Sailing Holidays Ltd

08/10/2026

One question 👇🏽

There are two perfectly good ways to deal with the fact that summer is over at home.

The first is to ignore it completely and join us for one of the final weeks of Greek sunshine this October.

The second is to put 2027 into the diary now and spend the coming months looking forward to clear water, steady breezes, little harbour towns and evenings that end around a taverna table.

If you can travel soon, there are only a few weeks left before this sailing season winds down.

If next year works better, booking early means more choice and plenty of time to gather the right crew.

Either way, Greece will be waiting.

Call 020 8459 8787 or email [email protected] and we’ll help you find the right holiday.

07/10/2026

A gentle reminder that “we should all go sailing together next year” is not technically a booking.

It is time to revive the group chat.

Choose the friends who remain cheerful while holding a fender. Identify the person who can be trusted with the helm.

Quietly establish who will be in charge of snacks, morning coffee and ordering enough food for the table.

Then choose a yacht and make it real.

Our most popular 2027 dates and yachts will naturally be the first to fill, especially for bigger families and groups of friends.

Send this to your future crew. Consider it the beginning of the plan.

06/10/2026

There is something deeply reassuring about knowing your sailing holiday is already in the diary.

While winter is doing its worst, you know that somewhere ahead there are warm mornings on deck, children jumping into the sea, sails filling in the afternoon breeze and long dinners beside a Greek harbour.

Booking early for 2027 gives you the best chance of finding the yacht, route and dates that genuinely suit your crew, particularly if you are planning around school holidays or hoping for one of our most popular larger yachts.

But perhaps the best reason is simply having something lovely to look forward to.

If Greece is calling again, now is a very good time to start planning.

05/10/2026

The final weeks of the sailing season always feel a little special.

The harbours are quieter. The light is softer. The afternoon breeze arrives and, for a few hours, nothing matters beyond trimming the sails and deciding which bay looks best for a swim.

By evening, you are tied up somewhere new, wandering into town in search of a taverna, a local glass of w**e and something involving far too much feta.

There are just a few weeks left to capture the last of the Greek sunshine before our yachts settle in for winter.

We would love to see you out there before the season winds down.

05/10/2026

There are just a few weeks left to capture the last of the Greek sunshine.

A few more mornings waking up on the water. A few more quiet bays, warm swims and afternoons spent following the wind towards the next harbour.

October has its own sort of charm. The pace is gentler, the sea has had all summer to warm up and the tavernas feel a little more unhurried.

You may want a light jumper after sunset, but dinner can still be eaten beside the water and the days still feel very far from autumn at home.

If you have been waiting for a sign to squeeze in one final adventure this year, this might be it.

Call us on 020 8459 8787 or email [email protected] to ask about the final weeks of our season.

02/10/2026

⛵ Last-minute cancellation!

A place has just become available on our two-week Corinth Canal Flotilla, starting this Sunday!

Sail through the historic Corinth Canal and explore the beautiful Greek islands along the way.

📞 Call the office now on 020 8459 8787 to enquire.

30/09/2026

Diving into October 💦

There is clear water. And then there is Greek-island clear water.

The kind where you can see the anchor resting on the seabed, count the fish beneath you and watch your shadow move across the sand.

You drop anchor in a quiet bay, climb down the steps and dive straight into a sea that has spent the whole summer warming up.

No pool lanes. No crowded beach. Just impossibly blue water and your yacht waiting when you finally decide to climb back aboard.

October is your last chance to swim from the boat this season, and there are still a few opportunities to join us.

We hope we get to see you in the water.

29/09/2026

There are just a few places left on our final South Ionian flotillas on 11th and 18th October, giving you one last opportunity to enjoy a week of sailing in the Greek Islands before the 2026 season comes to an end.

October is a fantastic time to be on the water, with warm days, beautiful sailing conditions and the islands taking on a quieter, more relaxed feel as the season draws to a close.

If you’re looking for to squeeze in a final week of sailing in the Greek Island sunshine, there are still a small number of yachts available.

Check out our offers here or give the team a ring on 020 8459 8787:

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

28/09/2026

A huge thank you to everyone who came to see us at the Southampton Boat Show.

It was wonderful to catch up with so many familiar faces, meet future sailors and welcome crew members past and present back to the stand.

Celebrating 50 years of Sailing Holidays made this year feel particularly special.

Reading the memories left on our postcard wall reminded us just how many friendships, family adventures, questionable moorings and unforgettable stories have come from five decades of flotilla sailing.

We may provide the yachts, routes and lead crews, but it is all of you who have made Sailing Holidays what it is.

Thank you for stopping by, sharing your stories and celebrating this milestone with us. Here’s to the next chapter, and to plenty more Greek islands, long lunches, sailing adventures and evenings on the quay.

Huge thanks to David Turner for the cracking photos!