The Season That Chose Us
We believe that the best sailing adventures happen outside the summer rush. While everyone else waits in line, we explore the Mediterranean when it’s still wild, warm, and welcoming. Our mission is simple: to offer high-end sailing holidays during Spring and Autumn, with beautiful boats, exceptional crews, and themed experiences from gastronomy to kitesurf, from hiking to mythology. We are skippers, chefs, guides, and travelers ourselves — and we know that the true luxury lies in choosing your own rhythm. And no, you won’t find us out there in August!
Not Just a Cruise
Of course, you can just sail, relax, and swim in quiet bays. But if you want more — more flavor, more motion, more discovery — we’ve designed sailing weeks with a theme and a soul.
Sail & Taste
A gourmet sailing experience with a private chef on board. Whether you want to learn Mediterranean cooking or simply enjoy the freshest flavors from local markets, this is the week to indulge. Wine pairings, hands-on cooking, and meals with a view — every day. ⸻
Hike & Sail
For those who love to move on land as much as at sea. Each day we drop anchor near a trail worth exploring: cliff paths, ancient monasteries, volcano rims. You sail in the morning, hike in the afternoon — and sleep under the stars.
Bike & Boat
Ideal for active travelers who enjoy fat tires and sea breeze. We plan routes on the islands, ferry your mountain bikes on board, and take you where cars can’t. Ride rugged coastal paths, stop in remote villages, and reunite with your floating home in a new bay each evening.
What Makes The Great Season Truly Great
Hidden Mediterranean Gems
We sail where others don’t. Off-the-beaten-track islands, secret coves, and authentic encounters
Top Skippers
Our crew members are not just captains — they are your personal consultants, local experts, and storytellers.
Themed Sailing Weeks
From cooking on board to volcano hikes, every week is a journey in itself.
Testimonials
“I’ve been sailing for 15 years. I love the sea — but I can’t stand August. With The Great Season, I finally sail when it feels like sailing again: quiet anchorages, real conversations, no rush, no chaos.”
Lara V. Skipper and Mediterranean Soul
“We’ve sailed in Greece before, but never like this. It felt like the islands were ours. Everything was curated: the food, the crew, the silence. We’re already planning the next escape.”
Emily and Sam, London
“Spring in the Aegean was a revelation. Warm enough to swim, cool enough to sleep, and no crowds. The kids made memories. We recharged. And we didn’t miss the summer at all.”
The Andersens, Copenaghen
