Skip to main content

Sailing vacation in the Azores

Experience an unforgettable sailing trip on board the KAIRÓS through the fascinating island world of the Azores! Start on Faial, where the legendary port of Horta welcomes sailors from all over the world. Continue to São Jorge, known for its dramatic cliffs and green “fajãs”. The highest mountain in Portugal is impressive on Pico. Back on Faial, your trip ends with one last view of the Atlantic and the breathtaking nature of the Azores. A sailing trip full of wild beauty, volcanic landscapes and a real spirit of adventure!

Routenkarte der Segelroute 6
Start / end
Horta – Horta
Arrival
Horta
Group size
Max. 12 guests
Places
Azores / Faial - Sao Jorge - Pico- Faial

Itinerary

Every sailing trip follows the conditions of nature. The itinerary shown is a non-binding orientation and can change depending on wind and weather.

Your sailing voyage begins in Horta on the island of Faial. Once on board, you get to know the yacht, the crew and your fellow travellers. Over a shared dinner on deck, you take in the view across the Atlantic and settle into the days ahead, filled with nature, sailing and discovery.

In the morning, we cast off. The yacht sets course for São Jorge as the volcanic islands of the Azores slowly drift past on the horizon. With a little luck, dolphins will accompany the ship. This narrow, elongated island impresses with its green high plateaus and steep coastlines.

Today there is time to get to know São Jorge more closely. The island is famous for its “fajãs” – fertile coastal plains at the foot of towering cliffs. Small villages, unspoilt landscapes and a relaxed atmosphere give you a true feel for the Azores. If you like, try the famous Queijo São Jorge.

The next leg takes us to Pico. Even from afar, the mighty Pico volcano dominates the landscape. At over 2,300 metres, it is the highest mountain in Portugal. Black lava fields, small coastal villages and spectacular views define this unique island.

Pico combines volcanic wildness with a centuries-old wine culture. Vines thrive between walls of black lava, their cultivation recognised by UNESCO as a World Heritage Site. The island also tells its story as a former centre of whaling – today it is more of a paradise for nature lovers and whale watchers.

Under sail, we continue on to Terceira. During the crossing, you enjoy the vastness of the Atlantic and the tranquillity on board. There is plenty of time to relax, read or simply watch the sea.

Terceira welcomes you with history and culture. The historic town of Angra do Heroísmo is a UNESCO World Heritage Site and impresses with its Renaissance architecture, elegant squares, churches and parks. Strolling through the old town, you experience the special charm of the Azores. To round off the voyage, you return to Faial, enjoying the Atlantic and the unique island world of the Azores one last time. At the festive Captain’s Dinner, glasses are raised to an unforgettable week full of experiences, sunsets and special moments.

Disembarkation and individual journey home. Your voyage comes to an end with unforgettable impressions of volcanoes, coastal landscapes and relaxed sailing.

Your sailing yacht

Our first ship — and with her this special sailing concept was founded in 2007. At 38 m long with 556 m² of sail area, KAIRÓS is a little smaller than CHRONOS and RHEA, which makes her all the more personal and lets guests lend a hand on deck.

KAIROS

Cabin equipment

  • Wardrobe
  • Hairdryer
  • Hand and bath towels
  • Air conditioning
  • 230 V sockets
  • Life jackets
Discover the yacht

Cabin A

The largest cabins on the KAIRÓS, with a fixed double bed and a spacious bathroom.

Cabin B

With bunk beds or a small double bed. Bathroom with WC and a classic yacht shower.

Included services

  • Accommodation on board in the booked cabin category
  • Nautical crew and service on board
  • Sea passage during the trip
  • Full board on board
  • Water sports from on board
  • Water, tea and filter coffee

Not included

  • Travel to and from the yacht
  • Transfers
  • Soft drinks, Nespresso and alcoholic drinks
  • One evening to explore the local cuisine ashore
  • Shore excursions and tips

Dates & prices

Sailing vacation in the Azores

 – 

Horta – Horta

Sailing yacht trip

Yacht: KAIROS

Spots still available
Cabin A (p.p.)
€ 3.800,–
Cabin B (p.p.)
€ 3.400,–
Request now

Sailing trip in the Azores

 – 

Horta – Horta

Sailing yacht trip

Yacht: KAIROS

Sold out
Cabin A (p.p.)
€ 3.800,–
Cabin B (p.p.)
€ 3.400,–

Sailing trip in the Azores

 – 

Horta – Horta

Sailing yacht trip

Yacht: KAIROS

Sold out
Cabin A (p.p.)
€ 3.800,–
Cabin B (p.p.)
€ 3.400,–

Island hopping in the Azores

 – 

Horta – Horta

Sailing yacht trip

Yacht: KAIROS

Spots still available
Cabin A (p.p.)
€ 3.800,–
Cabin B (p.p.)
€ 3.400,–
Request now

Sailing in the Azores

 – 

Horta – Horta

Sailing yacht trip

Yacht: KAIROS

Spots still available
Cabin A (p.p.)
€ 3.800,–
Cabin B (p.p.)
€ 3.400,–
Request now

Book now

Send us your request without obligation — we will get back to you personally.

Trip details
Personal information
Additional information
How did you hear about us?

The data sent to us via the form will be stored by us in accordance with our data protection regulations and will not be passed on to third parties under any circumstances.

Fields marked * are required.

Important information

You can easily travel to the ports in the Mediterranean with the usual airlines. The best way to reach Cape Verde and the Azores is via Lisbon. The return journey from the Caribbean to Europe is usually via London or Paris. For the return crossing to the Mediterranean, fly via London to Antigua. Depending on the duration of your journey, you should allow a buffer of 1-3 days for the return flight or book a rebookable ticket.

The cruise price includes: costs for the nautical crew and service, accommodation on board in the booked category, sea transport, full board on board / one evening per week to discover the local cuisine at your own expense, water, tea, filter coffee. The price does not include: arrival and departure, transfers, soft drinks, Nespresso and alcoholic beverages, water sports from on board, shore excursions and gratuities.

Sailing on the Atlantic is usually associated with the trade winds, which blow constantly in many parts. The weather can vary on long crossings, from calm conditions to heavy seas, and the influences of the Gulf Stream and crossing cold fronts require special attention. Up-to-date weather information is crucial for navigating through the various conditions in the Atlantic.

Life on board the Sailing-Classics yachts is very safe and well organised. The vessels meet the highest safety standards and are inspected annually. The captain and helmsman are graduates of a professional maritime college and undergo continuous professional development. The rest of the crew also receive intensive training in how to deal with emergencies. A compulsory safety briefing takes place at the start of every voyage. Furthermore, despite their speed, the yachts sail with remarkable stability – even in heavy weather, hardly any water comes on deck.

Both German and English are spoken on board the Sailing-Classics yachts. The language used amongst the international crew is English, whilst they communicate with guests in both German and English. On the KAIRÓS, we cannot always guarantee communication in German.

Meals on board Sailing-Classics are organised on a full-board basis and are included in the tour price. The day begins with a generous breakfast buffet, followed by a light two-course lunch and coffee and cake in the afternoon. In the evening, the on-board chef prepares a three-course dinner. On the final evening, the festive Captain’s Dinner is the culinary highlight. Once a week, a dinner is held ashore to sample the regional cuisine – this is not included in the tour price. Special dietary requirements and allergies can be catered for if notified in advance.

Sailing-Classics organises shore excursions using the crew’s motorised dinghies. On request, the crew will take you ashore and collect you again free of charge – simply let the team know in good time. In addition, in many sailing areas, the crew organises guided shore excursions with a local guide or accompanied by a crew member. The price per participant is communicated in advance and charged to your on-board account. Of course, you are also welcome to explore the surrounding area on your own.

The cabins on board the Sailing-Classics yachts are comfortable and practically furnished. Each cabin has its own en-suite bathroom with a toilet and shower cubicle, individually controlled air conditioning, a wardrobe, a hairdryer, and hand and bath towels. 230-volt sockets are available for charging electronic devices. A reusable water bottle is provided in every cabin and can be refilled at the water dispenser in the saloon.

At Sailing-Classics, you’re warmly invited to get actively involved in sailing – no prior experience or sailing licence required. You can help set and trim the sails, take the helm yourself, or lend a hand with other tasks on deck. The crew will be happy to explain the basics of sailing to you, show you how radar navigation works on the bridge, or give you a tour of the engine room. Those who prefer to relax can simply enjoy the passing scenery – the motto is: ‘Everything is possible, nothing is compulsory.’

To cancel your sailing holiday with Sailing-Classics, please send your cancellation request by email to info@sailing-classics.com. Written notification is required so that the cancellation can be processed officially. Depending on when the cancellation is made, Sailing-Classics’ tiered cancellation terms and conditions will apply. We strongly recommend that you take out travel cancellation insurance to protect yourself financially.
On-board ABC – everything you need to know

Related trips

Sailing trip in the Cape Verde Islands

We sail around the northern islands from Sao Vicente with the lively harbour town of Mindelo, across the still largely untouched tourist destination Sao Nicolau with towering mountains and bizarre rock formations to the eastern sandy island… Read more

From € 4.850,– per person

“Short” Atlantic Crossing

For sailors - a delivery trip from Gibraltar in Spain to the Cape Verde Islands off the coast of Africa and an opportunity to get to know the Atlantic. The goal is to move the yacht from one region to another. Sailing at night is included… Read more

From € 2.200,– per person