Sporades Islands Flotilla 2025: A Season with Lead Boat Dessa
There are some truly unforgettable experiences to be had when sailing through the Sporades Islands. The iconic Mamma Mia church perched high above the sea on Skopelos, scuba diving in the pristine marine reserve of Alonissos, or hiking up rugged hillsides to watch the sun melt into the horizon — these are the bucket-list moments.
But what makes a Sailing Holidays flotilla special isn’t just the scenery or the sights. It’s the joy.
This year, our lead boat Dessa and her crew captured that essence perfectly. Their photos from the 2025 Sporades season are a celebration of the simple, silly, and utterly human moments that make flotilla life unforgettable.
Sporades Clifftop Sunset
The joy of the everyday
It’s the first sip of something cold as the boats tie up for the night. It’s 12 adults, waist-deep in the water, playing tug of war like kids — not caring one jot what anyone looks like. It’s sundowners shared with new friends on the beach, laughter echoing across the bay.
In a world dominated by technology and distractions, these are the kinds of moments many of us forget to make space for. But on flotilla, they come naturally — because that’s what happens when you have good company, no schedule beyond the wind and the waves, and time to simply be.
Tug of War in the Sporades Islands
Adventure woven with connection
Of course, the Sporades provided their fair share of adventure too. From diving into turquoise waters to explore beneath the surface, to dropping anchor beneath pine-clad cliffs and hidden sea caves. From evenings spent in family-run tavernas, welcomed like old friends, to exploring historic monasteries bathed in golden light.
But it was the people who made it magic. The camaraderie of rafting up side by side. The shared pride of nailing a tricky anchorage. The belly laughs over punch party snacks that somehow taste better when enjoyed barefoot on the beach.
Getting together = half the fun
And we almost forgot to mention — the sailing itself in this part of the world is pretty epic too. But here’s the thing: it’s about so much more than the boats, the wind, the sea and the sunshine. The real magic lies in the way this combination draws together a certain type of life-loving folk. People who embrace adventure, laugh easily, and remind us that time spent well is often about who you’re with, not just where you are.
Lead Boat Dessa Crew - Sporades Islands
Memories to last far beyond the season
Looking back at the 2025 Sporades flotilla, it’s clear that the true highlight wasn’t any single sunset, swim stop, or island taverna. It was the collective joy of being out there together. A reminder that life’s best moments are rarely staged — they happen when you give yourself permission to slow down, dive in, and enjoy the company of other epic humans.
Here’s to Dessa, her crew, and everyone who joined us in the Sporades this year. Thank you for reminding us what sailing holidays are really about.
Anchoring in the Sporades Islands