The best way to learn to sail (on the cheap)
Despite growing up in a sailing town, I never tried sailing until I was in my mid-twenties. I always thought it was a pastime for wealthy people, and that you had to have money to participate.
If I’m totally honest, I never had much interest in sailing back then, so I never really looked into it. However, after going on my first sailing trip aged 25 to the Isles of Scillies, everything changed.
I was instantly hooked. I knew I wanted to live on a boat and use it as a way to travel. From then on, I’ve been learning to sail and travelled over 7,000 miles on sailing boats and learnt a lot, whilst spending very little.
In this blog, I’ll explain how you can learn to sail, and what I think is the best way to achieve certain sailing goals (competitive sailing, adventure crewing, skippering a circumnavigation or going on a sailing holiday).
Plus, explain which ways are the most affordable for achieving your goals.
You may be surprised to discover how many affordable ways there are to learn to sail in the UK.
DELIVERY CREW
After that first sailing trip with my friend to the Isles of Scilly, I got an unexpected opportunity: my friend connected me with someone looking for help delivering a boat from the UK to Portugal.
I had no idea what I was doing, yet somehow, I was being paid for the experience. I knew it was a total fluke, the kind of lucky break that wouldn’t happen again.
Nevertheless, there I was, sailing roughly 750 miles over the course of two weeks – and loving every moment of it. I took on various roles, from cooking to standing watch at night, whilst the skipper handled all the actual sailing.
Crossing the Bay of Biscay was an incredible experience, and I learned what it felt like to live and work on a boat. But in terms of actual sailing skills, I didn't gain much. For most of the trip, we sailed on a single point of sail, far offshore, which – ironically – can be easier than coastal sailing because there are fewer obstacles to worry about.
If you’re interested in getting involved in boat deliveries, there are plenty of opportunities available on crewing websites like Crewbay, Crewseekers, or through Facebook groups. Some gigs are paid, but many require you to pay for the chance to join, especially if you're lacking experience.
These opportunities are also great for mile-building, especially if you're working towards your Coastal Skipper or Yachtmaster RYA qualifications.
Whilst I found deliveries to be a fun adventure and a good way to learn about safety at sea, they’re not the best path to mastering the art of sailing. Still, it’s an incredible experience that every sailor should try at least once.
The first boat delivery I ever did (despite having no experience) back in 2021.
Hitchhiking on sailing boats
Similar to boat deliveries, you can find hitchhiking opportunities on the same crewing websites. Many skippers seek crew to help with chores and some of the sailing, especially on longer journeys.
That said, it’s becoming harder to find ‘free’ opportunities for this kind of experience – though it’s not impossible. Many boats now charge a weekly contribution to cover costs, but some still offer spots in exchange for help, without hefty fees.
For example, I managed to travel from the UK to Central America (about 7,000 miles, including an Atlantic crossing and another passage across the Bay of Biscay) with an experienced sailor, and I only paid for my food and immigration expenses.
Hitchhiking on boats like this offers a chance to learn a lot about off-grid living at sea, depending on how curious you are, how willing the skipper is to teach, and how well-equipped the boat is.
The boat I was on had all the modern gadgets, gizmos, and instruments. Many of the decisions were made using electronic tools that measured wind speed, direction, and apparent wind angle, which meant the sailing itself was often automated.
Whilst the trip was fantastic for learning about life aboard a boat and picking up the boat’s lingo (which is practically its own language), this particular boat wasn’t the best way to learn the ins and outs of actual sailing.
Since much of our sailing was downwind, driven by the trade winds, I ended up spending six months on the boat without really learning how to sail properly. However, I did gain valuable skills in provisioning, safety at sea, and living aboard for extended periods. And, of course, I met tons of adventurous people along the way.
It’s one of the best experiences I’ve ever had, and if you're not focused on becoming a skipper but want a taste of the sailing lifestyle, I highly recommend it.
Hitchhiking on sailing boats is one of the best things I’ve ever done.
Racing boats at a local sailing club
When I returned to the UK, I started racing on boats which for me has been a game changer. It’s been excellent for socialising and networking, I have loads of friends with boats now – and I’ve finally learnt how to sail.
Everything has been free other than post-sail beers and the occasional chipping in for longer race entry fees. Many clubs, including mine, accept people with no sailing experience.
Racing is great because you are constantly tacking, changing sails and pivoting around buoys and obstacles. Everything is fast-paced forcing you to build up muscle memory and to be able to react to things quickly.
Racing around the cans is great for learning how to optimise the boat on all points of sail. Off-shore racing teaches you to maximise performance whilst still being safe far from land.
Racing also pushes you to sail in bad weather, higher winds and quite frankly conditions a lot of cruisers would avoid altogether. Things often go wrong which is great for developing troubleshooting skills and what to do when you’re under pressure.
Racing regularly in regattas, local series, and national events not only accelerates your learning curve but can also save you a significant amount of money compared to formal courses.
I started racing on sailing boats in 2023 and it’s been a game changer for progression.
RYA Day Skipper course
After a season of racing, I decided to book my RYA Day Skipper course, mainly so I could get insured for my own future boat.
The course isn’t cheap and is primarily designed as an entry-level qualification or for those looking to charter a boat.
I found the theory portion extremely useful, thanks in large part to having an excellent instructor. However, the practical side felt like a complete waste of money for me, as I had already gained plenty of hands-on experience through cruising and racing.
You can think of your Day Skipper course a bit like your driving test, where you learn the basics and how to be safe, but you don’t actually learn how to sail. That comes after with practice.
If you’re new to sailing, this course could be valuable, especially for covering the basics of navigation, safety, and boat handling. But in my experience, racing is a far more effective way to learn to sail and improve your skills.
Day Skipper is one of many courses the RYA (UK) offers.
Go on a flotilla holiday
Personally, this option doesn't appeal to me as much, because I prefer the more adventurous side of sailing. Flotillas often involve a lot of motoring and tend to visit well-known tourist spots.
To be honest, financial constraints also mean this would never be an option for me. Chartering a boat or joining a flotilla can be expensive, and I prefer more budget-friendly ways of getting out on the water.
That said, for those with a bigger budget, combining the RYA Day Skipper qualification with a flotilla holiday abroad is a popular route. It can be a fun and relaxed way to explore new cruising grounds. However, the learning process may be slow unless you’re regularly taking these kinds of holidays.
Flotilla holidays are becoming more and more popular. Credit: Miguel Alcântara/ Unsplash.
Buy your own yacht
When it comes to developing true independence in your sailing and honing your problem-solving skills, owning your own boat is the ultimate step. At some point, crewing for others just won’t compare to the experience of managing your own vessel.
There are boats on the market for every budget – just be sure you can afford to run it safely and responsibly. A small day cruiser with a local mooring doesn’t have to cost a fortune, especially if you can find affordable storage for the winter months.
If you’ve already learned some basic sailing skills or have someone experienced on board, owning a boat will be more enjoyable and far less risky. That said, I’ve met people (though I wouldn’t recommend it!) who bought a boat with no prior experience and sailed thousands of miles right away.
Owning your own boat also means taking on the responsibility of learning maintenance, engines, and, depending on the boat’s size, even electrics and plumbing. It opens up a whole new realm of knowledge.
If you have the time and patience to buy a fixer-upper, it’s a great way to gain valuable hands-on experience with maintenance and troubleshooting – skills that will come in handy when issues inevitably arise in the future.
I bought a Hurley 18 in 2023 but it ended up being scrapped. A story for another day.
Dinghies
Most of the best sailors I know started with dinghy sailing and dinghy racing. This could partly be because many people begin dinghy sailing at a young age, giving them years of experience by the time they transition to larger boats.
That said, dinghy sailing is an excellent way to develop essential sailing skills, regardless of when you start. Everything happens quickly on a dinghy, with limited resources and no electronics to rely on, so you learn to truly feel the wind and understand how the boat responds to it. You become attuned to the nuances of sail trim, balance, and helming in a way that’s hard to replicate on a larger yacht.
Dinghies are also typically sailed short-handed, meaning you’re responsible for all aspects of sailing – steering, trimming the sails, and maintaining balance. With such limited space and fewer tools to assist, you develop self-reliance, quick decision-making, and the ability to handle the boat in a variety of conditions. These skills, honed on a dinghy, translate incredibly well when moving up to bigger boats.
In short, dinghy sailing builds a strong foundation that makes you a more skilled and confident sailor, able to respond quickly to changing conditions and handle boats of all sizes. It’s cheaper than owning a yacht and if you pay an annual sailing club membership you can have access to club dinghy boats for not too steep a price.
Dinghies are an excellent way to learn to sail. Credit: Kasia Derenda/ Unsplash.
Books and YouTube
Books and YouTube are excellent resources to supplement your sailing education. Whilst you won’t become a skilled sailor by using these tools alone, they’re invaluable for diving deeper into specific topics.
There are resources available for every level of sailing, whether you're trying to understand the different parts of a boat, perfect your sail trimming, learn essential knots, or study survival at sea techniques.
The RYA books are great for covering the basics and teaching the essentials, but don’t limit yourself to just their syllabus, or only practical and educational books. Sailing adventure books can be incredibly inspiring, showing just how far people can push the boundaries in this sport.
Reading is always a great way to learn. Credit: Pim Pouillot-Chevara
What is the best way to learn to sail?
Whilst I’m far from an expert, having explored many of these options, I have an idea of the best way to learn to sail depending on your goals.
Sailing holidays: If your main aim is to enjoy occasional sailing holidays, something like island hopping in the Mediterranean or Caribbean, the RYA Day Skipper course is a great fit. It’s more than enough to charter a boat safely for holiday cruising.
Crewing adventures: If you’re drawn to the adventurous side of long-distance sailing but don’t necessarily want to be a skipper, crewing on deliveries or boat hopping via crewing websites is your best option. You’ll experience life at sea, travel far, and build miles without needing to captain your own vessel.
Competitive sailing: If racing excites you, the combination of dinghy sailing and yacht racing is your best bet. Most of the top sailors have a background in dinghy sailing because it sharpens your skills quickly and teaches you how to handle boats under pressure.
Skippering a circumnavigation: If your dream is to sail around the world on your own boat, a mix of different learning experiences is probably best. Many people jump into this challenge right away, but it’s definitely helpful to understand ocean safety, boat handling in high winds, and problem-solving at sea. Racing or dinghy sailing, paired with some offshore or delivery experience, will prepare you for the challenges of long voyages. And of course, spending a season sailing your own boat, and understanding the systems onboard before you set off, will help you understand its quirks and how to repair it when things go wrong.
Whatever your sailing goals may be, I hope this guide has been helpful – especially if you’re learning to sail on a budget. No matter which path you take, I hope you enjoy the process and have as much fun learning to sail as I have. And, if you’ve got any more suggestions to add, please leave a comment below.
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