As the saying goes, “A rough day at sea is better than any day at the office.” You get out there a couple of times, you’re hooked, and now you’re considering taking the plunge: boat ownership.

However, don’t let dreamy visions of blue skies and clear water cloud your decision-making when it comes to buying a boat; there is quite a bit to consider. Whether you go for the traditional sailboat or a jet engine super yacht, they can both be very pricey and high maintenance.

Boat ownership can be fantastic, but before you throw off the bowlines and sail away from the safe harbor, here are a few things to think about:


With countless brands, styles and prices in the market – whether you want to buy new or used – it is important to do your research. Just like buying a car, try to shop around as many places on-island as you can. Remember, while you may get more for your money with a used boat, you will sacrifice on the warranty and although new vessels may not be trouble free, if you purchase from a local dealer, you will have the benefit of warranty service on-island. Check with experts like those at Harbour House Marina to get sound, professional advice.

There are also several brokers on the island that specialize in used boats.

Another popular option is boat sharing. If you have a group of close friends that have the same boating desires as you, then why not chip in and spread the cost? It will be much more affordable and you get to hang out with your buddies on the weekends. Everyone’s a winner and repair bills are shared. Bonus!

Sailboat vs Powerboat

Most shipmates fall firmly on either side of the boom with few straddlers, so you probably already know what you’re looking for, but if you still haven’t made up your mind here are a few pros and cons of both.

It is a very personal choice and depends a lot on the type of boating you will be doing. Sailboats are definitely more of a passion project, needing time and dedication to the skill of sailing and getting to grips with your vessel.

So, if you would prefer the minimal commitment of pressing a few buttons, drinking a few beers and impressing a few friends, a powerboat is probably a better partnership for you.


Unlike most things regarding island life, when it comes to boats, salt + sun = rust. They need a lot of tender love and care so make sure you have the time to devote to your new leisure pursuit or it may cost you in the long run.

Remember to wash your boat down with freshwater every time you take it out and use covers where and when you can. This will prevent a lifetime of grief down the line.


If you don’t have access to your own dock, there are a few options available on the island where you can tend to and hold your vessel. Harbour House Marina, Barcadere Marina at George Town Yacht Club and Cayman Islands Yacht Club offer extensive amenities and facilities on-site if you choose to dock with them. However, if you are lucky enough to live in one if the many residential areas situated on canals with docks attached, then look no further.


Before you get stuck between the devil and the deep blue sea with your new-found freedom out on the water, make sure that you and anyone else expecting to drive your boat has had the correct training and experience.

There are lots of courses to suit all sorts of watercraft on island so you can captain your boat safely. If you are interested in a sailboat, then the Cayman Islands Sailing Club offers courses for novices right up to advanced and even racing levels for the adrenalin junkies out there. For powerboats, there are several companies on island which are approved by International Yacht Training Worldwide that can show you the ropes. These can be found on their website: