Skippering a boat for the first time needn't be daunting, as long as you prepare. Matthew Diggle reveals how to make a success of taking charge

It’s a pity that skippering a boat for the first time can seem so intimidating.

Not much beats the feeling of being in charge of a yacht, deciding where to go, and taking the crew on an adventure.

And there’s a real sense of accomplishment at the end when you bring the crew and boat home safely.

For anyone who is new to sailing or who crews for someone else, following the RYA training path and becoming a Day Skipper is an excellent way of taking your sailing to the next level.

A moored yacht

As you gain confidence you can start to charter and explore new cruising grounds. Credit: Matthew Diggle

It shows that you understand the fundamentals and can take on more responsibility when other people feel daunted by the thought of being responsible for a boat and its crew.

With a bit of preparation and planning, skippering is well within most people’s capabilities, especially if you don’t bite off more than you can chew for the first few trips.

Preparation is the key. Simply put, you have to decide where to go, who to go with, and how to get there.

I thought it would be useful to share the lessons I’ve learned when I first started skippering for those considering taking their first steps.

Skippering a crew

Sailing boats are not particularly spacious down below so I generally don’t try to fill every berth onboard.

Even so, it is vital that the crew can get along together and this means that you have to choose who to invite carefully.

This is often a bit of a juggling act, trying to coordinate different people and boat availability, so in the end you’re unlikely to be able to please everyone.

Just offer some reasonable options and hope for the best.

A crew standing on a pontoon by a white yacht

Careful crew selection will contribute to a happy trip for all. Credit: Matthew Diggle

It is also important that people know what to expect, so they don’t sign up thinking that they’ll have a spacious cabin with en-suite facilities when they’ll actually get a space in the shared forepeak in a boat with a single heads.

Similarly, being clear about the nature of the trip – that this is your first time skippering –  will avoid adrenaline-junkies being frustrated by a gentle coastal cruise, or nervous novices being scared rigid during an offshore passage.

When skippering the first few times, it is well worth inviting an experienced and knowledgeable sailor to act as first mate.

But you should choose them wisely as you don’t want anyone who will take over or boss you about if you’re a bit slow working something out, or don’t do things in exactly the way they would.

What you really need is a calm and supportive person who will give you the space to experiment, have a quiet word in your ear if they are concerned that something is wrong, but who is capable of taking over if you are incapacitated in any way.

After all, you have to trust them to come back to pick you up if you have the misfortune to fall in, and you must be confident that they could get the boat and crew to somewhere safe if needed.

A man helming, while the skipper looks out to sea

A competent first mate will make your life as skipper much less stressful. Credit: Matthew Diggle

In return for the safety and security they provide, you should listen carefully to what they say and pay attention to their skippering advice.

You should also make it clear to the rest of the crew who the first mate is and that they may have to assume command.

It is also sensible to ensure that not all the crew are novices.

Coaching new crew is time-consuming, and sometimes time is in short supply.

It also takes up mental space while your head needs to be concentrating on skippering the boat.

This is especially true when coming into a berth.

Having one or two people capable of handling the fenders and warps will avoid the sort of situation I got into on one of my trips where I didn’t notice the crew were busy trying to remember how to tie the fenders so that when I got the mooring slightly wrong, they didn’t see we were drifting towards another boat and I ended up shouting.

In the end, someone from the other boat pushed us clear, but it definitely wasn’t my finest hour as skipper.

A crew of a yacht standing on the deck

With the crew briefed and kitted up, you’re ready to sail. Credit: Matthew Diggle

I usually send round practical information about arrangements, including advice about what to pack (and what to pack it in), about sharing cabins, what we will do about food, and also some reassuring words about the safety equipment on board.

More experienced crew members will probably already be aware of some or all of these things, but it is a good idea for everyone to have the same information so that there is a common starting point.

But I usually throw an extra sleeping bag in the car and make sure I check everyone’s equipped before setting off, just in case.

Organising a planning meeting, arranging to share lifts to the boat, or making some other excuse to get people together beforehand is a good idea.

The better people know each other, the more smoothly the trip is likely to run.

Encourage people to use email or social media to communicate, but make sure you ask for permission before sharing email addresses or phone numbers.

Keep your first skippering trip in familiar waters

Although it might be tempting to go exploring, you will probably have enough to think about without having to navigate around somewhere entirely new.

Indeed, the Day Skipper qualification says that you are only competent in ‘familiar areas’, but even here you might find yourself sailing from a marina or harbour you’ve not visited before.

If this is the case then do some research to get an idea of what to expect.

A skipper wearing a red lifejacket looking towards land from the cockpit of a yacht

Sailing in familiar waters will let you focus on skippering rather than navigating new hazards. Credit: Matthew Diggle

When you pick the boat up, take the opportunity to chat with the charterer and people on other boats nearby to get some local knowledge.

They’re likely to regale you with anecdotes about other visitors who have come to grief in one way or another.

Don’t let these tales put you off, just listen carefully and then you won’t feature in their next story.


Unless you have a particularly trusting boat-owning friend you will probably also need to use your Day Skipper qualification to charter a yacht.

Again, you are better settling for something which is not too adventurous or enormous.

This is not the time to have to deal with something much bigger than you’re used to or with extra sails, rigging, or masts that you’re not accustomed to.

The cost of the trip

One of the first practical aspects of arranging a trip is to sort out the finance.

You will need to cover the cost of the boat, together with mooring and fuel, and then decide whether to include food, meals out, and drinks.

I find that the simplest option is to share all the costs equally, and the first step is to prepare a rough budget so people have an idea of how much the trip is going to cost.

It’s generally better to over-estimate and then give people a small refund, rather than to try to collect an extra few quid from everyone at the end of the trip if, for example, there was a lack of wind and so the fuel costs more than you expected.

You also need to consider what to do about the cost of any damage.

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Do you trust everyone to stump up or would it be easier to include insurance in the basic cost of the trip?

You may find that potential crew are rather more enthusiastic about coming on a sailing trip in theory than they are in practice.

Asking them to pay a deposit when booking and the rest closer to departure is a good way of gaining commitment and preventing them from cancelling at the last minute.

Finally, record all expenses and payments so that everyone can check the figures and see that things have been divided up fairly.

This should help prevent disagreements.

There are a number of apps to make both the sums and payment straightforward.

Safety procedures

You are responsible for everyone’s safety and you should take this seriously, but in fact this usually isn’t too onerous if you are sensible and careful.

If you charter a coded vessel in the UK then it will come with a full set of safety equipment appropriate for its cruising limits.

All you will need to do is find where everything is stowed and familiarise yourself with specific details of the lifejackets, jackstays, and so on when you pick the boat up.

Then make sure the crew know how to use it, and do so at the appropriate time.

A fire extinguisher onboard a yacht

Brief the crew about safety equipment on board. Credit: Graham Snook/Yachting Monthly

I ask for an emergency contact number for each crew member, and in return let them have details of a shore contact.

I also ask crew members, in confidence, about any medical conditions that might affect them on the trip.

If someone falls ill you don’t want to be scrabbling about trying to find out if they have an inhaler or medication that could help.

Similarly, if you have to hand them over to an ambulance, the medics are likely to ask if they are allergic to common medicines.

There’s no need to share this with anyone beforehand, but I like to leave a copy with the shore contact and let the first mate know where the info is on the boat, just in case it were to be needed.

Catering for your crew

The first step when planning what to eat onboard is to check everyone’s allergies, likes, and dislikes.

With a modicum of thought it is quite feasible to cater for vegetarian, gluten-free, and other diets without making things too complicated.

There’s certainly no excuse for only offering a vegetarian crew member cheese sandwiches for every meal.

A crew eating dinner on a yacht

Good food on board boosts morale and can be a highlight of the trip. Credit: Matthew Diggle

On short, coastal trips I usually just cater for breakfast and lunch, and aim to eat ashore most evenings.

However, I like to have a simple ‘emergency meal’ on board, such as pasta and a jar of sauce, to make sure we can have a hot meal even if we end up at anchor rather than in a marina as planned.

I find that snacks, fruit, and biscuits are always welcome, and distributing a few chocolate bars can really lift the spirits during a hard slog or a long beat to windward.

Navigating your first trip

Once you’ve selected your crew, booked a boat, and decided on a cruising-ground, it’s time to start on the detailed preparations.

It is worth putting some effort into making the actual trip as straightforward and stress-free as possible.

Skippering means you’ll have lots to think about, so take any opportunity to ‘cheat’ by preparing things beforehand.

Your RYA training will have taught you how to work out tidal depths from the tables in an almanac, but why not print out some tidal curves for the time you’re away, in particular for any marinas you’re thinking of visiting?

Planning and navigation software packages can do this well in advance, and you can find information for the next few days online.

After all, you can still do things the traditional way if you want to impress your crew (or just to prove to yourself that you remember how) but if things are going wrong or time is short then having ‘one you prepared earlier’ can be a literal life-saver.

Weather forecasts

Similarly, you can download weather maps and forecasts for the next few days before setting off.

Obviously, things will change so you will have to re-check the forecast every day, but having a feel for the general weather pattern should help you decide whether to turn left or right when you leave the marina on the first day.

Unless you’re feeling particularly masochistic or determined to experience ‘life at an angle’, it’s not very clever to spend the first half of a trip on a hard beat only to find the weather system passes and you spend the second half on a hard beat back again, when setting off in the other direction initially would have resulted in a pleasant cruise, both ways.

A yacht sailing through waves

Plan a couple of route options in case the weather changes. Credit: Matthew Diggle

Finally, get hold of any information you can about places you might visit or that you might want to have in reserve as bolt-holes.

Printing out some sketch-maps and pilotage notes can help you stay up on deck rather than spending time below checking the charts.

Share your plan with the crew, but make sure everyone knows that you might have to revise it due to things like a change in the weather.

Picking up the boat

Try to pick up the boat before the crew arrives.

Taking the inventory and doing the handover is much easier if the boat is not full of people and all their kit.

Then put the kettle on ready to give the crew a warm welcome.

If you’re parking a car at the marina then it is sensible to leave as much stuff in it as possible, particularly bulky bags and rucksacks.

A set of dry going-home clothes (and shoes) together with a dry towel and a bag for damp kit is a good idea if you think you might arrive back cold and wet on the last day – and if you’re sailing in the UK that is pretty likely!

Briefing your crew

Brief the crew before setting off.

Keep this simple and to the point; you don’t want to worry people, but it is important to point out the key things.

I usually include:

  • Lifejackets and tethers
  • Fire prevention and extinguishers
  • Galley and gas safety
  • First-aid kit
  • How to turn off autopilot
  • Using winches safely
  • Starting the engine
  • VHF radio and sending a DSC mayday
  • Using the heads

Give a briefing that is appropriate for the crew, so you might have to have a couple of different briefings or even give one to the experienced people and get them to brief it on.

It’s a good idea to show people how to use pontoon cleats before setting off, rather than trying to explain this at the end of the day.

Other things about sailing the boat can be introduced gradually over the course of the day.

Consider having simple standing orders to make it clear what’s expected of the crew.

These should include rules about wearing lifejackets and tethers, such as ‘whenever you want to and whenever I tell you to’.


Remember to let your shore contact know when you set off, and also when (and where) you arrive.

Using the RYA SafeTRX app is a great way of ensuring that they are alerted if you’re overdue and it can also produce records of the trip that the crew may find interesting, but do keep your mobile charged during the trip or you might not be able to close the trip when you arrive, leading to possible confusion or concern.

When skippering, try to keep everyone involved in running the boat.

In challenging conditions it may be prudent to limit some tasks to more confident and experienced crew, but don’t let them dominate and hog the helm or other exciting jobs the rest of the time; make sure that everyone gets a turn.

Remember to be positive about everyone’s efforts, patient if you have to explain things, and gentle if you have to correct someone.

After all, they’re here to enjoy themselves and a harsh word may put someone off ever sailing with you again.

A crew member in wet weather gear

If you can, go with the wind when it blows up. Your crew will thank you. Credit: Matthew Diggle

Keep an eye on the crew so you’re aware if anyone is starting to suffer from seasickness or is getting cold, and deal with it before it gets too bad.

I find that putting seasick crew on the helm or persuading them to lie on a bunk with their eyes closed usually helps.

Hot drinks and an offer to pass up warmer clothes will help a cold crew member who is, perhaps, avoiding going below decks.

You are in charge of the boat and part of skippering is to ensure the crew have confidence in you.

So, remain calm at all times, or at least appear calm while you work out what to do next.

Don’t dither, it’s your responsibility when skippering to make decisions and when faced with a choice almost the worst thing you can do is nothing.

On the other hand, don’t be afraid of changing your plans if conditions change.

Don’t sail on regardless, hoping that things will turn out alright; shorten the trip if the crew are struggling, change the destination if the wind shifts.

Final words on first time skippering

Matthew Diggle, skippering for the first time

Matthew Diggle started sailing after signing up for the 2011-12 Clipper Race. Since then he’s cruised in UK waters and off the Italian and Croatian coast. Credit: Matthew Diggle

It’s always worth having a debrief at the end of the day and of the trip to reflect on what people enjoyed, learned or didn’t understand, and hopefully this will help ensure everyone leaves happy.

As a skipper you are allowed to have fun too, but it is different to going on a trip that someone else has organised.

It may seem hard work and a little daunting to start with, but you’ll get into your stride after only a few trips.

I find it immensely satisfying when crew tell me that they’ve enjoyed a trip, that they’ve learned new skills, and, most of all, that they want to come back.

So why not start planning a trip and gathering a crew now?

First time skippering checklist


  • Select crew with similar expectations
  • Mix of abilities and experienced first mate
  • Set expectations of boat and plans early
  • Email joining instructions ahead of time
  • Take a spare sleeping bag and waterproofs
  • Meet up before the trip if possible
  • Share shore contact details for the boat and get emergency contact for each crew

Cruising grounds

  • Stick to familiar areas for first-time skippering
  • Research new places you want to visit
  • Get some local knowledge from charter company or marina


  • Charter in an area you know
  • Opt for a modest-sized boat that will be easy to sail
  • Stick to white sails and don’t worry about spinnakers
  • Arrive before the crew to settle in


  • Decide what costs you will cover, and what you will split
  • Be clear with your crew about how much it will cost
  • Include a margin for extra fuel, and refund if possible
  • Ask for a deposit so crew commit


  • Check the boat has all the necessary safety equipment and where it is
  • Brief your crew on safety gear and procedures, above and below decks
  • Check if crew are on medication or have medical requirements
  • Check and fit lifejackets
  • Establish standing orders of when to wear lifejackets, who is in charge, and who first mate is


  • Check for crew allergies, likes and dislikes
  • Decide if you’re cooking on board or eating ashore
  • Have enough for breakfasts, lunches and a back-up meal
  • Take plenty of snacks, tea, coffee and milk


  • Print out tide times, tidal curves and weather forecasts beforehand
  • Plan a couple of route options to cover different weather scenarios
  • Aim to make the first sail an easy one
  • Prepare pilotage for new places you plan to visit


  • Let shore contact know plans/use RYA SafeTRX app
  • Share and rotate roles among crew
  • Look out for bored, cold or seasick crew
  • Distribute snacks and drinks regularly
  • Keep an eye on the big picture – passage plan, weather, navigation and safety
  • Teach crew if you have time, but don’t be distracted
  • Discuss plans, but you make the final decisions
  • Debrief at the end of the day and of the trip

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