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Trip type: Offshore
Crew size: Max 9
Region: Caribbean & the Americas
Adventure rating Intermediate
Experience Required Low to some
Starting from 12 days at £2299
1000 miles of offshore sailing across the Caribbean sea, from the Leeward Islands to Jamaica
This beautiful Caribbean offshore adventure sail from the Leeward Islands to Jamaica combines coastal sailing and training to start with an epic 1000nm of offshore sailing across the azure blue Caribbean Sea. You’ll be sailing in the powerful equatorial trade winds of this region with plenty of opportunity to improve your sailing prowess learning from a friendly and vastly experienced crew. The route takes us past the USVIs, Puerto Rico, Haiti and just to the south of Cuba, where we make landfall on the north eastern shores of Jamaica with its lush Blue Mountains, pretty bays and party atmosphere.
What can I expect onboard?
You’ll be central to the crew, with the famous Rubicon 3 ethos of full involvement for everyone, the highest quality training and the most gentle, supportive and friendly of environments. 90% + join solo making it brilliant for solo travellers. There is usually a 50:50 male to female mix, and the shared sense of learning and adventure makes for a very special atmosphere on board.
A huge offshore sailing adventure in the warm waters of the Caribbean and exhilarating trade winds. One you can’t miss!
We start with a few wonderful days training and exploring Antigua & neighbouring islands
This trip has spectacular offshore sailing
Night sailing under the Caribbean star scapes is a magical experience
1000 miles of offshore sailing across the Caribbean sea, from the Leeward Islands to Jamaica
This is a sample itinerary only showing some of the possible options for the route from Antigua to Jamaica. Start and endpoints can vary slightly so do check the ‘Date and Prices’ tab for specific details. The wind and weather at the time will shape what we can actually do and when.
We’ll all join the boat in Falmouth Harbour, Antigua. This is one of the Windward Islands in the Lesser Antilles and is full of maritime history. Its corrugated coasts has hundreds of little coves lapped by the turquoise water, while the sheltered bays have provided refuge for everyone from Admiral Nelson to buccaneers and modern-day sailors.
There will be a real sense of excitement for the adventure to come as we help everyone get their belongings packed away. After safety briefings and lunch, we’ll slip lines and head out onto the water to learn new skills, revise any existing ones and get up to speed for the sailing to come. We will practise tacking, gybing, rescuing a casualty who has fallen overboard and all the other skills we’ll need. This first night we may well anchor for our first evening at sea in the middle of the secluded horseshoe-shaped bay that is every bit as stunning as it is spacious.
Described by many as the perfect desert island, Great Bird Island really captures the imagination. It has wonderful snorkelling and great views if we hike to the top of the island. The island is a sanctuary for a variety of endangered wildlife species, including red-billed tropicbirds, West Indian whistling ducks and the extraordinary Frigate birds
Uninhabited Green Island is a truly gorgeous island just off the eastern shores of Antigua. Fantastic snorkelling again and with plenty of anchorages, this is another mecca for exotic bird sightings. We may also have time to explore nearby Nonsuch Bay with its flat waters, pleasant sea breezes, and barrier-reef protection.
The actual days we make this passage will depend entirely on the weather at the time, but it’s around 830nm to Jamaica, so we can expect to be at sea for around 5 days of magical trade wind sailing. If you haven’t tried it before, it’s hard to describe just how consistent and powerful the trade winds are, driven by the heat from the equator.
They will really power us along and in these yachts purpose-built for offshore sailing, you will really have the experience of a lifetime. Even so, it is always with mixed emotions that any sailor watches land disappear astern. With the Leeward Islands disappearing astern, we are out on the open ocean, away from the security and creature comforts we have been used to. Ahead lies the unknown of the Caribbean Sea, and it’s as a crew that we will take on whatever comes our way, from strong winds and big seas to flat calms, mirror-like water and not a breath of air. It all comes with a healthy sense of anticipation. The cooler temperatures of the open ocean is certainly welcome!
As the sun sets for the first time on our voyage, we will be sailing under the stars, in the inky blackness of the ocean. Far from any man-made light, and clear skies permitting, you will see a truly spectacular starscape. With 360° horizons, the stars can reach in a huge arc as far as the eye can see. With the wind in the sails and the yacht galloping through the waves, you’ll be storing away memories that will be with you for a lifetime. When it comes time for the watch change, it can be hard to tear oneself away from it, but a warm bunk and tiredness from a full day of learning and sailing always win out in the end!
No matter how special the night (and sometimes you can swap out the scene above for strong winds, crashing waves and driving rain!) sunrise is always so welcome. Now we can see everything clearly again, and we can make good any temporary fixes that might have been put in place through the dark hours. There is little that beats the new watch coming up and handing you a steaming mug of tea and some breakfast. Even though you may be tired, it comes with a wonderful sense of being alive. You are hundreds of miles from land, and except for your fellow crew, alone on the open ocean.
During the days, we need to keep track of our position and mark our progress on the chart. We need to sail south of Puerto Rico, the Dominican Republic and Cuba, with the infamous Guantanamo Bay just north of us.
The skipper and mate will be giving lessons on various skills, and one of these may be celestial navigation so you can start to learn how to bypass the GPS and locate your position using just the sun, moon or stars. There are also all the daily jobs essential to the smooth running of a yacht on passage. Everyone will be in a rota to help with cleaning, maintenance, cooking and navigation.
At some point on the fourth or fifth day, we should see the island of Jamaica with its jagged mountain range and lush green jungles appear over the horizon. However much we have loved our time at sea, the lure of land is always intoxicating, and more so when it is such an exciting landfall as this.
There is no real provision in the schedule to explore Jamaica, but we will make sure we do not arrive late – and if the trade winds have been powerful, we can certainly arrive a day or so early and if we do that gives everyone a chance either to do some serious R&R on the beach or to take a trip to somewhere like the Blue Mountains or the Blue Lagoon. We can’t promise it, but it’s fun when it works out. Whether we do or not, Jamaica is our final destination from this huge adventure.
Find all the information you need about our trips here, from the various trip categories to what to pack, connecting travel and more. The information here is generic across all our trips. For really specific travel details about your trip, click on the Dates & Prices tab.
All of our sailing trips are given one of three categories: ‘Coastal‘ – ‘Offshore‘ – ‘Skipper Masterclass‘. Whichever category trip you join, and whatever your previous experience (or rustiness!), you will be encouraged to be fully involved from the very start and receive high-quality Rubicon 3 training.
These are wonderful holidays that stay relatively close to shore and have no significant open-water passages. They are day sailing only and usually in quiet sheltered water. We sail to somewhere new just about every day and there is time built in to the planning to enable you to head ashore and explore everywhere we get to.
Self explanatory and if you’ve ever wanted to leave the coast behind and sail hundreds (or even thousands) of miles offshore out on one of the great oceans, these are for you. Each trip begins with a few days of coastal sailing, training and exploring while individuals and the crew as a whole get up to speed. Timings are very weather dependant. On our two weeks offshore trips, you can expect to have one main offshore passage of between 4-6 days, with the remainder of the time being coastal cruising at either end.
These are more intensive training courses, where we really focus on the skills and techniques needed to be strong crew or skipper on a prolonged passage through potentially technical areas. You will mix theory and practical tuition every day. Days are longer and there is less focus on exploring ashore and more on train, train, train. If you wish to supercharge your seamanship and sailing skills, these are for you.
All of our trips are open to crew aged 18 and above, but please the Fitness to Sail box below.
Anyone can join these trips. Wonderful for sailors of any experience level, if you are a beginner these are definitely the place to start. If you are at Yachtmaster or similar, there is still a huge amount you can learn and practise on these trips
As this is a Skipper Masterclass, no beginners are permitted to join. You must have RYA Day Skipper, ASA 104 or equivalent skills and experience. It doesn’t matter if they are rusty – that is what this course is here to address. This course is invaluable to all levels up to and including Yachtmaster.
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.
Unless stated otherwise on the ‘Dates & Prices’ tab, you must join the boat at 0900 hrs on the start day. It is important you are not late as the pre-trip briefing will start shortly after that time. You will disembark at 1200hrs on the end day. Exact start and end locations may vary depending on your trip date.
Five day trips sometimes start at 1800 on the start day (usually a Sunday) and will often end at 1700 on the last day.
Please see the ‘Dates & Prices’ tab.
We plan our routes very carefully and build in lots of spare time to ensure that we arrive at our end destination on time. However, particularly on offshore and ocean trips, we cannot guarantee that we will arrive by the end date. It is incredibly are (maybe three times in ten years?) but bad weather or mechanical issues mean it can happen.
On offshore and ocean trips, build some leeway into your trip home if you can. Maybe book the flight for the day after the end day, and / or use a flexible ticket where you can change the date if needed.
For long haul flights, especially those where we start and end in different places, we can sometimes find very good deals. If you cannot find a good flight, please do ask us to help by emailing us at firstname.lastname@example.org. Unfortunately, we cannot offer help with short-haul flights.
If you intend to travel on a one way ticket to meet up with one of our trips, without possessing an onward flight ticket – we recommend that you have a copy of your Rubicon 3 invoice with you and available at immigration to assist easy entry.
Your passport must be valid for at least 6 months AFTER your trip finishes. You should have at least 4-5 spare pages for visa, entry and exit stamps. If you have dual nationality you can only use one passport for the entire trip.
The situation regarding visas and passports can change rapidly and without warning. The information given here is accurate to the best of our knowledge but ultimately you are responsible for ensuring you have the correct visas. Please allow time for unexpected delays in obtaining any visas you require.
Around 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.
It is compulsory that you have adequate travel insurance before you board the yacht. We strongly recommend that you take this insurance out as soon as possible after booking your trip with us in case you suffer any medical issues or such like that prevent you from being able to join the trip.
Our page on travel insurance is found here.
You will be asked to provide the following details to Rubicon 3 if you have not already done so: travel insurance provider, insurance policy number, insurance emergency telephone number. You will also be required to give a copy of your policy with this information to the skipper on arrival with confirmation that the policy duration is sufficient to cover you for the entire duration of your trip.
We provide three meals a day on the boat, so if you do not wish to spend another penny, that is absolutely fine. Realistically, however, most crew like to have a few beers ashore and the occasional meal. Also please note that alcohol is not provided by Rubicon 3 so if you like a beer or wine in the evening please budget for this. You are very welcome to bring some duty free with you to the boat. Past crew estimate that £200 is ample to enjoy all there is offer ashore during the trip.
These are available in most major cities along our route and allow you to withdraw local currency only. We discourage you from relying on your ATM card as a primary source of funds in case it is lost/stolen/swallowed, or the machine isn’t working. Besides memorising your PIN, it is also important to be aware of your daily withdrawal limit and bank withdrawal costs.
You will be able to use credit and debit card just about everywhere
These cards are similar to normal Credit and Debit cards but they can be pre loaded with cash before you travel with a set amount allowing you to withdraw this cash using the card at normal ATMs. It is a more secure way to access cash on your trip and easier to use than travellers cheques, but again do not rely on these as your sole means of funds on a trip. Several banks and companies now offer these cards, but be sure to look into the rates for withdrawing cash when making your decision.
What equipment and clothing to bring for sailing – and how much to bring – are always the big questions for the crew and we totally understand that. The best generic guidance we can give is to imagine that you are going for a week in the hills or the mountains. If you think of that type of clothing and equipment, you won’t go far wrong.
Beyond that, we say don’t spend money unless you want to. The chances are that you already have most of what you need and a lot of fancy branded sailing equipment is both expensive and not very good. Especially when you’re fairly new to the sport, keep your money in your pocket.
The next question is always how much to bring. Within reason, you can bring what you like as we have quite a lot of storage space onboard the yachts. The usual airport allowance of 20kg / 44lbs of luggage is not a bad guide. Any more than that and you’ve probably overpacked!
What you pack your clothing and equipment in is vital. It needs to be in a soft bag that can be rolled away. Yes, that means no metal frames or hard backs. It needs to be in a duffel style bag. If you do bring a hard backed case or bag that cannot be rolled away, there is a good chance you will not be able to bring it on board. Something like this Sports Direct sack for just £12 is ideal.
Yes, to an extent. However, even in warm regions it can be chilly at night or when it rains. In Europe and the high latitudes, always bring hats & gloves and warm clothes. In the Caribbean, I would still bring them (as they are so small to pack) and just a lighter sweater for the evenings.
Don’t worry too much and if in doubt bring more. So long as you can keep warm, plus your usual toiletries and such like, you will be fine. If you have any questions, don’t hesitate to ask us. We’re here to help!
You will be issued with a foul weather jacket and salopettes. These are modern oilskins that will keep you completely dry and which we rate highly, but they are not Goretex or similar. If you have your own foulies and would like to wear them or have very high spec ones, then do feel free to bring them.
These will be c. 270-290N jackets with inbuilt spray hoods and personal locator beacons.
Fantastically warm, these all in one suits are incredible for when it gets cold up on deck. You will feel toasty warm all day long or through a long night watch. Essential gear for high latitude trips and RIB transfers in Svalbard!
Bring a fresh set for every day or second day you’re on board.
Bring a mix of thinner socks and some thicker, woolly socks If not a Caribbean style trip. A fresh pair every second day is a good guide.
For non Caribbean trips, these are great for upper and lower body. Merino wool is excellent but expensive. There are lots of options out there.
Bring a selection of T-shirts, polo shirts or long-sleeved shirts. You might be wearing a couple of these at any one time, so bring a few
Bring shorts. You never know when it will be hot and sunny!
A pair of thick hiking trousers, fleece-lined snowboarding trousers or our new favourite – softshell trousers. These will be what you wear just about every day, so bring a couple of pairs. Don’t go crazy – we buy ones costing between £50-70 and no more.
If you are on a Caribbean style trip then you will probably only need light trousers.
You need to bring at least two good, thick fleeces or jumpers. These are going to be critical to keep you warm, so choose carefully. We usually pack two mid-weight fleeces and one really thick woolly jumper.
If you are in the Caribbean, then one fleece is probably fine.
You will wear this pretty much every day, only changing up to your foul weather jacket when it rains. Any jacket will do that is showerproof, windproof and reasonably warm.
These don’t have to be sailing boots – even normal wellies will do fine. You can spend a fortune on Goretex lined sailing boots. They are great, but make sure you are going to be a regular sailor before investing. In the meantime, we’d stick to rubber sailing boots costing around £60.
There’s no dressing up on these expeditions, but bring a selection of shore clothes for the odd evening out. No restaurant owner likes people coming in wearing dirty sailing clothes!
We suggest bringing 2 sets of hats and gloves. If one set gets lost or wet, you need to be able to keep warm. We don’t really rate the thick sailing gloves. They are not good when wet, hard to get on and pretty expensive. Instead, go for a pair of thinner working gloves and a thick woolly pair.
If you’re in the Caribbean, just a wooly hat can still be nice for night sailing on occasions.
The classic neck warmer is a godsend when it gets windy and cold. Not for the Caribbean!
Wherever you are, bring one. You may want to jump in even when it’s icy, but also sometimes the best showers are in the local pool.
Great for exploring ashore, trainer style is fine. Just something comfortable to do an hour’s hike with.
Great for keeping cool onshore and essential for shower floors in marinas and ports.
It’s unlikely that you will be able to do laundry along the way, so bring enough sets of clothes to last you for the trip length. You can handwash some essentials if necessary but water is at a premium onboard so we don’t encourage this except on the longer trips of over 2 weeks duration. The start and end ports will nearly always have laundry facilities.
The boats are warm inside, so a medium weight sleeping bag is absolutely fine. If it has a long zip it’s better as it gives you more temperature flexibility but don’t worry and don’t spend money that you don’t need to!
If you are on a Caribbean style trip you can probably do without a sleeping bag and just use a silk liner or similar. The Caribbean is usually around 75°F at night, but just occasionally it can be colder: the choice is yours.
Toothbrush, toothpaste, shower gel, razor, deodorant and whatever else you need. We would bring a normal towel for comfort, but a travel towel is also good.
Sunglasses are essential at sea for every trip as the UV is reflected off the sea and can damage your eyes. They must be polarised or the damage can be even worse. Good strong sun cream is recommended for the same reason.
Life is pretty miserable if you forget these. Get a strap for the glasses in case they fall off.
We pretty much insist you bring some sea sickness medication, even if you don’t think you’ll be affected. This is a holiday for you and feeling queasy is horrible. In the UK, the brands that seem to work well are Stugeron and Kwells. If you have any other medications such as anti-histamine, blood pressure tablets, insulin, epi-pens etc, please don’t forget these.
Boats have lots of unfamiliar noises and yes, even the occasional snorer. Bring what you need to block out the noise and have a good night’s sleep.
If you’re sailing with us in the high latitudes in summer, the chances are the Sun will never set and it’s hard to get these boats dark. If that bothers you, bring a mask to make the world go dark again!
Any decent sized plastic or metal one is fine.
Don’t forget these, but put them in protective casings so they don’t get damaged or broken. Every bunk has two USB charging points, The boat has the UK 3-pin 240v AC power outlets, which can be used when are connected to shore power or when the generator is on. If your equipment has different plugs, bring an adaptor.
If your trip has an overnight passage in it, we would really recommend you bring one of these (unless it’s summer in the Arctic with midnight Sun).
These are really useful to carry with you.
This is a very good app. The chart pack for your area will cost you about £25 and then you can always see exactly where we are.
The fancy way of keeping your kit divided up, organised and dry (but plastic shopping bags work very well too!)
The boats have a UK (3 pin) 220 AC power outlet on board, that is available to use when connected to shore power or at sea when the generator is running.
Each bunk also has a USB charging point and a cigarette lighter style power point.
Cameras (incl. Digital & Video Cameras) – An easy to use ‘point and press’ will get you some good photos. For memorable shots, it may be worthwhile investing in an SLR camera, but be sure to get some practice in before the trip! Most towns and cities have internet cafes where you can download onto CD/internet sites – but don’t rely on it.
Drones – As the use of drones becomes more common, countries throughout the world are gradually updating their laws and restrictions on usage. The specific regulations will vary from one country to another, so do check the UK Foreign and Commonwealth Office advice for the latest information. As with cameras, use your common sense if you do use a drone and avoid operation in sensitive areas. If you plan to bring a drone on your trip with us please contact us first to ensure there will be a suitable place to store it while on your trip.
The internet and WiFi are available in many areas that we visit. Do bear in mind that the connections can be unreliable and will not always be as fast as you are used to at home. Once we have set sail, internet and phone signal will usually stop very quickly.
The UK Foreign and Commonwealth Office (FCO) offer country-specific advice, regarding not only security but also entry regulations, local laws and customs and health. We strongly recommend all travellers visit the FCO website, or the equivalent in their home country, to familiarise themselves with local conditions and issues in the countries they plan to visit before committing to a trip with us. You can view their website here.
If you have any questions at all about the safety or security of your trip, please do not hesitate to contact us and we will be happy to discuss your trip in more detail.
In cities – All major cities have their share of petty crime (just like our cities) and sensible precautions need to be taken. Wearing expensive looking jewellery or watches and carrying cameras will draw unnecessary attention to you. Leave valuables such as passports and excess money in your hotel safe (we recommend carrying a copy of your passport details page at all times). You may find a simple money belt is more discreet than a bag. Always be aware of your surroundings and when approached by people you do not know, use your common sense. At night in cities it’s best to use a taxi, rather than walking around the streets, single women in particular need to be careful and we would suggest that it is safer to be in a group.
Rubicon3 does not take responsibility for clients’ personal items and we advise you to not take items of value that are not essential for the journey.
It is essential that you have read, understood and accept our Booking Terms and Conditions, including our Guest Behaviour, Safety & Security Policy before you book. We take great care to ensure that these comply fully with the Package Travel Regulations. They also contain important information about possible financial liabilities you may have if you subsequently decide to cancel in the period before your trip start date. If you have any questions about these Terms and Conditions please do not hesitate to ask us.
We know you’ll have 101 questions about what life’s like onboard and just generally what to expect. Have a look at the video here of one of our customers telling you all about it. Below, we’ve answered lots of other common questions. Remember, if you have any other questions, just phone or email.
Ask one of our regular crew members what distinguishes the Rubicon 3 experience from other sailing they have done, and they will invariably reference our three golden rules. They are the foundation on which the whole experience is built and they are the one area that never changes and is non-negotiable.
Unfortunately many sailors have experienced shouting on board, and they know the unnecessary tension and anxiety that it causes. You will never find one of our skippers or mates shouting and no one else is allowed to either. Shouting is a clear sign of an inexperienced sailor who is not in full control.
We never step prematurely in to take a task off someone, thereby allowing them the space to think and (safely) make mistakes to best support their growth. There is nothing more frustrating than a keen fellow crew member telling you what to do, how to do it, or taking the job off you. You will always have the time and space to stop, think and come up with a plan.
Sailing is both blissfully simple and a sport that benefits from a great deal of experience. Especially on these larger, expedition yachts there are lots of ropes, winches, clutches and bits of equipment that can quickly become overwhelming. In a new environment, it can be hard even to remember one’s own name at times! No matter how straight forward the question, our skippers and mates are always there to help and will never look down on your for asking. It is what they are there for.
Training lies at the heart of the Rubicon 3 vision. We want you to learn the skills to be a central part of each adventure and to be able to go away and use the skills on other boats. The teaching syllabus changes quite a bit depending on the trip type. Full details of the syllabuses and qualifications below.
On Coastal trips, you can earn the RYA Competent Crew certificate. The price is included in the trip price.
Identify and describe the following cruising sailboat parts, areas, or systems and their functions:
Safety Equipment & Procedures
Navigation & Weather
Return to Dock/Slip
Basic sailing skills
For those wishing to learn how to be a watch leader or skipper of an ocean-going vessel, the Rubicon 3 Ocean Watch Leader Course is a must.
This course takes you through:
Please contact us for further details
A Watch Leader’s role & responsibilities
Total marks available: 105 Pass mark: 70
Free Ocean Watch Leader Course
When signing up as a Watch Leader, there is an additional fee of £150. This covers the additional training we give you. It also gives you free access to the Rubicon 3 Ocean Watch Leader Course, which we strongly recommend you take before starting your passage with us.
The RYA Ocean Qualifying passage
Are Rubicon 3 Ocean Passages suitable for Ocean qualifying passages?
What tasks do I need to complete onboard prior the exam?
Caribbean Offshore 1000: Antigua to Jamaica
Start date: March 27, 2023
End date: April 7, 2023
Start location: English Harbour, Antigua
End location: Port Antonio, Jamaica
Price : £2299
Our team are always here and can probably answer your question straight away. Whether it’s to check whether a trip is right for you ro to ask a question about flights, get in touch. We’rre here to help.
All customer money is held in the Protected Trust Service until your trip has run. This means it is 100% protected and should your trip not run for any reason, you receive a full and immediate refund. This is the gold standard of customer protection.
Adventure rating: High
Experience needed: Low to some
Solo crew: Welcome
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Adventure rating: Intermediate
Experience needed: Low to some
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Unless stated otheriwse, you should join the boat at 0900 on the start day. Each trip starts with an introductory briefing at this time, so it is important you are not late. You may need to arrive the day before and book a B&B or hotel (It is not possible to stay onboard before or after the trip).
We arrive at the end port on the penultimate evening, giving us time to head ashore and have a fun last evening together as a crew. Unless otherwise stated, the trip ends at 1200 on the end day. On the final morning we sign logbooks, give feedback and tips re next steps and clean the boat. We know sometimes the only practical flight leaves in the morning though so you may leave the boat anytime from 0500hrs on this day.
You can book your flights home for the afternoon or evening of the end day. We design our trips very carefully to be as certain as we can be that we will not arrive late and it is very rare indeed that we do.
This is distance sailing at sea, usually from one country to another, however, and delays can happen. Most people travel home on the end day. If you can boo your travel home for the next day, it both gives you a little time to enjoy the end destination and some extra security re making flights
You must ensure you have insurance that covers you specificallty for yacht sailing. Click on the ‘specific info’ to see what requirements your particular trip has.
Let us help you pick the perfect sailing holiday, course or just chat through your options.