There is something exciting about the extended anticipation of making landfall in a faraway place for the first time: the imminent meeting of expectations and reality, the inevitable differences from the mental pictures you’ve shaped.
Through our decade of offshore sailing, my wife, Mia, and I have been fortunate enough to experience that feeling many times in the islands and countries we’ve called in at, both aboard our boat and others we’ve delivered, including Bermuda, Cuba, Canada, Scotland, Ireland, Britain, Sweden and Finland. Few, though, have had the romance of the Atlantic Islands we visited first in 2012, and then again in 2017—the Azores and Madeira, Portuguese jewels of the eastern Atlantic.
The long way to Horta
Isbjörn, our Swan 48, was running down the miles on the home stretch, 300 miles from Horta, on the island of Faial. Under a dark black sky, just a few stars peeking out through some misty cloud cover, she flew along, touching double digits when surfing and making a steady 8.5 knots. The ocean was itself black under the inky sky, and the dolphins that streaked by the boat that night glowed. The phosphorescence was so thick anything that stirred up the water left a fluorescent trail, including Isbjörn—the comet’s tail behind the boat was 3ft thick and stretched for 100 yards in our wake.
“Sixty-two miles is a long way to sail if there’s no wind.” Mia was accidentally prophetic the day we made landfall in Faial, actually the second island you’ll pass on an easterly course from Bermuda (Flores is about 150 miles to the northwest), but traditionally the place to make landfall in the Azores.
Portuguese men-of-war glided by our stern in regular procession, and in that moment, it felt like Isbjörn wasn’t moving much faster than one of these jellyfish. The wind had shut down completely, and given that we were “technically” being competitive in the ARC Europe rally, I didn’t want to motor. The final seven miles took us nearly three hours in all. But heck, after 12 days at sea, what’s another three hours? It only made the champagne on arrival that much nicer.
Horta might be the most classic of all the classic landfalls in the Atlantic. During the transatlantic season in early summer, Horta is lousy with boats on their way to Europe. It’s also one of the most scenic and iconic marina views in deep water sailing—with boats rafted five deep along the outer seawall, which itself is covered in the rainbow colors of the wall paintings crews leave behind year after year, the top of the volcano on neighboring Pico clearly visible above the clouds in the background. To see this view in a joyful, sleep-deprived state from a sidewalk table outside the legendary Peter Cafe Sport is a special privilege.
However, while Horta’s attractions are well documented, in the Azores, cultural differences between islands only a few miles apart also become readily apparent, especially when you travel by boat, often with the only shelter being a recently created manmade harbor.
Running with the bulls in Terceira
The Azores have cows galore—cheese is both a huge commodity and a big part of what distinguishes the different cultures of each island.
“Is this cheese local?” Mia asked at a market in Horta.
“No, no, not local!” the woman replied.
In fact, the particular cheese Mia had chosen was from the neighboring island of Pico, visible literally over Mia’s shoulder and only a short ferry ride away. Not local.
Terceira, an island that’s an overnight passage to the east of Faial, has bulls and is known for its version of running with them. Mia and I first visited Terceira in 2012, when we delivered Kinship, a Saga 43, across the Atlantic in the ARC Europe rally, and the island immediately became our favorite spot in the Azores. We even decided to skip the rally’s stopover in Sao Miguel in order to get an extra day in Angra do Heroísmo, the historic and picturesque city on the island’s south coast.
Bulls literally helped defend Terceira from a Spanish invasion during the 16th century. When King Philip sent a fleet of ships there for a diplomatic takeover, his crew was met by not less than 600 bulls and subsequently defeated. The event is celebrated by a 33ft-tall, anatomically correct bull monument at the entrance to Angra do Heroismo.
Each village dotting the rugged landscape has its own day dedicated to bull running, a kind of culmination of the summer’s street festivals, where the bulls run wild through the village streets, six or seven guys trying to control a bull from the end of a long rope. Crowds of people stand off to the sides on balconies and behind walls. People tease the bull with umbrellas and red blankets. When we were back on the island in 2017, one of the ARC Europe rally crews wanted to get “in the mix”’ at a bull running and wound up gored, trampled and in the hospital, seriously injured.
In 2012, the first and last time I went to one of these, I have to say all I saw was fear and confusion in the eyes of the bulls as they trotted by, wondering what was happening and chasing off the teasing men while the spectators cheered. I’ll admit it was an interesting and fascinating cultural tradition to witness. However, I question whether it really needs to continue in our supposedly enlightened times.
Fast forward to 2018, and Mia I were planning our passage calendar for the fall and ultimately added a final trip from Lagos, on the Portugues mainland, to Madeira and back, 500 miles each way.
After a cold summer in the High Arctic, ending the year with a warm, dry passage to mystical Madeira, in particular, was just what the doctor ordered. We’d leave Isbjörn in Lagos for the fall and then return to cross the Atlantic in 2019.
Offshore, Isbjörn hurtled downwind. In full sunlight during the daytime, the deep ocean water was the bluest blue you’ll ever see. At night, the Milky Way was clearly visible overhead. Paul, one of our crew, mistook a bright star low on the horizon for a ship.
I’d almost forgotten what warm-weather sailing could be like. Shorts and T-shirts on deck. Bare feet. Just a sheet to cover within my bunk, with the portlight open for some fresh air and a breeze. Lounging on the foredeck to read a book and get some sun. This was easy.
We made landfall in Madeira after exactly three days at sea, closing the island at sunset and rounding the eastern tip after dark. The lights from the city illuminated the steep hillsides. With only 8-10 knots of apparent wind, our big white spinnaker pulled us forward at 6-7 knots, until we lost the wind entirely behind the high peaks and were forced to motor the last few miles to Funchal.
Funchal on Foot
We arrived in Funchal late on a Thursday night just before midnight and rafted alongside a big wooden ketch with a Danish family aboard on their way to the Caribbean. The boat looked like a miniature Ticonderoga. The varnish on her wooden spars glistened in the sun.
Friday was spent like many days after landfall are spent…being lazy. Mia and I wandered Old-Town Funchal, a much bigger city than I had imagined, and which reminded us of Ponte Delgada, the largest city in the Azores on the island of Sao Miguel. Like Ponte del Gada, Funchal is not really a sailor’s town—real people live there, and the bustling city would exist whether or not boats showed up in the harbor. Cities are for the locals, not the sailors.
Madeira towers out of the sea, steep cliffs dropping sheer into the ocean with little room on the coast for homes and businesses. Despite this, we were determined to explore our surroundings on foot. Walking, kind of like sailing, lets you travel the landscape at a human pace, observing the surroundings slowly enough to take them in.
We wound up at a tiny cafe to the east of Old-Town overlooking the ocean and a public bath down at sea level. There are few beaches on Madeira. Instead, at this public swim spot, lounge chairs sat perched on concrete shelves set into cliff faces. Floating docks were anchored just offshore with diving boards and ladders, and the unprotected ocean was right there. On calm days, this place looked peaceful enough. With a southerly swell rolling in during winter, it would have been anything but.
At the cafe, we took after the locals, sitting for hours at a two-person round-top table on the sidewalk, chairs facing not each other but the street, and watched the people and cars and mopeds go by while drinking coffee and orange juice. When in Madeira...
Jardim do Mar
There’s a book called Barbarian Days, a memoir on a surfing life by William Finnegan, that won the Pulitzer Prize. In it, a small village on the southwest coast of Madeira called Jardim do Mar is featured prominently. In the 1980s and 1990s it was called the Jewel of the Atlantic, a magical often overlooked big-wave surf spot way off the beaten path and hard to get to.
I’m no surfer, but I can relate to the culture and love the philosophy. When we added the Madeira passage, I knew I’d try to find Jardim and see it for myself.
We rented a 125cc scooter for the mission, the biggest, baddest I’d ever driven, and quickly discovered why they don’t do the 50cc models here—it’s hilly! The top of the highest mountain in the island’s interior is over 6,100ft, making it the third highest peak in all of Portugal. The cliffs and valleys are dramatic and endless. We passed one place, high up in a village on the side of cliff, where the only way you could access the isolated beach below was by ski lift.
The road to Jardim ended in a small village square, patterned with typical Portuguese paving—alternating black and white polished cobblestones in the intricate patterns that you’ll find throughout Madeira and the Azores, a different design on every street. In the center of the square, two small kids splashed and played in a fountain shooting up out of the ground.
The village itself has a population of just over 200 people. There’s a small guest house, a surfer hangout called Joe’s Bar, and a tiny boutique hotel. Otherwise, it’s residential houses, all nestled on a steep cliff and overlooking the midnight-blue Atlantic on three sides. There are no roads through the village, only narrow walking paths, also paved with the black and white polished cobbles.
We ambled down toward the shoreline, which was several hundred feet below us, stopping to admire the roofs and flowers on each small apartment. At the bottom, the path emerged onto a wide concrete seawall that lined the entire peninsula on all three sides creating a promenade along the coast. On the sea side of the wall, large concrete riprap was strewn about to protect the promenade from the same ferocious winter swell that made this place such a renowned surf spot. This is the same sea wall whose creation Finnegan lamented at length in Barbarian Days, as it destroyed the wave.
The coast of Madeira is so steep-to that the big swell that rolls up from the south only starts breaking a few hundred feet from shore, and even then, only at low tide. What used to be the surf lineup just offshore is now among the riprap. The surf breaks right onto the manmade barriers.
Despite the hills, I went for a run our last day ashore, during which I noticed a soccer field perched like an infinity swimming pool on the corner of a high retaining wall on the other side of a valley, with 15ft chain-link fence to keep errant balls in play (and out of the ocean, a thousand feet below). I stopped on the sidewalk under a shade tree and watched the locals play their Sunday morning game, teams of six a side with players of all ages. A young woman in a pink and black flowered dress sat on bleachers overlooking the field.
Beyond the chain-link fence, all you could see was ocean, a very long way down the cliff, and the marina in the hazy distance where Isbjörn was docked, awaiting our next day’s departure back toward mainland Portugal.
Earn it, baby!
As fate would have it, we paid for the lazy downwind sail to Madeira with a four-day beat back. However, it only served to make the short visit to Madeira that much more special. One day we were lounging in the sun drinking wine; the next we were heeled over at 30 degrees trying to stay on the toilet, experiencing that much greater an appreciation for where we’d just come from.
Islands are different than continents—not that long ago, within my grandfather’s lifetime even, the only way to get to them was by boat. Flying wasn’t an option. You obviously couldn’t just walk there. You had to sail.
Not only that, I think the same thing holds true today; you’ve still got to sail to these places to truly appreciate them. You’re missing something by taking a 90-minute plane ride from Lisbon. The islands in the Atlantic need to be earned: the charm of the cities with their tiled sidewalks and centuries-old architecture; the sight of the old whaling boats sailing around the harbor in Horta; that view from Peter Cafe Sport.
You can’t just fly to these places, not spiritually. Yeah, maybe you can fly to them physically, saunter up to the physical bar and order a physical beer. But that guy standing next to you who ambled up from the dock, who’s been at sea for two weeks, who’s put in the days, months, heck years of preparation to do it safely and confidently and with style...well, let’s just say he’s not buying you a beer when he sees the luggage tag hanging off your backpack. Sorry, it’s not the same. You can drink your physical beer, but you’ll never quench your spiritual thirst like that.
In this way, the Atlantic islands exist in two parallel universes: one of those who’ve earned them, and the one of those who didn’t. The sights look the same. All the colors are there. The flowers smell delicious in both of these universes, and the fish tastes great.
But in the universe of those of us who make landfall in these places, we who earned it, there’s a different texture to things that are reserved just for us. If you’re reading this having made a similar landfall of your own, you’ll know exactly what I mean. If not...well, you gotta go and earn it.