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Skippered Charters
Stress Free Tailor Made Holidays

Skippered Charter

Relax in luxury on a sailing holiday

Always desired a sailing holiday but have little or no experience, or no certification to go bareboat? Do you fancy being personally chaperoned on your sailing holiday to amazing settings each day and night?  Then a skippered yacht charter is the sailing holiday for you.

Skippered charters give you the freedom to do exactly what you want, whether it be swimming, snorkeling, exploring caves, or having a siesta in the shade.  Our experienced skippers will be able to take you places that most other yachts do not go, the hidden gem, secret places as well as mooring in the harbours, in busy high summer season.

This skippered sailing Greece holiday option is suitable for families with young children, it will give you the variety required by both adults and children alike.  Spend the mornings swimming and using the dinghy in bays, before setting off for an exhilarating sail in the afternoon, and finishing with a delicious meal in a local harbour, taverna or secluded bay.

For couples with little or no experience but wanting to explore and/or have a romantic holiday.  It is perfectly possible as we can tailor your skippered yacht charter to meet your needs.  Our skippers would all have a private cabin which helps give you the space to enjoy romantic meals and drinks in peace and comfort as well. We have found that this option is popular for honeymoon sailing as well. Read more about our honeymoon packages here.

Wondering what the weather is like in the Ionian and when to visit? See our Ionian Islands Weather post on our blog here.

Take part in the sailing:

The majority of our skippers are also qualified RYA instructors and they will be pleased to coach and encourage you to take part in the sailing as much as you like. A skippered sailing holiday in Greece is a flexible holiday and can be tailored to your wishes!

All of our skippers are highly qualified, experienced sailors. They are mature, sociable and understand that it is your holiday, their aim is to ensure you get to do what you want. All skippers are fully insured and employed by, or on contract to Sail Ionian.

If you aren’t sure which holiday is for you, go back to the Holidays summary page here or contact our office for advice.

View Our Yachts Here – all are available for skippered charters


Skippered yacht charters not only give you the reassurance and confidence to have the Greek sailing holiday of a lifetime but flexibility too. A crewed yacht has many advantages for families that want the experience of a sailing holiday without the pressure of looking after the boat.

The skipper will happily help choose a route that suits you and make sure that you have a stress free and comfortable cruise around the Ionian Islands. The skipper will sleep on board some nights, but not all nights if you wish. This gives you the security but also the opportunity to spend quality time together as a family.

This sailing holiday gives you the freedom to experience and enjoy your holiday exactly how you want to. It is your holiday and we aim for it to exceed your expectations!

You can view our Sailing Area here.

If you aren’t sure which holiday is for you, go back to the Holidays summary page here or contact our office for advice.

Sample Itineraries:

Best of The Ionian

Exploring the Northern Ionian

Quiet Escapes

Lively Nightlife

Skipper’s Recommendations

Top 10 Anchorages

Required Experience

Come as you are!

Learn about RYA

Book now

What's Included

Provided Support

Onboard Skipper

Trained in first aid

Weather Update

Sent daily by SMS

Support Rib

Support within an hour

24hr helpline

In case of emergency