7 of the Best Greece Sailing Tours and Holidays

by Paul Joseph  |  Published October 27, 2023

With its cruising season running from April through to the end of October, there’s ample time in the year to embark on a Greek sailing adventure.

(Photo: Tourradar)

Calm waters and a warm Mediterranean climate help to make the Aegean sea that flanks Greece’s eastern coast and its myriad of islands one of the world’s most popular sailing destinations. There are a wide number of Greek sailing vacations on offer, ranging from a single day through to several weeks at sea – some of which even incorporate sailing lessons into the trip. We’ve picked out 7 of the best sailing trips and holidays currently available.

Athens Sailing Getaway (2 days)

If you’re limited on time or budget but are keen to get a real flavour of Greece, this small-group tour could be the ideal compromise. As part of a group of up to 10 people, you’ll spend two days at sea and one night in a cabin aboard your charming sailing boat. In the company of a skipper and separate tour guide, you’ll depart from Athens before exploring the crystal clear waters of the Saronic Gulf. Highlights include trips to two beautiful islands where you’ll taste fresh seafood, pistachios and other local delicacies; hike in an abandoned ghost town; visit numerous Byzantine churches; and swim and snorkel in the sea. One breakfast and two lunches are included in the price. The tour ends back in Athens. From €259 per person.

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Kefalonia to Corfu (8 days)

(Photo: Tourradar)

Starting in Kefallonia and ending in Corfu, this 8-day tour takes in a total of 10 Greek hotspots in the Ionian Sea. Over the course of the trip, you and your group of up to 7 other guests – plus skipper, crew and tour guide – will set sail on a 15-metre yacht in pursuit of secluded coastlines, private islands, verdant rolling hills and orchards, historic Venetian architecture, inviting tavernas and some of the world’s most glorious azure waters. Each day, you’ll swim in picturesque bays and watch the sunset on the deck of your sailing boat before retiring for the night to your comfortable on-board cabin. As well as sleeping quarters, the yacht is also equipped with shared bathrooms with showers. A total of 7 breakfasts, 5 lunches and 2 dinners are included in the tour price. From €1,764 per person.

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Santorini to Santorini (10 days)

This 10-day round trip from Santorini offers the chance to explore some of the treasures of the Greek Islands. Aboard an 18-metre yacht, equipped with heated cabin, showers, kitchenette, common areas, and an outside deck space for sun-bathing or sleeping under the stars, you’ll be treated to an action-packed itinerary full of on-land activities, but with plenty of time for enjoying your yacht and its surroundings, too. Whether its exploring ancient archaeological sites and taverna-lined harbours, wandering through whitewashed villages, hiking across sun-kissed landscapes, snorkelling in the crystalline waters, or dining on fresh seafood, the trip is sure to leave you with memories to last a lifetime. The tour starts and ends in Santorini and is limited to people aged 16 and over. From €1,880 per person.

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Aegean Islands Tours (8 days)

(Photo: Bearing True South)

Bearing True South have been offering 8 day, fully guided Sailing trips to the Aegean islands for the past decade, to rave reviews. Guests travel in brand new, fully equipped sailboats, accompanied by a professional skipper as well as an English speaking tour leader. They visit 4-6 islands per trip and enjoy private, guided sightseeing tours in every place, focusing on architecture, cultural immersion, history and food. Almost everything is included in the trip, from pre-trip orientation, daily breakfast and lunch, all charter, fuel and docking fees as well as all local tours. From €2,160 per person.

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Ionian Islands Bike & Sail (8 days)

Explore Greece with the wind in your hair on both land and sea on this 8-day excursion. Starting in Corfu, you and your group of up to 20 will cycle and sail between Ithaca, Cephalonia and Corfu in the Ionian sea. Discover the famous island of Ithaca, said to have been the home of Odysseus, the unforgettable green bird sanctuary island of Lefkas, mountainous Kefalonia, and the beautiful olive woods of the small island of Paxos. Cruising from island to island, you’ll spend plenty of time ashore visiting fishing villages and historic sites by bike or just relaxing and enjoying the authentic Greek hospitality. The tour includes 7 nights accommodation in a twin cabin below deck with a private bathroom, and with 7 breakfasts, 5 lunches and 2 dinners also part of the package. From €2,071 per person.

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Mykonos Cruise (8 days)

(Photo: Sail In Greece)

Characterised by their white and blue architecture, traditional folk music, and general warmth and hospitality, the Cyclades are among the most famous island groups in Greece. Nestled in the heart of the Cyclades, the island of Mykonos  offers a flashy, cosmopolitan atmosphere thanks to its celebrity visitors and renowned clubs and bars. But there’s more to Mykonos than hedonism, with the island also teeming with charm and natural beauty. This 8-day sailing tour aboard  a traditional ‘gulet’ sailing yacht that accommodates up top 46 passenger invites guests to experience both sides of Mykonos. There’ll be onboard parties with drinks and music, plus the chance to walk the island’s stone-paved alleys, marvel at its eye-catching windmills, and generally take in the atmosphere of the island away from its raucous revelry. All accommodation is in comfortable on-board cabins.

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Sailing Tour & Lessons in Kos (14 days)

(Photo: Sailing Experience)

After a briefing in Kos, you and your fellow students will be ready for their 14-day intensive sailing trip among the Greek islands. Not only the quality sailing training you’ll receive, but also the wonderful journey itself offer an unforgettable and educational experience for all participants. You’ll set off from Kos towards Tinos with stopovers in Leros, Patmos and Ikaria. After mooring in  small idyllic fishing ports, a delicious local dinner awaits you in the evening. From Tinos, you’ll head to Siros and practice anchoring. The next day, it’s on to the beautiful little bay of Vathy on the island of Sifnos. Your return trip goes via Folegandros through the crater of Santorini and further to remote Anafi. Wake up the next morning and head back to Kos via Astipalea and Kalymnos.

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