A 5-Step Guide to Sailing the High Seas

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Want to go on a boat trip, but have no idea where to start because you’ve never done it before? You’ve come to the right place. Here, we break down the entire boat holiday planning process — from safety guidelines to planning your itinerary — into five easy steps. We’re even tackling the tough-to-answer questions like what to pack for your yacht charter. The world of sailing can feel especially exciting to beginners.

But before we get started, let’s talk licenses and skippers.

AT ZIZOO, WE OFFER TWO OPTIONS: you can either book a bareboat charter (aka a boat without a crew) or book a boat with a skipper (a person who’ll sail the boat).

Option 1: Bareboat

If you choose the first bareboat charter option, someone in your traveling group will need to be responsible for navigating the boat. This means that a designated person will need to have a valid boating license.

Option 2: Book a Skipper

If you don’t happen to know anyone with a boating license, then the “book a skipper” option is perfect for you. With this option, one of our Zizoo-vetted skippers takes over the responsibility of the boat and we provide all the safety amenities needed to enjoy a boat holiday without the stress of safely navigating the seas.

Now that we have the most important logistical hurdle sorted out, keep reading to find out how to prepare for your boat holiday.

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1. Plan Your “Sailing the High Seas” Itinerary

Now, let’s figure out where you’ll start your trip! Deciding which sailing route to take is one of the most important parts of a sailing holiday.

If you’re sailing a bareboat yacht charter (without a skipper), and you’ll be navigating the seas without a guide, you should arrive at the marina with an exact travel itinerary in mind. Have fun with it! The beauty of a bareboat trip is the freedom to customize your route. You are, essentially, your own captain.

One essential consideration you should make when figuring out your itinerary is what and where you’ll eat. When planning your stops, it’s a good idea to plan your meals along with them. Remember, once you begin your trip and you’re many kilometers out at sea, there won’t be an opportunity to pop into a grocery store or restaurant. But don’t look at this factor as a limitation. This is where you have the opportunity to be really creative. You’re on the water, meaning that if you’re a seafood lover you’ve hit the jackpot for the freshest varieties available. If seafood isn’t quite your taste, no worries, your many marinas stops mean you’ll have access to the best local cuisine, whether it’s at a restaurant or at a local market. Whatever your culinary preference, just make sure you know how the saying goes, you can never be too prepared.

Sailing the high seas: learning basic nautical terms boat with rope on water
Sailing the high seas: learning basic nautical terms.

2. Learn the Basic Nautical Terms for Sailing the High Seas

Stand tall and proud on your deck and revel in the greatness of the wind in your sails and the sun dancing on your face. To do so, let’s have you not only looking but also speaking like a captain. Here is our list of basic nautical sailing terms that will have you feeling like an expert in no time. You might even impress your skipper with how much you’ve learned!

  • “Aft” – the front of the boat
  • “Anchorage” – a beautiful bay, cove, or marina where you can drop anchor for the night
  • “Bareboat” – a boat charter without a skipper and crew
  • “Below deck” – the area of a boat where the cabins and galley are located
  • “Bow” – the back of the boat
  • “Fender” – the cylindrical bumper used to protect the sides of the boat when mooring
  • “Galley” – the kitchen
  • “Helm” – the captain’s steering wheel
  • “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” – these are no longer ‘ropes’, rather ‘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 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
Sailing the high seas: learning the sailing basics on a sailboat
Sailing the high seas: learning the sailing basics.

3. Learn the Basics of Sailing

Though sailing with a skipper will mean you’ll always have someone on board to explain all the basics, it’s always useful to come prepared. Knowing a few basics off the top of your head will make your experience a much more interactive adventure AND give you an appreciation for your whole journey when you know you’ve had a hand in steering the vessel. Besides, since you’ve already learned the basic nautical terms, you’ll be able to pick up the sailing basics pretty quickly. Here are some tips for you and your crew before boarding the boat and start sailing the high seas.

Here’s what you should know:

  • How to read the wind and how to use it to your advantage: There are two major ways to do this. You can either read the wind by looking at your sails, or by reading the wind’s affect on the waters. Once you get this down, you can move on to reading clouds and using these readings to predict the weather forecast.
  • The mainsail, jib, and genoa: The main sail is just that: the larger, primary sail on a boat. The jib and genoa are terms often used interchangeably and refer to the smaller secondary sail.
  • Which lines (aka, the sheets) lead to which sails: The best way to figure these out will be through on-the-field experience, but looking at a few illustrations here and there beforehand wouldn’t hurt.
  • How to operate the winch: So, first things first: What’s a winch, you may ask? A winch is essentially a hand crank that lets you adjust the tension on a rope. Learn how to use one and you’ll prove a helpful hand when on board.
  • How to navigate: Obviously, you can’t learn how to navigate a boat the weekend before you go on your trip, but you can and definitely should skim through the basics to get a sense of the lay of the land. You can also download a few sailing apps on your phone to give you real-time numbers on weather conditions, marine traffic, and other forecasts.
  • Last, but not least don’t forget to watch the boom! The boom is the horizontal portion of the rig which can swing back and forth without warning. It can cause serious injury, and even death, so seriously — watch it!

4. Pack Appropriately for Your Boat Holiday

Packing for a summer holiday on the seas is different than packing for one on dry land. As the saying goes, less is more. Swimwear, t-shirts and shorts, a smart casual outfit, boat-appropriate shoes, and a jumper will be your basic clothing needs. The same idea goes for your packing materials; leave the bulky, hard suitcase at home — a soft duffel bag for storage purposes is easier to carry and stow on board. For when you do hit dry land, be sure to bring an outfit or two for a night out on the town. (There’s honestly nothing more relaxing than the feeling of being on steady ground, combined with that of a crisp, clean outfit.) If you’re looking for a more in-depth guide, check out our ultimate sailing packing checklist or the preparation checklist for your next boat trip.

5. Day Trips on Land

One of the most undersold parts of a sailing holiday is the many opportunities it grants you to sightsee several destinations in a single holiday. Once you dock at your marina of choice, you’ll have time to shake off your sea legs and explore what dry land has to offer, including beautiful seaside towns, secluded islands, and ancient cities. If it’s your first sailing holiday, switching between sea and land will give you the best of both worlds! Check out our destination guides to discover what each of our locations has to offer.

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Now all that’s left for you to do is pick a date, destination, and boat. Did we mention there are over 30,000 to choose from in over 500 destinations worldwide? If you’re struck with indecision, you can also check out our Super Deals where you can select from our biggest savings of the moment. Or let one of our holiday planners help you  — just fill out a request form in the right-hand sidebar and someone will be in touch with you for a zero-pressure chat soon.