5-Step Guide to Sailing the High Seas

man-on-a-boat-How to sail basics Zizoo

So you want to charter a yacht. But it’s your first time? Check out our 5-step sailing guide.


Chartering a yacht and sailing the high seas may seem like a huge task. And you’re right, it can be.

Sailing is not as easy as lounging around on deck with champagne and a tan.

If this is the kind of sailing holiday you’re looking for, no problems! Perhaps you’d prefer to sail with a skipper. Sailing with a skipper removes all the stress of operating a boat, planning an itinerary and ensuring the safety of the boat and crew.

However, if you do want the full sailing experience but are a little nervous about stepping away from the marina, we’ve put together an easy 5-step guide for beginners.

You’re probably asking yourself, “Surely there must be more to sailing than five simple steps?”

And you’re right. There is.

For this episode, we’re taking more of a first-timer approach to sailing; a guide to sailing for the seaside novice, if you will.

Check it out and rent a boat now!

1. Plan Your Itinerary

Deciding where to sail is one of the most important parts of a sailing holiday. If you’re sailing without a skipper, you cannot simply turn up to the marina and set sail if you do not know the area.

Plus, you want to make the most of your holiday, right? Then you’ll want to see all the best spots and swim at all the best beaches.

Along with planning your itinerary, it’s a good idea to plan your meals. You’ll need to know where the next grocery store is if you’re planning on cooking and stocking the boat with delicious local cuisine for breakfast.

After booking a boat, our team of local experts can help you plan your entire route. We’ve also got a couple of sail Croatia and Turkey sailing routes here on the lobster, with more countries to come.

2. Know Your Basic Nautical Terms

“Aft” – this is the front of the ship.

“Anchorage” – a beautiful bay, cove or marina to lower the anchor for the night.

“Bareboat” – a boat charter or hire without a crew.

“Below deck” – where the cabins and galley are.

“Bow” – and this is the back.

“Fender” – the cylindrical plastic items used to protect the sides of the boat when mooring.

“Galley” – the kitchen.

“Helm” – the steering wheel, the Captain’s driving area. Do not get in the way here.

“Jibing” – the opposite of tacking, when you turn the stern of the boat through the wind so the wind switches to the other side of the boat.

“Lines” – whatever you do, don’t call the ropes, ‘ropes’. Call them ‘lines’.

“Luffing” – when the sails begin to flap and lose their tight stretch, due to changing of direction or loosening the sheets.

“Mast” – the long pole holding the sails and rigging.

“Mainsail” – the largest sail, set by the stern.

“Port” – this is the left side of the boat when you’re facing forward.

“Starboard” – this is the right side of the boat when facing forward.


“Telltale” – the little wind indicator on the sails.

“Tacking” – when you turn the bow of the boat through the wind so the wind switches from one side of the boat to the other.


3. Learn the Basics

If you’re sailing with a skipper, they explain all the basics after you board, but it’s always useful to be prepared. When you’re sailing bareboat, however, and your captain is asking you to trim the sails, it’s helpful to be able to put down your mojito and know what to do.

Here are some basic tips for you and your crew before boarding:

– Know how to read the wind and how to use it

– Know the mainsail, jib and genoa

– Know which lines (aka, the sheets) lead to which sails

– Know how to operate the winch

– Know how to navigate

– And always watch the boom!

4. Pack Appropriately

Packing for a summer sailing holiday is different to packing for a regular holiday. We know they always say to pack as little as possible, but you really have to apply this mindset when packing to go sailing. Swimwear, a couple of t-shirts and shorts, a smart casual outfit, boat-appropriate shoes, and a jumper will be your basic clothing needs.

The same goes for what’s on the outside; leave the bulky, hard suitcase at home – these are not welcome on a sailboat. In tiny quarters, a soft duffel bag or backpack is best.

Check out our ultimate packing checklist for a complete guide.

5. Get off the Boat

Get OFF the boat, you say? That’s right. One of our favourite parts of sailing holidays is getting off the boat. Exploring idyllic coastal towns, secluded islands and ancient cities is the best part of finally arriving somewhere by sea.

If you’re a natural born landlubber and it’s your first time sailing, the chance to depart that rocky boat will be one of your highlights until you get your sea legs. So, on a first-time sailing holiday, be sure to schedule plenty of stopping points and shorter sails on your trip.


Think you’re ready to go? Take a look at our fleet and or start planning with our destination guides. You can also find some great seasonal deals that allow you to save up to 40% on your boat holiday. 


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