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Ocean Sailing Azores to Gibraltar TOP029_13

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Ocean Sailing Azores to Gibraltar

Join the crew sailing Azores to the island of Gibraltar on a 15 night ocean adventure combining open ocean sailing and navigating the islands.

The Azores are rarely passed during Atlantic crossings but this beautiful chain of volcanic islands has so much to offer. Join as a novice sailor and get your sea legs for the first time or if you’re more experienced you can apply for one of the RYA Ocean Qualifying Watch Leader positions for your Ocean Yachtmaster.


  • 12oo nautical miles of experience
  • 3 RYA Ocean Qualifying Watch Leader positions available
  • Gain theoretical and intensive practical instruction on every aspect of ocean crossing
  • Optional celestial navigation course
  • Swim in warm Portuguese waters off the coast of Madeira

The ocean sailing Azores to Gibraltar itinerary is simple but spectacular. Join the crew in Ponta Delgada and immediately head west to Madeira. If you’re lucky the winds will be behind you and will give you the chance for a long spinnaker run – speeding across the sea. You’ll spend a few days resting and exploring Madeira before heading out for the famous straits of Gibraltar.

Navigate the famously busy shipping lanes and make your way up the north coast of Morocco before setting sights on La Linea and home. When it’s all said and done you’ll have 1200nm of open-ocean sailing under your belt and nice long lie-in at one of the most famous sailing stopovers.

This sailing adventure is open to all and no experience is required. The routes and course are both designed to be accessible to all. However, if you’re looking to build on previous experience then three RYA Ocean Qualifying watch leader positions are available. To pass your RYA Ocean Yachtmaster, you need to have skippered or been a watch leader on an ocean passage. Your capable and professional instructors aim to teach you everything you need to know about ocean crossings including instruction on weather routing, passage planning, victualling, pre-departure tasks, international routing considerations, and so much more.

Join this group of highly qualified skippers and increase your knowledge base and confidence as you sail from the Azores. Enquire today to get the full trip notes and to get a detailed course outline.


Day 1: Joining day

Join the boat between 1200 and 2000hrs. Get your belongings packed away and relax. The physical and mental stuff will come in good time, but for now it’s time to settle in and relax!

Day 2: Initial training, skills and drills

The first day is all about gently getting up to speed, both as individuals and as a crew. We’ll revise all the key sailing concepts, tacking, gybing and do some super realistic man overboard exercises to make sure we’re prepared for the deep ocean. We’ll find a lovely bay or port to stop in overnight, while we make final preparations for the passage.

Days 3-7: Ocean passage to Madeira

Nearly 700nm of open ocean lies ahead and it gives us the perfect opportunity to get into the rhythm of life on the open ocean. Hummingbird is one of the best ocean crossing yachts ever built and you will soon come to appreciate her qualities. As we head out into the Atlantic, we will train on drogues, storm sails, storm board and more. You can make huge gains in your ocean going skills but there’s also plenty of time to sit and marvel at the beauty and wilderness all around. You’ll be helming and navigating on a 24 hour watch system and as the Sun drops below the horizon, the stars come out to play. Complete silence excerpt for the wind in the sails and the sound of the hull cutting through the waves. It’s magical!

Day 8: Rest and recuperation on Madeira

A short stop on the beautiful island of Madeira is the reward. Exactly ho long we get will depend on the speed of the previous passage, but we will certainly aim for 1-2 days. Warm with lots to see, we love this island.

Days 9-15: Ocean passage to Gibraltar

From Madeira we’ll head east bound for the famous straits of Gibraltar. A second ocean passage is the very best way to embed all those new found skills. What seemed baffling on day one will be going like clockwork now and you can really focus on taking your learning to the next level.

It’s a real privilege to be able to set out to sea again so soon after the first passage. There are few times in life when we get to do something like this and as land disappears for a second time, it is always a very special moment. Weather and time permitting, we may be able to make landfall in Tangier before finally pulling in to Europe’s most southerly point and the famous naval enclave of Gibraltar.

Day 16:  Debriefs, 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

Be ready for the challenges and rewards of ocean sailing

Ocean passages are superb adventure sailing holidays if you are an ambitious sailor, traveller or you just have a huge desire to get out on the open ocean. For some crew, it’s all about the challenge of sailing a powerful yacht from one country to another, with no land in sight for days on end. For others it may be the navigational challenge, the beauty of the wildlife you will see or even just the breathtaking solitude that the ocean provides.

Even though no experience is required, you should be confident that you’ll enjoy sailing for a prolonged period of time. These passages mean you will be at sea for 4-5 days at a time. You will be part of a watch system helping sail the ship day and night and the yacht never stops moving (unless we’re becalmed!) Even simple tasks like cooking a meal or getting in to your bunk require that bit more determination and there’s no doubt that you’re going to be tired at times.

Of course, it is these challenges that make it so hugely rewarding. The nature of the environment means you live very much in the moment. You will learn a great deal about yourself and those around you and the bonds formed can be lifelong. Edmund Hillary once said, “It is not the mountain we conquer, but ourselves.” and that could just as well equate to the ocean.


More Details


  • No previous sailing experience is needed
  • Maximum of 8 crew on most trips
  • Over half the crew join the boat alone
  • Average age range is 35 – 65 yrs
  • Most crews are evenly split male & female
  • Everything is included – you just need to get to & from the start / finish

Travel & Joining Times

Travel to Ponta Delgada on November 16, ready to join the boat after midday and before 2000hrs if possible. You’ll find you usually have to change somewhere like Lisbon. Watch leaders should join the boat on November 15th, ready to start studying by 1000 hrs if possible. The airport (IATA code PDL) is a short taxi ride from the marina.

Disembark in Gibraltar on December 1st. The airport is very nearby (IATA code GIB)

The Ocean Crossing Masterclass
Whichever qualifications you have, skippering a yacht offshore or internationally is quite a step up and not something to be undertaken lightly. There are much greater weather routing issues and international regulations to deal with. You are going to be in amongst heavy commercial shipping, interacting with foreign port controls and coming across unfamiliar situations on an almost constant basis. On top of that, away from land, your crew and yacht are entirely reliant on you to keep things moving along successfully. It can be stressful, tiring and difficult. It is also one of the most rewarding types of passage making you will have as a skipper. There is nothing quite like pulling in to a foreign port, having crossed a sea on a yacht that you skippered.

Your current qualifications may not have given you what you expected
If you’re like almost every other client of ours, you’ll have got your Day Skipper or Yachtmaster, with the expectation that afterwards you would be free to roam the seas and head off to all corners of the world. The reality is that you are probably not ready to do that. Even the Yachtmaster is really a ‘licence to learn’ – the equivalent of passing your driving test. As we all know, it’s only once a new driver is let loose at the wheel that their education really begins!

What a new ocean-going skipper needs
Getting offshore sailing experience is often tricky, even more so if it needs to be an RYA ocean qualifying passage. It often involves just jumping on a long-distance yacht delivery and making the best of it. But let’s be honest – anyone can head off to sea and have a successful voyage. That doesn’t necessarily make the skipper competent or safe. It just means that nothing went wrong that time. To be competent and safe, a developing skipper needs to experience offshore and international passage-making in a controlled environment. Able to plan the routes and make the decisions but with expert backup and advice at every stage. This is the very best learning environment. No theoretical exercises. This is a real ocean passage, dealing with real situations at every stage.

What you get on the Masterclass
Every Ocean Crossing Masterclass has two highly experienced instructors on board. While you victual, plan and execute the passage, they will constantly feedback, teach you more and demonstrate further techniques. It is quite different from crewing for a delivery skipper; with this expert tuition your skills and experience will improve rapidly.

Get some training in celestial navigation
A ocean passage is a superb opportunity to use a sextant and navigate your way using just the Sun, Moon, planets and stars. If you would like to use the sextant on-board, you must have prior training. Look to come on our intensive two day celestial navigation course  held in London. Enquire for more information. Places go quickly.

The Boat

60′ expedition sailing yacht

The yacht is a stripped-out ocean going yacht designed with safety and simplicity in mind. Originally built for the Clipper round the world yacht race, she has more than proved her seaworthiness with three successful circumnavigations of the globe. Her long fin keel means she has exceptional stability and the cutter rig gives a versatile sail plan that can be quickly matched to conditions as they change.

The yacht is equipped with a full suite of navigation equipment, including paper charts, GPS, an electronic chart plotter, AIS and radar. Just as importantly we have our trusty sextant on board, and as often as possible we get everyone navigating using this type of traditional method rather than being constantly glued to the instruments.

Huge amounts of space

A large yacht, she has a great deal of space down below. The headroom is around 8’ in most areas and all crew have large amounts of personal storage space. The accommodation area is mostly open plan, with a series of bunks measuring 6’ 7” in length giving you plenty of room to yourself. There is heating throughout to keep us warm, while a well equipped galley allows us to make some great meals underway, often with freshly caught fish. The saloon has books, a TV & DVD player, games and a selection of films.

Highest safety rating possible

The boat has the MCA’s top rating: Category 0. This means that they have designated her and her equipment fit to sail unlimited distances off shore for any period of time. This rating requires the top rated life rafts, an EPIRB, advanced medical kit, satellite communications, three different watertight compartments and more. There is no higher standard for such a yacht. Most sailing schools will be using Cat 2 rated yachts, limited to no more than 60nm offshore. These expeditions are true adventures, often heading far out to sea and to remote shores, but safety remains at the centre of everything we do.


16 November 2017 – 1 December 2017 (15 nights)


£1,640 crew

£1,790 watch leader

£400 deposit secures your place.

Whats included


  • All foul weather clothing
  • Lifejackets
  • All on-board food and accommodation
  • All training and certification


  • Flights
  • Transfer to or from the airport
  • Travel insurance. This needs to cover yachting that is more than 12nm offshore. Buy it early so that your flights are covered in the event you have to cancel.


  • Sleeping bag
  • Waterproof boots
  • Warm clothes

Kit List

On-board, we provide top quality foul weather kit and life-jackets. You will need to bring the following kit.

Sleeping bag
We recommend a good 3 seasons bag that can open up fully. A silk liner can really help keep your bag clean and comfortable.

Dry bags
About 4 dry bags, ranging in size from 5 to 20 litres. These will keep your kit dry, electronics safe and such like. Maybe get ones with windows so you can see what’s inside. Pack a little silica gel pouch in each one to really keep things dry. If you don’t have dry bags, plastic shopping bags are decent alternative!

I-pod, camera, kindle etc. Put them in a waterproof cases wherever possible. Writing materials, pens etc. Each bunk has a USB charging point, so bring a lead.

Head torch
It has to have a red filter, but other than that, don’t go for anything fancy or expensive.

We like ones that are a bit waterproof and that really come down over the ears. A wide brimmed sun hat can also be a great second hat.

Have a thin woolly pair and a nice thick pair for night helming and such like. Bring more than one set, because they’ll get wet and then they’re useless! We really don’t rate most expensive sailing or skiing gloves, not least because their liners tend to pull out when wet making the glove impossible to get back on. Mittens really are ideal.

Base Layers
There really is no need to buy expensive or technical base layers. If you are on one of our colder expeditions, some woolly long-johns and a couple of long sleeved base layer tops will be your best friends.

Underwear and socks
Bring enough that you can wear a fresh set every day for up to a week. Why not?

Light weight long sleeve top
For hot sunny days and sunburn issues

1 pair long trousers for day to say sailing
There really is nothing to beat fleece-lined snowboarding trousers. Warm, weather proof and cheap. Why pay hundreds more for inferior kit?

Mid layers
These are what will keep you warm, so bring plenty. Thick fleece jackets and woolly jumpers are great. Duvet jackets are also very good, though you have to keep them dry.

Mid weight jacket
Something to wear as an outer layer that is windproof and at least shower proof. If it gets really wet, then you swap it out for our foulies!

Sailing boots
You can spend a fortune but you really don’t need to, especially if you’re just joining us for one or two legs. We’ve sailed in £30 rubber sailing boots and they are absolutely fine (and dry). We’ve also sailed in £200 ocean sailing boots and been wet. If anything, go for rubber sailing boots to start. I fyou think you’ll sail regularly the Musto HPX Ocean boots are great as are the Dubarry Ocean boots.

Other footwear
Flip flops are great once we’re ashore and a pair of cross-trainers or light hiking boots can also be invaluable for exploring ashore in muddier areas.

Sun glasses
They should be polarised and have a safety strap

Tooth brush and toothpaste; small bottle of shower gel; deodorant; SPF 15+ Sun cream (the sea reflects the sun and you will burn); towel (it doesn’t need to be a travel towel). Ear plugs can be very valuable.

Swimming gear and goggles

A knife / pliers combination
Not essential but very nice to have.

An internationally recognised credit or charge card and some local currency for when you first arrive.

Some shore clothes



We love this sailing company’s ethos – to help people do three things: sail, train and explore. They are passionate about enabling people to experience life out on the open ocean, building sailing skills and exploring some beautiful countries. After years of training people to become professional sailors, and having covered thousands of miles between them, the company Founders  realised that so many people had dreamt of setting off across an ocean, but hadn’t the skills, the boat or crew to make those dreams come true.

The company now runs expeditions on a specialised 60’ yacht to some of the most exciting places out there – often largely inaccessible from land. With no previous sailing experience required, the two instructors will guide you every step of the way as you develop your sailing skills, maybe even earning an RYA qualification during the week. Exploring on land as they go is just as important and the bikes and a kayak mean you can head off and enjoy everything there is to see along the route.

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