Planning a cruise: Secrets of successful skippering

When planning a cruise more than a few days out it is rare that the navigation and weather stars align, allowing you to choose your destination, the time to leave and also the time to arrive and have a successful trip. If you think about why a trip hasn’t gone so well you were probably trying to choose more than one of these parameters. You can always choose one. Choose two and you can quickly make problems for yourself. Try for all three and you are very lucky if your plan survives at all.

For cruising in the UK, I think weather is always the biggest factor but there are many others we can consider when deciding where we want to go and how to get there. In reality, many of the skippering decisions we can make that will ultimately affect the success of a trip happen long before we start entering our waypoints into our chartplotters. These decisions we make (or our chartplotters make for us), become our routing strategy.

Some may think strategy is something only racers should concern themselves with, but in many ways, cruisers have just as much or more to gain from good routing strategy. Both groups are trying to get to their destinations quickly and efficiently but in general, those on cruising yachts usually sail short-handed and with crew of mixed sailing ability. Trying to do too much, worsening conditions or a lengthy delay will wear far more heavily on those cruising than on a fully crewed racing yacht.

When thinking about planning a cruise I work from two mantras: ‘Passage planning is an art so there is no harm in trying for a bit of elegance’. The second is a military saying: ‘The plan is nothing, planning is everything’. To me, these come together as: come up with a great plan that you are confident will work and everyone will be happy with. However, don’t hesitate to dump it the second it doesn’t look right – but don’t worry, the planning you did in the first place should stand you in good stead to come up with something that will most likely be equally as good.

So what should we be thinking about when planning a sailing trip? Strategy is a tricky subject as there are rarely clear-cut options to take. It’s easy to go around in circles considering the various factors but the trick is to embrace the challenge.

Even if it’s not clear to start with, ask the right questions and an elegant plan should bubble up, eventually.

Planning a cruise: What do you want to do?

Let’s talk about what we want to do and where we want to go. As the certainty of weather forecasts diminishes after about a week, if your trip is longer than this, your return trip is very much at the mercy of the weather gods. This isn’t a problem if you have lots of time but nearly everyone’s most unpleasant trip usually started because they needed to get back or it seemed easier to head home rather than stay where they were. I think the desire to just head home increases the more experienced you are but do remember your crew. Many people have been put off sailing because they’ve had to sail in what they perceived were horrific conditions.

Get acclimatised

Think about acclimatisation. Unless you sail most days, it always takes a little while to settle back into being on your boat and to get comfortable, cruising fit and work through any boat issues.

I always plan a short trip (no more than four hours) for my first passage after a prolonged break (more than a few weeks). This gives me time to sort things out, run the boat and crew through a few manoeuvres, and still get to somewhere different in the first day or so. Crucially I can assess on a short passage how the crew will cope with what we have planned and if necessary alter it accordingly. If it’s the first trip of the season, I generally don’t leave the mooring for a few days and check and test everything while I just get back into the swing of living on board again.

Come back with the wind

For trips lasting up to a week (about the limit of forecasting certainty), I would always recommend ‘coming home with the wind’. Beating to windward, if you are ever going to do it at all, is much better to do when you are fresh and full of anticipation for the trip to come. Whilst beating towards your destination will take about a third longer than a straight rhumb-line course, if you reef for comfort rather than speed, even a day beating to windward (as long as you are making progress) can be OK early on in a trip.

It’s all about the sea state

Remember it is the sea state that makes things difficult and how the boat moves that unnerves people the most. Short, sharp waves can make things dangerous and unnerving but it doesn’t take long to get used to well-behaved bigger waves when sailing mid-Channel.

Sail a triangle

Linear trips present more planning problems than triangular ones. Rather than head out for a trip along a coast with many headlands and their associated tidal gates, think of a route that has a crossways leg. As an example from Portland Bill, Alderney and Dartmouth are about the same distance away and you’ll be ‘offshore’ for about the same amount of time travelling to either of them. Also, with predominantly southwesterly winds or if there is a prolonged easterly, you’ve a good chance of a better sail back if you head across the Channel. There is a psychological barrier to crossing the Channel but with chartplotters accurately letting you know where you are and when you will get there, it isn’t quite the sail into the unknown that it used to be.

Picking The Tidal Cycle

Think about the cycle of the tides and how they will help or hinder your plans. For example, I much prefer going to the Isles of Scilly on springs. Spring high-tides are in the morning and evenings in the south-west and because distances are short, I can quickly move between islands and not lose a day ashore. Springs also bring the added benefit of being able to see most of the rocks at low tide (which you can go and have a look at when ashore) and also reducing the swell if you are in one of the pools that get cut off.

Conversely, if you haven’t been to the Channel Islands before, going on neaps keeps the tidal streams manageable but the downside is that marina access times are much reduced and around the middle of the day. This all works for me but there will likely be equally valid reasons to go on the other tidal cycle depending on your circumstances – some people prefer neaps in the Isles of Scilly because they can remain afloat in some anchorages that would be off limits during spring low tides. The key when assessing these types of recommendations is to understand the rationale behind them and make the tidal cycle work for you.

Get the transitions right

Be wary of inadvertently making life more difficult than it has to be. Be sure to think about the link points between each main leg as these can often help or hinder. For instance, before a particularly long or challenging sailing leg, try and set yourself up for success. Give yourself the best night’s sleep you can. This may be on a pontoon or buoy to save you getting up to check the anchor; or anchoring may be the best option if things are a little loud in the marina. Leave with the boat in good shape and well-stocked – setting off clean, warm, dry and well-fed will always make any trip a more pleasurable experience.

You can’t have it all

Remember, with our changeable weather, it is a very rare occurrence that you can pick your destination, time to arrive and time to leave with absolute certainty more than a few days out. You can always pick one, two if you are lucky, but be wary of making plans in advance that depend on all three. If you find yourself doing this you may be setting yourself up to fail; for example sailing from a drying harbour to another drying harbour or through a tide race, without an all-tide alternative. It is no coincidence that all of the anecdotes in this article occurred because either the time to leave, time to arrive or the destination was unrealistic.

Increasing miles doesn’t necessarily increase fun

Finally, having said all of the above, remember an increase in nautical miles travelled rarely equals an increase in fun or increased justification for the boat. It is the experience that counts and I think of a boat as having three interchangeable roles. In no particular order (and forgive the analogies). First, it can be a holiday home which doesn’t have to move to enjoy being in it. Second, it is a lovely thing to go out in for the day and just enjoy the art of sailing, picnicking in a picturesque location and just ‘being on the water’. Third, it is the best motorhome I could think of having for travelling far and wide to places new. This gives us many options when all we can guarantee is the day we are going to arrive.

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Consider the crew

Knowing those on board’s tolerance and experience is crucial. Unfortunately, for the majority of people, only by experiencing worse conditions than previously encountered does their tolerance increase. A common mistake is to try and expand their tolerance zone for them. It might work in some cases but get it wrong and they will go backwards. It is a very personal thing. We used to have a saying in the Marines, ‘Go at the pace of the slowest man’. This works for sailing too – having people who are scared and unhappy on the boat does nothing for the success of a trip.

What is the skipper’s role?

The key to a successful trip as skipper is making sure the whole trip sits well within your ‘skippering’ capacity.

I think there are two ends to the skippering scale. One end is that of ‘facilitator’ of the sailing trip, characterised by you being the only experienced sailor on board who pretty much has to do everything. This is by far the most taxing so it pays to be conservative with your aspirations or build in lots of down-time for you to properly relax and not worry constantly about the boat and how much effort you need to put into the next activity. If you don’t, you may run out of steam before you get back. An early indicator of this is you starting to feel the crew don’t seem grateful for the efforts you are putting in.

The other, much less taxing mode, is ‘first among equals’ where you are able to share most of the responsibilities and much of what you ask to be done requires very little explanation or instruction. This other end of the scale is by far the most rewarding and relaxing position to be in as skipper but it’s not likely to occur unless you make it happen yourself. To start with, it takes real effort and patience usually when you don’t have much more of either to give (a good reason for taking it easy).

Instead of thinking about teaching your crew in terms of techniques and skills (the ‘how’), think of it and explain it in terms of the ‘what and why’ and how it relates to them. When reefing for instance, instead of describing the sequence of coloured ropes to let off and tighten, explain the need to de-power the sail so it’s easy for them to slide it back down the mast and tightening the topping lift to stop the boom falling on their heads. It is easy when under pressure to close down and do things yourself. It is well worth the effort to think about how you can usefully include everyone. It won’t take long before those on board have enough knowledge to work things through for themselves.

Planning a cruise: Where and when do you want to go?

How far is it?

Having chosen a destination, the traditional place to start planning a leg is to work out in detail how long it’s going to take. I will stick my head above the parapet here and suggest that this is the only use for any autoroute function on a chartplotter that doesn’t take tidal streams, weather and tidally corrected courses to steer, into account.

How fast will I go?

First you need to have worked out a reliable planning speed. My rule of thumb for calculating it is to plan on 1 knot lower than the speed I notice the boat seems to do when going well. Errors create errors so do confirm the speed you think you do is correct. I use my boat speed through the water but Speed Over the Ground is OK if you’ve removed the tide. I don’t adjust planning speed for different points of sail but would if there are a few knots difference between the respective performances.

Do I have to beat?

Be wary of assuming you can motor at your normal speed when you find yourself in rough seas. Some boats struggle to draw enough cooling water into the engine when heeled or when going over big waves that expose the inlet. Us cruisers don’t tend to beat to windward but it’s surprising how fast a boat will go upwind particularly if the tide is with you. To calculate how long it will take: add or subtract the cumulative tidal stream to or from the straight-line distance, work out the time it will take for that leg using your normal planning speed and add a third extra time; it is surprisingly accurate.

Constraints

Now look for what is going to try and hinder you. Check for constraints at your exit port (often overlooked), the destination port, tidal gates around headlands, big tidal streams, obviously the weather and look at how all of that shapes the contingency plans you will need to build in. Hopefully everything will fit together nicely but sometimes it just won’t, so don’t try to force it.

Try and keep things flexible – try and maintain your options so the time you have to leave doesn’t become the critical factor to the success of the trip.
I also don’t like stacking time gates on top of each other unless distances are short.

For example, having to meet a tidal gate at a headland and also arrive before a falling tide stops me getting over a bar. One problem that creeps up on us is having to be in port before a forecast increase in wind makes a portion of a trip difficult.

Unless I can guarantee lots of time to undertake a journey I would pick a closer destination or not go. Remember, the more experienced you are, the more likely you are to fall into the trap of thinking you’ll get away with it; you may think you have, but your crew may not.

Day or Night?

It goes without saying that doing things in daylight is the much preferred option but for a long time, making landfall was much easier just before sunrise so we could use the lights ashore to orientate us before the land turned into an indistinguishable mass. We used to plan for this. Nowadays, a quick bearing taken from our plotter points us to hopefully what we need to see ashore and we can orientate ourselves from there. However, sail for long enough and there will be parts of your trip you will need to do in the dark.

Remember you probably have a choice about which part of the journey needs to be in the dark. My rules of thumb are to try and not do anything new and try not to leave in the dark. By doing anything new, I mean something like an unfamiliar port entry but it also includes making sure I sail for a good few hours of daylight before the transition into night. This allows time for everything to settle down on board and for everyone to have got into the rhythm of it all before we lose the daylight.

Leaving a port in the dark can be psychologically challenging. First, you are mostly likely going against your body’s natural rhythm of expecting to be winding down (particularly if you have had a bad day which is why you are leaving in the dark anyway) or wanting to be asleep – and that takes effort. Secondly, you are leaving a place of relative safety for something less so.

It is surprising how strong just a light wind sounds and how ominous a dark horizon can look. Combine all of this with a lack of night vision, with no time to develop it as you navigate out of a port, and you can quickly find yourself questioning your wisdom of leaving at all.

Enjoyment not achievement

It’s ironic that with modern-day navigational techniques it is almost the default position to be asked by our chartplotters where we want to go, what time we want to leave or what time we want to arrive. Undoubtedly, navigational calculations and how we track our progress have become much easier but we shouldn’t forget this is just computational output. As skippers, we are responsible for the outcome of our trips and it shouldn’t just be judged in terms of safety. Many a safe trip has been a miserable experience.

Although safety is always paramount, enjoyment should be the aim and with a little forethought, planning and design, we should be able to come up with a reasonably enjoyable trip regardless of the weather and tides. Remember, we should never try and have it all, but if you keep looking, you will definitely find that those rare but enjoyable days are out there.

Planning your cruise

How long?

It is helpful to categorise your cruising plans into timeframes as I think they should be approached slightly differently.

Extended Cruising: four weeks or longer

This is probably the least risky to plan for as long as you don’t expect to take half your time getting there and the other half getting back. Work in weekly stages with a general direction of travel in mind and take the conservative options when heading home. Better to lose a day or two of your holiday and get back in favourable conditions, rather than ruin your trip by pushing it to get back when you know conditions aren’t right.

Long cruise: two to four weeks

I think this is the most complex timeframe to plan for. It’s long enough away to want to push your boundaries and have an adventure but too long a duration to feel that staying local is appropriate. As it’s well outside weather forecasting certainty it’s these long cruises that definitely suit a crossways leg. I prefer to adopt a ‘hub and spoke’ approach – pick an all-weather port that has good facilities and bad weather options and is within easy travelling distance to other interesting places. Then, depending on the weather, day-sail or overnight to other destinations as the weather allows. Most of us anchor and creek crawl with our tenders and this is the same technique but on a larger scale.

Short Cruise: up to two weeks

There is trouble to be found when trying to make the most of a couple of weeks away. Up to a week, a good mantra to adopt is to always come back with the forecast wind (and keep an eye on it).

I think the key is to be conservative. Doing a long leg first is tempting. I always do a short first leg to check the boat and settle and assess the crew. Unless you do it all of the time, skippering is hard work, and planning a week where you are constantly ticking off destinations will not be relaxing.
Crossing the Channel is easily achievable and the hub and spoke approach works but even with 10 days, you will be hard pushed to get to visit more than one hub.

Weekend break: two to three days

I think it is crucial to work with the weather. Sea state and the boat being overpowered in gusts are the biggest factors to consider. We have a few short standard trips we do, depending on the weather and we do them both as a family and also with friends.

When introducing friends to boating it is crucial they enjoy themselves. That means skippering has to be easy (I am also one of the hosts) and I don’t want to have to spend all of my time facilitating or teaching. Just being on the water is often enough for new sailors and with tenders, paddleboards and other toys there is often more than enough to keep those on board entertained.

What is Achievable?

I rarely if ever enter a port I haven’t researched first and always buy pilot or cruising guides for the areas I am visiting. They contain lifetimes’ worth of information and although expensive, I think their usefulness justifies the expense.

When planning, I find it easier to think of destinations in terms of time to get there rather than distances. The following charts highlight locations that can be reached in a single summer daylight passage (no longer than 18 hours) with a planning speed of 4.5 knots.

This may seem a little conservative but as you can see, there aren’t many places you won’t be able to get to. Invariably, in good conditions most of us would arrive in less time than indicated.

When cruising I either choose the start date and let the weather dictate the destination or choose the destination and let the weather dictate the start and end time. I never expect to choose both, but sometimes I will get lucky.

West Country

Plymouth and Falmouth are great hubs to base from with excellent transport links and mooring/berthing options. You could easily explore each harbour by boat for a week in bad weather. Dartmouth is a little less connected but the River Dart is sheltered and amazing for several days’ exploration. The Isles of Scilly is a great destination but shelter is limited if a storm blows up so always have a fall-back anchorage planned and know how you are going to get to it.

Across the Channel

Crossing the Channel can appear a bit of a challenge when you haven’t done it before but the distances involved are really no more than when heading along the coast. The Channel Islands are still my favourite place to go and because winds from the northern sectors are light or shortlived, getting home again often isn’t problematic. Make sure you leave the UK properly. A good source of information is the RYA: https://www.gov.uk/guidance/sailing-a-pleasure-craft-that-is-departing-from-the-uk

Channel Islands

Both Guernsey and Jersey are great destinations in themselves but also good hubs to branch out from. Don’t be tempted to try and ‘do’ all of the islands in one go unless you have more than a few weeks to spare. If you haven’t been before, I’d stick to one island and go on day-sails. The Channel Islands also make a great launch point to explore the adjacent French ports.

France has recently increased the numbers of ports of entry for small boats. Further details: https://www.theca.org.uk/news/france-easier-check-in-out

A question of weather

Using the actual weather for the two weeks following the time of writing, I thought I would create a hypothetical example of where I thought I would go if I was planning a cruise with my wife for a two-week period. I would assume my arrival at the boat on Friday night or Saturday, giving myself Saturday to sort myself out and think about going on Sunday or Monday.

Saturday’s forecast

From the Saturday forecast it looked like a trip from Dartmouth to the Isles of Scilly could be on the cards if we left on Monday. Having already sailed the boat a few times this year we would be happy to head straight out on a longish leg. There was a two-day weather window with SE Force 4-5 winds (about our comfortable limit) to get to the Scillies. All being well, we could leave on Monday morning for the Helford River and the tides worked for a daylight passage to St Mary’s on Tuesday. Two consecutive days is about as much as we would want to sail without a break.

As the wind was forecast to stay light for the following week, with a glorious weekend in the middle it would be worth the initial effort. With westerly winds forecast for the end of the following week (wanting to come back with the wind) and with some added assurance with that being the predominant wind direction, getting back looked workable too.

Once in St Mary’s, we would branch out from there to the other islands after a couple of days.

Sunday’s forecast

By Sunday morning, however, the weather forecast had changed sufficiently to make the trip look precarious. Sunday’s wind remained the same SW Force 4 but the wind was due to increase SE Force 5-6 on Monday before veering SW Force 4 on Tuesday. I worked out that we could probably rush to leave on Sunday and beat, probably to Salcombe or perhaps further, and then on Monday have a very long, spirited sail to the Scillies. The rest of the forecast still looked good for the trip so I could probably justify it.

The problem was Force 5-6 is outside of our self-imposed ‘comfortable’ limits and it would still be about a 24-hour sail. Then came the temptation to change the planning speed. With a Force 5-6 wind behind us the boat will do 6.5 knots. A planning speed of 5.5 knots becomes realistic – that makes it only a 20-hour sail. So still achievable.

And this is the point when I should really be having a word with myself! Setting off short-handed in marginal conditions isn’t relaxing and not much would have to go wrong before we would be having a hard time. Worse, my wife isn’t as experienced as me and a real concern of hers is always her ability to manage the boat should anything happen to me (hence our Force 4-5 comfortable limit). By going for it, I would make her trip deeply uncomfortable – not the best start to our two-week holiday.

Making a decision

But how to make the most of our precious hypothetical two weeks? With the wind picking up on Monday to SE Force 5-6 staying in the River Dart is probably the wisest thing to do. Up the river is sheltered so we could have a night or two at anchor or stay in the town and make the most of shore power to top up our batteries and have hot water. On Tuesday, the wind reduces to SW Force 4 and further drops and goes NW/W Force 2 on Wednesday and Thursday. This would be more than enough of a window to put the Channel Islands in scope.

We could keep an eye on the sea state on Monday and look to go early on Tuesday for St Peter Port in Guernsey or head out on Wednesday, possibly having to motor. We could spend a couple of days in port before using the nice weather over the weekend to explore Herm and Sark or at a push Alderney before returning to Guernsey, either to St Peter Port again or Beaucette Marina at the north of the island. We would need to keep an eye on the wind but the forecast has favourable winds to return to Dartmouth for much of the following week.

Putting it into practice

Dartmouth to the Isles of Scilly

Just as I was putting the finishing touches to this article I was looking forward to a trip from Dartmouth to the Isles of Scilly. A friend had asked me to help him sail there as he was competing in the World Gig Rowing Championships and wanted to use his boat as accommodation. Coming with us was another former Marine who was rowing for another team.

Dartmouth to the Isles of Scilly is 120 miles or a 26-hour trip for us and we had a deadline to be there no later than the May bank holiday Friday morning when the first race started. Needing a decent weather window we looked to keep that whole preceding week free. Ideally, we would have a long sail to either Falmouth or Newlyn and make the shorter trip to St Mary’s from there.

By the preceding weekend, an area of low pressure was centred over Ireland. This was to give us westerlies due to back southerly, increase Force 6-7 on Sunday into Monday before backing southeasterly and die away to nothing on Tuesday into Wednesday.

My crew mates were a Coastal Skipper I had never sailed with before and who hadn’t sailed for a year, and a current Day Skipper who hadn’t done any proper night sailing. Fortunately as both are former Marines, their resilience was a known quantity.

Our Options

Go Monday morning

SW Force 5 increasing Force 7 backing southerly. 2.5-3.5m seas

The two main concerns were how much progress to windward we would make getting around Start Point to begin with and the size of the head-sea for the main leg. Start Point is dangerous in S or SE winds so we would need to go wide. A starboard tack lee-bowing the tide could see us safely out to sea and once past Start Point we could tack and ease off to a fetch as the winds backed. It would be very hard work to begin with but get slightly easier for the rest of the trip. It would be exhilarating in parts and unpleasant for most.

Leave Tuesday Afternoon

SW or S winds Force 6-7 backing southeasterly becoming Force 1-2. Reducing 2-2.5m seas

This looks like a great time to leave if you didn’t take the rest of the weather forecast into account or look at the wave heights. The key consideration was again getting around Start Point. The boat can’t motor into wind in 1.5m-2m waves so we would need to balance using the tide to help us make progress as we beat toward Start Point but arrive when the SW-going tidal stream was easing. The best time to pass Start Point worked out to be around 1900-2000. But this meant we would need to beat to windward and do it well against big waves and, if we were delayed, in reducing wind and light; not an easy combination. Once around Start Point, it would be a nice straight sail in decreasing winds with the hope the sea state reduced enough to allow us to motor before the wind completely died.

In summary, it would be a tricky start, an OK-to-good middle in the dark, and as we were due to arrive in daylight, a good end.

Leave early Wednesday morning

SE to SW Force 1-2. Reducing 1.5m seas

As the wind was due to drop completely it would be helpful to use as much of the tide as we could to get around Start Point. The sea state was of concern and we would need to balance the tidal stream going against the residual swell at Start Point but we would know pretty quickly if that was going to be a problem. The downside was we would be off Land’s End in the dark and would need to be careful around the traffic separation scheme. It would also mean an 0500 start (daybreak), which meant not the best night’s sleep the night before and it could mean a night entry into Hugh Town.

Other Considerations

For all options we could use either Plymouth or Fowey (a bit out of the way), Falmouth/Helford River or Newlyn as all-conditions ports of refuge or as stop-overs. Issues at The Lizard were considered for Monday but discounted for Tuesday and Wednesday because winds would be light and we could stay offshore. We would also use the St Mary’s Sound route to Hugh Town as to me it seemed the easiest to use at night.

We also had planned New Grimsby Sound as a secondary location if we needed it, but would have had to have waited for the tide to get over Tresco Flats. Finally, I was coming home once we got there and pointedly didn’t book my ferry ticket as I knew it would affect any decision I would make if we needed to adjust the plan.

What we did

It was a unanimous decision not to go on Monday. I’m sure we would have made it but it wouldn’t have been good preparation for the gig championship.
We seriously considered Tuesday, but I disliked it because my biggest concern was the real possibility of finding out that we couldn’t all beat to windward in what were tricky conditions.

I felt this wouldn’t have really become apparent until we were offshore, heading around Start Point probably in fading light. Worse, we then wouldn’t be able to motor in the big seas which would have made for a miserable night lolling about.

Although none of us wanted to motor, in the end, going on Wednesday appeared the least worse option and was the one we went for. The wind did blow itself out quite quickly on Tuesday afternoon and we would most likely have struggled to motor. As it was, the sea was much reduced by Wednesday and we had no problems chugging our way west.

It was a dull and uneventful trip but fortunately in good company. We only managed to sail for about an hour. We arrived slightly earlier than expected in the dark and we tied to a buoy just as daylight broke on Thursday morning. Whilst we achieved the aim – we got to the Isles of Scilly on time – it won’t go down as a great trip. Despite giving ourselves what we thought was enough of a weather window, our set destination and date of arrival forced our hand.

From Saturday the wind went easterly and had we set off on any day that following week, we would have had a great sail. To our relief the winds reverted to southwesterlies by the following weekend and we had our best sail to date this year heading home.

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