How long should our sailing holiday be for? Seven days, or longer?

You may think that a love of sailing holidays means the pleasures of boat life are without limit; that time will just meld together with the environment, that when one view tires just weigh anchor and find a new horizon to gaze on. This is true, but there comes a time when the most satisfying horizon is the one that takes you home. 

Deciding on a holidays’ duration has a lot to do with the destination. Some itineraries absolutely need more than a week to do them justice, while others can be tailored to suit the amount of time that’s right for you and your travel companions.

 Many factors will affect your decision

The length of charter you decide on will depend a lot on the sailing experience, dynamics and objectives of the group you are taking sailing. Budget is an obvious limitation too, but for now let’s assume cost is not a limiting factor in your sailing holiday planning. 

Allow me to share a trade secret. Professional charter boat crews know that the most important times of charter are the first hour you’re all aboard, and the last day before you disembark.  

This book-end approach to the psychology of group chartering says a lot about the full boating holiday experience: Make the group comfortable as quickly as possible then keep them happy to the very end. That’s a rather obvious aim, but one not always achieved. 

Time and time again I have witnessed the inevitable roller coaster of personal emotions that emerge during just one week of charter, and it’s an experience more than likely to play out for you. 

Many of the charters we at Sail Connections arrange are for experienced groups of sailors who are right at home from the start. For others however - family members, partners or friends sharing the sailing holiday experience for the first time – stepping aboard a charter boat can be as foreign as boarding a spaceship. That can also apply if you have some familiarity with boats, especially if it has been a while since you last sailed. The departure from ‘normal’ can be a challenge. It’s that very step away from normality however that makes the sailing holiday so special.

Chartering with skipper or full crew 

When you hire a crew or skipper, you get the benefit of professionals who understand that unease can and does arise. It’s part of their jobs to make things comfortable for everyone. While there to serve they also assume control, taking important responsibilities out of the group leader’s hands so that all aboard can relax and enjoy the sailing vacation experience. 

Once everyone has settled into life aboard, you and your crew have the status of guests, and the process begins of relaxing into a holiday without comparison. Your first night afloat is filled with the sensations of having arrived on holiday at last. Your group is convivial but reserved, familiarity not quite established just yet, but soon it will be. 

By the next day as body and mind adjusts to the new surroundings, the motion of the waves and the feel of the breeze, the full impact of your boating holiday takes hold. The anticipation has become reality, everyone is feeling relaxed and happy as the journey begins in earnest. There’s some impatience to get on with what you came to do. 

As routines are established and priorities sorted, general excitement gives way to quieter enjoyment as everyone settles into boating life. Buoyancy - a nautical word - accurately sums up the mood on board. A natural high pervades, all are loving life, it’s as good as it gets.  

Every headland passed reveals a new wonder, as the days tick by packed with fun and relaxation. Talk turns to achieving what you all came here to do, making the most of a limited period each in your own way. It has taken time to get into active mode, and it’s now or never. You fully embrace the experience that just gets better as familiarity with your environment grows.  

Then as time flies and the holiday’s inevitable conclusion draws near, there’s a change of tone aboard as you all start to anticipate going home. At this stage your paid crew really prove their worth. They help you wind down slowly, and it’s only as the base comes into view the sense builds that vacation’s end is near. A planned gesture – a final meal together or excursion - crowns a wonderful time had by all. 

On a bareboat charter 

The dynamics within a bareboat charter group can be quite different without professionals aboard to carry responsibility. It falls on the holiday organiser, often the boat’s designated skipper, to lead the group experience. Leadership is critical and it starts with planning, the needs of everyone aboard kept firmly in mind. Good communication leads to full involvement and a happy crew. It’s so important to share knowledge of what’s to happen from the start, taking time to convey shipboard rules and how everyone can and must contribute. 

While the leader leads, crew members know that this is the leader’s vacation too. The leader’s role is a result of their knowledge and experience, which must be respected. The final decisions of the skipper, who is responsible for the boat and everyone’s safety, should never be openly challenged. 

Best practice means starting the first day with everyone understanding how the charter should end. Leave enough in the tank so that the final day of charter can be looked back on most favourably, having been as pleasant as every day that preceded it. 

Your charter broker is your best sounding board 

A competent broker will always be happy to advise and comment on your planned itinerary, providing recommendations as well as critical assessment when necessary. A key aspect of that is in deciding the length of your charter. So let’s get back to that. 

European charters are rigidly scheduled on a 7-day turnaround. If chartering in Greece, Croatia, Italy or elsewhere in the Mediterranean, your charter duration is set by weekly increments. If you need longer than seven days, you’re looking at 14, or 21. Elsewhere generally, bookings are more flexible, as long as you book early and get the pick of the dates available. So what follows largely applies to non-European charters. 

For a mixed group of friends or extended family, one week is a good length of time to holiday aboard a boat. By the end of charter you’ve had a taste of boating life and your break has given you a reset. The odds are you’ve all had a great time, enjoyed the company, been freed of stress, and are ready to return home.  

In my view, a shorter charter of say five days – a duration often requested for cost or time-pressure reasons – doesn’t work anywhere nearly as well. Charter operators know that there’s an adjustment period, that’s why most charters are sold for a minimum seven days.  Those extra two days can prove the most rewarding – so you don’t want to miss out on them.  

Is there an optimum charter sailing duration? 

If organising a charter for a less-experienced group, I suggest you book the best boat with the best level of service you can afford for one week. That’s the conservative approach – time enough for all those great outcomes mentioned above, while leaving your charter with a determination to return, vowing to do what it takes to get there. Back home, you reflect on what a wonderful experience you had, on a holiday format that’s well worth repeating! 

A seven-day charter is not however long enough to fully cross over into boating life. On a charter of 10 days or longer, a group that starts out reserved gets the chance to mould into a team. These longer charters are almost always bareboat, the boat’s full crew comprising friends or family who will self-define roles on board and be considerate and appreciative of others. If you are lucky enough to have such people to charter with, they become invaluable companions on this and future trips, the essential ingredient for making the boating lifestyle your reality. 

Pushing the charter out beyond a week has its rewards: a great way for friends and families to connect, for everyone to find their strengths and work on their weaknesses, to get in touch with nature, and yourself. 

In conclusion, I can only stress that charter duration is an important consideration before booking. In seeking your broker’s advice, be sure to explain what you and all members of the group want to get out of your sailing holiday - everyone’s hopes and expectations, as well as their special interests. The better the brief, the better the guidance.