For some time I’ve suffered from an affliction that arrives in the form of a shoulder-mounted gremlin, who maintains silence until I arrive on a tranquil island for some much-needed downtime. Then it pipes up with a word that can’t be ignored…

“Circumnavigation”

God damn. It always sounds so romantic and intrepid, the concept of rounding an island on the sea, but nature also has her way of ensuring that we continue to do silly things by painting upcoming pain-fests as baths of honey.

In reality, these sweet, ever-huggy thoughts don’t last forever. Not when the ocean is gently bopping you on the head and your poor weedy arms are trying to pump out 25,000 paddle strokes in 12 hours.

Emms and I are enjoying an extended honeymoon in Thailand, as you might have read earlier. We’ve spent our first weeks on Koh Phangan, the middle island in a chain of three in the Gulf of Siam, which also includes Koh Samui and Koh Tao. It wasn’t long before I wondered whether some kind of adventure might interfere with our bliss, and slowly a plan developed to paddle round each of the islands.

The decision was made partly because of the distances. Long ago, in 2014, some friends and I paddled around Martinique in the Caribbean. It took around 10 days and was intended to be the first of a series of twenty-five mini-journeys that might go some way towards padding the gaps in between my longer 1000-mile+ trips. Each one, I proposed, would be on a Stand Up Paddleboard, at least 100 miles in distance, and in a different country from the previous paddles.

In order of circumference, Koh Samui is 75km around, Koh Phangan 50km, and Koh Tao 25km. Which comes pretty darn close to 100 miles in total.

We have ourselves a little challenge. As Koh Phangan is the current base this is where we’ll start. The maths are easy. My average speed on an inflatable SUP hovers around 3.5miles per hour, including the odd water and photo break. The sun rises at 6:15am and sets at 5:55, so with Twilight I’d have twelve hours to cover a touch over 30 miles. Normal speed + a couple of meal stops and this felt more than doable. 

When you’re away only between sleeps then preparation is minimal. We’ve already got our boards here, inflatable 12 foot Pathfinders by Lakeshore. Mine’s called Mud, after its maiden voyage on the Mississippi. And then I gave myself a £20 budget for the whole day, which is hearty living in these parts.

I was excited, I really was. It had been a while since my last adventure, largely because that waterbike trip along Norway’s rugged coastline had properly kicked my ass, but as we pulled ourselves out of bed at 5:30am I didn’t even hold the slightest envy knowing that Em would be right back in the bed as soon as I paddled off. 

Morning thunderstorms were 50% likely but this is normal during late monsoon season, and the grey-blue surface was mirror-calm as I headed north along the coast, Emms and the co-working hub’s two dogs – Jay and Bruce, bounded alongside briefly until their beach ran out.

Pace was fast, it felt great to be on the move. After half an hour I was into new territory, far beyond my previous recreational paddles. This newness is forever a motivation and for the entire morning I’d be treated to a convex coastline, each headland acting as a carrot before the next one would slowly reveal itself. I was being pulled around the island two or three kilometres at a time, with the rest entirely secret – a reward I had to work for.

The night before I’d made a map for Em with distance markers around the island and my estimated time of arrival at each spot. She anticipated renting a moped (for a massive £7 per day) and coming out to find me, but the eastern half of the island is only accessible by boat or 4x4, so I didn’t expect to see her before lunch.

I hit my first mark, which always feels good. 3 hours after starting I’d covered 18km and it was time for a breakfast. A wide open beach seemed to offer plenty of cafes and I paddled in under the curious gaze of holiday-makers, confused by this man who had apparently come in off the sea. “Passport?!” asked one bearded tourist, jokingly. I grinned, shrugged with a wink, and ordered eggs and coffee. 

After ten the wind picked up but, at least for the backside stretch of the island, it was mostly to my tail. This is rare in SUP, where as a rider you’re doing a half-decent impression of a sail. In years-worth of adventure and expeditions I can recall perhaps ten days of solid tailwind. 

We whizzed along, Mud and I, swell and wind encouraging us both south. Headlands were often mounds of strewn, house-size rocks, toppled into the ocean over the centuries then smoothed over by salt water and nature’s encouragement. The swell to my back would bounce off the rocks and return to whence they came, offering a confused, mogulled landscape as a reminder that this wasn’t all simple.

Over halfway I popped into a small, isolated cove and landed on a beach where the early seeds of a party were developing. It’s easy to forget that most foreigners come here to howl at the moon and spread their well-earned cash widely over a considerable amount of cheap cocktails and Asian beer. This was a party I’d been invited to, and dropping in was worth the endless, wide-eyed, “You paddled around the island to get here?”

This is what I love about water travel. When you make it a habit, the world is your oyster. The secret coves and offshore islands become a playground, while the rest of the world still looks out to sea and wonders what it might be like, one day, if they ever headed out there. The truth is, for a few hundred dollars and a recognition for modern-day inflatable technology, this freedom can now be carried around the world, and then becoming a sea creature is just an easy, daily decision. I said my hello’s, waved goodbye and left the soon-to-be-drunk in their spot of paradise. 

At Mile 20, my two-thirds marker, my enjoyment of the day changed. The wind and tide had switched and I only realised as I rounded the boulders of Haad Riin, the southern-most point of the island. From here, home was north west, then north, and immediately the wind howled in my face somewhat inexplicably, because it had never blown in this direction before. My pace halved, the next two miles was akin to crawling through mud, uphill.

By the time I caught sight of Emms and her camera, I was a mess. We collapsed into a raised bar roughly shaped out of driftwood to become a pirate ship. Flags fluttered in the increasing wind and I stared along the coast, no longer a mysterious cascade of headlands — just the ten mile infinity beach that left nothing to the imagination. When you can see your upcoming challenge laid out from the beginning, the incentive to explore with effort is greatly decreased.

A mound of chicken and a bit of prodding from my masseuse wife was just, just enough to get me on my feet again. This was it, the final stretch, and I wasn’t looking forward to these final four hours into wind. 

The wall. Marathon runners will be familiar with it. Endurance adventures offer them up at least once a usual day. Beyond the new perspectives and exercise, the thrill of optimism-paid-off and a gentle notch-in-the-self-confidence-belt, the value of a self-set adventure is in hardening the mind more than the muscles. More is gained from the battle than freewheeling.

Two hours later I could still look back and see that damned pirate restaurant. But the distance ahead had been reeled in, inching slowly and painfully towards the island’s main port of Thong Sala. This, with the ever in-and-out of local ferries, kept me focused. Mother Nature can try to splash, drown, blow and exhaust, but the most likely danger on any venture is man. And man at the control of a big metal craft that doesn’t expect or care for a lone paddler down below — this is a dangerous creature.

This safety is up to me. The boats stay their course, they have their channel. I just need to pick my moment. The safest route would have been under the beach-side struts of the pier but the tide was out and my fin dragged on the sea-bed 100m away from shore.

Once past the port I was on the home straight. 6 kilometres left, around an hour and a half into the wind. Problem is, the sun was already licking the horizon and twenty minutes of twilight was the cushion before darkness.

I was beat. Lifting the paddle for each stroke was now an effort and the easiest thing to do would be to go to land, deflate the board and jump in a taxi. Perhaps finish off the rest of the distance tomorrow. I want to do this yet I don’t want to, and my solution is always to carry on until the giving-up solution is not the obvious one. I started with the intention of paddling around an island and just because I’m tired, hungry and out-of-energy, and just because my enjoyment of the scenario has greatly decreased, I must hold onto the original intention because I once knew going all the way round would be good for me. 

So, going to land packing up is the easiest thing to do until the easiest thing to do would be to carry on regardless and arrive back where I started, without having to deflate the board tonight, then inflate it once again tomorrow (or in four days when I’m ready for a paddle again).

My hands were screaming, and I finally found a reason to begrudge the temperature of the water. The sea is 28 degrees here, and while this is lovely for a quick sun-escaping dip I actually missed being able to cool-down my hands and feet, long-numb from gripping paddle and board. Cold water is an elixir for claw-finger. After my Mississippi paddle in 2011, three months of paddling left me with slightly curled fingers for two months afterwards. It would have been longer were it not for the chill of the lower river.

For the last hour I was in pitch darkness. The wind has slowed and I was alert to the danger of incoming fishing boats. What I didn’t expect was an enormous whooshing of water to my right, an out-rushing of air and the circular retreating wave from a smooth, rounded back. At first I thought, ‘how the hell did I paddle so close to that rock without noticing?’ but then I realised that I’d paddled this bay before and there had been no rock before. In the ever-so-pale combined light of the stars, the final refractions of sunlight from far below the horizon and the luminescence of coastal road lights over a kilometre away, I wasn’t able to make an exact identification, but I’m around 90% sure that a Whale Shark just surfaced five metres away from me, and then disappeared forever.

Twenty minutes later the end of my paddle was out of sight, and this meant that I only saw the turtle when it was beside me. It shat itself and mightily kicked downwards, throwing up a shower of sea water and leaving my little heart panting like Freddie Kruger had just jumped out.

Finally a familiar noise, “Woooo whoooop.” Em! Immediately post-wedding we’d venture to the Lower Mississippi and she’d picked up the paddler’s call. There she was, Jay the dog a faithful Boy Friday on her board, and suddenly we were paddling alongside the Srithanu channel navigation tower, a three metre high lighthouse that takes us three minutes to paddle to from our beach.

From the beach where I started this morning. From the start of this little journey. And the end. 

Twelve hours and forty seven minutes after setting out, Mud’s nose touched the sand again. Koh Phangan had been circumnavigated.

With a couple of hundred Baht to spare, the day’s budget of £20 had been spent. But this included Em’s moped hire and a good lunch for both of us, and welcome-home treats in the shape of a pizza, three large Leo beers and a Magnum each. I managed a few slices, slid the Magnum down, sipped about a quarter of one beer, then passed out.

• See the photo story with more images from this mini adventure

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