For new sailors, I’d recommend a week sailing around the Greek Ionian Islands. It’s a wonderful introduction to sailing: beautiful turquoise bays, short hops between islands, pretty harbours, traditional Greek tavernas and plenty of opportunities to swim, explore villages and enjoy life ashore.
You don't need to be an experienced sailor. You can charter a yacht with a professional skipper, learn a few sailing skills along the way, and enjoy the holiday without the pressure of being responsible for the boat.
Day 1 — Arrive in Lefkada
Easy start · Marina and town
Arrive, meet your skipper, settle into your yacht and learn the basics of safety and life aboard.
Onshore activities: Explore Lefkada Town's colourful streets, browse local shops and enjoy your first Greek dinner at a waterfront taverna.
Day 2 — Meganisi
Short sail · Swimming and village life
Sail towards Meganisi, with a stop in a sheltered bay for a swim. Your skipper can show you how to steer, handle ropes and understand the sails.
Onshore activities: Wander around Vathy harbour, visit a traditional café or take a walk up to Spartochori for lovely views over the bay.
Day 3 — Ithaca
Island scenery · Walking and culture
Head towards Ithaca, the island associated with Homer's Odyssey. Enjoy the coastline and practise sailing under supervision.
Onshore activities: Explore the pretty harbour village of Kioni, walk its narrow lanes, find a beach or enjoy a long lunch overlooking the boats.
Day 4 — Discover more of Ithaca
A flexible day · Walking and local food
Keep this day relaxed, with a short sail to another bay or harbour depending on the weather.
Onshore activities: Walk inland through olive groves, visit Vathy's waterfront, browse local shops or take a taxi to a scenic viewpoint. This is also a good day for a longer lunch ashore.
Day 5 — Fiskardo, Kefalonia
Pretty harbour · Coastal exploring
Sail to Fiskardo, one of the Ionian's most attractive harbour villages, known for its colourful buildings and waterfront.
Onshore activities: Browse boutiques and galleries, take a coastal walk, find a beach or settle down for a seafood dinner. If conditions permit, explore a nearby cove by dinghy.
Day 6 — Kastos
Quiet island · Snorkelling and relaxation
Enjoy a quieter stretch of the Ionian, with time for a swim and perhaps a little more hands-on sailing.
Onshore activities: Explore the small village on foot, have a leisurely coffee, snorkel in clear water and enjoy a relaxed meal at a local taverna.
Day 7 — A final swim and return
Gentle sailing · Farewell to Greece
Sail back towards Lefkada, stopping for one last swim if time and weather allow. Your skipper will manage the return passage and yacht handover.
Onshore activities: Enjoy a final coffee or lunch ashore before departure, depending on your travel arrangements.
The itinerary is flexible rather than a fixed passage plan. The skipper will adjust destinations and sailing distances for the weather, daylight and the crew's comfort. The route above is a proposed outline, not a guarantee that every stop will be possible.
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