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Sailing trip Azores

Azoren
Azoren rund

Atlantic islands between volcanoes and whales

The Azores rise from the sea in the middle of the Atlantic: green volcanic islands, steep coasts, wide horizons and impressive nature make this area unique. Discover the islands around Faial, São Jorge and Pico with the KAIRÓS – intense, pristine and shaped by the open Atlantic.

Our Azores cruises take place in May and start and end in Horta on Faial.
From there, you sail between the central islands of the archipelago – past volcanic landscapes, green cliffs and small harbour towns. The short distances between the islands allow for varied stages, while the open Atlantic feeling remains tangible at all times. The Azores are among the most pristine and unspoiled areas in Europe.

Quick Facts about sailing trips in the Azores

Highlights

  • Volcanic islands in the middle of the Atlantic
  • Whale and dolphin watching with a bit of luck directly from the ship
  • Pristine nature, green landscapes and spectacular coastlines

The best time to travel

Our sailing trips to the Azores take place in May – one of the most beautiful times of the year for the archipelago. The islands are particularly green, the temperatures are pleasantly mild and nature is in full bloom. At the same time, conditions are usually stable for sailing between the islands.

Sailing conditions

The Azores offer a real Atlantic sailing area with changing conditions, open stretches and noticeable Atlantic swell. At the same time, the comparatively short distances between the islands make for varied daily stages. The area is particularly suitable for guests who want to experience nature-loving and pristine sailing.

Arrival

Arrival is via Horta Airport (HOR) on the island of Faial. From there you can reach the port of embarkation in a short time by taxi or organized transfer.

Top highlights & sights in the Azores

Horta - legendary sailing port in the middle of the Atlantic

Horta - legendary sailing port in the middle of the Atlantic

The small harbour town of Horta on the island of Faial is one of the most famous sailing ports in the world. For decades, yachts have stopped here on their Atlantic crossings, creating a special maritime atmosphere.

The famous harbour pier with its painted crew graffiti, small cafés and the view of the neighbouring island of Pico give Horta a very special character. At the same time, the town is the ideal starting point for sailing trips through the Central Azores.

Pico - volcanic island and home to Portugal’s highest mountain

Pico - volcanic island and home to Portugal’s highest mountain

The island of Pico is dominated by the volcano of the same name, the highest mountain in Portugal. The striking cone is often visible from afar and dominates the entire landscape of the island.

In addition to its volcanic nature, Pico is also known for its wine landscapes, which are a UNESCO World Heritage Site. Black lava rock, small villages and spectacular coastlines create an impressive backdrop between the Atlantic and the volcano.

SMI Vista do Rei 01 1980

São Jorge - green cliffs & pristine nature

São Jorge is one of the most pristine islands in the Azores. The elongated volcanic island impresses with steep cliffs, lush green slopes and the famous “fajãs” – small, flat coastal plains at the foot of the cliffs.

The island is quiet, unspoiled and authentic. Small villages, traditional agriculture and spectacular views make São Jorge a perfect destination for anyone who wants to experience the Azores off the beaten track.

Atlantic, whales & wide horizons

Atlantic, whales & wide horizons

The Azores is one of the best regions in Europe for whale and dolphin watching. With a bit of luck, sperm whales, dolphins and other sea creatures can be observed directly from the ship.

The open Atlantic feeling accompanies the entire journey: clear air, wide horizons and constantly changing light moods create an intense atmosphere that makes this area so special.

Your sailing trip - optimally planned

Your sailing trip - optimally planned

Would you like to know whether the Azores is the right destination for you or do you have questions about travelling to Horta?
Our experts will be happy to advise you personally and help you find the right cruise with the KAIRÓS.

Pristine sailing in the heart of the Atlantic

Pristine sailing in the heart of the Atlantic

A sailing trip to the Azores means nature, vastness and a real Atlantic feeling. Between volcanic islands, green slopes and a deep blue sea, you will experience an area that is much more pristine and rugged than classic Mediterranean destinations.

Whether sailing between the islands, going ashore in small harbour towns or gazing at the volcanoes on the horizon – the Azores combine intense nature experiences with relaxed life on board and an extraordinary atmosphere.

What our guests say about their time on board

  • Travelogue by Heinz-Dieter Heibach

    Transit Cruise on the KAIRÓS: Portimão, Portugal – Valencia, Spain

    Who would have thought it!!! When I saw my wife Barbara poring over a Sailing-Classics brochure with sparkling eyes in October 2025, I had no idea that we’d be booking a delivery cruise on the KAIRÓS just a short time later. But let’s take it one step at a time. For the two of us, as recreational sailors with our little ETAP 23iL, it was actually unimaginable that we’d ever get to sail on a large two-masted yacht and even lend a hand ourselves. After a last-minute informational meeting with Ms. Sturm at the Stuttgart sales office, we were certain: We were going to take on this voyage, and so we eagerly awaited the start of the trip in June 2026. For us, the focus was on sailing the KAIRÓS rather than just hopping from bay to bay. There were just ten days between the end of my own trip and our flight to Portugal. On that trip, I’d previously sailed solo from South Holland across the English Channel to southern Brittany, and then continued on with Barbara for a few more weeks in the Bay of Biscay. Days before her arrival, we were already tracking the KAIRÓS via Vesselfinder on her journey from the Azores to Portimão. The joyful anticipation grew.

    When we finally saw the KAIRÓS in person for the first time, we were really looking forward to checking in the next day.

    Captain and Sailing-Classics CEO Seren Elgün warmly welcomed us—ten passengers—aboard along with his seven-member crew. The very next morning, after a brief stop for a swim near Portimão, we set off for what would be our last anchorage for the time being, near Faro. This gave the guests plenty of time to settle in on board and get familiar with the KAIRÓS. After all, the upcoming nonstop voyage to Valencia would be quite demanding during our first two days at sea.

    Off the Strait of Gibraltar, winds of up to 47 kt from the east were forecast. Later, while tacking toward Tarifa, the anemometer even registered 50 kt. The boat, the crew, and, of course, the guests were put to the test. However, I thoroughly enjoyed steering the 153-metric-ton KAIROS close-hauled through waves up to 4 meters high. On our little ETAP, I had last sailed in the English Channel with a broad reach and winds of up to 32 kt. On that boat, you’re much closer to the elements. It was nothing like the majestic experience on the KAIROS. Together with Seren, I sailed through the Strait of Gibraltar on the third night. There was relatively little ship traffic, and Tangier at night, along with the Rock of Gibraltar, glowed almost mystically against the dark backdrop of the mountains behind them. After the hardships of the Atlantic, the conditions in the Mediterranean Sea the following day felt like sailing on a duck pond. We watched dolphins, as well as tuna and barracudas hunting; two sunfish (Mola mola) were drifting on the surface; and later, my personal highlight: a pod of six pilot whales, which I first noticed because of their loud songs. These extraordinary creatures accompanied us at a leisurely pace for about half an hour. Pure joy!

    And then there were those sunsets at sea, time and time again. I love them!!! The crew took excellent care of us, even in the toughest conditions. The ship’s engineer found a quick solution to even the smallest problem, and the ship’s command—including the captain, first mate, and deckhand—always made everyone on board feel safe, not just the sailing novices among the guests! Over the remaining days, we cruised—with several stops for swimming in the middle of the open sea—all the way to Valencia, where, after 711 NM, we performed an anchoring maneuver under sail. Hats off! After one final night at anchor, there was a touch of melancholy in the air that last morning. At breakfast, everyone spoke in hushed tones. The crew prepared everything for our departure. Over the past seven days, we—crew and guests alike—had become a temporary unit! I’m very satisfied and happy that I was able to actively support the regular crew with ship handling and maneuvers. In particular, the watches with Captain Seren Elgün helped me improve my seamanship quite a bit, especially when it comes to handling a tall ship.

    After tears had been shed—not just by the crew—as we said our goodbyes, we checked out and drove to the harbor with the second group. There, from the shore, Barbara and I gazed thoughtfully at “our” KAIRÓS for what would be our last time—for now.
    Read the full review
    July 8, 2026 Travelogue by Heinz-Dieter Heibach
  • Captain Nico and his crew did a great job

    An all-round successful trip

    It was an all-round successful trip, from the organization and information beforehand to the support and care on board! Captain Nico and his crew did a great job, so that I felt very comfortable the whole time on board and enjoyed the trip very much. All crew members were always attentive, kind and helpful! The fellow passengers also very quickly became a harmonious and cheerful community. I will remember this trip as a very special experience and will be happy to recommend you to others.
    Read the full review
    Reiner after the Atlanticcrossing W-O on the CHRONOS
  • What a feeling...

    A wonderful Atlantic crossing

    I experienced a wonderful Atlantic crossing and still think about it every day. What a feeling to be out there "all alone" for 3 weeks; that will always be a part of me.... And then the nice conversations with great people, as they say: all in the same boat. The crew were great; with Sandy and Agi I felt it always seemed like it was their first day on board, so full of energy and friendliness; a hearty Merci, as we say here in Switzerland.... It was an incredible experience for me and I'm already looking forward to another sailing trip (this time with my husband).
    Read the full review
    Irene
  • It was a dream trip...

    A dream trip across the Atlantic

    It was a dream trip... Every morning during the RHEA cruise I got up in the dark and, after greeting the night shift crew, sat down on a bench with a headlamp and started writing into the dawn. Organizing your life - is there a better way to do this than during a three-week crossing through an empty world (which is by no means empty under the keel)? ... A wonderful time, ... especially the two stops that allowed us to take a dip in the 5,000 meter deep Atlantic. So all this will remain unforgettable, a lifelong dream...
    Read the full review
    Peter
  • Bianka and Dirk after their Cape Verde cruise on the CHRONOS in November

    A very successful mix

    Very successful mixture of sailing, excursions, culture and background information. The crew on board was great!

    Bianka and Dirk after their Cape Verde cruise on the CHRONOS in November
    Read the full review
    Bianca and Dirk
  • Every aspect of the trip was first class

    The whole trip was fantastic

    I wanted to let Sailing-Classics know about my experience on the April 6th to May 5th Atlantic Crossing from Antigua to Mallorca on Chronos. Everything about the entire trip was fantastic. The captain Jan Dobrogowski did an amazing job of managing the adventure. Every aspect of the trip was first class and professional. All of the crew worked really well together and were professional, friendly and relaxed all at once. Managing safety, the route, the weather, the schedule and the various guests' personalities is not a small endeavor. So congratulations and a big thank you to everyone.
    Read the full review
    Kerry

Experience the Atlantic under white sails

Discover our sailing trips around the Azores

stylish, authentic, unforgettable

We have the answers for you

FAQs about sailing in the Azores

In May there are usually mild temperatures, spring-like conditions and good conditions for sailing trips between the islands.

The Azores are particularly suitable for nature-loving guests who appreciate pristine landscapes, the Atlantic feeling and varied sailing conditions.

The start and finish port is Horta on the island of Faial.

Yes, the Azores is one of the best regions in Europe for whale and dolphin watching – with a little luck, sightings are possible directly from the ship.

Yes – on the Atlantic all the more so: the wind sets the course. The route can be adapted depending on the weather and conditions, so that you experience the finest harbours and the most pleasant days of sailing.

Yes, short shore excursions are part of the programme: from small harbour towns and traditional villages to natural highlights such as the fajãs on São Jorge or the wine landscapes on Pico.

A lot is already prepared for you on board – towels, shampoo and usually also sun protection products are available. For the Azores we recommend dressing in layers, sturdy shoes for going ashore, a windproof jacket and rain gear. It is best to travel with soft bags, as they are easier to stow in the cabins and offer more space than suitcases.

Our cabins are comfortable and well-designed, with a wardrobe, shelves and storage space under the beds. There is plenty of space for the duration of the trip; foldable travel bags are better suited than hard-shell suitcases.

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