Take to the waves: how to plan the ultimate family sailing holiday

Ropes clinking on the mast, uninterrupted horizons met by clear waters and deserted coves that invite you in for secluded swims — sailing holidays allow families to leave their daily routines behind and explore the world from a new perspective. However, if you're new to the seas it can be difficult to know where to start. 

What makes a family sailing holiday so special?
The perfect combination of action and relaxation, a sailing holiday allows families a unique bonding experience, with the potential to learn a new skill in a relaxed, safe environment. Not only will you gain a new perspective of the coastline from the water, you’re able to stay in a different place each night — and saves you the chore of re-packing. With the option to do as much or as little as you like, a sailing trip gives you the opportunity to spend serious quality time together as a family, without distraction.

Where should I start?
If you’ve never tried a sailing holiday before, one of the best options is to book a skippered flotilla holiday. A flotilla is a group yacht holiday in which you sail with another group of yachts on a suggested route, with a lead crew — comprising a skipper, host and technician — on hand for support. You can take the helm yourself, or hire a skipper to sail the yacht so you're free to relax and enjoy the journey. Fancy getting involved? Gather any budding young crew members and your skipper will happily show you the ropes. 

If you'd prefer to sail at your own pace, a bareboat sailing holiday is a more private option, where you can plan your own route and opt to hire a skipper to navigate it for you. Or, you can choose a fully skippered package where all the essentials are included in your booking, making it perfect for those who don’t know where to start. Skippered trips are a great option for families, as skippers offer not only seamless sailing experiences, but also unparalleled local knowledge. This will mean you can discover the best beaches, restaurants, bars and any hidden gems that the area might have to offer. 

Sailing can be daunting for those new to the water, but an operator such as Sunsail can provide experienced skippers and trustworthy yachts on plenty of tried-and-tested itineraries. Some of their flotillas also include a children's co-ordinator on certain departure dates for added entertainment. As a result, it’s always best to speak to a holiday planner who can direct you to your family's ideal destination — whether you want to discover deserted snorkelling spots, explore the best traditional tavernas or find the most picturesque anchorages for a relaxing sundowner.

Do we need special kit?
By choosing a reputable operator, you shouldn’t need any specialist sailing kit. All safety equipment — including lifejackets — will be provided. However, you do need to pack a good set of beach towels, a plentiful supply of reef-safe sunscreen (sun reflected off the water is much stronger than it is inland), sunglasses (preferably polarized, to remove glare) and rash vests/shorts/suits for the water. While going barefoot is generally the norm on a yacht, good, grippy footwear that won’t mark the decks (no black soles) and that you don’t mind getting wet is helpful. It’s worth packing a light windproof jacket for that occasional sea breeze, too.

Which kind of yacht should I choose?
There are two types of yacht — monohull, the traditional single yacht shape, and catamaran. A monohull is arguably the better choice for more experienced sailors and single families as they can be more compact and tend to ‘heel’ in the wind (sail on an angle). Catamarans, on the other hand are much more suited to first timers. They offer a more balanced sail that lessens the risk of sea-sick sailors, as well as dual hulls ideal for combined families.

Where can I find the best family-friendly ports/destinations?
Sailing in the Mediterranean and Ionian seas is unbeatable for families. The waters are calm and warm, the breeze isn’t too strong and countries such as Greece and Croatia offer exciting opportunities for exploring islands unreachable on shore-based holidays. 

Sailing the Ionian Coast offers a unique view of classic isles like Kefalonia and Ithaca, while in Croatia, Marina Agana is the perfect springboard for exploring the Dalmatian Coast and its 1,000-plus islands. These include the cultural havens of Brač, Šolta and Hvar in the south and east, as well as the untouched Kornati Islands in the north and west.

For those who want to go a little further afield, the British Virgin Islands are a fantastic choice for families, thanks to year-round warm weather, sheltered harbours, short hops between islands and a fascinating pirate history. 

What other off-yacht experiences should I consider?
A family sailing holiday isn’t just about swimming, sunbathing and learning the difference between a clove hitch and a reef knot. Simple off-yacht activities range from beach barbecues, snorkelling and island walks to cultural excursions and cookery classes. Why not combine your sailing holiday with a little history and leave from Dubrovnik, one of the world’s best preserved medieval walled cities? Or, immerse yourself in world-beating cuisine at some of Europe's top restaurants — the coastline is your oyster.