When the tow rope is released, two of the strongest Azorean whaleboat crewmembers leap forward and haul up the mainsail gaff as quickly as possible.

The secret is not to power up the huge main too early, before the halyard has been made off on its rudimentary jammer made from whalebone.

Once the sail is raised, you can turn towards the wind and sheet in, but there is definitely a skill in learning how high to point and just how much power these slender hulled rowing gigs can handle on the wind.

A capsize and there is definitely no coming back.

Relaunching Azorean whaleboat racing

Welcome to Azorean whaleboat racing, where the top crews are truly athletic, able to not only row and hike hard, but also raise and lower the main mast, which is literally a 9m tree trunk, cut from the locally grown cedar forest at the base of Mount Pico.

I’ve had the enormous pleasure of racing on everything from IMOCA 60s to Extreme 40 catamarans and more recently even traditional luggers, but the experience of sailing the Azorean whaleboat left a huge impression on me.

The design of an Azorean whaleboat, which was used right up until the 1980s to hunt and catch giant sperm whales migrating through the Azores archipelago, has changed very little over time.

While I might feel uncomfortable about their past history, few could argue about the sailing skills that were required to get these boats launched into the Atlantic swell, ready for an almighty battle when a whale was spotted from lookouts placed strategically around the island.

When the invitation came from Ana Brum, mayor of Lajes do Pico, to join a small select group visiting Pico Island in the Azores archipelago, with the chance to sail on board these original hunting vessels, I had no idea what a voyage of discovery this would be.

It was a chance not only to race these remarkable boats, but also to get to know their history as a vital part of Azorean culture and economy going back over a century.

In fact, ‘Whalers’ have been used in expeditions and for exploration for well over 200 years. These versatile little double-enders, which are fast and could be rowed in both directions, were part of the British Navy right up until the 1970s.

So versatile are they, that Commander Robert Fitzroy chose to take four whalers on board HMS Beagle to explore Tierra del Fuego, and Ernest Shackleton managed to partially deck a whaler and sailed 800 miles across the Southern Ocean to South Georgia.

The powerful Azorean whaleboat differs from its North American cousins due in part to the competitive racing experience throughout the Azores archipelago.

The boats are longer to accommodate an additional crewmember, making them faster when under oars. The massive 50m2 mainsail features a 4m gaff and 9m-long boom.

Speed, stealth, and sails

The top recorded speed, by successful whaleboat racer Filipe Fernandes, is over 12.4 knots.

Traditionally, speed and stealth were needed to get close to the whales, before launching a harpoon by hand. Once alongside the whale the sails were quickly dropped.

Azorean whaling no longer exists (it was banned in 1984 by international convention), so instead the traditional hunting boats are now part of a thriving racing scene.

Though the whaleboat crews had often informally raced one another, the first regattas took place shortly after the whaling ban in the 1980s, and there is now a series of regattas from Pico and neighbouring Faial.

Pico has the largest fleet, with several dozen whaleboats, both restored original boats and others newly built.

“Without these regattas, all these whaleboats would be gone, but they are a healthy story of change and adaptation,” Fernandes explained.

Fernandes was born in the beautiful village of Lajes do Pico and is an avid whaleboat racer. He selected a young crew, which he systematically trained once he was awarded the captaincy of their local boat, Maria Armanda.

The Maria Armanda has a unique history – it was the last Azorean whaleboat to hunt a sperm whale in a final protest hunt in September 1987 after the whaling ban, while captained by Fernandes’ uncle. Fernandes is now the champion whaleboat racer in Pico.

I joined Filipe for the day along with Italian foiling supremo, Luca Rizzoti.

After a quick refreshment in the local tavern and a chance to recruit an extra crewmember, we headed down to the newly-restored boat house to prepare the whaleboats.

Rigging a whaleboat

At just under 12m and with a slender 2m beam, the Azorean whaleboat weighs around 800kg.

While Rizzoti was busy suggesting how much weight could be saved with carbon, Filipe’s secret weapon, Jose – also known as ‘The Ox’ – arrived and picked up the 9m mast like a toothpick and pushed it up into the air.

A neatly hinged mast step kept the mast foot in place before it dropped into its step. Two quick stays were attached with quick-release knots and we were all ready to launch.

Wooden chocks are placed under the keel and down the slip into the water – no requirement for a trolley!

Once afloat, I noticed there were both oars and smaller dragonboat-style paddles, which made it much easier to navigate the rocky channel out of the marina.

That said, the moment we could raise the sails, we did – it seems that it’s tradition to only use the oars when competing in the rowing races.

With four boats on the water, I joined one of the newest captains, Beatriz Azevedo, who’d just taken over the Marie Celeste from her father that season.

Beatriz gave me some welcome tips as we headed out of the marina and soon we were powering along with Portugal’s highest volcano, Pico, as a backdrop.

In an idyllic warm autumn breeze I could not believe how efficient these boats were, given the waterline length, with no centreboard and just a tiny foresail for balance and to help when tacking the boat through the wind.

Racing whaleboats

After a brief practice session, we fell into formation for our first race start. And as you might expect, it’s not a traditional start line.

Each boat started with their sails lowered while in a line, being towed by a launch, who would announce over the radio a one minute countdown.

As the start signal flag was lowered, I had to cast adrift the boat behind me and simultaneously turn towards the wind as Beatriz’s father hoisted the mainsail.

I was a little slow with my turn, so the sail started filling before reaching the top, making it difficult to raise.

The result was not the best start for us, but we were still in the game and not too far from Filipe, who was now powering away to windward.

The Azorean whaleboat has a slender hull, making it extremely efficient through the water. With the slightest breeze, we comfortably powered up.

With six crewmembers sitting on the windward side, some hiking with their feet under the wooden thwarts, I estimated that we were doing around 5-6 knots upwind.

The large mainsail is made from a soft cotton-like polyester, which was controlled by a single (non-purchased) mainsheet. At times the helmsman has to help the trimmer pull it in.

With more mainsheet, you feel as if you could point higher, but boatspeed soon suffered if you tried too much.

The key was staying in the breeze, and with the wind slowly dying under the lee of Pico mountain we headed more offshore in search of better pressure.

The race course is quite short, perhaps no longer than a one mile beat to windward, followed by a downwind leg and then another lap, finishing on the downwind run.

On the downwind leg you can really sail these boats very deep, with the mainsail at 90° to the hull and weight forward.

We got to play a little on the Atlantic swell that picked up the hull and gave us a nice little surge in speed. I was in my element, playing on these waves, steering deep into the troughs and looking for every inch to gain on the leaders.

We soon found ourselves back in the hunt and with a slight overlap at the leeward race marker, we gained a place and were just behind Filipe as we turned back upwind.

The pure passion was evident in our captain and crew’s eyes.

Beatriz was beaming, as her proud father looked on. She had entrusted me with the helm and we were gaining on the lead boat after again finding more wind offshore.

At the windward mark we crossed in front of Filipe and now we just needed to hold them off on the final leg downwind.

We worked every wave and gust and as we crossed the finish line, Beatriz handed me a red flag to raise. I was unaware of its significance, but later learnt that traditionally a red flag was used to indicate a successful kill.

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Tweaking tradition

Back ashore, we headed over to the Museu dos Baleeiros, a wonderful museum that looks sympathetically at the heritage of Azorean whaling and a must-visit if you arrive in Pico Island.

There are historical films of early whale hunting, and visitors can see whaleboats up close.

Since whaling was banned in the Azores it has been replaced with a number of whale watching boats and tours operating from Pico.

Many species of whale can be seen in the islands, including humpback, blue and baleen whales. In the summer the sperm whales return and still provide valuable tourism income.

“South of Pico Island is a superhighway for cetaceans,” explains Fernandes.

“People used to ask around in the streets “Who caught the whale?” because they heard the firecracker and knew the boats had gone out. Now, people are asking, “Who won the race?”

The following day we visited a boat club named Clube Náutico de Santa Cruz, where we met João Silveira Tavares, a boatbuilder that had reconstructed more than 20 Azorean whaleboats since 1997.

Looking around his shed it was striking that not only had the boats changed very little over the years, but that they are still built using traditional methods. It takes nearly five months to build a whaleboat, employing a single shipwright.

Some of the boatbuilding skills required are sadly dying out as young people head away from the islands to study, many not returning until much later in life, if at all.

Filipe is worried about this, and part of his vision for the whaleboat fleet in Pico is to design a smaller, lighter version of the traditional whaleboat, which he calls the ‘Calf’.

A 4-5 person version that can be rowed and sailed by 12- to 16-year-olds would open the door for younger crews to get involved.

It’s hoped this venture might breathe new life into the class and encourage young people on the island to learn some of these important boatbuilding skills before they are lost.

The scenery around the island is breathtaking and there is an abundance of forests, particularly the non-native Japanese cedar which grows straight and tall, providing excellent masts and spars for the whaleboats.

On our final day, we ventured into one of the forests to select and cut down a tree that Filipe had been eyeing up for his 2024 whaleboat campaign.

As we walked through the forest, I looked up at one of the tall cedars, placing my hands around its tall trunk and checking if it was straight. Perhaps, I thought, I’ll be back one day to choose myself a mast.

Life on Pico

Pico Island is one of the nine volcanic islands that make up the Azores archipelago in the North Atlantic Ocean. Its dramatic landscape is dominated by Pico Mountain, the highest peak in Portugal.

For centuries, Pico Mountain has been an important landmark for sailors navigating through the Atlantic Ocean and often a safe refuge for those caught out by a North Atlantic storm.

It was rumoured that Christopher Columbus made an unplanned stop after being forced here by a storm.

On a clear day its peak (2,351m) can be seen from over 80 miles away and for boats crossing the Atlantic from Newport, Rhode Island, or New Bedford, Massachusetts, (another historical whaling community) it became an important stop en route to Europe.

The Portuguese first settled the island in the 15th Century and early settlers farmed wheat and olives, but it was the presence of American and British whalers in the waters of the Azores at the end of the 18th century that stabilised the economy.

Sperm whale hunting became the island’s primary industry until it was abolished in the 1980s.

The last whales to be killed were captured from Pico in 1987, while Pico was also the first island in the archipelago to adopt whale watching as part of its tourism industry, and tours began in 1990.

Today, Pico is a popular tourism destination for hikers and nature enthusiasts who come to explore the mountain’s rugged terrain, and unique flora and fauna.

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