Tips for New Skippers on Their First Charter

In my experience, the difference between a stressful holiday and a genuinely enjoyable one usually comes down to attitude, preparation and a few simple habits you can start from day one. I’ve spent the last decade giving tips to new skippers and helping new sailors get to grips with their yacht and crew, and have seen some recurring themes in the best of them.  

Unfortunately, the first bareboat charter can be a nerve-racking experience for many. As a newly qualified skipper, you have to start somewhere, and the calm, warm Ionian is a sensible choice. With no tides and easy line-of-sight navigation, the area is perfect for those starting out on their first sailing holiday. We are also well practiced at offering support for new or rusty sailors and their crews, helping to make the experience as relaxed as it can be.  

It’s probably been a little time since you passed your Day Skipper, and you might not have been on a yacht since them. So, the handover may well be your first time onboard in a few months. At Sail Ionian we email a copy of the Yacht Manual to guests a couple of weeks before the charter, so you can have a look through in advance and see how all the systems work. If you get the time when you first get on board, have a good look around the yacht before the handover starts and note down any questions. It’s important to slow things down and take a few notes during handovers. 

This is a good time to ask any other questions you might have too. Our staff at the base are your best source of tips for new skippers, so use them fully. I’d also suggest discussing a route, either on a video call before you arrive in Greece, or with base staff once you’re onboard.

New skippers often fall into the same trap: they look at a chart covered in beautiful islands and think they can visit all of them in a week. The reality is very different. Trying to cram in too many locations leads to tired crews, rushed meals and a schedule that falls apart at the first sign of a blustery day. It’s important to realise that as a novice your first charter should have modest ambitions. It doesn't matter if you don't get to see all the islands on this trip - you can use that as a reason to convince your crew to return next year!  

For a first week I’d even advise staying around Meganisi - at least for the first few days until you have got used to the boat and the crew have relaxed a little. It's a good tip for new skippers that the area immediately to the north of the island is known as the Inland Sea and is the most sheltered area in the Ionian. It’s bordered by Lefkada to the west and the mainland to the north and east. There are enough bays and harbours around Meganisi alone to spend an entire week there without going anywhere else! Most charter yachts will start from bases around here on a Saturday or Sunday, before heading south to Kefalonia and Ithaca, making it nice and quiet mid-week. That means easier mooring for the novice bareboater!  

If there’s one piece of advice I always give to clients planning their first Ionian bareboat, it’s this: book an assisted sailing day on day one. As a new skipper, you not only have to familiarise yourself with a yacht you’ve never sailed before but also help a crew who are most likely less experienced than you. Teaching whilst trying hard to recall everything you’ve learnt is very hard. A professional skipper on board for the first day helps a huge amount, giving you pointers and at the same time keeping a professional eye on your crew, and teaching them to be safe.  

Try to structure that first day so you’re not trying to go anywhere in particular. You will get far more valuable time with the skipper if you’re not plugging away on a 3-hour passage in a straight line. In my experience, most guests benefit much more from hours spent in and around harbours practicing mooring, anchoring and long lining, than in sailing.   

The most important tip for new skippers is about slowing down. New skippers often rush around: hauling anchor, hoisting sails, without a real plan or a crew that understands what is happening. Take some time on a morning somewhere quiet to think about what you want to achieve that day. Is it realistic and relaxed? Go through the day logically, step by step and consider anything that sounds difficult or confused, or that you’re not sure how to do. Once leaving your mooring, take everything at a very slow pace. There is no need to rush. Prepare the boat and plan each action carefully. Take time to brief the crew on what is happening and talk through the plan for the day. Then talk through each manoeuvre before you do it. Make sure you have told them the order you want things done and explained why and how. Even if they think they know, tell them again, one of them (or you!) will likely have forgotten something.  

Finally, always expect wind speeds to increase. The Ionian can be confusing to a new sailor as you are often in the lee of an island. Rounding a headland can suddenly expose the boat to much stronger winds. There’s a reason every teacher tells students to reef early. If it's your first charter, I would even suggest always having one reef in the main sail for the first few days. Remember your crew are probably new to this as well and can easily feel out of their depth and frightened. Holidays are for sailing slowly, not for racing.  

Being a new skipper on your first Ionian bareboat is a big moment. If you approach the week with these habits in mind, you’ll finish not just with a tan and a handful of photos, but with a genuine sense of confidence and a crew who trust you enough to return next year. And that, for me, is what being a skipper is really all about.  

This post was written by Tom Fletcher