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Adventure sailing holiday: Azores explorer

Adventure sailing holiday: Azores explorer





The mid-Atlantic, volcanic archipelago of the Azores is one of the most spectacular cruising grounds in the world. Being at the junction of the Eurasian, North American and African tectonic plates, the Azores are a geological hotspot, with vast craters and volcanoes explore fringed by gorgeous villages, green fields and millionsof flowers.  We have nine islands to sail between and explore. The islands are also a real hotspot for whale sightings. Sperm whales are the resident species and most frequently sighted. They live in the waters around the islands all year round, feeding on the giant squid that lurk deep down in the depths of the Atlantic

Sailing location image
Route Map Image

These are the available dates and routes. To book your place, please select the dates from the drop-down above the ‘Add to Cart’ button.


  • Start date / place: June 20 2022. Horta, Azores
  • End date / place: July 01 2022. Horta, Azores
  • Full price: £1,899
  • Deposit: £475


  • Start date / place: July 04, 2022. Horta, Azores
  • End date / place: July 15, 2022. Horta, Azores
  • Full price: £1,899
  • Deposit: £475


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



This is non-refundable. On making payment, your berth is guaranteed.

Paying the balance
The balance of the invoice can be paid at any time. It must be received by Rubicon 3 90 days before the trip start date or your place will automatically be cancelled. We will remind you of the date nearer the time.

Cancellations and moving trips
Our expedition sailing yachts only have between 7 and 10 berths on them. When you book, you are committing to take one of these places. Due to these very limited numbers, we will often have turned away someone else who would have liked the berth. Unlike many other holidays, please understand this gives us little if any flexibility to make changes or to move trips. We will always endeavour to assist you (& the earlier you tell us the better), but unless we can find someone else to take your place, we usually cannot move your booking.

This is a typical sailing itinerary for the Azores explorer expedition. What makes an adventure holiday so special however is that there can be no fixed itinerary and no part of this is guaranteed. The wind and the weather ultimately shape what’s possible each day but everything is very flexible within that.

Joining day

Join the boat and get your belongings packed away and relax. There’s plenty of things to do in the future but right now it’s about relaxing, finding your way around the boat and enjoying the surroundings. After lunch, we’ll start to show you the boat, issue lifejackets and oilskins and teach you the most important skills when on board.

Briefings and training

Today is all about getting up to speed with the boat. Whether you are a complete novice or more experienced sailor, everyone benefits from detailed introductions, safety briefings and training sessions. You will have two highly qualified instructors to guide you through every aspect that you need to know to have a great sailing holiday. By lunchtime, we should be casting off the lines, and it’s time to learn the ropes. You’ll be hoisting the sails and working through all the critical sailing manoeuvres such as tacking and gybing, reefing and knot tying! By the end of the day, everyone on board should feel comfortable with the basics – even though there’s more to learn and practice every day. We may anchor overnight.

Sail to Flores

Flores, Azores

It’s around 130nm to the island of Flores, so we can expect a full day of sailing and then experiencing the sun setting over the Atlantic horizon and we will be sailing through the night, under the stars, experiencing the full thrill of open ocean sailing. Only briefly however, as by lunchtime the next day we will be arriving at Flores

Flores is the most westerly island in the Azores and a UNESCO biosphere reserve. It is probably the most beautiful island of the Azores archipelago, with a landscape of vast green hills and crater lakes. It has huge waterfalls and monolithic seacliffs, and isolated, whitewashed fishing villages, perched above the ocean. There is so much to explore on this island, not least Faja Grande, a wonderfully easy-going and welcoming little hamlet which has the honour of being the most westerly settlement in Europe.

Flores has one of the most famous natural monuments of the Azores, the rock ‘Rocha dos Bordões’. We can also bathe in the natural pools next to the black rocks at the Poço do Bacalhau, and visit the enormous cavern of Gruta dos Enxaréus. To fit it all in, we’ll likely spend a day and half exploring Flores.

Sail to Pico island

Pico Island Volcano

It’s another sail of about 130nm, so another wonderful taste of sailing out in the Atlantic and another night at sea. Now the crew are fullof stories and memories about the Azores, so there is loads to chat about through the night, drinking hot chocolate, star gazing and living the moment.

Pico is an island covered in vineyards, producing wonderful rich wines. It is also home to the Montanha do Pico, a huge 2351m stratovolcano which dominates the landscape. It is  an island of fascinating volcanic landscapes: at Arcos do Cachorro in the north you’ll see some of the most unusual lava formations in the Azores, where the volcanic coastline is perforated with grottoes, tunnels and arches. In the south, there are the lava caves at Gruta das Torres – formed just 1500 years ago.

Pico is also the original home of whale watching in the Azores – where French conservationist Serge Viallelle first demonstrated that whale tourism offered a more sustainable future than whale hunting.

Sail to Angra Do Heroismo (Terceira Island)

A much shorter sail today, with Terceira being just 60nm from Pico. It gives us a lovely full day sail, but we will also be tucked up in the harbour long before it gets dark and can sample the wonderful hospitality and have a really fun evening on the island.

Terceira is Portuguese for ‘third’ – as in ‘the third largest island’ and ‘the third island to be populated’ during the Portuguese Age of Discovery. The island is home to the Azores’ oldest city, Angra do Heroísmo. its cobbled streets, historic architecture and friendly population give the city a real charm. As a protected UNESCO world heritage site, the city’s stately 17th and 18th century architecture bears witness to Angra’s golden age, when the city blossomed economically, culturally and architecturally.

Inland, the island has a very volcanic landscape of criss-crossing lava flows and spectacular cave systems – most famously at Algar do Carvao: a unique 3000-year-old volcanic chimney and one of Portugal’s most-fascinating natural attractions.

Sail to Praia Da Graciosa (Graciosa Island)

Another shorter sail, with Graciosa being 45nm from Terceira. This small island is so peaceful, very rural, but with a violent volcanic past that is all too evident at Furna do Enxofre. A unique geological phenomenon, this enormous lava cave is an extraordinary sight: 200m in diameter with a 50m high vaulted ceiling made-up of volcanic prisms, it has its own underground sulphurous lake, and it’s only accessible via a vertigo-inducing 80-year-old stone spiral staircase. The Azores has more than its fair share of impressive geological phenomena, but Furna do Enxofre is one of our favourites.

Sail to Velas (Sao Jorge Island)

It’s now a 40nm sail to Sao Jorge. The island’s long, slender shape is quite unlike any of the other islands of the Azores. It was formed by a linear volcanic fissure – a tectonic plate boundary which extends 200km east all the way to the main island of Sao Miguel. The island is famous for it’s fajas – coastal plateaus which are home to many of the island’s smaller villages. The fajas are formed by different processes – by ancient landslides in the north where the seacliffs are steepest, creating the best natural swimming pools in the Azores. The cliffs on the south coast are less-steep and many of the southern fajas were formed by lava flows.

Sail to Horta, Faial Island

Our final sail brings us back to Horta. Faial itself has an amazing history. It was a crucial resupply point for Portuguese ships trading in Brazilian gold in the 16th & 17th Centuries, a 19th Century H.Q. for telegraph cables connecting Europe with the USA,  a safe-haven for seaplanes making the first trans-atlantic crossings in the 1930s, and  a communications hub connecting the D-Day landing beaches to the USA during the battle of Normandy in 1944. One of the Azores’ most arresting volcanic landscapes is Faial’s western peninsula at Capelinhos. Over a thirteen-month period (from September 1957 to October 1958), two overlapping volcanic eruptions created over 2km² of new land, allowing geologists their first opportunity to study a submarine eruption from beginning to end

Debrief, clean up and goodbyes

It’s always amazing how quickly everyone has become firm friends, and the boat and its routines seem so familiar. Yet it’s time to wrap it all up and head home. We’ll get the boat back to how we found it, sign logbooks, exchange emails and disembark by 1200hrs.


  • You should join the boat at 0900hrs on the start day. It is important you are not late.
  • You will disembark at 1200hrs on the end day.
  • For exact start and end locations, please see the ‘Dates & Prices’ tab



    • You can fly into Jerez (IATA code: XRY). Ryanair, British Airways and Iberia all fly there. From the airport, a taxi takes about 30 to 40 minutes and costs about €55 to Cádiz. There are also frequent trains from Jerez to Cádiz which arrive at the station inside the old town (see below).
    • You also fly into Seville (IATA code: SVQ) which can often be easier


    • Arecife airport (IATA code: ACE) is well served by many airlines and is close to the marina



    These adventure sailing holidays are open to anyone aged 18 – 70 years. No previous sailing experience is required for this route


    We provide the foul weather clothing, life-jackets and all other technical equipment you will need. You need to bring a sleeping bag and some waterproof boots.

    See more information and the full kit list here


    We believe that as many people as possible should be able to head out to sea and have a great adventure. However, it is essential for everyone’s safety that you are in a fit enough state to be on board. Ability to complete the five exercises below is a pre-requisite for joining as a crew member. They are not designed to be physically taxing and almost everyone should be able to complete them. Rather they are in place to check that you have the stability and basic physical condition to be on-board. If when you join the vessel the skipper believes you are not capable of completing these exercises, you will probably not be allowed to embark. If you have any doubts at all about your ability to complete these exercises safely, you must contact your doctor before attempting them.

    Fitness to sail


    Four weeks before your trip start date, you will be sent final joining instructions. At this time you will be asked to complete our medical declaration. At the time of booking, it is your responsibility to be sure that you will be able to pass all the criteria at the start date of your trip. If you cannot pass the criteria you will probably be refused permission to board.

    See the Medical Declaration here


    • All crew must have adequate travel insurance in place for your sailing holiday.
    • We strongly recommend that you arrange insurance as soon as you book. This ideally will cover you for any mishaps, medical or otherwise, in the build-up to your holiday so that should you have to cancel, you can reclaim you fees.
    • Please note we will not refund your money or cancel your invoice due to medical issues that disqualify you from joining your trip.
    • For our latest guidance on travel insurance, please read here.


    For a full explanation of what to expect with the various trip ratings please click here.


    • Oilskins
    • Fladen immersion suits. These will keep you warm in even the coldest, windiest conditions.
    • Ocean-spec lifejackets. These are the best on the market.
    • All on-board food and snacks.
    • Daily sailing lessons and tuition from two highly experienced instructors.
    • RYA sailing qualifications can be earned where applicable.


    • Your travel to and from the start and end points.
    • Travel insurance (see our travel insurance page here)
    • Any alcohol – but feel free to bring your own or buy some along the route.
    • Any meals you eat ashore.


    Everything’s included except for flights, travel insurance, a sleeping bag and some waterproof boots. There are no hidden extras.

    • These expeditions have small numbers of people on board. When you book, you are committing to being a part of the crew.
    • These are genuine adventure sailing holidays and you will be helping sail the boat, planning where we go, navigating, cooking and keeping the boat clean and tidy.
    • When you book, the deposit is non refundable. It is possible to cancel subsequently, however you may still be liable for the balance of the invoice, depending on how close you are to the start date when you cancel.
    • Please ensure you have read and agreed to the T&Cs and Trip Notes before booking.