Sailing voyage Z05-26: Family Sailing Holiday in the Azores

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

This family sailing trip is perfect for families with children. We take a little more time in port, leaving plenty of opportunities for swimming, walking, and exploring the islands together. Life on board is relaxed – we sail shorter legs, take more swimming breaks, and enjoy ice creams in the harbour. It’s a wonderful way for kids to discover sailing, life at sea, and the natural wonders of the ocean – from dolphins to volcanoes.
Children aged 9 to 11 receive a 50% discount on the trip price.

During this sailing voyage, you’ll discover the central Azores archipelago – a stunning collection of islands, each with its own unique character. We start in Horta, on the island of Faial, a lively sailors’ town famous for its colourful harbour walls, painted by visiting yachts from all over the world. After boarding and sharing a first meal together, we prepare for our departure the next morning.

Our first sailing day takes us to Lajes do Pico, on the southern coast of the island of Pico. Along the way, there’s a good chance of spotting dolphins – and with a bit of luck, even whales. Lajes is a charming little harbour with a fascinating maritime museum, home to a beautifully preserved wooden whaleboat. Until the 1980s, whales were still hunted here under sail and sheer muscle power – today, those same sleek wooden boats compete in spirited sailing races between the islands, an impressive sight of grace and speed.
Although my own ancestors were whalers, I am, of course, strongly opposed to whaling. Still, the museum offers a fascinating glimpse into a time when people needed meat to survive – an important chapter of the Azores’ maritime history.

The next day we set sail for Velas on the green and rugged island of São Jorge. It’s a stunning passage between the islands, with sweeping views of the Atlantic and the volcanic peak of Pico on the horizon. We spend an extra day here to explore the island – a paradise for hikers, full of green valleys, waterfalls, and dramatic cliffs. Don’t miss the natural swimming pool on the eastern coast – crystal-clear ocean water surrounded by volcanic rock, perfect for a refreshing dip after a scenic walk. At Café Nunes, you can taste coffee grown on Europe’s only coffee plantation. In the evening, the harbour comes alive with the hauntingly beautiful calls of Cory’s Shearwaters, the seabirds that nest along the cliffs.

From Velas, we continue to Terceira, mooring in the historic port of Angra do Heroísmo, a UNESCO World Heritage Site. We stay another day to discover the island’s highlights: its charming old town, cosy cafés, and volcanic wonders. A must-see is Algar do Carvão, an ancient lava cave that lets you descend deep into the heart of the earth. And in Biscoitos, you can swim in natural lava pools that open directly into the ocean – a truly unique experience!

Our voyage ends in Praia da Vitória, on the east coast of Terceira. On the final evening, we go out for dinner together in a local restaurant and toast the journey with a beer back on board. The next morning, after a special breakfast, everyone disembarks around 10:30 – filled with lasting memories of a week of sailing, nature, and island adventure in the heart of the Atlantic.

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 holidays 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!)
– Optional tips. These are, of course, entirely voluntary, but always appreciated. Any tips are shared between the skipper and crew, as some guests assume that a tip is primarily intended for the Bosun, while the skipper is just as much a part of the team that makes the voyage possible. Contrary to what many guests assume, the skipper on board the Cherokee does not receive the highest salary.

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’.

Sailing holidays 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’.

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

Sailing holidays discounts can not be combined with each other.

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

Private charter

You can also rent the ship and crew for a privat charter. Then multiply the price with 7. For a private charter, you can choose one of the offered sailing holidays, provided there are no other bookings for that sailing journey. If you would like more information on private charter, please contact us.

Sailing holidays with your own private cabin

If you are a solo traveler and would like the comfort of a private cabin (room), you can reserve it for 1.6 times the price (for crossings, it will be 1.9x).

Extend your sailing holidays with an extra day B&B

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 € 125 per person. This automatically applies when booking multiple trips in a row.

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.