Liveaboard Lifestyle Explained



Your Hosts –

Hi there. I’m Paolo. I was born in Siena, Italy. I skipper our beautiful Oyster 56’ foot Mono Hull sailing boat Sea Pearl.


And I’m Jenny. Paolo’s wife and chef / first mate on board Sea Pearl. I was born in Brisbane, Australia.


Jenny) Together, we are sailing Sea Pearl, our third boat after our 34’ and 48’ foot boats, around the world – maybe? Maybe we’ll get all the way around the world and maybe we won’t, but we intend to spend the next 10 plus years trying.

Paolo) We have both enjoyed fulfilling careers while also sailing on our boats, and other people’s on weekends and holidays. Until we decided that living on board our boat full time and sailing her to the far corners of the earth is the only thing that makes sense to us.

Jenny) This is not a path that we have chosen lightly. The most enjoyable and satisfying part of our journey is that we are always learning new things every day. Every day is different, and we would like to share what we are discovering with you.

Paolo) If you or your partner has been bitten with the same sailing bug that we have and you are considering getting more involved in the sailing lifestyle, then this is your opportunity to jump in. Or if you want your partner or family to see first-hand what it’s really like to live on board a sailboat, and maybe even buy a boat of your own, then this is the perfect way to introduce them. Why not “try before you buy” and come sailing with us?



Jenny) We don’t have a fleet of bare-boat charter boats to rent out to you and let you work it all out for yourselves. We’re not selling a luxury pampered 5 Star Cruise where you don’t have to lift a finger. We are inviting you and your family, onboard our boat, to experience for yourselves what your future could look like.

Paolo) Spend some time living with us on board Sea Pearl and we can show you how we live day-to-day. You can pick our brains about every aspect of the sailing lifestyle, as we share our experience with you and your partner, or family and friends. 

Jenny) Paolo bought his first boat with his father at 22 and has sailed over 70,000 miles as a skipper. I have always dabbled with sailing boats growing up in Australia, but I didn’t take my first RYA sailing course until I was 40 years old. We met each other through sailing and our combined passion for sailing has propelled us to explore the whole of the Mediterranean and North Africa, after which we sailed Sea Pearl across the Atlantic to the Caribbean.

Paolo) If you come sailing with us, I can show you how our boat is set up for short-handed sailing and how we sail our boat. You can get as involved as you like. Helming the boat, setting the sails, dropping the anchor and picking up mooring balls. I can explain how the weather effects every decision we make about where and when we move Sea Pearl, and then experience the consequences of those choices. I will show you what it takes to look after a boat, and your family, and keep you all running well and SAFE.

Jenny) We’ll even show you how to move around the boat while it is under sail or at anchor, if this is unfamiliar to you. We have been doing this for so many years now that it has become second nature to us. But we can show you techniques and tips that will allow you to become more confident and safer onboard Sea Pearl and possibly, therefore, your future boat.

Paolo) Planning and maintenance take up more of our day than actual sailing. We can show you what it takes, and what skill sets are important to become familiar with to enable you to look after your own boat and plan your next steps. But it’s not all about the boat. Just as in OUR daily Liveaboard Lives, you will have plenty of time to relax, enjoy the water, explore and mix with the locals and other cruisers.

Jenny) Cleanliness, food hygiene and meal planning are extremely important in the Caribbean’s very hot weather. I can show you how storing every last item on your boat – where it is accessible depending on frequency of use – is so important for safety on passage. I’ll show you how to plan ahead with your food; what is appropriate to prepare when you’re going to be sitting in the cockpit at anchor surrounded by turquoise waters and sea life, or meals that are more manageable while sailing between the islands.

Paolo) We can show you some of our favourite local bars and restaurants and take you to the hidden gems we have found while exploring the Caribbean. There are many different aspects to boat life that you may not have even considered, so we will not only talk you through these, and show you how to acquire a new skill – you’ll also get to practice these new techniques for yourselves.

Jenny) This is a hands-on liveaboard lifestyle experience that will allow you to “try before you buy”. To experience for yourselves a window into a life that you and your partner have been dreaming about, watching other people enjoy from the beach or land, on YouTube, or via TV documentaries. Now you and your family can experience it for yourselves, asking all the questions you need the answers to. 

Paolo & Jenny) Come sail with us in the Caribbean on Sea Pearl this season.