Share the post "Living on a Sailboat: A Look into Andrew’s Lifestyle"
While some rent boats frequently to enjoy the pleasures of sailing on the open water, others go a step further, embarking on a life at sea by living on a sailboat. Meet Andrew—a passionate sailor, seasoned adventurer, and storyteller. Living aboard a beautifully restored 54-foot Jeanneau Sun Odyssey (54DS) with his wife, Hiba, and their 5-year-old son, Arthur, Andrew has spent the past two years exploring the Mediterranean, from Greece to Spain. A lifelong sailor with years of experience living abroad, Andrew is also the creator of the Ocean Cruisers Podcast and the Odyssey Sailing Festival.
We had the chance to dive into his journey, his unique lifestyle, his path to embracing the sea, and what it involves to live and work while cruising the world.
How did your dream of living on a boat begin?
Andrew: Living full-time on a sailboat and traveling has been a dream of mine since I was 18. Back then, I had this wild plan to save £30,000 with a friend, move to Australia, buy a boat, and live on it. The idea was to work part-time in the fields and to spend the rest of the time sailing. It didn’t work out in the end, but the idea of living on a boat stuck with me. Years later, after spending a lot of time in the corporate world, I realized how unfulfilling it was for me. This strengthened my will to live life aboard. While it drained me mentally, it also gave me the chance to save up enough to finally make this dream happen.
What inspired you to transition to living full-time on a boat, and how did the journey unfold?
A: I’ve always been around boats. My dad had a few small ones, so being on the water felt natural. When I was 18, I was on a trip to the Lake District with a friend. It got me thinking about living on a boat, though it felt more like a daydream back then. Life got busy; I worked in the energy industry and got caught up in the grind. By the time I was 32, I was tired of chasing material things and wanted a simpler, happier life. My wife and I moved to Spain near a marina, planning to work hard and save for our dream boat.
Then Covid happened, and it was a wake-up call. It made us realize how unpredictable life is, so we sped up our plans. We didn’t wait for the perfect boat; we just found one that suited us and our three cats. After a few charters to get some experience, we decided to dive in fully. We’ve been living on the water ever since, and honestly, I wouldn’t change a thing.
What have been the biggest challenges of living on a sailboat for the past two years?
A: It depends on your location and the weather. For example, last year in the Balearic Islands, the winds could be unpredictable, which made the boat rock violently at anchor on some nights. We had sleepless nights bracing against the movement and securing things that were flying around. In Greece, on the other hand, we can find well-protected anchorages to sleep peacefully.
Weather issues aside, we can fall asleep under the stars at night, and within minutes we can be on the beach every day. For us, there are no downsides.
What are the best things that come with living on a boat?
A: There are a couple of different aspects of living on a boat that are really great. One is family. Instead of the traditional 9-to-5 life, you’re constantly with your family, your children. This lifestyle forces you to work on yourself: you become more aware of your voice and the words you use because you need to be mindful of their feelings. Being stuck in this smaller space all the time means there’s no room for things left unsaid. You learn how to communicate and be as open as possible.
And the other thing is nature. I believe we’re meant to be surrounded by nature, water, trees, grass, sand. Maybe it’s an old-fashioned view of life, but it makes sense. If you’re in a bad mood, have had a bad day, all you have to do is pop your head out, and you’ll see a beautiful beach, or a glorious sunset. It puts things into perspective, reminding you that small problems are insignificant, and it keeps you in touch with the big picture.
Is there a moment, from the last two years, that is particularly memorable?
A: After I finished fixing up the boat in Greece, I went straight to Spain to pick up my family. The first anchorage we stopped at once we were all together was Cala Bassa, on Ibiza. I remember that day as absolute bliss, and it’s still, after two years, one of my favorite memories onboard. The beach was paradise, and the afternoon was just perfect. I remember my wife being happy by my side, my son playing in the sand by the water, and our boat in the background. It was lovely because it was then that I realized what this new chapter of our life would be like, and that every day could be like this if we worked at it.
It’s actually funny, because that afternoon was so perfect, but the following morning we were hit with 40-50 knots of wind, and rain coming sideways through the cockpit. It was kind of scary, but we got through it alright, and we still look back at that first evening as a sweet memory.
Could you tell us more about your Odyssey Sailing Festival and what it consists of?
A: Sailing is unique because it brings people together—whether you want to relax on a beach, aboard a boat, or connect with others who share the lifestyle. My podcast celebrates this each week by featuring inspiring individuals who live on the water, travel the world, and share amazing stories and advice.
To deepen this sense of connection, I launched a week-long sailing festival. The goal was to create an unforgettable itinerary with multiple boats, a vibrant community, and inspirational skippers admired for their skills and experiences. To do this, I invited amazing guests I’ve featured on my podcast such as Brady and Blue, Glen from Below Deck, Laura Dekker, Dustin Reynolds, and many more.
This festival is not just about sailing—it’s about experiencing life on the water. During the trip, participants get to meet incredible people, enjoy great food, fish, snorkel, and be inspired by the skippers leading the way. The inaugural event in the British Virgin Islands in 2023 was a huge success, with attendees eager to return. Since then, we’ve hosted another one in Greece and plan to return to the BVI next. By 2025, we aim to take the festival global, exploring destinations like Australia, Fiji, or French Polynesia. This is just the start of an incredible journey for sailing enthusiasts worldwide.
What advice would you give to people interested in a lifestyle such as yours?
A: I think that before taking the big step of buying a boat, you should try many different boats, with different configurations, in different locations. The lifestyle of living on a boat may seem very nice and romantic, but the logistics—the maintenance, the upkeep—are harder. You see too many people buy a boat, only to sell it again at the end of the season because they can’t deal with the challenges.
I advise people to listen to my podcast. I talk to people around the world who are living on boats, and we regularly discuss the challenges, difficult situations, and hacks to make life easier and safer onboard.
Another piece of advice I would give is to charter boats on platforms like yours. This is a great way to test a variety of different boats, and see what life on board could be like. By renting different boats, you gain valuable sailing experience, and get to understand what works or doesn’t work for you. That way, when it comes time to buying your own, you’ll know what you like and what fits your needs better. The charter industry gives everyone the opportunity to try boating. It also serves as a huge learning experience for less experienced sailors (or even experienced ones).
Stay connected
Andrew’s journey is proof of the adventurous spirit of life at sea many sailors experience. Living aboard his 54-foot Jeanneau Sun Odyssey with his family, he’s explored the Mediterranean and managed to build a thriving sailing community through the Ocean Cruisers Podcast and Odyssey Sailing Festival.
To join that community and follow Andrew’s projects and adventures, feel free to connect with him on Instagram at @oceancruiserspodcast and listen to his podcast. There, you’ll find valuable advice and stories about his life at sea, as well as the experiences of his inspiring guests.
For those inspired to try this lifestyle, follow Andrew’s advice and start by chartering different boats. Gain experience, and find what suits you best!
Ready to set sail? Click&Boat has everything you need to begin your adventure! 🌊
Stay connected with the sailing community:
- Follow Hiba on Instagram: @hibaonaboat
- Check out the Odyssey Sailing Festival on Instagram: @odysseysailingfestival
- Visit the Ocean Cruisers YouTube Channel: OceanCruisers
- For more about Andrew’s journey and projects, visit the official website: www.theoceancruisers.com
- Follow Click&Boat on Instagram: @clickandboat
