Sailing Trips in Greece

Sailing Trips in Greece with a Professional Skipper

Joining a sailing trip in Greece with an experienced skipper is one of the best ways to explore the Greek islands — even if you have no sailing experience yourself. On these small-group sailing adventures, a professional skipper takes care of navigation, route planning, and daily logistics, allowing you to simply relax and enjoy the journey.

On board, a dedicated chef or host prepares fresh meals throughout the trip, making these sailing holidays in Greece a relaxed and all-inclusive experience at sea. With local knowledge guiding the route and great food shared with fellow travelers, these sailing trips combine island hopping, comfort, and unforgettable moments in one of the Mediterranean’s most beautiful sailing regions.

Discover Greece on a Small-Group Sailing Trip

With one of the longest coastlines in Europe, Greece is a dream destination for sailing. Joining a sailing trip through the Greek islands offers a relaxed and immersive way to explore this beautiful region. Expect turquoise bays, white beaches, dramatic cliffs, and charming harbor towns where traditional tavernas and the easy rhythm of Greek island life invite you to slow down and unwind.

With an experienced skipper and welcoming host on board, your sailing trip in Greece becomes a seamless and all-inclusive experience. Fresh breakfasts are served on board, drinks are included, and your accommodation on the yacht, port fees, and other boat-related costs are all taken care of. The crew plans the route and guides you to the most beautiful islands and hidden gems along the way — leaving you free to relax, enjoy the journey, and soak in the magic of sailing in Greece.

What does a typical day on board look like?

MORNING

Waking up on a yacht during a sailing trip in Greece is a peaceful way to begin the day. Start with a refreshing morning swim in the clear Mediterranean water or enjoy a quiet cup of coffee on deck as the harbor slowly comes to life. Soon after, a generous breakfast is served on board and shared together in the cockpit — the perfect start before another day of sailing and island exploration.

MID-MORNING

After breakfast, the skipper gathers everyone briefly to outline the day’s sailing route and highlights along the way. Then it’s time to set sail. If you’re curious about sailing, you’re welcome to get involved — from helping raise the sails to learning a bit about navigation — while those who prefer can simply relax on deck and enjoy the sunshine. As the yacht glides between islands, there’s plenty of time to unwind and take in the beauty of the Greek sea.

LUNCHTIME

As lunch approaches, we stop in a quiet, peaceful bay where we put down anchor for a few hours and enjoy a lunch prepared with local ingredients. There will also be plenty of time for sunbathing, swimming and enjoying your surroundings. Perhaps you’ll take the dinghy out to explore the nearest beach?

AFTERNOON

After lunch, we sail on to one of Greece’s beautiful harbours, towns or villages, where you will spend the night. Some light snacks are served on arrival and the skipper will tell you more about the day’s destination.

Our Destinations

Join our sailing trips in some of the world’s most beautiful cruising regions. During the summer season, explore iconic Mediterranean and Baltic destinations such as Croatia, Greece, Italy, and Sweden. When autumn and winter arrive in Europe, our sailing journeys continue in the warm waters of the Caribbean.

Whichever destination you choose, the experience remains the same — a carefully designed, all-inclusive sailing trip where the crew takes care of the sailing, planning, and onboard hospitality. All you need to do is relax, enjoy the journey, and discover new places at sea.

Your questions answered

Our sailing trips are designed to be simple and mostly all-inclusive, allowing you to relax and fully enjoy the experience at sea. Each sailing trip with a professional skipper and host includes:

A qualified and certified skipper with strong local knowledge and extensive sailing experience
A dedicated host who prepares breakfast and lunch on board, along with a drinks package during the trip
Accommodation in a double cabin on the yacht
Bed linen and towels
Boat-related costs such as port fees, LPG, and diesel

Many sailing trips also include return flights from selected departure airports as well as return transfers between the airport and the marina.

The only additional costs during the trip are typically evening meals ashore and any personal spending for shopping or other purchases during the journey.

During your sailing trip, the crew ensures everything runs smoothly so you can fully relax and enjoy the experience at sea. The host takes care of meals on board, preparing and serving breakfast and lunch while creating a welcoming and social atmosphere for everyone on board.

Our sailing trips include breakfast, lunch, and a drinks package with water, soft drinks, and wine or beer served with meals. In the evenings, the yacht typically docks in a harbor town or island village where guests enjoy dinner ashore and explore the local restaurants and cafés.

Your host and skipper are always happy to share their favorite recommendations, helping you discover the best places to dine and experience authentic local cuisine along the way.

Staying on a yacht during a sailing trip is a comfortable and unique experience. While life on board offers many of the conveniences of home, yachts operate with limited space, water, and electricity, so guests are encouraged to use resources thoughtfully — for example by keeping showers shorter when the yacht is anchored or moored.

Guests stay in a private cabin aboard a sailing yacht or catamaran, depending on the trip. Each cabin accommodates two people, so solo travelers typically share a cabin with another guest. Depending on the yacht model, cabins may feature either double beds or bunk beds.

All yachts are equipped with comfortable sleeping areas, a kitchen (galley), bathrooms with showers and toilets, and several spaces to relax and socialize, including the cockpit, the foredeck, and the interior saloon.

While sailing, phones and small devices can be charged through 12V power outlets. When the yacht is docked in a marina with shore power, 220V outlets are also available. Some yachts are equipped with generators, allowing the use of 220V power even when not connected to shore electricity.

In many destinations, marina facilities also provide additional showers and toilets that guests can use during the trip.

When Is the Best Time to Go Sailing in Greece?

The sailing season in Greece typically runs from April to October, offering a long window to explore the Greek islands by yacht. Each part of the season has its own unique charm depending on the type of experience you’re looking for.

From April to June, you can expect pleasant temperatures around 18–25°C, great sailing conditions, and fewer crowds in the island harbors. This period is ideal for travelers who prefer a more relaxed atmosphere and comfortable weather.

July and August mark the peak summer season, with warmer temperatures often above 30°C and lively harbors and villages throughout the islands. It’s a vibrant time to sail, with long sunny days and a lively Mediterranean atmosphere.

In September and October, the pace slows again. The sea remains warm, the weather is still comfortable, and many travelers appreciate the quieter harbors and more relaxed rhythm of the islands during this late-season sailing period.

We sail with these yachts

Excess 15

If you are a large group who still wants a quick-sailing catamaran, the Excess 15 is the perfect choice.

Dufour 530

Dufour 530 is a classic monohull boat perfect for larger groups who want to enjoy good sailing and pleasant spaces.

Excess 11

Excess 11 is a modern, smooth-sailing catamaran with ample space for a comfortable sailing holiday.

Dufour 48

Dufour 48 is a modern monohull boat which sails well – for a safe and pleasant holiday in the Mediterranean.

Fountaine Pajot 44

For those looking for that little extra – maximum comfort paired with optimal performance.

Which routes do we sail in Greece?

Our sailing trips in Greece typically depart from the charming harbor of Preveza and nearby Mytikas Marina, located just north of Lefkada along the beautiful Ionian coast. From here, the journey begins into one of the most scenic sailing regions in the Mediterranean.

Each sailing route is carefully planned by the skipper, taking into account weather conditions, wind, and the preferences of the group. This flexibility allows every trip to feel unique while ensuring a safe and enjoyable sailing experience.

Along the way, your island-hopping adventure may include stops at some of the Ionian Sea’s most beautiful islands, such as Lefkada, Kefalonia, Ithaka, and Meganisi, where picturesque harbors, hidden bays, and authentic Greek villages await.

What our clients say

"Boon was incredible to work with. I used them to broker a yacht in the Philippines and it was one of the best trips of my life….and I am a frequent traveler with high expectations. Polina is a seasoned professional and responded to all of my requests and questions in lightning speed. The contracting process was painless. It’s rare to receive this level of concierge service these days. HIGHLY RECOMMEND!"

Amber Z.

"Kaarel and Polina were incredibly helpful throughout the whole process. I would definitely book a charter yacht through them again."

Sophie D.

"We had the most amazing experience! Everything went perfectly smoothly from start to finish. The team was incredibly helpful, kind, and genuinely on our side — something that’s rare to find, especially when dealing with the often tricky world of boat rentals. Thanks to Boon Yacht OÜ, we enjoyed the most beautiful trip on a yacht in Croatia, completely stress-free. Their professionalism and personal touch made all the difference. We can’t wait to book our next adventure through them again — highly recommended! ⛵✨"

Epp S.

"We had an amazing experience with Kaarel and Polina providing great ideas and support for our charter"

Meelis K.

Sailing Trips in Greece

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