Sailing Holidays Ltd

10/09/2026

The best thing about an October sailing holiday is that no two days feel quite the same.

One morning begins in a lively little town. The next starts in a peaceful bay with barely another boat in sight.

There are proper sailing days, slow lunches, swims from the stern and evenings spent discovering family-run tavernas or a tiny cocktail bar tucked away behind the harbour.

It is relaxing, but never boring. Active, but never exhausting.

And when you return home, it feels as though you have been away for far longer than a week.

Call 020 8459 8787 or email [email protected] to explore October with us.

09/09/2026

Trying to choose the right yacht for a group of friends?

Have you been wondering which flotilla would suit your family?

Thinking about learning to sail, returning for another route or securing one of our most popular yachts for 2027?

Come and have a proper chat with us at the Southampton International Boat Show.

Tell us who’s coming, how much sailing you’ve done and what your perfect holiday looks like. We’ll help you work out where to begin.

Find us on Stand H46 from 18 to 27 September.

Tickets are £19.99 with code SAILHOLS and include two free under-16s.

Get your tickets: https://www.southamptonboatshow.com/

08/09/2026

You could spend the October half-term trying to entertain everyone at home.

Or you could wake up on a yacht in Greece.

The children can swim from the boat, help with the ropes, take a turn at the helm and explore somewhere new each day. The adults can enjoy the sailing, the sunshine and the rare pleasure of nobody asking what the Wi-Fi password is.

Then everyone meets again around a taverna table in the evening, tired in the very best possible way.

If your school dates line up with our October sailing, this could be a family half-term you’ll be talking about for years.

Call 020 8459 8787 or email [email protected] to find out more.

Read our article on October Half Term sailing to find out more!

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

07/09/2026

Caption contest 😉 Leave us your thoughts in the comments...

But...joking aside - Save the date. We’re heading to the Southampton Boat Show

You’ll find the Sailing Holidays team on Stand H46 from 18 to 27 September 2026.

Come and say hello, catch up after your latest flotilla or start planning your very first one. We’re always happy to talk about yachts, routes, RYA courses and Greek islands for far longer than most people consider reasonable.

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

We would love to see you there.

Click here to book tickets:
https://www.southamptonboatshow.com/

07/09/2026

September means summer is over - right?

We’re not entirely convinced.

In Greece, the sea is still warm, the sun is still shining and there are still islands to sail around, bays to swim in and waterfront tavernas waiting for you.

October sailing is one of the loveliest ways to avoid slipping straight into autumn. The pace is gentler, the harbours are quieter and the whole experience feels a little more relaxed.

If you’re not ready for summer to end, perhaps it doesn’t have to.

Call us on 020 8459 8787 or email [email protected] to find out what’s available this October.

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!