Sailing voyage Z01-26: Island Hopping through the Central Azores

Dolphins, volcanoes, and charming harbours in the heart of the Atlantic

This sailing trip takes you through the central Azores archipelago – a stunning collection of islands, each with its own distinct character. We begin on the island of Terceira, setting off on a short coastal leg to the beautiful harbour town of Angra do Heroísmo, a UNESCO World Heritage site. Along the way, we sail between the iconic Ilhéu das Cabras, two uninhabited green islets rising dramatically from the sea.

The next day, we make a longer passage of about 55 nautical miles to the island of Pico – a full day of open-water sailing. With some luck, we may spot dolphins or even whales along the way. By evening, we’re gliding along Pico’s rugged coastline, dining at sea and sipping coffee as the sun sets behind the towering volcano – Portugal’s highest peak.

We moor in Lajes do Pico, a charming little harbour with a small maritime museum that houses a beautifully preserved wooden whaleboat. Until the 1980s, whale hunting was still done here under sail and with sheer muscle power – a fascinating glimpse into Azorean history.

From Pico, we sail to the legendary sailors’ port of Horta on the island of Faial, known for its colourful dockside murals painted by visiting yachts. We spend a full day here to explore the island. One highlight is Capelinhos, a lunar-like volcanic landscape created during the 1958 eruption. Beneath the partially buried lighthouse, a modern museum tells the story of volcanism in the Azores.

Our next stop is the wild and green island of São Jorge, where we stay another day to discover its natural beauty. A true gem is the natural swimming pool on the island’s eastern side – crystal-clear ocean water framed by volcanic rock columns. It’s the perfect way to cool off after hiking through the island’s lush forest trails. Afterwards, we stop for coffee at Café Nunes, which serves beans from Europe’s only coffee plantation. In the evening, the harbour at Velas comes alive with the eerie and enchanting chorus of Cory’s Shearwaters.

We then continue around São Jorge’s scenic north cape to the charming island of Graciosa, enjoying another full day at sea. This tiny island offers a peaceful harbour and a chance to slow down. We stay an extra day to descend into the Caldeira, an ancient volcanic crater where the earth still gently bubbles. After a scenic hike and a picnic lunch at the crater’s rim, we unwind in the warm waters of a nearby thermal spa – or, for the brave, a refreshing dip in the sea.

The journey ends back on Terceira, in the harbour of Praia da Vitória, where we wrap up this unique and relaxed sailing adventure with dinner in a cosy local restaurant and drinks by the water.

The daily distances vary, depending on weather and tide, between 12 and 55 miles. The above schedule depends on weather, wind and tide, if necessary we can change destinations.

Land excursions are not included in the price and are of course not mandatory.

Read more about our sailing holidays around the Azores

Information about this sailing holiday

Participants of this sailing holiday

Sailing holiday Prices 

The price is the rental cost for the ship with crew, including food and drinks on board, hence full board. The price mentioned is per person.

Included in the price:

– Food and drinks on board.
– Fuel, water, shore power, harbour fees and tourist tax.
– 1 towel set and bedding incl. duvet and, of course, a life jacket.
– For after sailing there is also wine and beer on board, based on average use. Should we run out, then you can purchase more yourself.

Not included:

– Your transfer, meaning your journey to and from the ship
– Sailing clothes and boots, you can rent these from us if you would like.
– Possible shore excursions such as renting a van, or visiting a museum etc.
– Food and drinks ashore, the last evening we will go out for dinner and this will be at your own expense. ( Should you wish to treat the crew as a thank you for a lovely sailing holiday, it would of course be greatly appreciated!)

On some of our sailing holidays, it is possible to book an extra overnight stay on board based on Bed & Breakfast (B&B, so without dinner) for €75 per person. This automatically applies when booking multiple trips in a row.             

Duration & Time on Board

The listed trip duration refers to full calendar days. Since you embark on the first evening and disembark on the final morning, your actual time on board is on average about 1.5 days shorter. We use this format to keep our trips comparable with other providers – but we like to be transparent about the real time you’ll spend on board.

Sailing holidays discount

Customer Discount:
If you book a second sailing holiday with us within a year, you’ll get 2.5% off the ‘board price’.

Group discount:
If you book a sailing holiday as a group (more than 3 passengers), you will receive 2.5% discount per person on the ‘board price’.

Youth Discount:
If you are under 29 years old, you will get 5% discount on the ‘board price’.

Discounts can not be combined with each other.

Bonus Discount:
€25 extra discount when you choose a vegetarian menu on board.

Sailing holiday with your own private cabin

If you are a solo traveller and wish to enjoy the comfort of a private cabin (small room), then you can reserve it for 1.6 times the price (for crossings, category A, the rate is 1.9x).

Sailing holiday categories

Category A:
Offshore crossings, includes also sailing throughout the nights. Passengers will also be grouped in the watch system.

Category B:
Offshore sailing holidays, there will be no sailing throughout the nights, but occasionally a late arrival at the harbour (or an early departure), depending on the weather.

Category C:
Relaxed sailing holidays with shorter sailing distances, including more time for sightseeing and sometimes a nice land excursion.

Category D:
Sailing holiday specials, from ‘Sailing holidays with Yoga’ up to expedition sailing. Not every season available.

Category E:
Sailing holiday’s with extra sailtraining.

Category F:
Sailing holidays with also small children on board.