroad to connect two oceans.

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Real Latin american experts

  • Finn Clennett
    Finn Clennett - Travel Expert

  • Juliet
    Juliet Ellwood - Travel Expert

    After graduating with a degree in Anthropology and History and having been fascinated by Latin America since childhood by the book featuring photos of Nazca, Juliet first visited the region in 2003. Since then, Juliet has visited the majority of countries in Latin America but has particularly extensive experience with Peru, a country she loves for many reasons but not least, its incredible archaeological richness and delicious food!

  • Kathryn
    Kathryn Rhodes - Travel Expert

    Kathryn backpacked across Argentina, Chile, Bolivia and Peru before joining us. She has a degree in Philosophy and French and is a keen netball player.

  • JLA
    Julia Golden - Travel Expert

    Julia’s passion for Latin America was sparked during an unforgettable year-long journey that began in Brazil and continued all the way to Mexico. Along the way, she experienced the continent in many different ways, from vibrant cities and remote villages to breathtaking landscapes and hidden natural wonders. Exploring such a diverse range of destinations gave her a deep appreciation for the region’s cultures, people and scenery, and inspired her love of creating memorable travel experiences for others.

  • Maggie
    Maggie Wilson - Travel Expert

    Maggie visited Latin America on her first backpacking trip when she was 19. Since then, she has taken every opportunity to travel, and has managed to explore a lot of the region in subsequent trips.

  • Mary
    Mary Anne Nelson - Travel Expert

    Born in the Atacama Desert in northern Chile, Mary’s insider knowledge and dry sense of humour make her a highly valued member of the Tailor-made Holidays and Group Tour sales team.

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