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When you sail the Greek Islands, you'll discover the Ionian Sea is the most relaxing area of the Greek Islands, with tall cliffs offering sheltered sailing conditions and a warm temperature, which makes them the ideal location your Greek Island sailing holiday.

Sailing Holiday in Greece


Sail Greek Islands, Myrtos Beach


Explore Kefalonia and visit the world famous Myrtos Beach and Melissani Caves, it's a real adventure day.

Blue Caves


Swim inside the Blue Caves (Lefkada) after breakfast to start your day. This is a real secret spot, not even the locals know it.

Porto Katsiki


Check out the famous Porto Katsiki beach (weather permitting) and take your paddle board on an adventure.

Sailing Greece - Dine out


Dine in Fiskardo, with some of the best restaurants, ever!

Melissani Cave


Take an excursion to the famous Melissani Caves as part of an adventure day.

Sail in Greece - Swim Stops


Enjoy and lap in the shallows of the water or grab your snorkel and explore the rocks and the surrounding bays.


7 Days   From € 1,590 pp

Yoga Sailing Greece





Check in time is 5 PM at Lefkas Marina

You will be greeted by the crew and will have a glass of Proceso waiting for you upon arrival at the boat.

Sailing Holidays Greece


Spartochori, Meganissi

We set sail once we're all boarded and head straight to the port of Spartochori, where you can sneak in a quick swim before dinner, or enjoy cocktail on the boat.  We eat dinner at the restaurant we dock 'Med Style'.



Local taverna 

Cocktails on the boat 

Sailing in Greece
Ithaca (Vathy)


Vathy, Ithaka

We start the day right by leaving early and having a swim at the Blue Caves (Lefkada) right after breakfast, then after a leisurely sail we spend the afternoon at the breath-taking Tilemachos Beach, before heading to the port Vathy, legendary home of King Odysseus. 


Activities:  Swim / snorkel in the Blue Caves, Paddle boarding 

Evening: Bars, Local tavernas, Cocktails on the boat 

Sailing Holiday


Everything you need to know on how to get to the Ionians coming from your designated locations.

Kefalonia (Sami)


Sami, Kefalonia

After leaving the port of Vathy, we stop for a morning swim and breakfast in a beautiful bay before heading to Sami for an afternoon of activities. We dock in the port of Sami up against the restaurants, for a real Mediterranean style yachting evening. Sami has a lot of attractions including:  The underground Melassani caves, hire a scooter and go to the beautiful Myrtos Beach for spectacular views, take a wine tour or arrange a dive.

Activities: Swim / snorkel, Paddle boarding, Melassani Caves 

Hire a scooter / car, Road trip to Myrtos Beach, Road trip to Assos 

Beach day, Wine tour, Horse / donkey riding, Scuba diving 


Evening: Bars, Local tavernas, Cocktails on the boat 



Fishkardo, Kefalonia

Another amazing day ahead and depending on the group and your wishes, we can either have a beach day at the spectacular White Pebble Beach, then anchor for the evening in Foki Bay, OR we have an early start to beat everyone else and go to Fishkardo to get a place on the town quay for a guaranteed 'hop on, hop off' experience.  


Activities: Swim / snorkel, Paddle boarding, Cave jumping and exploring Hire a scooter, Beach day


Evening: Bars, Spectacular restaurants, Cocktails on the boat 

Lefkas Sivota


Sivota, Lefkada

Today we sail to the famous Porto Katsiki beach which has postcard-perfect white cliffs, white beaches and the bluest water for lunch, swimming and laying out before heading to the traditional town Sivota, where we have a spot waiting just for us.  We eat dinner at the restaurant we dock 'Med Style'.


Activities: Swim / snorkel, Paddle boarding, Explore the rugged coastline, Beach day 

Evening: Bars, Traditional tavernas, Cocktails on the boat

Sail Greek Islands



Today is a day with plenty of short swim stops, including the famous Papa Nicholas Cave and a couple of other secret spots along the way. We spend the evening in the small fishing village of Kalamos and you'll experience Greek hospitality at it's finest. 


Activities: Swim / snorkel, Paddle boarding, Beach day


Evening: Cocktail bar, Traditional taverna, Cocktails on the boat 




We stop for breakfast and morning swim before we head to our final beach with bar, so you can sit in the shallows, sip a cocktail and enjoy our final swim before the port of Lefkada. Lefkada has a great selection of traditional restaurants and bars, including a Cuban bar where you can enjoy a Cuba Libre and dance the night away. 


Activities: Swim / snorkel, Paddle boarding, Cocktails on the beach

Evening: Bars, Traditional tavernas, Cocktails on the boat 

Lefkas Sivota .jpg



Saturday: Lefkada: Check out at 9am. Sadly it's time to say good bye, until next time.  


Please note the itinerary may change without notice due to weather, sailing regattas or other reasons.

Departure on Saturday, providing no significant boat damage from previous week.


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Introducing our beautiful Lagoon 42. This catamaran is one of the best models in the industry and is popular choice for sailing holidays.

Catamaran charter


Here is our Lagoon 42 up close. Look how beautiful it in the cobalt blue ocean.

Gay Sailing Greece Forward Cabin


These cabins are situated on the front part of the catamaran. It's not as big as the Master but some couples prefer it here. 

Gay Sailing Greece Master Cabin


These cabins are situated on the rear part of the catamaran. It a bit bigger than the Forward cabin and is more for shared charter.

Sailing in Greece


We offer the most inclusions and the best value for money!


You're greeted with Champagne upon arrival


Seven days/nights accommodation on your luxury private yacht


Half board: your hostess will prepare your breakfast & lunch


Full friendly crew: Skipper & hostess. Learn how to sail or test your skills with your qualified skipper.


All your onboard costs included: Your weekly marina & port fees, *fuel, final cleaning fee, tourism taxes.  No hidden charges or 'departure taxes'.
*fuel paid at end of week for private charters


Wifi (4G unlimited data)


Bring-Your-Own (BYO) alcohol.


We also have a Snorkeling gear on board for your usage.


Crew dinners and fuel are excluded  for private charters



The Girls sailing Greece
Hydra Beach


Everything you need to know on how to book your sailing holiday trip. It's very simple, it'll make your booking as "smooth sailing" as possible.

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When you sail the Greek Islands, you'll discover the Ionian Sea is the most relaxing area of the Greek Islands, with tall cliffs offering sheltered sailing conditions and a warm temperature, which makes them the ideal location your Greek Island sailing holiday.


When you think about sailing the Greek Islands, you think about the tranquil bays, the calm weather, small villages and sites of natural beauty for you to explore.  This itinerary has it all, so join us for your Greek Island sailing holiday as we explore the Blue Caves (Lefkada), discover the Melissani Cave, visit the home of Odysseus in Vathi, and of course the spectacular sailing around the Greek Islands.


Whether you want a cabin or a private yacht charter when you sail Greece in 2021, we offer a fully crewed cabin and private charter with a fully qualified skipper and hostess, so you don't have to lift a finger on your Greek Island sailing holiday. We take care of the provisioning, cooking and cleaning, giving you more time to relax and take in the beauty of your Greek Island sailing holiday.

If you like what you've heard, then this trip is perfect for you, so confirm your dates, gather your friends and either book a cabin or hire the boat to yourself on a private charter for your Greek Island sailing holiday.


Book your Greek Islands sailing holiday now!

Explore Europe’s Most Peaceful Islands with Sailing Holidays in Greece

There’s no better way to unwind from the everyday difficulties you encounter than by breaking routine and embarking on one of our sailing holidays in Greece. Med Sailing Holidays has created special holiday packages suited for couples, families, and friends to enjoy the natural beauty and modern comforts of a yacht tour through the Greek Ionian Islands. Below, we explore the ways in which you can get the most enjoyment out of our all-inclusive packages or bareboat yacht charter in Greece.

Tips for Getting More Value out of Yacht Holidays in Greece

We’ve set the opportunity before you to enjoy the best yacht holidays on the market. Our team has created high-value tours that showcase the relaxation and beauty found only on the Ionian Sea. Consider several key ways in which you can maximise your holiday’s value:

  • Take your choice between our all-inclusive chartered voyages and our bareboat charter in Greece. If you aren’t sure of what to bring on this voyage, then we can take care of all the details for you. Otherwise, if you’re an old hand at assembling this kind of holiday and are experienced at sea, we’ll provide you with a high-quality yacht with an experienced captain to get you where you’d like to go. 

  • When you book family sailing holidays in Greece, we’ve laid out several key destinations that you can visit. We recommend visiting each of these islands and seeing beautiful locations such as Lefkas, Meganisi, Vathy, Sami, Fiskardo, Sivota Bay, Kalamos, and Ormos Vrako. These islands are the most peaceful locations in the Ionian Sea and have sights that you won’t want to miss.

  • If your group is smaller and you don’t need the privacy of an entire boat to yourself, you can get the full experience for a fraction of the price by booking a cabin. You’ll still have access to the whole crew, accommodations, and sights that you’d have by booking your own boat.

Myths about Greece Sailing Holidays

Each person who contacts us has a different idea about what a yacht charter entails when visiting the Greek Islands. Here are several of the most common myths that we encounter:

  • Your sailing holiday isn’t just several days of you seeing things from your boat. You’ll have the opportunity to get up close and personal with the most beautiful sights that the Greek Islands have to offer, including the Blue Caves, Melissani Cave, and the mythical home of Odysseus in Vathi.

  • You don’t have to be an experienced sailor to charter one of our yachts and explore these beautiful islands. In addition to the boat and essential materials, you’ll also have our crew at your service. These exceptional mariners will ensure a safe and enjoyable holiday, as they take pride in showing off the beauty that Greece has to offer.

  • Sailing holidays don’t have to be wall-to-wall excitement and endless parties. Instead, our crewed yacht charter in Greece gives you time to unwind with calm days on a beautiful sea. The continual relaxation is punctuated by visits to the most beautiful spots in the Ionian Sea.


With these myths cleared up, you should have a better idea regarding what’s involved in our charter packages.

What Sets Med Sailing Holidays Apart Regarding Yachting Holidays in the Greek Islands

Any time you charter a private boat with a company, you’ll get a distinct experience. Our charter holidays stand out from the other options for several reasons:

  • Our all-inclusive options truly let you unwind. You don’t have to worry about cooking, cleaning, or choosing the regular supplies that you’ll need for a holiday. Leave all those details to us.

  • We’ve scouted out the best locations at each of the islands and will take you to spots that are known only to the locals.

  • Our boats are well-maintained and suited to host you for your full stay in tremendous comfort. You’ll have the privacy and space you need to relieve stress and enjoy the Ionian Islands’ unparalleled beauty.


Let our passionate team show you the best holiday you can have during your stay in Greece. Each day will reveal new wonders, and you’ll have a hard time choosing which part of the holiday was your favourite.

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