Exploring a far-flung cruising destination without making an ocean passage

What a difference 18 years can make. Entering the harbor at the picturesque town of Velas on the island of São Jorge in the Azores, I am remembering the last time I was here. “Disastrous” is a word that comes to mind. Back then there was nothing but a short seawall for visiting yachts to land on, and after one day laying here aboard my old Alberg 35 yawl, Crazy Horse, I was summarily evicted by the harbormaster, who regretfully informed me the monthly freighter was coming in ahead of schedule and needed to land on the wall. Immediately.

Peering out my companionway, I could see the ship approaching, maybe a half mile out, and before I knew it, as soon as I started my engine, the harbormaster and his friend suddenly cast off my lines. The boat’s caprail was smashed to splinters as I pulled away from the wall. Then, as soon as I cleared the harbor, a surprise gale blew in from the southwest, and I spent the next eight hours running off before a vicious 50-knot breeze. I didn’t make it into another harbor until the following afternoon and spent the next two days after that fixing up my poor caprail.

If you had told me then that my next visit to Velas would be aboard a chartered Dufour 375 bareboat, I would have laughed at you.

Not that the Azores, an archipelago of nine Portuguese islands sprawled across 370 miles of open Atlantic Ocean, isn’t a great sailing destination. Back in my Crazy Horse days I was totally captivated by the islands and spent nine months enjoying their dramatic volcanic topography, the verdant sub-tropical foliage, the exquisite architecture, the amazingly friendly people and the surprisingly low food prices.

But parking was often a problem. The islands have virtually no natural harbors, anchoring along the steep-sided shore is usually out of the question, and the few moorings in those days were grossly unreliable. I managed to visit seven of the nine islands during my stay, but I did have a few skin-of-my-teeth experiences in the tiny man-made harbors.

Since then, fortunately, the Portuguese government has been busy building marinas. When I first visited the Azores in 1992, while crewing on a big Alden schooner, there was just one of these—in Horta, on Faial—but now all the islands, save for Corvo and Graciosa, have marinas, and one, São Miguel, the largest island, even has two. This not only makes it possible for transient bluewater cruisers to visit multiple islands while sailing through, it also makes bareboat chartering perfectly feasible.

SAIL’s editor-in-chief, Peter Nielsen, and I (together with one imported photographer, Graham Snook, from the U.K.) became the very first charterers to visit from the United States when we hopped aboard the Dufour 375 Insula, managed by SailAzores, last May. For me this was like a return to Valhalla, as I do love these islands, and being able to sail here again was a real treat.

Our week-long adventure started in Horta, which is still the most cruiser-centric community in the archipelago, as it has been since Joshua Slocum put in here about 120 years ago. Superficially, at least, I doubt the town has changed much in the interim. Replete with traditional architecture, basalt mosaic sidewalks and palm trees fronting its waterfront promenade, it still has a friendly, sleepy Old World feel.

The social center for sailors is Peter’s Café Sport, which has been frequented by most every bluewater adventurer who has crossed the Atlantic since the middle of the last century. Run now by Jose Azevedo, grandson of the famous “Peter” Azevedo who first welcomed yachtsmen here many decades ago, the bar is arguably the most famous sailor’s watering hole on the planet, and its walls are festooned with layers of fascinating memorabilia. The walls of the harbor itself, meanwhile, have likewise served as a canvas for artistically inclined crews and are covered with literally thousands of graffiti paintings left by visiting boats.

Before leaving we first spent a day touring Faial in a rental car and were particularly impressed with the exotic volcanic wasteland that is Capelinhos, on the island’s northeast corner. For over a year starting in 1957 this was the site of an ongoing eruption that destroyed two villages and led over a third of the island’s population to flee to the United States and Canada. Today, nearly 60 years later, it is still devoid of vegetation, and has a surreal alien aspect that is both chilling and awe-inspiring.

The following day we enjoyed a leisurely beat over to São Jorge in moderate wind, under a blazing blue sky with vibrant wisps of transoceanic clouds tumbling by overhead. Arriving at Velas, where I smashed my rail all those years ago, we found not one but two boat basins with floating docks—one for the local fishing skiffs and one for visiting yachts, where we were greeted by the effusively friendly harbormaster, who personally took our lines and welcomed us ashore.

All the Azorean islands are volcanic, but each has a unique geographic personality, and São Jorge’s is perhaps most extreme. It is essentially a steep ridge plunging straight up out of the water, girded on all sides by very high cliffs, with a few flat tongues of land, known as fajas, splayed out at their bases. We enjoyed one full day here, touring Ouvidor, the largest faja on the north coast, sampling local cuisine at Calheta, on the south coast, then finally settling down for a sumptuous dinner aboard Insula back in Velas, where hundreds of shearwaters came home to roost on the cliff overlooking the marina as the sun went down. Meanwhile, out in the channel offshore, we could see a pair of local fishermen casting lines from a small boat as a river of dolphins streamed by.

When it came time to sail over to Pico, the high island across the channel from São Jorge, we weren’t so lucky with weather. It was a good day to wear foulies, as we had intermittent rain squalls passing through, punctuated by a blustery north wind. Sailing off on a broad reach for the eastern tip of Pico we enjoyed some fine sailing nonetheless, then had fun after we rounded the corner playing the intermittent katabatic gusts that tumbled over Pico’s high central ridge onto its southern shore.

Pico is the tallest Azorean island, and its primary terrain feature is an impressive 7,700-foot conical volcanic mountain that towers over the neighboring islands in this central portion of the archipelago. A day earlier, as we explored São Jorge, the mountain’s peak had been capped with a light frosting of snow that had fallen during the night. But now, as is often the case, it was shrouded in ethereal mist that gave it an ominous air of mystery. Sailing at last into its lee, we fired up the engine and motored the last couple of miles to Lajes, where we found a small marina and several pairs of helping hands to take our lines.

Immediately after tying up, we headed to the local whaling museum, mere footsteps from our dock. Whaling used to be a very big deal in the Azores. The waters around the islands are thick with marine mammals, and Azoreans first learned the business of capturing them when they signed on as crew aboard the American whalers that came to hunt and provision here. They started hunting on their own locally in the middle of the 19th century, using traditional whaleboats propelled by sails and oars, and continued doing so in the very same sort of boats until the International Whaling Commission banned whaling in the mid-1980s.

When I was here on Crazy Horse I met middle-aged men who told me tales of rowing out to harpoon baleias by hand. They were clearly proud of this, and that same sense of pride is manifest today. Touring Pico in a car, we found an old boathouse in a small village just down the road from Lajes where a group of men showed us two whaleboats, immaculately maintained, that they race against other whaleboat zealots on the island. The walls of the shed were covered with photos of men who had both fished and raced in the boats, and there was a glass case filled with a very impressive collection of trophies.

Besides being the epicenter of Azorean whaling tradition (and the current whale-watching trade) Pico also has a remarkably diverse landscape. From closely cultivated vineyards set off behind mazes of black rock walls, to forests of tall pine trees, to groves of bamboo and eucalyptus, to other-worldly Alpine pastures looming far above the island’s treeline, to the barren volcanic crater at the very top of the island, Pico is the island most worth exploring in detail of the three in the archipelago’s central group.

After another full day spent lingering here, our appetites certainly were not sated, and as we sailed back to Faial in a light southwesterly the following day we regretted that our visit was already coming to an end. This is probably the biggest challenge of chartering in the Azores. Every island is worth exploring at length, but they are very spread out. Take my own example: I’ve now spent a total of nine months cruising the islands on my own boat, plus one week on a charter boat, and still there are places I haven’t seen yet.

Thank goodness I can come back again and explore some more if I like, without first sailing thousands of miles over the open ocean.

Cruising Notes

There are two flights a week from Boston to Ponta Delgada on São Miguel, and you can catch a puddle-jumper from there to Faial or Pico, where SailAzores maintains bases. A new base just opened in Ponta Delgada, so you can sail out of there, too. If at all possible, I’d recommend taking two weeks so you can explore more widely. If you have only one week, it is best to sail from Faial or Pico in the central part of the archipelago, where there are the most islands in reasonable proximity to each other.

All marina fees are included in your charter fee, and SailAzores will make sure there is both space for your boat and people to
greet you in every marina you visit. On the two islands without marinas they will even make sure there are secure moorings to which you can tie up. The company’s fleet of Dufours ranges in size from 37 to 45 feet. You may want to favor a smaller boat, as the marinas on some islands are small with little room to maneuver.

This is not the BVI. To charter a boat here you need a fair amount of experience, as the sailing can be challenging, ranging from simple coastal hops to true ocean passages in sometimes strong weather. You don’t need a certificate, but you will be closely queried as to your experience. Also, chartering in the Azores has proved very popular with Europeans, so you need to book well in advance. The season runs from April through October; prime time is from May through September.

You can make arrangements through SailAzores to have rental cars waiting for you on each island. Alternatively, it is relatively easy to hitchhike around the islands, as people are very friendly, but traffic in some places is thin. English is widely but not universally spoken.

Cruising in Portuguese waters you are required to book in and out of every port you visit, which isn’t quite as onerous as it sounds. You can usually book out of ports the day before you actually leave; also, because officials see the SailAzores charter boats all the time, they do seem inclined to cut them some slack.

Many thanks to Nicolau Faria, Joao Portela, Anabela Costa, and Emidio Goncalves of SailAzores (sailazores.pt) and the Azores Tourism Board

Photographs by Graham Snook