Skippered Yacht Charter Guide
Want to know more about what’s involved if you book a skippered yacht charter holiday? Ever wondered how involved you can get, whether to invite your skipper out for meals, and how much to tip? We've put together a handy guide to hopefully answer all these questions, and more.
Updated April 3, 2025
Sailing is a great way to enjoy the open water and explore new places. But if you're not a sailor, or if you don't have the time or experience to learn how to sail, a skippered yacht charter is a great option.
One of the many delights of a sailing vacation is that it doesn’t require you to ever take the helm or hoist the mainsail, let alone batten down the hatches.
If you have the correct licence for bareboat yacht charter (for example an RYA Yachtmaster or an RYA day skipper licence) and relevant sailing experience, you can choose to bareboat charter, where you are the captain and your friends and family are the crew.
If you happen to be new to sailing or just want to put up your feet while on holiday, a skippered charter is the answer, where you hire a professional skipper to look after the boat and setting the sails for you while you relax.
Key info
What to Expect on a Skippered Yacht Charter?
What is a skipper?
Your experienced skipper is a qualified professional captain whose job is to use their sailing skills to make your skippered sailing holiday as enjoyable and relaxing as possible, allowing you to join in with as much or as little as you wish.
There are a few things to keep in mind when planning a skippered yacht charter. First, you'll need to choose a sailing area. There are many great places to sail, from the beaches of the Caribbean to the Adriatic Coast's beautiful bays.
Once you’ve chosen a destination, you’ll need to decide on the type of yacht you want to charter. There are many different sizes and styles of yachts available, and whether you choose a sailing yacht, catamaran or motor yacht will depend on your budget and the sort of experience you’re looking for, so talk to your broker and you’ll be sure to find one that’s perfect for your group.
Want to know more about what’s involved if you book a skippered charter holiday? We thought you might and have put together the following guide which will hopefully answer all your questions.
What Should I Expect?
- Choice of stunning destinations
- Freedom to create your own itinerary
- Chance to relax on board and leave the sailing to a professional
- An opportunity to learn some sailing basics under instruction from the skipper
- Inside knowledge from a local expert who can take you to the best beaches and secluded bays
- Privacy - it's just your group and the skipper onboard
How does it work?
When you arrive at the base, your qualified skipper will be there to meet you and your group, helping with check in to your chosen yacht. They will be responsible for sailing you to your chosen destinations for the duration of your holiday.
You can sit back and relax for the entire time or if you would like to use the opportunity to start learning some basic skills, the skipper will be happy to show you the ropes (as it were!).
For many, a skippered yacht charter tends to be more about the holiday than the sailing. So having someone else at the helm will enable you to make the most of everything else a yachting holiday offers – swimming off the back of the boat, snorkelling, sunbathing on deck or simply relaxing in a hammock.
Top Skippered Yacht Charter Destinations
Itineraries
How far you go each day will depend on your itinerary, but on average the skipper will sail the yacht for three to four hours a day between morning and afternoon, stopping for lunch on the way. In the evening, you will dock at a port or harbour and then are free to either eat on board or go out for dinner.
We provide suggested yacht charter itineraries for each sailing destination, but these are only ever suggestions, and you are welcome to adapt them as you please.
Our advice is to sit down with the skipper at the start of your trip and work out your preferred route. Also, if you have any specific ideas for activities – such as trying out water sports or visiting historic places of interest en route – just ask the skipper and he can advise on where to go.
Who are the skippers?
Our skippers are professional sailors. They have excellent local knowledge, so can make recommendations on where to go and what to see.
This gives you a huge advantage – they know where the best spot is for a tranquil lunch in a secluded bay and the best restaurants in town when you dock at night. They will even book you a table.
Where can I sail?
Because most skippers are freelance captains, you can find a skippered charter yacht everywhere there are charter yachts, from the Mediterranean to the British Virgin Islands, and the Balearic islands to the Indian Ocean.
See more details on our destinations via the button.
What sort of yacht should I choose?
Your skipper will sleep on board, so you will need to allocate them a cabin. Otherwise, the type of yacht you choose is up to you.
And of course, we are on hand to offer suitable recommendations based on the size of the group travelling and any specific requests you have.
Read our guide on choosing the right yacht to give you a good idea of what will suit you, and then ask your HELM broker to find the right fit for you
Use our yacht charter experience builder to help us create the perfect sailing holiday for you.
Will the skipper get on with my crew?
Yes, all the skippers we work with are incredibly personable, friendly and adaptable individuals, who are as skilled at adapting to their social environment as they are at controlling the yacht.
Skippers tend to be relaxed, approachable people, always happy to entertain kids and adults with funny anecdotes and stories from their days on the water. They are also very professional and discreet, and good at giving your family space if required.
It's really up to you how much you want to involve your skipper in your trip.
What about feeding them?
In general, skippers are very happy to either join in with your group of do their own thing when it comes to evening meals. If eating lunch onboard the yacht, you will need to make sure the skipper is included in your lunchtime plans.
- Include your skipper in your plans. If you prefer to do your own provisioning, you will need to plan ahead and make sure you have enough food and drinks for the entire crew. Be sure to pack a variety of foods to suit everyone's tastes, as well as plenty of snacks and drinks.
If you are eating ashore, you are welcome to ask the skipper to join you, or if you'd rather have time apart, we recommend you give the skipper an allowance of €30-40 per day to feed themselves.
- Consider the skipper's dietary needs. If the skipper has any dietary restrictions, be sure to take them into account when planning your meals. For example, if they are vegetarian or vegan, you will need to make sure you have plenty of plant-based options available. You will be told these in advance.
Should I add a hostess?
Having an exceptional hostess on board can really enhance the relaxation of your sailing vacation.
A skippered charter is a self-catered holiday, so you will need to buy enough provisions before you embark (and en route) for your group and the skipper. These will include food, drink, cleaning products and toilet rolls.
If you’d like a hand with the catering, you can add a hostess. Your hostess will keep your yacht clean, prepare drinks and snacks as well as help with the shopping.
A hostess would double up as a competent crew to aid the skipper, and prepare two light meals a day (usually breakfast and lunch) as well as a potential 3rd meal on one or two of the days. They will also ensure the daily cleaning the communal areas and clean dishes after each meal.
Bear in mind that just like the skipper, the hostess will need their own cabin.
When will I find out my skipper's details?
We understand that you may wish to contact your skipper before your charter, to help build a rapport before you spend a week together.
When we get their contact details varies, but our Charter Management team will put you in touch with your skipper shortly before your charter, so you can get to know each other and plan itineraries.
To give you the best possible experience, we'll send you a skipper preference sheet. Once completed, our Charter Management team will send it along to the base team, so everybody can know what to expect and look forward to a wonderful week.
Please be aware that your skipper may be on a charter the week or two before yours begins, and so they may be slightly delayed in responding to any messages.
Anything else to be aware of?
The skipper is there to sail the boat and will always respect your privacy. That said, in our experience, our guests always form a genuinely close bond with the skipper during their holiday and are often sad to say goodbye!
Tipping is customary but not obligatory. It is however greatly appreciated by the crew who will consistently go above and beyond to make you happy.
We generally recommend 5-15% of the charter price.
Is my skipper insured?
Yes - all the skippers HELM use are fully insured professionals, with skipper liability insurance, which protects them from third-party claims while operating a yacht.
They are insured against and responsible for the safety of the yacht and its passengers for the duration of their charter contract, which means if the worst happens and the skipper incurs some damage in the course of manouevring the boat, their insurance will pay out, not yours.
Your damage/security deposit insures you against any possible breakages or damages you may cause (or if you are willfully negligent).
If in any doubt, please ask your HELM broker.
Next steps
Now you've got the lowdown on what to expect, it's time to get on the water and plan the best holiday you'll ever have!
For more advice on creating your perfect sailing holiday, email us at [email protected] or phone (+44) 0207 632 7567
Need some help?
If you are unsure about charter or boat selection, contact us at HELM to help you decide.
We only choose boats that are in excellent condition, and we are here to help you every step of the way and to make sure the whole process is as easy as possible.