Sailing trip Azores

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 harbor 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.

Our sailing trips around the Azores

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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

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.

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.

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 cab or organized transfer.

Top highlights & sights in the Azores

Horta - legendary sailing port in the middle of the Atlantic

The small harbor 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 neighboring 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

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.

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

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

Would you like to know whether the Azores is the right destination for you or do you have questions about traveling 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

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 harbor 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

5 stars +
The crew really read every wish from our eyes. The food was excellent... If I had to award stars for cuisine and service, it would be 5+. .. We had...

High praise
This is the fifth time we have enjoyed a trip with Sailing Classics, this time between the Greek islands. And in November we want to sail across the Atlantic with...

Everything optimal
I will remember these two weeks for a long time to come, because there was a good balance between shore leave, swimming, sailing and wonderful weather. The crew was outstanding...

blick-auf-die-segel-der-chronos-vor-der-amalfikueste
A special experience
You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time...

blick-von-der-chronso-auf-den-sonnenaufgang
A special experience
You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time...

Absolutely marvelous charter
It was an absolutely marvelous charter. Loved every minute of it. I have chartered boats a number of times, and I have never had such a friendly, positive, and accommodating...

It was marvelous
About 10 days ago, we had zero sailing experience and no idea what to expect as a family with two young kids (ages 5 and 7) boarding a 3-night charter...

A special experience
You are probably more than aware that sailing on the Rhea is a particularly beautiful experience. It was a special experience for me. Not that it was my first time...

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...

A great pleasure
I would like to express my great pleasure at having taken part as a passenger in the wonderful, eventful and indeed exhilarating voyage with the RHEA on the occasion of...

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 – even in the Caribbean, the wind sets the course. The route can be adapted depending on the weather and conditions so that you experience the most beautiful bays and most pleasant sailing days.

Yes, regular swimming stops, snorkeling opportunities and short shore excursions are part of the program: from beach visits to small towns to nature highlights such as the frigate bird reserve on Barbuda.

A lot is already prepared for you on board – towels, shampoo and usually also sun protection products are available. For your summer sailing vacation, we recommend light, comfortable clothing, sturdy shoes for shore excursions, swimwear, possibly a windbreaker and a sun hat. It is best to travel with soft travel 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, and foldable travel bags are the best option instead of hard-shell suitcases.

Caribbean under sail - perfect for solo travelers

Discover our special offers for solo travelers in the Caribbean:

🎉Christmas & New Year’s Eve without single cabin supplement

🏝️Bis 31.03.2026: half single cabin supplement on all Caribbean voyages

⛵Tip: Combine two weeks and secure a multi-week discount