Sail Together, Independently
Flotilla Sailing Holidays
Skipper your own yacht alongside a small fleet of fellow sailors, with a lead boat and experienced flotilla skipper guiding the route, social evenings ashore, and support on hand whenever you need it.
Available Flotillas
Sail independently by day, raft up together by night — the easy way into flotilla sailing.
Ionian Lefkas Flotilla
Based in Nikiana Harbour on the sheltered east coast of Lefkas, this is one of the gentlest introductions to flotilla sailing in the Mediterranean — short hops between islands, light Ionian breezes, and a lead crew on hand every day. Two routes alternate week to week: one threads north to Ithaca's fishing harbours at Fiskardo and Frikes, the other loops south past Meganisi and the quiet anchorages around Kastos and Kalamos. Combine both for a two-week holiday.
Ionian Kefalonia Flotilla
Sailing out of Agia Eufimia on Kefalonia's north-east coast, this flotilla explores some of the most photographed corners of the Ionian — Ithaca's deep-water harbours, Fiskardo's pastel waterfront, and the beaches around Assos beneath its Venetian fortress. An alternate route swaps across to Zakynthos for the shipwreck coastline and Zante Town.
Southern Ionian Explorer Flotilla
A one-off, two-week season-closing voyage that links the whole southern Ionian into a single itinerary — from Lefkas down through Kalamos, Ithaca and Kefalonia, across to the ancient site at Olympia via Katakolon, and on to Zakynthos, before looping back north. Priced as two weeks for the cost of one, it's the longest flotilla route Medsail offers in Greece, sailing once a year at the very end of the Ionian season.
Kefalonia to Korfos Explorer Flotilla
A one-way, end-of-season delivery voyage that repositions the fleet from Kefalonia in the Ionian to Medsail's winter base at Korfos in the Saronic Gulf. The route heads east via Ithaca, along the Gulf of Patras beneath the Rio-Antirrio bridge, through the Gulf of Corinth past Galaxidi and Antikyra, then finishes by transiting the Corinth Canal itself before reaching Korfos via Epidavros. Runs once a year, at the very end of the Ionian season. Note: this is a fixed one-off delivery route, so the exact overnight schedule can vary slightly with weather — contact us for the confirmed day-by-day plan.
Saronic Gulf & Corinth Canal Flotilla
Based at Medsail's winter home in Korfos in the Saronic Gulf, this flotilla alternates between two routes each week — one exploring the islands of Poros, Hydra and the little harbour of Perdika, the other heading north to transit the Corinth Canal and visit the mainland town of Galaxidi. Varied, sheltered sailing with some of the most dramatic scenery in Greece, and one of the longest seasons of any Medsail flotilla — April to November.
Sporades Flotilla
Sailing out of Skopelos, this flotilla explores the pine-covered Sporades islands made famous as the Mamma Mia backdrop — quiet anchorages, the marine park that protects the Mediterranean's monk seals, and some of the clearest water in the Aegean. An alternate Pelion route crosses to the mainland coast beneath Mount Pelion. Stronger meltemi winds make this a step up from the Ionian flotillas.
Dodecanese Flotilla
Based in Kos, right on Turkey's doorstep in the south-east Aegean, this flotilla alternates between two island-hopping routes — one to the amphitheatre-shaped harbour town of Symi via Nisyros and Tilos, the other to Kalymnos, Lipsi and Leros. Warm, reliable sailing among some of Greece's least-crowded islands, with the fortress of the Knights of St John overlooking Kos harbour on the way out and back.