MID-ATLANTIC CRUISE: Bareboat Chartering in the Azores

Sailing to Sao Jorge

While dawdling about the North Atlantic in my old Alberg 35 yawl Crazy Horse I spent nine months in the Azores in 1995 and ’96. The beautiful nine-island archipelago just sucked me right in. With its dramatic volcanic topography, verdant sub-tropical foliage, sumptuous mid-ocean cloud formations, amazingly friendly people, low food prices, and exquisite architecture it seemed to me a paradise on earth. But if you had told me back then there would one day be a successful bareboat charter operation in the islands, I would have laughed at you.

Not that the sailing is bad. Much of the time it is perfectly splendid, with interestingly variable breezes and occasionally challenging conditions to keep you honest. The big problem was parking. The islands have virtually no natural harbors, anchoring along the steep-sided shore is usually impossible, and the few moorings you were apt to find in those days were grossly unreliable. During my time there I did manage to visit and explore seven of the nine islands, but I had a few skin-of-my-teeth experiences in some of the tiny man-made harbors, and one acquaintance of mine actually lost his boat after he left it in the harbor at Vila do Porto on Santa Maria on a seemingly solid mooring that failed.

Azores map

But that was then. When I first visited the Azores, as crew aboard Constellation in 1992, there was just one safe haven for yachts, at the marina in Horta on the island of Faial. By the time I returned on Crazy Horse in 1995 there were two more. One was a new marina at Praia da Vitoria on Terceira, where I was the first American ever to visit. (I remember I was very pleased when I learned they weren’t charging for dock space, but I wasn’t so pleased when I found an enormous dead pig floating next to my boat the morning after I checked in.) The other was a new marina at Ponta Delgada on Sao Miguel, where Crazy Horse was one of three transient yachts to winter over.

Nowadays there are marinas on all the islands but two (Corvo and Graciosa), there are two marinas on Sao Miguel (at Vila Franca do Campo, as well as Ponta Delgada), and the existing marinas at both Horta and Ponta Delgada have been greatly expanded. This not only makes it possible for transient bluewater cruisers to easily visit multiple islands while sailing through, it also (gasp!) makes bareboat chartering perfectly feasible.

The first such operation, SailAzores, was started just three years ago and runs a small fleet of Dufours, ranging in size from 37 to 45 feet. Their clients are mostly from central Europe, and last week SAIL‘s editor-in-chief Peter Nielsen and I (together with one imported photographer, Graham Snook, from the UK) became the first bareboat charterers ever to visit from the United States. For me it was something like a return to Valhalla. I love these islands and being able to sail there again without having to first make a major ocean passage was a real treat.

Faial from above

The town of Horta on Faial, seen from on high

Pico from Horta

A classic view from the Horta marina, with the 7,680-foot peak on the island of Pico seen in the distance

Horta waterfront

The main drag in Horta, as seen from sea level

We started our tour at Horta, which has long been Sailor Central for transatlantic bluewater cruisers, as far back as Joshua Slocum. We had only a week to spend, and as you can see on the map up there, the islands are quite spread out, with 370 miles of open ocean stretching between the easternmost and westernmost islands. So we limited our exploration to three of the islands in the central group, taking a day on each to explore by car.

For anyone else coming to charter here from the States, I’d recommend taking two weeks if at all possible. This will give you time to visit all the central islands, plus shoot over to the east and/or west. There is a fair chance you’ll be weather-bound for a day or two, so having extra time in hand is always a good idea. If you’re lucky with the weather and feeling ambitious, it is possible to visit all nine islands during one two-week cruise.

Duncan Sweet

My man Duncan Sweet (on the right), originally from New Hampshire, has been operating Mid-Atlantic Yacht Services in Horta for over 20 years now. He helped me sort a few problems on Crazy Horse way back when, and now tells me he’s looking to sell his business so he can go sailing again

Azorean sidewalk

A typical sidewalk in Horta. You see these basalt mosaics on the streets of most Azorean towns. Even the crosswalks are inlaid!

Horta paintings

For decades transient sailors have left paintings on the harbor walls in Horta. A few charter guests do it, too, but personally I think this is uncool. The unwritten rule is that you have to cross an ocean before leaving a painting here

Horta tiles

The wall paintings are surprisingly impermanent. You see few that are more than few years old, and the paintings I made for Constellation (1992) and Crazy Horse (1996) were long gone. Dieter on Lady Summerfield, as you can see, didn’t take any chances and solved this problem by making his mark with tiles

Kids painting

A pair of cruising kids wielding brushes

Nielsen at Cafe Sport

Boss Nielsen makes the scene at Peter’s Cafe Sport, the most famous sailor’s bar in the world

Golden Hind

The marina at Horta is one of the best places in the world to ogle bluewater boats. You always see a fascinating array of offbeat vessels. My favorite this visit was this Golden Hind 31, which looked to be about the same vintage as my old Golden Hind Sophie

The highlight of our tour of Faial was a visit to Capelinhos on the island’s northeast corner. From September 1957 through October 1958 this was the site of an ongoing volcanic eruption that destroyed two villages and led over a third of the island’s population (about 2,000 people) to emigrate to the U.S. and Canada.


Capelinhos today. The lighthouse was formerly on an exposed headland, but now is inland, and all the land you see there on the right, nearly 3 square kilometers, was created during the eruption

Capelinhos eruption

Capelinhos during the eruption. Faial’s main volcanic caldera (or crater) in the center of the island was also involved, as the lake there drained away and fumaroles of boiling clay and mud appeared on the crater floor

Wasted village

A wasted village, post eruption. Fortunately there were no fatalities, but there was a great deal of property damage

We had a marvelous sail from Horta over to the town of Velas on Sao Jorge the following day. It was a beat, but the wind was moderate, 10-12 knots, and we were able to lay Velas after just two tacks. There’s great little marina there now that’s perfectly secure, with an extremely friendly harbormaster, but when I last visited Velas on Crazy Horse back in 1996 the only place to park was right on the seawall.

My second morning there the harbormaster came down and told me I had to leave immediately, as the monthly freighter was coming in ahead of schedule. He and a buddy cast off my lines post haste, before I was ready, and the boat’s caprail on one side was smashed to pieces as I pulled off the wall. Then, as soon as I cleared the harbor, a surprise gale blew in out of the southwest, and I spent the next eight hours running off to the north in a vicious 50-knot breeze. I didn’t make it to Horta until the next afternoon, and then had to spend the next two days after that fixing up my caprail.

So, yes. This time I really did appreciate that marina.

Sailboat and Pico

Another sail spied en route to Velas, with the top of Pico just peaking out of the clouds

Nielsen lounging

Boss Nielsen demonstrates his power-lounging technique as we approach Sao Jorge

Velas from above

The town of Velas, seen from on high, with Faial in the background. You can see the wondrous yacht marina in the lower righthand corner of the harbor, directly across from the evil wall. The smaller marina in the upper corner is for fishing boats

And yes, as I said, the current harbormaster is exceedingly friendly. So friendly that after we toured the island by car the following day he arranged for us to use the local pilot boat as a photo chase boat so Graham could snap pix of us sailing by the town.

The one downside to the marina, I should note, is that at night the high cliffs directly above it are inhabited by a vast flock of very noisy shearwaters. They sounded like deranged children and cackled with glee until well after midnight.

Velas dragon

Downtown Velas, with dragon emerging from pool

Velas garden

The public garden in Velas. The little stone house you see behind the lamp-post furthest left is filled with dozens of parakeets

Velas duck

One of many weird ducks that lives on the waterfront in Velas. Unlike the shearwaters, they had nothing to say


Sao Jorge is a long, tall spine of an island, girded round on all sides by very high cliffs. Along the coast there are a few flat tongues of land, known as fajas, that are prized for their habitability. This is one of the biggest ones, Faja do Ouvidor, seen from on high

Channel dolphins

Dolphins and a pair of recreational fishermen enjoy an evening outing in the channel between Sao Jorge and Pico

Dinner shoot

Journalistic incest. I shoot Graham shooting Nielsen as he prepares a dinner onboard

Pico with snow

In the local parlance: Pico wears a hat. Our first morning in Velas we found it had snowed on high across the channel during the night

After one full day on Sao Jorge, we sailed around to south shore of Pico and had good wind most the way. First a steady breeze from behind us as we scooted down the Sao Jorge channel and around the eastern tip of Pico, then lots of erratic blustery gusts as we sailed west with the high land of Pico towering above us. After only a wee bit of motoring, we landed at last in the town of Lajes, which is unusual among Azorean harbors in that it has shoal water. We squeezed into the marina there with no trouble and soon after tying up headed for the local whaling museum.

Whaling used to be a big deal in the Azores. The waters around the islands are thick with marine mammals, and Azoreans first learned about whaling when they signed on as crew aboard American whalers that came to archipelago both to hunt and reprovision. By the middle of the 19th century, Azoreans were hunting on their own in local waters from small open boats. Pico, and Lajes in particular, was the focus of much of this activity until as late as 1984.

Lajes marina

The mountain of Pico, shrouded in cloud, as seen from the marina in Lajes. That’s our boat, Insula, on the right, with another SailAzores Dufour 375 right next to it

Lajes museum

Inside the whaling museum. Whale watching instead of whale hunting is now a significant source of income in Lajes

Whaleboat model

A museum model of an Azorean whaleboat, with all relevant gear. These were the boats used right up until 1984, and there are many men on the islands still alive today who once worked in them

Pico coast

South coast of Pico near Lajes

Whaleboat in shed

Though Azoreans stopped whaling, they haven’t stopped building and maintaining whaleboats, which they now race under both sail and oars. We found this example in a boathouse in a small village near Lajes. On the wall you can see photos of crew members and a case full of trophies

Whaling launch

Azoreans are also still maintaining the old motor launches that were once used to tow whaleboats out to the hunting grounds

Fishing skiff

Many Azoreans are also still fishing from small wooden skiffs in the traditional style. You’ll note, however, that they do install electronics

Alas, we lost the vaunted Snook, our photographer, on Pico, as he had to catch a ferry back to Faial to hop a flight home to the UK. Nielsen and I spent an extra day on the island, then motored back to Horta in a bit of rain the following afternoon. There we had a chance to dine again at Cafe Sport with our friends from SailAzores and were introduced to Jose Azevedo, the current proprietor and grandson of the famous bar’s original founder.

The next day we flew to Sao Miguel and lay over one night before catching our flight back to Boston. Again, thanks to the extremely gracious tourism board, we had a car at our disposal and were able to tour around a bit before moving on.

Jose Azevedo

Jose Azevedo gave us a personal tour of his family’s famous scrimshaw museum. Among the items on display is a well-known photo he took of a huge storm that hit Faial in February 1986. You can see a human face in the immense sheet of spray above the rock on the left


This is but a small portion of the Cafe Sport scrimshaw collection, which most likely is the largest in the world. This set of sperm whale teeth is adorned with likenesses of various famous sailors and members of the Azevedo family

Sao Miguel coast

The north coast of Sao Miguel

Sete Cidades

Sao Miguel has three major volcanic calderas, two of which are inhabited. This is the village of Sete Cidades, situated on the floor of the western caldera, as seen from the crater rim


This is the village of Furnas, which is inside the eastern caldera

Furnas hot springs

Hot sulphur springs outside Furnas. This suggests to me that this volcano is not entirely inactive

Cheoy Lee ketch

An old friend on the hard in Ponta Delgada. Back when I last visited the Azores very few locals had yachts, as there was no place to keep them. Now, with all the marinas, local yachts are quite common. This was one of the first ones, an old Cheoy Lee ketch that was imported to Ponta Delgada the winter I lived in the marina there. She was berthed right across from Crazy Horse, and of course I was both surprised and pleased to find she is still hanging out there


How Much Has It Changed?

All of you with distant memories of the Azores will be pleased to know the islands have actually changed very little over the last two decades. The harbors everywhere have been greatly improved, and there are a few more tourists than there used to be, but otherwise I was very pleased to find things were much as I remembered them. The one exception was Sao Miguel, which now has divided highways traversing part of the island and a cruise ship dock in Ponta Delgada. Gack! Cruise ships also visit Horta, but they cannot land there and evidently do not spend the night.

Stuff You Need To Know

This ain’t the BVI people. To charter a boat here you need a fair amount of experience, as the sailing can be challenging at times. You don’t need a certificate, but you will be queried closely as to your experience and background and may be turned away if these are found wanting.

No, the tourism board will not give you cars to drive like they did us, but you can easily rent them and can make arrangements through SailAzores to have a car waiting for you wherever you go. Alternatively, you can just hitchhike your way around when exploring each island. This is how I got around when I stayed here before. People are very friendly and often stop to pick up hitchers, but in some places the traffic is very thin.

All marina fees are included in your charter fee, and SailAzores will make sure there is space for you and people to greet you in every marina you visit. On the two islands without marinas they will make sure there are secure moorings for you to stay on.

One downside to cruising in any Portuguese jurisdiction is that you have to book in and out of every port you visit. The Portuguese love their paperwork, but in the Azores at least everyone is very nice about it. You can usually book out of ports the day before you actually leave, which simplifies things, and since officials see the SailAzores charter boats all the time they do seem willing to cut them a little slack.

The charter season runs from April through October. The best time to come is May through September. If you’re interested in doing this, be sure to plan ahead. The summer season this year is already all booked up.

English is widely but not universally spoken.

Many Thanks To

Nicolau Faria, Joao Portela, Anabela Costa, and Emidio Goncalves of SailAzores

The Azores Tourism Board

2 Responses
  1. joe g longo

    looking for passage to azores ,and am intrigued with what i,m seeing on the computer and feel that i may be able to contribute in various ways to the historic and ecological preservation of the archipelago. although i have some maritime experience,i have also participated in salvage ,reuse ,recycling ,environmental stewarship,agriculture ,forestry, and general sustainability ,i welcome any feedback regarding my possible contribution as a volunteer with these concerns in mind.yourstrully,joe longo,167 bleecker st nyc ,ny,10012,u.s.a.

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