The Portuguese were the first to discover the route from Europe to Asia by sea. This goal was achieved by explorer Vasco da Gama, who sailed some 24,000 miles over two years, travelling south along the coast of Africa and around the Cape of Good Hope. With the help of a local navigator, da Gama crossed the Indian Ocean and reached the coast of India at Calicut, making history on 20 May 1498.

While the local Hindu population initially welcomed the arrival of the Portuguese sailors, the Muslim merchants saw them as competition for the spice trade. The Portuguese fleet was also met with hostility when the monarch of Calicut, the Zamorin, deemed their gifts inadequate as gold had been expected. As a result, the Portuguese had to leave Calicut immediately.

The voyage was deemed a success nonetheless, and the King of Portugal, Manuel I, declared the issuance of a 10-cruzado coin (known as a Português) made of pure gold to celebrate this pioneer voyage to India.

In a subsequent voyage to the east, the Portuguese sent a larger fleet commanded by Pedro Álvares Cabral to capitalise on da Gama’s discoveries, and a trading post was set up in the kingdom of Cochin, India. Some violence ensued amid efforts to secure a trading post at Calicut. From then on, the Portuguese proceeded to establish various trading centres and factories in India, including Tangasseri, Quilon and Kannur, establishing the Portuguese government in the east.

Portuguese general Afonso de Albuquerque subsequently captured Goa in 1510 and Melaka in 1511, as part of the Portuguese trade expansion to China and Southeast Asia.

Southeast Asia saw a trade boom between the 15^th and the mid-17^th centuries – a time known as the Age of Commerce.

Several factors contributed to this economic growth:

1. The geopolitical instability in Southeast Asia led to port cities expanding and proliferating, further aided by the power vacuum of the declining Srivijaya empire and the Majapahit empire's inability to control trade.

2. The demand for spices spiked in China and the West. In the early 1400s, Admiral Zheng He introduced pepper to North Sumatra and West Java, creating a pepper trade boom in the region and driving up demand. European demand for spices also surged after the signing of a treaty between Venice and the Mamluk rulers of Egypt for reliable spice purchases in Alexandria in 1345.

3. In 1371, Chinese maritime trade saw a revival as the Ming Dynasty tweaked the ban on private overseas trade by allowing an alternative arrangement: tributary trade. This was a precursor to Admiral Zheng He’s expedition in 1405 , which strengthened ties with various newly-minted port cities, and encouraged the cultivation of spices such as pepper. Despite the maintenance of the official ban on maritime trade, weak enforcement aided in the flourishing of Chinese trade. From 1429, through Ryukyu, Chinese traders developed trade networks between Southeast Asia, Ming China, Korea and Japan. The demand for Southeast Asian spices in China was so huge that Chinese soldiers received pepper as part of their salary.

4. New maritime trade routes established by European traders also increased population sizes. Major cities including Ayutthaya, Pegu, Hanoi, Demak and Melaka exceeded 50,000 people. When the Portuguese sacked Melaka in 1511, the city was estimated to have a population of between 10,000 and 200,000.

After the Portuguese conquered Melaka, the Sultanate resettled along the Johor River. Singapore's fortunes returned as it became the proxy port for conducting foreign trade with the re-established Johor Sultanate. The Europeans' entry into the Southeast Asian markets sustained the trade boom. Between 1510 and 1670, Southeast Asian pepper exports saw a 550 percent increase. In addition to the Portuguese trade, Muslim trade routes were also re-established by the 1560s as they could carry more pepper and spice to the Mediterranean than the Portuguese.

The entry of the Dutch trading conglomerate, Verenigde Oost-Indische Compagnie, in 1602 marked the monopolisation of long-distance trade’s most lucrative aspects, taking profit out of Southeast Asian hands. Singapore’s position as a proxy port under the Johor Sultanate hung precariously in the balance. In 1603, the Santa Catarina incident off the coast of Changi foreshadowed power shifts in the region from the Portuguese to the Dutch, and unrest in the Straits saw a decline in trade.

In 1613, an Acehnese attempt to destroy all the Johor Sultanate’s ships in Singapore’s harbour forced the Sultanate to relocate to Riau, displacing the need for Singapore as its proxy port. As with other ports, the Dutch also reduced Singapore’s trade to a bare minimum by forcibly shifting the sea trade routes away from the Straits of Melaka to the Sunda Straits. Within a century, the Age of Commerce in Southeast Asia came to an end.

Throughout its 700-year history, Singapore was no stranger to turmoil. The 16^th century saw Singapore’s destruction – and its eventual rise to greater heights.

After the Portuguese takeover of Melaka in 1511, the Laksamana was said to have moved to Singapore. Historians have speculated that since the Laksamana’s job was to engage foreign trade, his presence would have naturally drawn more merchants to call at Singapore and revive the weakened port. This, coupled with the retreat of the Melaka armada to Singapore, was enough reason for the Portuguese to attack the port of Singapore, as well as Johor and Bintan.

In August 1526, the Portuguese claimed to have destroyed a town at the mouth of the Singapore River during their journey through Keppel Harbour towards Maluku, Indonesia. Portuguese chronicler João de Lisboa offered insights about Singapore’s location, observing that the route from Melaka to Maluku passed between “two mountains which are only a small crossbow shot apart” – possibly referring to the waterway between Labrador Point and Sentosa. Northwards lay a bay on which the settlement Çimquapura (Singapore) sat. De Lisboa added, “This settlement was destroyed by us.” But despite the destruction, the town was later rebuilt according to Portuguese sources.

When the Johor Sultanate was established around 1530, Singapore became an integral part of Johor’s riverine economy. For more than a century, Singapore was a flourishing port until the Dutch arrived in the region.