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Living & working on a sailing boat: the pros and cons

Updated On 3rd January, 2022

There is something about the idea of living and working on a sailing boat that is so romantic. Moving from marina to marina, coast to coast, country to country, all while simultaneously travelling and working sounds like bliss. If you’re wondering what it’s like to live on a boat or to work on a boat, or if you’re considering living on a boat or working on a boat, this is the post for you.

It’s not all glamorous, but it can be fun! If you’re ready for a huge adventure, full of highlights, compromises and challenges and everything in between, living on a sailing boat could be just what you need. Learning to expect the unexpected, to prepare for anything and everything, and to embrace spontaneity are just some of the things you’ll get out of working on a sailing boat. It’s a unique way of life, and it’s not for everyone, but if you’ve made it to this post and you’re thinking of living on a sailing boat, you might be ready to take the leap.

I have lived and worked on boats all over the world so I’m obviously biased in thinking living on the water is a fantastic experience! However it’s not all plain sailing and I’ll talk you through some of the pro’s and con’s of living and working on a sailing boat for me. Spoiler alert: I definitely think that the benefits outweigh any inconveniences, but keep reading to find out why!

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Living and working on a sailing boat: the pros and cons... ​

Living and working on a sailing boat: the pros and cons...


1. The freedom to choose where you want to be and where you want to go next.

This is an obvious starting point and is probably one of the key motivating factors for most people when they choose this lifestyle. The world is your oyster and your travel plans are only limited by your imagination (and both you and your boat’s capabilities!). This is definitely one of the biggest pros of living on a sailing boat for me. 

Living and working on a sailing boat: the pros and cons... ​

2. Living in the moment.

Life is what happens when you’re busy making other plans. It can be challenging to be present in our busy and chaotic lives. We can also be tempted to constantly worry about the future and dedicate so much energy to our plans that we forget to focus on the present moment. Life is fairly unpredictable when you’re living on a sailing boat and appreciating the small things and being flexible with any future plans is so important. 

3. You bring your home with you.

You might think you have to leave a lot behind when living and working on a sailing boat, but that’s not necessarily the case. Sailing away can be the ultimate form of escapism but you also have the luxury of bringing your little home with you on your travels. 

You make the call whether you want to sail off into the horizon by yourself or share the experience with people close to you or furry friends. I’ve sailed with a little dog who would constantly be on the lookout for dolphins to chat to and would be too excited to sleep once she had spotted them! Another friend has a cat as his crew who can paddle board to the beach (assisted by his captain) and wander around onshore with his GPS tracker before making his way back on board. 

Living and working on a sailing boat: the pros and cons... ​

4. Every day is an adventure.

When you’re living on a sailing boat, nothing is as easy as living on land but it’s also more exciting! Even going to the shops can involve an unexpected hike to find civilisation and trying not to sink the dinghy if you have been over ambitious with your purchases.

5. Home is where the anchor drops.

Wherever you want to go, you can find a good location on the water, and if you change your mind, you can change and go wherever the wind takes you! Launching the dinghy and arriving somewhere ashore for the first time never gets old and watching your home bobbing around on the water waiting for you is also very special.

6. You meet like-minded people from all over the world.

Sailors tend to be very friendly people and living on a boat throws you into a worldwide community of all sorts of different people with something in common. I also think it’s quite entertaining how quickly you start to spot people who live on boats by the telltale signs of being tanned, sun-bleached clothes, waterproof bags (you never know if you might have a mishap on your way to shore) and the fact that they’ve probably already introduced themselves to you. 

See more top tips for making friends when travelling here.

7. You can work on board with the Internet.

Even relatively recently it was difficult to imagine how queuing at internet cafes or walking around a town scanning for any potential WiFi networks would become less and less common. There are much cheaper and more reliable mobile internet options now which make being connected whilst on a boat a reality and living and working on a sailing boat much more feasible. Remote working in general is much more widespread and makes this lifestyle more compatible with a ‘normal’ job.


1. The weather can change all your plans.

It takes a bit of getting used to when you first start living on a boat that any ideas you might have about what you want to do need to be run past the weather gods first! If the conditions aren’t right, you won’t be going anywhere and you need to have a Plan B, C and even D to hand. 

2. Supplies are limited.

Living on a boat means being aware that you are working with limited resources especially in terms of water, fuel, electricity and food. The more luxurious the boat the less obvious this might be but the point still stands that if you turn on the tap it’s coming from your supply not the mains. This can be a bit tricky to get across to guests who could happily use up a whole water tank with one shower! It can be quite eye-opening how much we use or how little we can consume if we are careful.

See more sustainable travel tips here.

Living and working on a sailing boat: the pros and cons... ​

3. Lack of space.

Space could be seen as your ultimate limited resource to which the only solution would be a bigger boat, but the harsh reality is there will never be a big enough boat if you don’t adapt your mindset. Living with less is definitely a challenge as you try to predict what you might need most. The small space doesn’t just affect material things; think carefully about who you choose to have onboard too!

4. Keeping your boat afloat isn't easy.

It may look like you are living the dream and let’s be honest, most of the time you probably are. Especially as you are less likely to share with your friends an update on a very glamorous morning spent fixing a toilet than a beautiful sunset photo. So you can’t blame anyone who underestimates how much time you will need to spend maintaining your boat. Keeping your boat afloat is a bigger challenge than you may initially imagine; cruising is described by many as fixing your boat in exotic locations, and this is something you should definitely consider before you start living on a boat!

Living and working on a sailing boat: the pros and cons... ​

5. Saying goodbye is hard.

It can be difficult feeling transient and although you are definitely part of a wider community, frequently saying goodbye to friends is a reality when you’re living on a sailing boat. The flip side of meeting so many fantastic people is that they will be on the move too but your paths may cross again sooner than you think! You can also choose to move around slowly or base yourself for long periods of time in the same area to feel like you’re creating more of a base. 

6. Working on a boat with the Internet is easier than before, but not easy.

Internet becomes another factor to consider in your plans as to when you need to be connected and when you can be sailing without any signal. For remote working on a boat this could mean planning any longer passages for the weekends if you’re trying to work a traditional 9-5 Monday to Friday schedule, or making sure you have a certain amount of control over when you work.

Living and working on a sailing boat: the pros and cons... ​

I think if you’re looking for an easy life sipping cocktails and watching the sunset, it’s probably better just to have a holiday on the water and not to spoil the illusion! But if you’re up for an adventure, and a steep learning curve, you’ll realise that your sundowner in your unusual home is priceless. 

Have you ever thought about living on a sailing boat?

Have you got any top tips for working on a sailing boat? Anything you’d add?

Love as always and happy adventuring…

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