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It was mid-autumn on the high seas, and we were halfway across the Taiwan Strait, beating into a northeasterly wind. It could have been a much kinder southwesterly, had we sailed a week earlier, but we were starting a new life, a sailing adventure, and saying goodbye to Hong Kong had taken a lot longer than we thought it would. I winched our reefed mainsail in just a little tighter, and tried to point a degree higher, as we clawed our way upwind into a cold grey rain towards Taiwan.

The notorious currents of the Taiwan Strait, which have earned it the nickname the Black Ditch, were kicking up a steep two-metre chop, knocking us back every time we built some momentum. But then, it had taken some time to build enough momentum just to leave port. To explore the seas on my own sailing boat was a dream I’d been harbouring for three decades.



Finally, my girlfriend and I bought an old but solid boat, and spent several years repairing and upgrading her. We saved money and sketched out our plan on a world map hung on our bedroom wall. Then the pandemic hit.

We spent the time working through our long list of equipment to buy, repairs to make, subscriptions to cancel and moved as much of our administrative lives online as possible. There would be no forwarding address. Finally, on a cool October dawn last year, we cast off from our mooring on Middle Island and pointed Teng Hoi’s bow towards the rising sun.

Our plans were simple – go east to Taiwan, and then north, following the string of Japanese islands until, well, we hadn’t thought that far ahead. We knew we wanted to discover the far-flung islands and little ports. What we didn’t expect was how tightly woven together they were by centuries of maritime trade, piracy, wars and colonial rulers.

As we sailed through our East Asian maritime history lesson, we would gain first-hand knowledge of what has been the core of this fraught, conquered and still-contested region’s centuries-long story. By the second day of our voyage, everything above and below deck was sodden, as the seas breaking over the boat revealed leaks in our hatches. We were heeled over, with all the detritus of offshore existence – life jackets, rain slickers, cushions, empty food wrappers, a stray coffee cup – collecting in a pile on the low side of the saloon.

The objects made a clattering migration across the boat with every tack. But nothing was going to diminish our high spirits as we slowly made our way across the strait. At night I lay in the cockpit, watching the mast sway back and forth across the dark, star-studded sky.

During the day, we dodged fishing boats and watched sea birds circle our vessel. There is no stopping once a yacht is at sea, so we fell into a rhythm of three-hour watches, one person on deck while the other person slept. It was the longest voyage we’d made together, just the two of us, and we were proud of ourselves when the mountains of Taiwan appeared on the horizon.

The long, slow approach into a foreign port under one’s own sails can make a sailor feel like a swashbuckling adventurer. Three and a half days out of Hong Kong, such fancies were dispelled five miles from the harbour when our VHF radio crackled to life. The Taiwanese port authorities asked us who we were, where we were from and where we were going.

We answered their questions with confidence, knowing we had completed our pre-arrival documentation online. When a boat is registered, it is issued something like its own national passport. When a boat leaves a country, it receives a port clearance document, evidence that the boat and crew have cleared customs and immigration.

Port clearance, registration and crew passports are requested when the boat arrives in a new country. Under normal circumstances a boat is allowed into safe harbour for this process, while the crew are quarantined on the boat until the paperwork is complete. In Taiwan, however, long-standing geopolitical fears and an overbearing bureaucracy turned those processes on their head.

As we motored into the harbour, the port authority radioed and asked us to turn around and wait outside the sea wall while they checked the paperwork we had filed online. After a few hours of bobbing in the sea, our radio sounded and we were invited to moor at a coastguard dock for further inspection. We were metres from the dock, about to cast our mooring lines ashore, when the inspectors changed their minds and commanded us to turn around and leave the port, back out into the gloom of the early evening.

“We are a small vessel with only two crew, and we are tired from a long crossing,” I told them over the radio, the tension clear in my voice. “You are putting us in danger by sending us back to sea.” We were slowly idling out of the harbour, hoping the officials would soon change their mind.

“Can’t your motor go faster than that?” they radioed back. “Speed up, and go at least five miles out. Wait there until we radio you.

” I gritted my teeth and did as I was told, knowing that the voices on the radio held all of the power. We spent several hours drifting in circles five miles from land, feeling sorry for ourselves, before we were allowed back into port. We secured our lines in the darkness, watched by a group of apologetic officials and marina staff.

“Welcome to Taiwan,” they said. “It shouldn’t be this way.” We prepared for winter and moored our boat in Tainan, Taiwan’s oldest city and former capital, filled with reminders of the famous foreign sailors who had arrived long ago, and faced far more hostility than we had.

This year, Tainan celebrates 400 years since the Dutch arrived, built Fort Zeelandia in the swampy delta of the Zengwen River, and turned Tainan into a major trading hub. Examples of Dutch architecture still stand throughout Tainan’s historical districts, and museums tell the story of how the ocean-going Europeans turned Taiwan into another link in their global trading empire. Then came Zheng Chenggong, also known as Koxinga, the Ming general and pirate who drove the Dutch out of Tainan in 1661.

Koxinga’s exploits are retold in statues and gardens around the city, and we’d hear his name again as we sailed north. The Japanese took control of Taiwan in 1895, following their victory in the first Sino-Japanese war. Today, half a century of Japanese colonial rule is visible at every turn, from the design of buildings and roads to some of the island’s famously sluggish bureaucracy.

Back then, Imperial ships plied the waters between Taiwan and Japan, cementing Taiwan’s place in the long chain of islands we were planning to hop our way up on our way north. Many of the waves of sailors to arrive on Taiwanese shores have been driven by geopolitical shifts, just like the most recent wave of Hongkongers who have made Taiwan home. We soon felt right at home, overhearing snippets of Cantonese on the streets and eating dim sum in émigré cafes.

Over these winter months, we lived the adage that yacht cruising is just repairing your boat in exotic locations. I spent months negotiating repairs to our engine, and undertook a long list of upgrades, including the installation of a heating system, anticipating colder weather ahead. In spring, we returned to sea, rounding Kenting at the very southern tip of the island, where we caught the first fish of our voyage, a glittering green mahi-mahi.

After a season on land it took some time to readjust to life on the water. Before departure we cooked up a big pot of pasta, making for easy salads or quick hot meals when the seas were rough. We refamiliarised ourselves with all of the handholds in the boat, swinging like monkeys from deck to saloon, and perfected the art of hurried trips to the toilet as the boat swayed and plunged through the waves.

When we arrived at Japan’s Ishigaki Island, in keeping with seafaring tradition, we raised a small yellow flag – Q for quarantine in flag semaphore – as we approached port, to signal that we needed to clear customs and immigration. We felt nervous following our experience in Taiwan, but though there was a sea of paperwork for us to complete, the Japanese officials were welcoming and organised. Each of the masked officials boarded Teng Hoi in turn, wielding translation devices to ask myriad questions.

They also looked through our cupboards and refrigerator, insisting we throw away fresh vegetables and rice, in case they carried foreign insects or disease. When the immigration official stamped our passports we lowered our yellow flag and in its place raised a small Japanese national flag, called a courtesy flag. Japan had long been mostly off-limits to the yacht-cruising community due to its onerous bureaucracy, but that has changed in recent years with rules for visiting boats overhauled.

We were granted a Closed Port Permit, which enabled us to visit the hundreds of small Japanese fishing ports technically closed to foreign vessels, and moor in them for free. Still, even with the rules having been relaxed for cruising yachts, there are few foreign vessels visiting Japan – we saw none of the swarms of foreign visitors currently experienced on more well-trodden tourist paths throughout the country. Ishigaki marks the southern edge of the erstwhile Ryukyu Kingdom, a tributary state of Ming China, which ruled the string of islands from southern Japan to Taiwan for about 450 years, ending in 1879, when the islands were annexed by the Meiji government of Japan.

On Okinawa Island, about 230 nautical miles to the northeast, traces of Ryukyu culture can still be found in local dialects and the cuisine, such as the indigenous liquor awamori , distilled from long-grain rice. But the Ryukyu legacy is buried under several layers of colonial pain. In local eyes, Japan remains an outside power, and the wounds from the violent American military occupation following World War II are still raw.

Take the story of the Battle of Okinawa. Despite being fought on land, this was a story about sailors, which drew our interest when we arrived on the island. The Japanese Navy, short on ships, tunnelled underneath a hill in southern Okinawa for their last stand.

Thousands of sailors crammed into the tunnel network, and then committed mass suicide rather than surrender. The islands were returned to Japanese rule only in 1971, but the Americans still maintain 30,000 active military personnel there – a sensitive point among locals. While fellow sailing yachts were few and far between, we encountered more Japanese fishing boats as we continued north.

The long, narrow craft with high, flared bows zigzagged between the islands day and night, dropping and lifting nets, and creating an obstacle course for us. One of Japan’s most spectacular natural treasures, the island of Amami and neighbouring Kakeromajima form a long, sinuous strait bordered by beaches, tiny islets and bays that invite exploration. Most tourists stay in the big towns, ferried to a few choice beaches in day boats, but with our own yacht we were free to anchor where we liked to explore the coastline.

Hiking in one remote bay, we stumbled upon shin’yo , or suicide motorboats, developed during World War II. The small wooden boats were tucked into dark, overgrown caves carved into the shoreline. They had been disarmed, but even with their explosive charges removed and their wooden hulls rotting, they were seemingly poised at the ready to launch and repel any intruders.

Nowhere has that idea of being on the defensive shaped local history as much as in Hirado and Nagasaki, neighbouring ports on the west side of Kyushu, the most southerly of Japan’s main islands. Hirado, on a small island of the same name, was an important port for trade with Korea and China for centuries before the first Portuguese ship arrived in 1550, when Francis Xavier founded a Christian community, marking the first interaction between Japan and the West. The Dutch sailed onto the scene in 1609, building Hirado into one of the major international shipping ports of its day.

Hirado is also the island where the Ming seafarer Koxinga was born, in 1624, before driving the Dutch out of town, and then out of Taiwan. Legend has it that Koxinga’s Japanese mother was collecting clams on the beach when she went into labour, and while giving birth, leaned on a large rock – now a tourist attraction. We rode a brisk wind, pushed along by a flood tide just as the sun was setting into Hirado, a snug little port, its entrance guarded by a small island that turns the strong tidal currents into a tangle of waves and whirlpools.

The pleasant port town is surrounded by hills studded with centuries-old Japanese and European architecture, and we cast our lines ashore in front of the rebuilt Dutch trading post, metres away from where, some 400 years ago, European ships had unloaded silks, cotton and spices from the south in exchange for Japanese copper, silver and rice. The Dutch East India Company built an impressive warehouse here in 1639, the first Western-style building in Japan. But then – a common feature in Japanese history – the hosts grew nervous at the growing might of maritime traders.

In 1641, Japan’s Tokugawa shogunate insisted the entire building be demolished. The reason? The Christian year 1639 carved into the stone gable: far too blatant a display of European power. Japan forced the Dutch to move their operations to Dejima, a man-made island in the heart of Nagasaki port.

By the time we sailed into Nagasaki, nearly four centuries later and moored only steps from Dejima, reclamation meant it was no longer an island. However, careful reconstruction and refurbishment of historical buildings have transformed Dejima into a lively museum site, detailing Japan’s long-standing love-hate relationship with maritime trade. The warehouses smelled of tarred hemp rope, and ornate parlours and dining rooms told the story of how bored Dutch traders were kept isolated from Japanese society.

And there, moored right where the heavily restricted Dutch trading ships had first anchored, coastguard officials came to check on us. We’d become used to these visits. Curious, somewhat aimless questioning, and requests to see our documents.

Just checking. Par for the course. “Nagasaki is very beautiful,” I said, sticking to simple words I hoped would bridge the language gap.

And sometimes, speaking a few words in a foreign language conveys more than one could hope, or hope to mean: “There is Dejima,” said the official, smiling, and pointing towards the stone walls of the ancient port. “Many ships have come here before.”.

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