The Ultimate Guide to Sailing Holidays for Families Who Love to Cruise


Sailing boat moored by island - Sailing Holidays Greece

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If cruising has given you a taste for waterborne breaks then how about taking your passion to another level with a sailing holiday? Learning to sail, chartering a yacht or joining a flotilla sailing holiday are all ideal vacations for adventurous families. Here’s our ultimate guide to sailing holidays for families:

Sailing Holidays for Families Who Love to Cruise

The best location for sailing holidays in Europe

Greece is the perfect place to experience sailing holidays for families, particularly if you are novices at the helm. This is for a couple of reasons. Not only are the waters around the Greek coast and islands incredibly beautiful; they are also warm. If you do end up in the sea it’s not going to be such a shock to the system. 

The Ionian Islands are a favourite destination for sailing holidays as there are plenty of pretty harbours and bays where you can drop anchor for a swim. Island hopping in this sheltered region is the perfect way for sailing beginners to learn the ropes. 

To find out more about sailing holidays in Greece with a skipper or flotilla holidays then click here.

Sailing holidays for beginners

If you are an absolute beginner and don’t want the pressure of being responsible for navigation and steering then how about booking a sailing holiday with skipper? The vessel might be a tad smaller than a cruise ship but you can sit back with the same assurance that you’re going to make your ports of call. Plus there’s never an excuse to miss sundowners on deck!

If you’re feeling adventurous but have no sailing experience then you can still get hands on. A flotilla holiday during which you’ll sail with several other boats will give you the guidance you need from the lead crew while also the support of other families and groups learning at the same time at you. There’s training on hand from skippers during your sailing holiday, plus social events at the end of each day.

Sailing boat deck - Sailing Holidays Greece

Sailing holidays – what to pack

It comes with the territory that a sailing holiday allows for less luggage than a cruise. So what are the essentials? Here’s a quick guide to what to pack for sailing holidays aside from your usual travel documents, first aid kit, medicines, toiletries and undies:

  • Light weight t-shirts and shorts
  • Sunglasses
  • A lanyard for attaching to sunglasses and mobile phones
  • A jumper or zip-up cardigan
  • Warm trousers
  • Factor 50 sun screen
  • Swim suits – two so you can dry one and wear one
  • Rubber soled shoes
  • Towels
  • Travel washing detergent
  • Pegs for hanging washing 
  • A waterproof bag for your camera, wallet and valuables when you leave the boat
  • A beach bag
  • A sarong or beach shirt
  • Sun hat
  • Wind proof jacket
  • Adaptor plug
  • Any sailing qualification certificates.

Whatever ends up in your bag, go back through and rationalise it. Do you really need t-shirts for each day? Or could you freshen a couple up with a quick wash? And will you really be needing your whole makeup bag? Space is at a premium on this type of boat!

Sailing holidays with children

While the luxury of having several hours to relax each day while sailing might be your idea of bliss, your kids will have other ideas. Make sure the sailing holiday itinerary you choose has plenty of stops for swims and exploring ashore. 

Zakynthos beach - Sailing Holidays Greece

A flotilla sailing holiday will give your kids opportunity to make friends with children travelling on the other boats. Older kids might also like to get involved with the steering of the boat.

If you are travelling with young children be aware that many charter companies providing a skipper will ask for one adult in your party to help, so parents are unlikely to get any down time to dive into a book while the boat is underway.

Can you go on sailing holidays with toddlers and babies?

Sailing holidays with toddlers and babies are not for the faint hearted. Do so only if you want to be on edge the whole time. We’d advise against it – holidays are for relaxing after all. You may also find it difficult to find charter companies that can accommodate you. Save the sailing adventure until the little ones are a bit older and plan another cruise!

Safety for kids on sailing holidays

Make sure your sailing holiday company can provide lifejackets in sizes suitable for your children. If not, then you’ll have to bring them with you. Also enquire about guard rail nets if you are bringing younger children.

Sit down with the kids for a chat well before your holiday and talk about how everyone should behave on a boat: the skipper’s instructions should always be followed, life vests should always be worn; and there’s no running on deck.

Kit out your kids with non-slip shoes, sunglasses, hats and factor 50 sun cream. Make sure they drink plenty of water each day too. You’re going to be exposed to the elements and even when the sea breeze is cooling you the sun is still baking hot.

Activities for kids on sailing holidays

Here are some ideas for keeping kids entertained during your sailing holiday:

  • Get you kids to record their holiday in their own shipmates’ log 
  • Bring travel board games to play below or on deck. Pack some extra dice – they’re bound to roll overboard!
  • Charades, I-Spy and Who Am I are all easy games to play wherever you are in the world
  • Make a story bag before you set sail, adding lots of random objects. Each person plucks an object from the bag and uses it as a prop to tell the next part of a collaborative tale
  • Take turns at being a look out for pirates
  • Bring story CDs and books for evening entertainment.

If all else fails bring a tablet loaded with games and movies, plus the charger!

When to go sailing in Greece

The Greek coast is lucky to have mild weather all year round so the sailing season runs from April to November with the most popular months being July and August. If you would like to get out on the water with less competition for sea space and lower prices then aim for May or October Half Term. If you have the luxury of being able to travel outside the school holidays then April, May and June are wonderful months to visit Greece when the green islands are at their lushest.

Greece flowers and sailing - Sailing Holidays Greece

Have you experienced a sailing holiday with kids? What are your top tips and destinations? We’d love to hear about them.

Disclosure: this post may contain compensated links.

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If cruising has given you a taste for waterborne breaks then how about taking your passion to another level? Read our guide to sailing holidays for families #sailingholiday #holidayinspiration #GreekIslands #sailing #travel #cruiseblog #travelblog #SailingGrece #familysailing


Claire Hall Tin Box Traveller


  • admin

    Donna and Sarah ( Cruising For All ) Sarah Christie and Donna Vallance are experienced travel writers and cruise enthusiasts specializing in cruising. They are passionate about exploring new destinations and have dedicated themselves to sharing their knowledge and insights with fellow travellers. They provide valuable information, tips, and recommendations for all cruisers. They strive to make cruising accessible and enjoyable for everyone, regardless of their interests, budgets, or accessibility needs. Their articles and reviews are well-researched, comprehensive, and written to help readers make informed decisions and have unforgettable cruise adventures.

1 thought on “The Ultimate Guide to Sailing Holidays for Families Who Love to Cruise”

  1. We went sailing around Greece years ago before kids. Absolutely loved it. Great post Claire and stunning photos


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