How to Travel As Crew on Sailing Boats

Travelling by sail is unlike anything else. The sense of fulfilment you get after days or even weeks of hard work and patience to reach your destination is incomparable to the quick, detached feeling of hopping on a plane or train. Sailing transforms travel into a true adventure.

Even with today’s advanced weather forecasting, you never really know what’s around the corner, and that’s part of what makes it so exhilarating. And, whilst most boats are far from carbon free travel, sailing can go a long way in mitigating the impact your travels have on the environment.

If you’re an adventurous traveller, this might be the perfect way for you to explore the world. However, let’s be realistic: sailing isn’t for everyone. 

Whilst some of the best moments of my life have been out at sea, it’s not always smooth sailing – it can be challenging, and sometimes uncomfortable. But if you’re eager to learn new skills, test your limits, and embrace adventure, this blog is for you.

In this post, I’ll cover why travelling by sail is great, how to find a boat and plenty more useful information about how to travel as crew on sailing boats.

Travelling by sail can get you to destinations like this (Bequia, Saint Vincent and the Grenadines).

My experience of travelling on sailing boats 

My first experience travelling by sail was back in 2021, when I took a few trips, including sailing along the south coast of England and helping with a boat delivery from the UK to Portugal.

By that point, I knew I wanted to continue exploring the world by sail. Since then, I’ve become hooked on the adventure and freedom that sailing offers. Some of the best moments of my life have happened at sea.

My real love for this way of travelling took hold after I spent three weeks sailing across the Atlantic Ocean. This was part of a much larger trip where I sailed from the UK to Costa Rica stopping in the Canary Islands, Caribbean, and Panama along the way. 

Overall, I was travelling by sail for seven months and covered thousands of miles. The best part? I started with next to no sailing experience and I didn’t even know how to sail.

I did my longest trip on a Voyage 500 Catamaran which I stayed on for six months.

Why Travel By Sail?

Travelling by sail is incredibly liberating. It’s exhilarating being carried across the ocean by the wind. It allows you to connect deeply with nature – you'll witness breathtaking wildlife and enjoy every sunrise and sunset from the water.

Sailing also opens the door to destinations that would otherwise be inaccessible, allowing you to immerse yourself more fully in a country’s culture. And depending on the boat, you can visit places that might normally be out of your budget, making even unaffordable locations affordable.

One of the things I love most about sailing is the sense of anticipation as you slowly approach a new destination. It gives you a true appreciation for the sheer scale of the world and its oceans – something you don’t experience with faster, more conventional forms of travel.

Another big draw is the close-knit relationships you build with your crew. Living, working, and relying on each other creates bonds that go deeper than most other travel experiences. Some of my closest friendships have been forged on these journeys.

And of course, your accommodation moves with you – no more packing and unpacking, just the freedom to explore as you go.

Morning coffees in remote and beautiful places is a definite perk of travelling by sail.

Is travelling by sail right for you?

Sailing is unlike most other forms of travel – once you’re on a boat, there isn’t always an easy way out. Whilst Instagram and social media may portray it as an idyllic lifestyle, the reality can be quite challenging at times. In fact, it's probably challenging for everyone at some point. So, before you dive into life at sea, here are some important things to consider:

Do you get seasick? 

Seasickness isn’t the end of the world, and in fact, many seasoned sailors deal with it at some point. The intensity, however, varies from person to person, so it's smart to gauge how you react before committing to a long journey. Start with a few shorter day sails to see how you handle the motion. Even if you do experience some seasickness, it’s not a deal-breaker – there are effective remedies like medication, wristbands, or natural options to help manage it.

How flexible is your schedule?

My friend Max once told me, “You can have a place or a time, but you can’t have both.” When sailing, the wind and tides dictate your schedule. If you want to travel by sail, you need to embrace flexibility and let go of fixed timelines. You might plan to reach a destination by a certain date, but nature or the boat may have other ideas. The adventure lies in being open to where the sea takes you.

Check out this YouTube episode where I join my friend Max as crew in Central America.

How do you handle authority?

On a boat, the captain is in charge. You’ll follow their decisions on where to go, when to leave, and how long to stay. Some captains are more laid-back, whilst others run a tight ship. Either way, you won’t have full control over your schedule, and that can be hard for some people. If you prefer a relaxed atmosphere, it’s essential to have open discussions with the captain before setting off, to align expectations.

Are you good with people?

One of my first captains, Sophie, once told me, “Being at sea is less about sailing and more about managing relationships.” When you're sharing a confined space with others for long periods, patience, communication, and flexibility become essential. You’ll experience moments of stress, exhaustion, or vulnerability, and so will your fellow crew. How well you navigate these interpersonal dynamics is crucial for a positive experience.

Are you a team player?

Sailing is a collaborative effort. You’ll need to pitch in, whether that’s taking turns with night watch shifts, cooking, cleaning, or stepping up when someone is seasick. Living on a boat quickly turns your crew into a family of sorts, where everyone relies on each other. Being a team player isn’t just helpful – it’s essential for safety and harmony on board.

Working as a team is a crucial aspect of travelling by sail.

How do you handle fear?

Sailing can be unpredictable, and sooner or later, something will go wrong. Whether it’s encountering rough weather, an engine failure at a critical moment, or even the boat being sunk by orcas (yes, that really happens!), you need to be able to stay calm under pressure. Sailing requires you to face unexpected challenges with resilience and a level head.

How much luxury do you need?

Whilst sailing can feel like a dream come true, it’s often not as glamorous as it seems. Depending on the boat, you may go days (or weeks!) without a proper shower, be sharing a cabin with someone, be woken up by wildlife, or spend sleepless nights fixing things when they inevitably break. If you’re after the romanticised version of sailing without the rough patches, you might prefer a charter boat experience. But if you embrace the real sailing lifestyle, you’ll see discomfort and things going wrong as part of the adventure.

You’ll see dolphins and plenty of other wildlife when sailing.

What kind of boat is right for you?

If you're still excited about travelling by sail, that's great news! And if you’re unsure about some of the above points, maybe it’s time to push yourself outside of your comfort zone and give it a go anyway. Choosing the right boat and crew is crucial for a positive experience. Here are some key things to consider before you embark on your adventure:

How much experience do you have? 

The amount of experience you have will determine in some part which boats you go on. It’s important to be honest about how much sailing you’ve done and what you know, otherwise things could get dangerous on the boat. It will be obvious right away whether you know what you’re doing. If someone thinks they can rely on you and then it turns out they can’t, they probably won’t be happy. But the reality is many boats prefer people with little experience, so it shouldn’t be a barrier to entry.

How much comfort would you like? 

The size and type of boat greatly affect your comfort at sea. Larger boats, especially over 37 feet, are better suited for international cruising, whilst smaller boats can feel cramped and more affected by ocean movement. Catamarans offer more comfort since they don't heel (tilt) as much, making them a more luxurious option. However, monohulls, though less stable, provide a more traditional and thrilling sailing experience. 

Monohulls can be less comfortable than catamarans, but also more exciting. Credit: Christian De Stradis / Unsplash.

What sort of experience are you looking for? 

Are you after a relaxed trip exploring new places or a more intense, delivery-style sail? Consider factors like downtime, sailing time versus port stops, and the crew’s lifestyle – whether it’s late-night partying or quiet evenings. Ask about diet, shared interests like diving or surfing, and equipment onboard. Will you be anchoring more often or staying in marinas, which can be pricier and less scenic? The crew can make or break your experience. So choosing the right people to sail with is just as important – if not more so – than choosing the right boat.

How much are you willing to pay? 

Costs can vary greatly depending on the boat and captain. More often than not, you'll need to contribute to running costs like fuel, marina fees, and repairs. Expenses can range from hundreds to thousands per month. Factors like the boat’s size, skipper’s wealth, and crew size affect the price. However, compared to backpacking, which can have similar costs, travelling by sail often provides a richer and more unique experience for a comparable price. Make sure you agree on finances upfront, so there are no surprises down the line.

Where do you want to go?

Deciding between national or international travel will shape your adventure and where you’ll meet the boat. National trips, like coastal hopping, are ideal for beginners. International voyages offer more remote, stunning destinations but require extra time, preparation, and flexibility. Consider the cost and logistics of reaching the boat’s departure point, and ensure you have the necessary visas for the countries you’ll visit.

International cruising can take you to beautiful tropical destinations.

How to find a sailing boat

There are several ways to find sailing boats, whether you're looking for short-term crewing opportunities or long-distance voyages. I’ve personally connected with boats through crewing websites, social media, word of mouth, and even spontaneous encounters, like at a paddle out protest. The key, however, is finding the right boat, not just any boat. With the considerations mentioned earlier, you should now have a clearer idea of what suits you best.

Crewing websites
There are whole sites dedicated to helping match boats and crew. Crewseekers, Crewbay and Findacrew are amongst the most popular, but there are others too. This is a great way to find boats in specific areas and to see the different types of opportunities available. However, you may have to pay for a subscription to have access to contact details. It’s worth putting a decent amount of effort into your profile on the site you choose, because crewing is becoming more popular and you’ll want to stand out from the crowd.

Facebook pages

Facebook also has a number of crewing pages, including global and regional groups. The best part about this is it’s totally free and they are frequently updated with boat owners looking for crew or people offering to join a voyage. 

Crewseekers is one of many ways to find crewing opportunities.

Marina notice boards

If you’re based near a marina, check out the notice boards. You may find an advert for vessels looking for crew. Whilst you’re there, consider creating a notice of your own. List relevant details like your experience (if any), age, the languages you speak, and any valuable skills like cooking, mechanical expertise, or first aid.

Atlantic Rally for Cruisers (ARC) website

For those specifically interested in a transatlantic journey, the Atlantic Rally for Cruisers (ARC) website is an excellent resource. The ARC supports hundreds of boats annually in their crossing from the Canary Islands to the Caribbean. Although you’ll need to pay to access contact details, the advantage here is that all registered boats adhere to safety protocols and use advanced weather forecasting, providing an added level of security.

Boat knocking 

Last but not least is the good old fashioned way, where you can simply rock up at a marina and knock on each of the boats. There are no guarantees but I have seen this work multiple times, particularly in marinas which are well-known to long-distance sailors. For example, Las Palmas in Gran Canaria, Shelter Bay in Panama and many of the larger international marinas. This approach requires confidence, but it could lead to spontaneous opportunities and all adds to the sense of adventure.

Boat knocking in large marinas can be a good way to find boats. Credit: Matt Thornhill / Unsplash

Safety 

One of the most important factors to consider before stepping aboard is safety. Once you're underway, there’s no easy way off the boat until you reach the next port, so you need to trust both the boat and the captain. Ultimately, your wellbeing is in their hands, so here are some essential things to check before setting sail:

• Captain's experience: Make sure the captain has enough sailing experience to handle the boat safely, especially in challenging conditions. Ask about their experience with similar passages and how long they’ve owned or managed the boat.

• Boat condition: A well-maintained boat is a safe boat. Ensure that everything onboard is in good working order, especially critical systems like the engine, sails, rigging, and navigation equipment. Any known issues should be addressed before embarking on a long journey.

• Alcohol and drugs: Surprisingly, some boats have a culture of drinking or even drug use whilst underway. This is a huge red flag – it can impair judgement and compromise safety. Clarify the boat’s stance on substances before you commit.

• Crew size and dynamics: Sailing with just one other person can be intense, especially if you’re strangers. It’s usually more comfortable to have multiple crew members. If you're concerned, especially as a woman, it's reasonable to ask for another female crew member. A considerate captain should be open to this.

• Safety equipment: Ensure the boat has basic safety gear like a liferaft, flares, VHF radio, and lifejackets for everyone onboard. For offshore passages, satellite devices such as an EPIRB or PLB are reassuring in case of emergency.

• Meeting the skipper: If you don’t know the skipper, meet them in advance or, if that's not possible, ask for contact details of previous crew members. Their feedback will give you insight into what it's like sailing with that person.

Pacific Panama was one of my favourite places whilst travelling on sailing boats.

Conclusion 

By now, you should have a clearer sense of whether this lifestyle calls to you. If it does, don't be afraid to take the plunge. There are countless ways to find your first boat and get started, whether through crewing websites or by simply showing up at a marina. Just remember to choose wisely and stay mindful of safety – but most importantly, stay open to the adventure that awaits.

If you’re ready to embrace the uncertainty, test your limits, and feel the true freedom of travelling by sail, it might just become your favourite way to explore the world.

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