How to Become an Ocean Sailing Cruiser

Four main components of becoming an ocean sailing cruiser include: getting experience sailing in the ocean, thoroughly understanding the boat you’re going to cruise on, developing a robust toolbox of resources, and finding a way to ensure your wife/husband/partner/family (whoever is joining you) want to be a part of your dream.

One of the biggest questions we get asked by readers and our Britican Experience guests is, ‘I’m not as young as I used to be and don’t have loads of time. I don’t want to learn to sail on a dinghy, spend time learning on a lake and years later be able to get out onto the ocean. How can I become a proficient ocean sailor sooner rather than later?’

Of course, like most things, there’s more than one way to accomplish a task. If you want to become an ocean sailor, buy an ocean-going boat and hire a Liveaboard Sailing Cruiser Captain to take you out every day teaching you until you feel capable and competent to head out into the sunset.

Before doing that, however, it’s best to make sure you like to sail.

And if you’re like most ocean sailor dreamers, there is usually someone else that needs to buy into your dream – perhaps your wife, partner, or even family? Getting them to see the benefits of sailing might be your biggest challenge? Perhaps you need to get yourself capable and competent so that they feel safe and secure?

The transition from a land-based life to becoming an ocean sailing cruiser has many facets. There are the education and experience necessary for knowing how to sail and maintain the boat. There is getting to know the boat – each boat is different and has its various quirks and systems of operation.

Then there is the acceptance of living with daily troubleshooting and learning how to become resourceful. Add on top of that the aspect of having to convince your other half that heading out to sea is a good idea!

Below I’ve laid out six options, you can do one or many, to get ocean sailing experience to grow your experience and confidence. Each of these ways can also act as a means to get a partner/family to buy into the dream. The more experience you get, the less unknows you (and your partner) will have, and the easier it will be to make the firm decision of ‘yes – it’s time to make the dream happen and go out and buy the boat.’

Getting Experience To Become An Ocean Sailing Cruiser

1. Take a course or courses.

The two main sailing education systems are the American Sailing Association (ASA) and the Royal Yacht Association (British). Both offer theory and practical-based education. For a couple of weeks, you might do an online course about plotting a passage, navigation rules, sailing terms, and how to read tide charts and then you’ll get on a boat for a week and apply the theory.
Both associations have a variety of courses allowing students to gradually increase their knowledge.

Courses are not necessary. In most countries, you don’t need any kind of certification to buy and operate a boat. The courses, however, are beneficial to learning the basics. They’ll provide the education but realized that it’s when you get your boat that you’ll truly gain solid experience.

It’s so much easier and less stressful sailing at night, calculating tides, or navigating through a heavy traffic area with a professional first before doing it yourself.

Sailing courses, however, only teach you to sail and sailing is actually the easiest (but an integral) part of living the sailing life. The courses may or not be ‘fun’ for you or your partner. Simon loved all the courses he took whereas I didn’t care for them at all. I didn’t like the pressure of having to be ‘tested’. And the stress of learning while sailing caused me to be quite seasick the whole time.

Different approaches work for different people.

2. Do a Flotilla vacation.

A sailing flotilla is nothing like a course! It’s where a group of sailboats all set off at the same time and are required to arrive somewhere around the same time. A common misconception is that the boats sail together – that’s not accurate. What happens is that you attend a morning briefing from your ‘Lead Boat’.

The lead boat is usually three people consisting of a captain, hostess, and mechanic/electrician. They move around on their own boat but are nearby to help you if you have any issues. The Lead Captain explains where you’re going for the day and good spots to stop. The Hostess arranges meals and rum punch parties and the Mechanic/Electrician is on standby if something breaks.

The Lead Crew explains where you are and where you need to sail by 5 pm. Options are given for where you might want to stop for lunch or a swim. The Lead Crew orientates you to the boat, explains the basics, and helps you direct you out of the anchorage or mooring. You sail and operate the boat.

When you arrive at your destination, the Lead Crew will again help you to anchor or to tie lines on a dock. Usually, some sort of social function is set up by the Hostess and you get together with other newbie sailors to discuss your trials and triumphs for the day.

For ten years Simon and I did Flotilla holidays/vacations. We did them in Greece, Turkey, and the Caribbean. Every time we left, I cried because I truly didn’t want to go back to land!

In order to do a Flotilla holiday, you need to take a course – RYA, ASA, or Charter Companies offer them. Once you’re on the boat, you will take charge of it but you’ll have the Lead Crew around if you need any help. It’s an excellent way to get to experience the fun side of sailing – it’s all about sailing, socializing, enjoying the beautiful beaches and wonderful deep blue sea!

Sailing Flotillas, however, show you the fun side of sailing. It’s not a true-to-life sailing lifestyle experience. It will, however, provide you with real tangible sights, smells, and feelings about how awesome the sailing life is. For many, it’s a Sailing Flotilla vacation that ignites the fire.

3. Do a Bareboat Charter.

If socializing isn’t your thing or you want to take the next logical step forward after doing a sailing flotilla, Bareboating might be a good option. Again, you need to take a short course to be able to charter a boat. With a Bareboat charter, there is a representative on hand to tell you about the boat and be available if issues arise however you’re good to go wherever you want. You can drop anchor and stay in a beautiful bay for a night and head off to another amazing one the next night.

This option provides you with more freedom to go where you want when you want. With both Flotilla’s and Bareboat Charters, you can often choose a boat that’s the same or similar to one that you want to buy – perhaps you’re interested in Catamaran’s or want to test out a Monohull? Chartering a boat also will allow you to test out different sailing destinations. If you’re interested in the Mediterranean and the Caribbean but don’t know which one to start from, consider doing a charter or charters in each area to get an idea of what the sailing conditions are like and so forth.

Bareboat Charters will allow you to test out your knowledge and confidence enabling you to gain experience on someone else’s boat. It’s a great test to determine that you can, indeed, take command of a boat. Bareboating, however, won’t teach you much about maintaining and servicing a boat, troubleshooting, or the normal day-to-day life of a cruiser. Also keep in mind, that the sailing part of the sailing lifestyle is the easy part!

Just one more note about Bareboat Charters – you can also hire a Captain for a day or two to help you get going. If you feel you’re almost ready for a Bareboat but worried about that very first try, get a Captain and he or she can show you everything you need to know over the course of a day or two.

4. Join us on Britican or other liveaboard Boats that offer Charters.

Both Flotillas and Bareboat charters are an excellent way to see different locations, test out a variety of boats and get to grips with the fundamentals of sailing. They are, however, a vacation. You won’t learn about sailboat maintenance, longer passage planning, weather routing, and the day-to-day realities of living on a boat.

If you want to learn about the ocean sailing cruiser lifestyle, consider joining us on Britican or another liveaboard sailing boat Charter. By doing so you’ll not only learn how to sail (or what you need to know to be comfortable handling a boat) and experience a particular sailing destination you’ll also see what the whole lifestyle is like. You’ll be able to see the good and the not-so-good parts of the cruising life.

When you come out with us, we’ll help you determine what you need to know, get right to it and work on increasing your knowledge and experience so as to enable you to get out sailing your own boat sooner rather than later.

Since we’re not a school there’s no set syllabus. If you need to learn how to anchor and pull up mooring balls or service an engine or what to do in squalls, we can focus on those things specifically. In-between learning your core objectives we’ll be able to share information about anything and everything to do with the sailing life.

And the cherry on top is that you still get the ‘vacation’ side of things. With us, we go to amazingly beautiful anchorages so that we can swim, snorkel and/or dive. We take the dinghy to a deserted island, have a picnic, do a hike and swim back to the boat. Fantastic restaurants offer delicious delights. In other words, it’s the full package – education and experience and all the fun stuff too. Find out more about our Britican Experiences here!

5. Volunteer to do a Boat Delivery.

Charter companies and private boat owners are often looking for help to move a boat from one place to another. A boat delivery is nothing like a sailing vacation or a liveaboard Charter. Chances are that you won’t even sail because motoring can often be quicker, but the experience can be excellent.

At the beginning of the Caribbean season, many boats need to be moved from the east coast of America down and at the end, boats need to be moved out of the hurricane zone. Many boats are moved from the Caribbean to the Med and vice versa.

Delivery captains are often looking for help doing night shifts and sharing various jobs. Generally, Captains want you to have a certain level of experience and know that you can handle a long passage. After you’ve taken a few courses and/or have done a Bareboat charter it might be worth doing a delivery. Many pre-cruisers do deliveries to find out if they can handle a long passage. Often the weather isn’t ideal because deliveries are based on schedules.

No, you won’t get an insight into the lifestyle and it might not show the fun side of things, but you’ll truly see the reality of a long passage. Many pre-cruisers just want reassurance that they can handle the not-so-fun side of sailing and boat deliveries can offer this kind of experience.

5. Buy a small boat to learn and practice on.

If you’re close enough to a body of water, it might be worth buying a smallish boat to learn on first. With a smaller boat comes smaller costs and you can get out and practice your sailing skills without worrying too much about costly mishaps. Furthermore, if you discover that you really don’t like boating, it’s not a massive investment of time, money, and energy.

My husband, Simon, and I started off doing sailing Flotillas. After ten years of doing week-long sailing vacations once a year we decided to get a boat. We purchased a 35’ Moody Sailboat and put her on the south coast of England. At the time we thought that only rich people purchased a boat and sailed around the world!

Every weekend and when possible, we’d go sailing for a week at a time. We sailed during the off-season and learned an enormous amount of information. The south coast of England is very tidal and extremely busy. It was a great opportunity to understand how to sail well and to be able to navigate busy areas.

Had we known it was possible to just buy a big boat perhaps we would have skipped buying the smaller boat? Or, perhaps the confidence we gained by having the small boat enabled us to finally say, ‘screw it – let’s sell up and sail around the world.’ After less than two years of sailing our smaller boat, we purchased our 56’ ocean cruiser.

6. Buy an ocean cruiser and hire people to get you up to speed.

As mentioned in the introduction. If you know that the sailing life is for you and your partner/family are supportive just go buy a boat and get people on board to show you how to sail and manage it.

You can even make sailing/boat lessons a condition of sale. Many new boat owners ask the old owner to stay on the boat or do a delivery together. This will enable the new owner to get to know how to sail the boat, what maintenance routines to follow, and ask any/all questions they can think of as and when they come up.

Otherwise, get a boat and hire a captain for a couple of weeks to go on a passage learning as you go. Then spend the first several months trying to fix things yourself and then watch the expert you hire when you can’t figure it out. Make friends with cruisers around you and get involved with their issues so you can learn from others. Spend several months going out locally. Start off doing day sails and then anchor for a night. Take longer and longer passages all the while servicing, upgrading, and getting to know your boat.

In short, get a boat and start using it immediately so that you can quickly figure out how it works, how to fix it, and have the necessary resources (books, people, videos, mindset) around you to eventually become more and more self-sufficient.

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The biggest mistake we see pre-cruisers make is to get a boat and spend all the time making it perfect rather than getting out and sailing it. If you want to become an ocean sailing cruiser in the shortest period of time you need to get out and sail on the ocean.

Learn How To Become An Ocean Sailing Cruiser On Britican

Britican Experience Feedback – Murphy & Stephanie, January 2021

“I used to be a sailor. I sailed a nice Beneteau monohull and enjoyed great times with friends sailing around the shallow gulf waters in Texas. As time went on work and kids became more demanding, and sailing, sadly, became a very occasional pleasure and the boat went to live with someone else. Now that the kids are grown, I often find myself thinking of the sea again.

Should I buy another boat? Do I even remember enough about sailing to charter and not look like an idiot? Hmm…my fiancé is from Wyoming and thinks boats are for water skiing. Is that a problem? Maybe. Lots of random thoughts and worries about the subject. I resubscribe to Cruising World. Wow! Beautiful boats! Can I possibly handle that big yacht on page 3?

Well, if I was ever going to circumnavigate (I know. That’s a bit of a leap.)

I needed to find a way out of the torturous mental maze I found myself in. During my nautically oriented wandering in cyberspace, I stumbled across SailingBritican.com featuring Simon, Kim, and Siena Brown and their tales of living and sailing on their beautiful Oyster yacht, Britican.

After a number of months following Kim’s tales of family life, glorious sails, repairs, leaks, beaches, and the sailing community, I decided to give them a call and take them up on their offer to share what real life is like on a cruising sailboat- sailing, cooking, fixing, navigating and all the things that make up the cruising life. So, my fiancé, Stephanie, and I braved the COVID maze and met the Britican and its crew in St. Martin in late January. I was hoping that Stephanie wouldn’t hate it and that I would find I could still sail a bit and maybe handle that big Oyster.

What a great time we had!

I remembered how to tie a knot or two. Stephanie helmed that big Oyster all the way from St. Barts to St. Martin like she’d been doing it for years. (With a big grin on her face!) I even learned how to replace the impeller on the generator, which would have worked if we’d had the right part. All in all a great week and a real confidence builder for both of us.

Simon, Kim, and Siena are great teachers with great knowledge and greater patience. They also like to have fun which we had a lot of. I recommend the Britican Experience to anyone who is wondering if the cruising life if for them.” Murphy Lents

More on our Britican Experience and Dates Available here.