3 Things Retirees Need to Know About Planning a Sailing Trip

For some people, retirement means long afternoons spent in a comfortable armchair reading a book, or perhaps pottering around the garden in a pair of comfortable slippers. 

For others, reaching the end of working life means just the opposite – it means breaking the shackles and living your dreams, hitting the high seas in search of adventure. 

Stories of intrepid pensioners abandoning the workaday world in favour of a life sailing around the world abound. While most couples spend their latter working years paying off the mortgage, some focus on raising the funds to buy their own boat.

Other stories tell of retirees who have no previous experience of sailing ending up spending considerable lengths of time living aboard a boat – such as this US couple who, despite starting out as novices, spent 8 years sailing the Caribbean. 

Perhaps your nautical aspirations don’t extend quite as far as living on a boat full time, and you would instead just like to get a taste of the sailor’s life on a holiday. How would you get started, especially if you have no previous sailing experience? 

Here are some key things you need to know before embarking on your maritime adventures.

Get the right travel insurance

Not surprisingly, sailing is considered a fairly high-risk activity for travel insurance purposes, which means that your ordinary, everyday policies are not going to cover you. For older travellers, this is further complicated by age. Once you reach 60, travel insurance providers consider that the older you are, the higher the risk you will make a claim, especially for medical care. They therefore start to ramp up the premiums accordingly. 

The answer is to look for a specialist provider who caters for the needs of older travellers. Do your research and select the right over 60’s cover for you, then at least you can set sail with peace of mind that you are covered for all eventualities.

Learn the ropes

If your ultimate goal is to self-sail, then one thing you cannot do is jump into a boat and expect to sail off into the sun set. There’s a lot to learn, and it is a case of taking baby steps. To start off, look for chartered cruises, either on day trips or short holidays, where you will have a qualified captain and crew take care of the sailing side for you. 

Chartered cruises are a great way to find out if sailing is for you. They will usually operate on fixed routes, which for many people is just fine. But if you want the freedom to wander wherever the wind blows, then you need to take the next step and learn to sail yourself. A great option here are so-called skippered charters, where you get to sail yourself with a qualified captain on board to show you how it is done.

Carry the essentials

The big difference between a sailing trip and almost every other type of holiday (except, perhaps, an extreme wilderness camping adventure) is the need to be self-reliant on board. Once you hit the open water, that is it – no more shops, no more amenities, and probably no more contact with other people, unless you need to radio for help in an emergency. 

That means you have to stock up on everything you will need, at least between port calls. So food, water, a full first-aid kit, clothing, sunscreen, modes of entertainment to keep you occupied during downtime – all of it needs to come with you.

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