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How to get first-time skipper experience and prepare yourself for sailing

How to get first-time skipper experience and prepare yourself for sailing


Yachtsmen often say: "If you put to sea, you need a license, and if you want to return, you need knowledge".

Obtaining a license is not a problem, what is difficult is to sail a yacht properly, even for experienced skippers. You have to consider big winds, steering failure, anchor cables fouling, etc.

A novice skipper may panic and make a mistake, therefore putting the crew’s life and sail safety at risk. Before you sail alone for the first time, you better get some experience. You may take part in a sailing school’ training trip, become a member of another skipper’s crew, or participate in a flotilla.

In this article, we will tell you how to prepare for your first sailing alone. The next article will be dedicated to the most suitable routes for unexperienced skippers.

Where you get the first sailing alone experience

Practice plays a big part in boat sailing as well as in car driving. You have many options on how to get a record in the logbook and build your nautical miles. The simplest and most available options are:

1. Sign up for a school training trip

Many sailing schools offer trips and expeditions that may become your first skipper experience. Routes vary in difficulty, giving access to the most spectacular places on the map. You may take part in a training trip along the coastline of Italy, an expedition around Iceland or a yacht delivery across the Mediterranean Sea from one regatta to another. The more difficult the conditions are, the more you can learn. You will get the knowledge of how to sail a yacht in variable winds, in different tidal conditions, face all sorts of navigational troubles. You can monitor the wind in real time on live wind map.

The advantage of training trips is that a captain you sail under is not only an experienced skipper but a certified instructor. Their mission is not just to sail but impart their knowledge and skills to the others.

Besides, if you have been trained at the same school, you would probably with the captain, it will be easier to find a common language. In addition, such schools usually offer discount programs to their graduates.

These schools often offer all kinds of training trips:

2. Sail with more experienced captains

On the Internet, you can find many offers from captains for those who have a skipper license and little yachting experience, especially when they need to urgently find a crew member. You can search for such ads in social networks, yachting groups or captains’ personal pages.

From time to time experienced captains search for mates for sailboat transfers or regattas, where an extra pair of hands comes in useful.

Newbies just need to pay for a ticket and meals. You will have a great opportunity to practice and build your nautical miles, besides your skillful work may also be awarded. But mind that new crew members are often accepted by referral. On your part, you should be careful with captains you do not know, especially if they offer some dubious affairs.

3. Go to your first charter

Old whales say: you become a captain only when you charter a yacht by yourself and take all the responsibility. You may gain experience as a deckhand, but it is incomparable with the role of a skipper. What are your options?

Sailing on your own. How do people sail alone for the first time? Some novice skippers are so confident that they rent a yacht and put to sea right after the sailing school graduation. It is okay. If you are one of such bravehearts, just make sure that you have enough knowledge and skills to manage a sailboat and a crew, and not just in perfectly calm waters. For a start you should rent a small yacht, for example, 34-36 feet long. It is much easier to manage and moor.

Sailing under the mentor skipper. A safer option is to take a mentor to your first trip – an experienced person, who would control how you deal with the duties of a skipper and come to assistance should any difficulties occur. You take all responsibility, you make all decisions, but you will be able to call for the advice of a more experienced skipper.

4. Taking part in a flotilla

Another variant is taking part in a flotilla in which a group of chartered yachts set sail together on the same route. It is usually led by an experienced captain, the rest of the skippers follow his path. You rent a yacht by yourself, recruit a crew and run alone. In this case you really feel freedom at the helm, and a flotilla organizer takes care of many issues, making your skipper life easier. You sail on a proven route, all hidden rocks taken into account, and also participate in the evening master classes for novice skippers. In such conditions the risk of doing something wrong, breaking something and, as a result, losing a deposit paid for the boat is minimal. After that you will be able to sail confidently and without assistance.

Flotillas may be organized in yacht schools, charter companies or by private captains. For example:

There are also international websites (and applications) that help captains and crew members find each other. The formats and conditions for participation may vary. You can find positions both for professionals (paid) and beginners:

What is special about the route for novice yachtsmen

If you have little experience, you should choose waterways comfortable enough to strengthen your sailing skills. Which parameters should be considered here?

1. Safety

Do not sail far away from the coast. (By the way, this is how the Portuguese sailors made their way to Asia during the Age of Discovery: they sailed along the coast of Africa.) If something goes wrong, the official services or other yachtsmen will have enough time to rescue you.

In any case, find out the main types of life-threatening incidents that can happen to you on board to avoid them. According to the Boating Safety Guide of the Brown and Crouppen Law Firm in the US, these include "сollision with another recreational boat or fixed / submerged object, grounding, capsizing, falling overboard", and many others.

Speaking about the latter, "the vast majority of boat accident fatalities in 2021 were by drowning (81 percent), and 83 percent of those who drowned were not wearing life jackets."

Take the short routes with enough anchorages, where you can stay at night or hide in case of bad weather. You may use wild bays, protected from the wind and waves, or fully-equipped marinas. Study the pilot book carefully so that you always have an alternative where to anchor or moor.

For example, in high seasons there are stores of boats around many popular ports. If you arrive late or have not booked a place in advance, you will have to look for an alternative. You should study water areas in specialized literature (printed, not electronic), paper maps and also in applications like Navionics Boating. These are the basics that all yachtsmen use. There are also applications for online booking, for example, Navily (worldwide), MySea (worldwide), ACI Marinas Berth Booking (Croatia).

2. Well-developed infrastructure

Sailing is much more pleasant when it is comfortable. In marines you can always be helped to moor. Such assistance is very valuable, especially when the superyachts of billionaires swarm around, it is scary to pass them by, let alone mooring nearby.

Yacht marinas are perfectly equipped: they have a shower, toilet, water supplies, electricity, restaurants, where you can have a dinner after a hard passage.  Besides there are supermarkets, yacht shops or chemist’s within walking distance.

An additional advantage is when the locals speak your native language or at least are fluent in English.

3. Stable weather conditions

Even an experienced skipper gets exhausted if the weather changes five times a day and squalls come suddenly. It usually happens because of local hard topography, waterway peculiarities or an adverse season.

For example:

  • Crossing the Bay of Biscay is not an easy task even for a trained crew, especially in late autumn or winter when hurricanes may occur. It is no use hoping for ideal conditions. Yachtsmen may wait for a favorable forecast for a whole week.
  • In summer the weather in the Mediterranean Sea is quite stable and predictable, but in inter-season and winter yachtsmen way face some certain unpleasant surprises.

You should monitor the forecast carefully in order to avoid undue risks. It is better to wait out in a sheltered marina for one day than to try to “punch through”. Why tear the sails and exhaust yourself and your crew? A raging sea is not the best place to search for thrills, especially for a novice skipper. In order to monitor the forecast, you may use the application, where you simply need to open the SAIL weather profile.

4. Coherent navigation in water areas

There are different sailing areas varying in difficulty. The routes may include fairways, canals, locks, the ship traffic is very busy there. For instance, in the English Channel, a commercial sea route, a yachtsman meets about 1,000 nautical signs, and it is rather difficult to pass the channel (especially in the night). In the Bosphorus it is better to use the services of a marine pilot who knows the water area.

In such places you will need all the knowledge about tides, streams, navigational signs and COLREGs (International Regulations for Preventing Collisions at Sea) acquired at a sailing school. But recognizing warning signs on the map and distinguishing running lights is one thing, and handling a situation is another.

Among the main challenges for a novice skipper are drops of depths, where the risk of running aground increases, and also high tidal fluctuations. In Europe the strongest fluctuations are observed in the North Sea (northern Atlantic coast of France) and off the coasts of Holland and Belgium. If you miscalculate the time of tides from the tide table, it is easy to get trapped, because the entrance to some marinas is only available at certain hours when the water reaches the desired level.

If you are not ready to complicate your skipper duties, it is wiser to choose simpler waterways where the depths are even, all underwater cliffs have long been marked on the maps, and tidal fluctuations can be neglected. For example, Fethiye Bay or Turkey.

How to plan a voyage

While sailing, a captain needs to keep a huge amount of information in his mind, solve numerous problems at a time, so the better you are prepared, the easier the voyage will be. What exactly should you do?

1. Define goals and objectives

You should better write them down: what do you want to get from the campaign in the whole? What skills are important to you in the first place? Do you want to build as many miles as possible or rather visit interesting places on the route sailing at a leisurely pace? And so on. Just ask and answer these questions to yourself before the trip.

Your crew wants to be aware of all your plans and intentions. Anyone would be disappointed, if you promised a sunlit deck, warm sea, ice mojito and nightclubs on the shore, and in the end the crew would have to wrap up in waterproof during long passages and practice storm tactics.

2. Study the water area

Today you can get access to all necessary information as well as technical capabilities, so:

  • read books and websites;
  • download applications with detailed maps;
  • request feedback from experienced skippers who have already traveled the same route;
  • inquire what time of the year is more suitable for travelling, what local specifics should be taken into account;
  • take note of any useful advice and recommendations, addresses of charter companies, lists of cafes, phone numbers of
  • drivers or interpreters – you never know what and when will come in handy;
  • think about how you will take meals, where you will buy the basic products and drinking water, how often you will be able to provide yourself with food.

3. Select and plot a route

Voyage planning is an essential part of any yachting school program. For that you will need planners or applications, such as Navionics Boating, where you can plot your route and make up an approximate daily schedule.

You will have to calculate how many miles and hours an average passage will take, where it is better to stay overnight, define the most difficult spots on the route.

4. Find a reliable charter company

If you do not have your own yacht, it is worth finding a company that has a good charter fleet. It is better to study several companies and compare their offers and conditions. You will thereby have a possibility to choose a yacht suitable for your trip at a reasonable price. It can be a single-hull sailing yacht or a catamaran. The newer the yacht, the less technical problems it will have.

Here it is important to answer these questions:

  • Do these companies maintain their boats well? Do they keep the yachts clean and in good condition?
  • Do the companies have all the documents and licenses?
  • Is your boat driving license enough or not?
  • How do the companies perform the delivery and acceptance of vessels?
  • Are there any additional costs?
  • Do they have insurance for their vessels?

Charter business specialists will help you find the answers to these and many other questions. First of all, explore the recommendations of friends and acquaintances, search for positive feedbacks. Do not accept any questionable offers from little-known companies. And trust your intuition, but only if you have no other opportunity to get recommendations or feedbacks.

5. Prepare documents

In order to charter a yacht, a skipper must provide a valid boat driving license for this type of vessel - International Bareboat Skipper Certificate.

Most sailing schools work according to international IYT (International Yacht Training) or RYA (Royal Yachting Association) systems, there you can take a 2-week sailing course, and that will cost 950 euros (RYA courses are held in English only). These are the most popular courses for future yachtsmen. Earlier we compiled a list of schools and reviewed popular sailing licenses.

A basic sailing license allows for daytime coastal navigation with family or friends on a yacht up to 78 feet long. It is also enough for chartering a yacht in most countries of the world.

Depending on the country, the charter requirements may vary. For example, in Turkey it is enough to have an IYT International Bareboat Skipper license, in Greece you will need a certificate of no lower than Yachtmaster Coastal level. In many European countries an ICC license is required, and at least one of your crew members must have a VHF certificate.

A skipper also needs to obtain a yacht insurance. It is very important especially for inexperienced captains.

A transit log for the entire crew is issued before the voyage. It is a special document needed for entering the waters of certain countries. It “opens” and “closes” the borders. Yacht agencies and charter companies usually take care of this. To obtain a transit log it is necessary to provide a list of crew members and their passport data.

And of course you must have a valid visa of the state which you are travelling to. You can check whether you need one on the websites of embassies, consulates and visa centers in sections like “Visas for Foreigners” and such.

The basic minimum of documents:

  • International Bareboat Skipper License or higher;
  • Yacht Insurance;
  • Yacht Charter Commercial License;
  • Transit Log;
  • Visa.

6. Download useful applications

While you have access to fast Internet at home, you should select programs and applications that may be useful in a yacht trip:

  • Navionics Boating (iOS, Android) is perhaps the best digital atlas, with detailed descriptions of waterways.
  • Windy App (iOS, Android) shows the current weather forecast which will always be at hand (it can be used offline).
  • Anchor Alarm (iOS) и Anchor Mate (iOS) or Anchor Watch (Android) allow to sleep peacefully overnight – the signal will inform you of the danger immediately.
  • Tides Planner (iOS, Android) helps to predict the tidal changes correctly.

7. Make a list of useful things

Any member of the crew and especially the captain should pay attention to their equipment. This refers not only to clothes and personal hygiene means. Some items are better be brought along, if you do not want to look for them somewhere or lend:

  • a hand and head light
  • a multitool
  • walkie talkie
  • water hose adapters and universal adapters
  • a 12V triple adapter
  • a mask for diving
  • a lighter
  • small carabiners
  • scotch tape and an adhesive tape
  • extra ropes
  • sewing kit

You should also have a first-aid kit with medications for seasickness, ointments for burns and cuts and so on.

8. Take more experienced yachtsmen on your crew

Of course, you can manage a sailboat alone, especially a small one, but it is rather complicated, slow and inconvenient. Consider taking at least one or two yachtsmen to become your mates during the trip. If you have studied together at a sailing school, it will be even easier to understand each other. They may be your acquaintances who have taken part in cruises or regattas; they may know how to handle certain situations on board. Or they may be familiar with an upcoming voyage route. They are not afraid of seasickness and take a strong roll of a yacht easier than those who sail the sea for the first time.

9. Solve the meals issues

  • Decide where and how the team will take meals, on board and on land.
  • Find out where it is better to buy food and drinking water; how often you will have an opportunity to resupply on the way. Find out which restaurants or cafes you can visit if the crew will not be willing to cook on board, check their menus.
  • Take more water - at least two liters per person per day.
  • Ask experienced skippers what you should take with you from home if you are used to specific or rare products and drinks.
  • Take provisions for future use, but find out if there is a refrigerator on your boat. For example, most cruise sailing yachts do not have a freezer, so taking a week supply of meat or chicken is a bad idea. Vegetables and fruits also go bad quickly, but cereals, pasta and canned food remain in good condition for the whole trip.

10. Set a budget (Ship’s fund)

Ship's fund represents total expenses of the crew during a voyage. The amount of the fund depends on certain situations. The expenses usually include:

  • fueling (sailing yachts need less fuel than motor yachts)
  • mooring rent, including electricity and rewatering
  • food and water
  • household items
  • other expenses

On average a one-week-long cruise goes for 150 euros of additional costs per person. If a yacht is chartered, you are required to make a security deposit to cover possible expenses in case of breakage; it is returned if everything is fine. Usually it comes to 2000-3000 euros. This amount is shared by all members of the crew.

11. How to improve skills and sail more confidently

With every trip our experience will grow and you will probably want to explore more complicated waterways, discovering an amazing sailing world.

There are certain steps for skippers who already have an International Bareboat Skipper license and want to improve their skills.

For example, according to the IYT system:

  • IYT Yachtmaster Coastal is a coastal yacht captain, who is allowed to sail not only at daytime, but also at night.
  • IYT Yachtmaster Offshore is a sea captain who is allowed to sail up to 150 nautical miles from the coast.
  • IYT Yachtmaster Ocean is a captain for whom all the oceans of the world are open.

Anyone can enroll in the International Bareboat Skipper course, but there is a number of requirements for an applicant who wants to join a Yachtmaster program. You must have a certain number of nautical miles in the logbook; besides you need to confirm your experience as a skipper, and provide a medical certificate.

Along with standard programs you may take master classes which are held in the evenings or on weekends in local yacht clubs and various marinas. For example, “Racing Practice” courses, where legendary athletes, masters of sports, prize-winners of international competitions and participants of the Olympic Games share their experiences.

The real skippers study throughout their lives, always learning something new about sailing. The more knowledge and experience you get, the more confident you become as a skipper, even in the most difficult situations.


  • In order to officially charter a yacht as a captain and travel around the world, you need an International Bareboat Skipper license. It can be obtained at any yacht school based on international IYT or RYA systems. A course costs 950 euros and lasts two weeks.
  • The four main ways to gain practical experience after studying at sailing school are: enrolling in a school training trip, sailing with more experienced skippers, going to your first charter and taking part in a flotilla.
  • Routes for beginners differ from those for experienced skippers. They are safer, they have a well-developed infrastructure, stable weather conditions and coherent navigation in water areas. You should also choose a reliable charter company to rent a yacht.
  • While selecting and plotting a route, pay attention to the goals and objectives and the water area; take more experienced yachtsmen on your crew, check the yacht carefully. Take useful things on board, install the Windy App application for navigation and weather tracking.
  • After gaining the first experience you can improve your qualifications by taking additional courses in one of the international systems: IYT or RYA.


This post was originally published on the blog on August 5, 2019.

Text: Alyona Shkarupeta, professional sailing writer and specialist from Turkey. Ivan Kuzentsov contributed to this gudie

Cover photo: Unsplash

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