Sailing Holidays Ltd

02/09/2026

Summer does not have to end just because the school holidays do.

October in Greece is one of those secrets we are almost reluctant to share.

The sea has had all summer to warm up. The harbours are quieter. The midday heat softens and there is more room to linger in the places everyone rushes through in August.

You still wake up on the water. You still swim from the boat, sail between islands and wander into town for dinner. But everything feels calmer, slower and somehow more Greek.

It is the perfect antidote to the sudden return of darker evenings and everyday routines at home.

If you are not quite ready to let summer go, book yourself something better to look forward to.

Call us on 020 8459 8787 or email [email protected] to discover our October flotillas.

01/09/2026

Let's talk 2027... because many of you already are!

There is a particular sort of happiness that comes from knowing the family holiday is already in the diary.

Not just any holiday, but two weeks in Greece waiting for you.

Mornings on deck. Children jumping into the water before breakfast. Long sailing days that end in little harbour towns, with dinner outside and stories that will be repeated long after everyone has gone home.

Our most popular yachts and peak summer dates are often the first to fill, particularly the larger boats that work so well for families and groups of friends.

A week or two at Villa Meandros is also up for grabs.

Booking early means more choice. The right yacht for your crew. The route you really want. The dates that work before diaries, school holidays and everyone else’s plans begin to close in.

If you already know you want to sail with us in 2027, now is the time to turn “we should do that” into something real.

Call the team on 020 8459 8787 or email [email protected] and let’s get your next Greek adventure into the diary.

31/08/2026

October doesn’t have to mean darker evenings, digging out the jumpers and admitting that summer is over.

It could mean waking up on a yacht in Greece.

Breakfast overlooking the harbour. A few hours sailing. Lunch and a swim in a quiet bay. Then an evening wandering through a small town in search of a waterside taverna or a quaint cocktail bar.

Late-season sailing is a lovely way to stretch summer just a little further, particularly if you prefer quieter harbours and a more relaxed pace.

If that sounds better than settling into autumn at home, come and talk to us.

Call the team on 020 8459 8787 or email [email protected] to ask about our late-season sailing.

P.s. if you can sneak away in September - ask our team about recent cancellations.

30/08/2026

Save the date. We’re heading back to the Southampton International Boat Show.

The show runs from 18 to 27 September 2026 and you’ll find the Sailing Holidays team on Stand H46.

Come along, say hello and talk to us about Greece, flotillas, yachts, routes, RYA courses or the holiday you have been promising yourself for years.

You don’t need to arrive knowing exactly what you want. Tell us who you are travelling with, how much sailing you have done and what your dream week in Greece looks like, and we can help with the rest.

Use our ticket code SAILHOLS to get tickets for £19.99, including two free under-16s.

We would love to see you there.

Click here to book your tickets:

The Southampton International Boat Show will be back in Mayflower Park on 18-27 September 2026!

27/08/2026

October in Greece moves at a slightly different pace.

The harbours are calmer, the water has had all summer to warm up and the busiest weeks of the season are behind us.

You can still fill the days with sailing, swimming and exploring. There is simply a little more room to linger over lunch, take your time on the quay and enjoy the islands without feeling as though anyone is in a rush.

If you like your holidays warm, relaxed and just outside the main summer crowds, October might suit you very well indeed.

Call the team on 020 8459 8787 or email [email protected] to ask about our late-season sailing.

27/08/2026

For those of you looking for a last-minute escape, we currently have a Beneteau 361 and a 323 ‘couples yacht’ available on our one week South Ionian Flotilla with 30% off the per-person rate, including flights this weekend.

September is our most popular month of the year, and there’s not much availability left now. You can see the last of our September spaces on our website.

October is looking just as good weather-wise – perfect for sailing, swimming and dining ashore – and we still have a few one-week flotillas available, as well as two-week favourite “coming home to Corfu” flotillas from 18th October.

If you’re tempted, get in touch and we’ll help you find the right flotilla.

Click here to find out more or call the team on 020 8459 8787 or email [email protected]

Award Winning Flotilla Sailing Holidays in the sunny Greek Islands...

26/08/2026

Our 2026 RYA programme is almost full, so we are already looking ahead to next year.

There is something rather satisfying about taking the helm of your own yacht and realising you know what to do.

For many of our flotilla skippers, the journey begins with an RYA course.

A week of practical learning in Greece can give you the skills, experience and confidence to start imagining a very different kind of family holiday. One where you choose the crew, take charge of the yacht and sail from one Greek island to the next, with our lead crew never too far away.

If 2027 could be the year you learn, improve or prepare for your first flotilla, get in touch with the team.

25/08/2026

A flotilla day can feel wonderfully long.

Breakfast on the quay. A swim before leaving. A gentle sail or motor to a bay for lunch. Another swim, because nobody is in a hurry. Then the afternoon breeze arrives and carries you towards the evening’s harbour.

By sunset, you have sailed somewhere new, swum in impossibly clear water, eaten very well and met another collection of people you would never have crossed paths with at home.

Nothing has been rushed, but somehow the day feels completely full.

That might be the real luxury of a sailing holiday. Not doing nothing, but having enough time to notice everything.

24/08/2026

Which route is best for younger children?

Do you need to be an experienced skipper?

What happens if you need help mooring?

Which yacht works best for two families?

And, most importantly, where are the best waterside tavernas?

These are exactly the sorts of conversations we love having at the Southampton International Boat Show.

Come and find us on Stand H46 from 18 to 27 September.

Tell us who you are travelling with, how much sailing you have done and what your ideal holiday looks like, and we will help point you in the right direction.

Tickets are £19.99 with code SAILHOLS, including two free under-16s.