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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.



Sailing with Med Sailing Holidays, was the best ever experience. We had a great time, I was spoilt with having great skippers. I felt very safe all the time. Geoff the head skipper of the company is a very competent sailor. We had loads of fun and visited many islands and experienced many wonderful cafes and restaurants. And what can I say about the islands and the colour of the water, very much what you see in magazines. Croatia & Greece are amazing places to visit, I was fortunate to be able to sail both areas. The locals are very hospitable



Just spent an amazing week sailing around the Ionian islands with skipper Delaney and hostess Kat. They were wonderful and the islands were beautiful. The food was amazing and the boat was beautiful. Can’t fault the wonderful 7 days we spent on board and would love to do it all again.



The sailing swimming and sunning aren’t even the best parts of this incredible vacation...nor are the amazing views of the Aegean Sea, the snorkeling in the clearest blue water you’ll ever see or exploring the adorable Greek ports. These things are all top notch, each detail flawlessly and effortlessly attended to. The best parts? Take this trip and let’s compare!!


Med Sailing Greece

Sailing Greece highlights

  • The best Greek sailing itinerary in the market (in our opinion)

  • Full crew provided on all voyages (Captain & Hostess)

  • Book a cabin for a fraction of the price of a whole boat, or

  • Book a private charter for you own group

  • Completely hassle free - we'll take care of everything 

  • No previous sailing experience required

  • Get away from the hordes of tourits

  • Learn to sail (if you want) with your qualified skipper

  • Daily swim stops in the crystal clear water

  • Trips suitable for professionals, couples, families and a mature audience

  • Explore Kefalonia and visit the world famous Myrtos Beach!

  • Swim inside the Blue Caves (Lefkada), explore Melissani Cave and enjoy the breathtaking beaches.

  • Check out the famous Porto Katsiki beach

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

  • Let your taste buds come alive with the local food and wines

  • Wander the streets of Vathy, Ithaka the home of Odysseus from Homer's Odyssey

  • Take in the sights and relax as we sail the coast

  • Golden sunsets and sunrises like nothing you've seen before

  • A sky full of stars at night, with no light pollution

Sail Greece Itinerary

What's included?

  • Champagne arrival

  • Seven days/nights accommodation on your luxury private yacht

  • Luxury Lagoon 42 catamaran

  • Champagne arrival

  • Early check in

  • Full crew: Skipper and hostess

  • All your onboard costs included:

  • Your weekly marina & port fees

  • Fuel (up to €200)

  • Final cleaning fee (€250)

  • Local taxes

  • Half board: your hostess will prepare your breakfast & lunch

  • BYO alcohol

  • Snorkelling gear

  • Learn how to sail or test your skills with your qualified skipper

  • A private yacht for a fraction of the cost to do it yourself

  • Always a small group on board

  • Wifi (Limited data)

  • No hidden charges or 'departure taxes'

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

Greece Inclusions




1. Spartochori (Meganisi)

2: Vathi (Ithaki)

3: Sami (Kefalonia)

4: Fiskardho (Kefalonia)

5: Sivota (Lefkas)

6: Kalamou (Kalamos)

7: Lefkada (Lefkas)

Day Stops (Highlights)


1: Blue caves (Lefkada)

2: Papa Nicholas Cave

3: Porto Katsiki

4: White Pebble Beach

5: Pristine Beaches 

The Girls sailing Greece

You will start your Greek Islands sailing holiday in Lefkas town on Lefkada Island. If you arrive early, you can explore the wonderful Greek Island and her beautiful postcard beaches.


If you have a day or two on the island before your trip, be sure to hire a car and explore the island, you'll have fantastic views, perfect beaches and you'll be spoiled for choice with the local restaurants.

After checking in, we're off to Meganisi to start your Greek Island sailing holiday.

Greece beautiful beaches

Our first stop of your Greece sailing holiday is Meganisi.  Meganisi offers the charm of a small port, like only the Greeks can do!

We will be berthing in a family owned and operated restaurant and pier. Nothing says Greek hospitality like the locals running around in preparation for us. We will dine on the water's edge as the sun sets over the bay.

In the morning we'll set sail off for the Blue Caves of Lefkas to kick-start your Greek Sailing Holiday in style! Prepared to be amazed.

Private Charter Greek Islands
Vathy (Ithaca)

Sailing the Greek Islands is a magical event, so while on your yacht charter, we will take you to a place of legend; Ithica, the home of Odysseus, the King who left his wife and home in pursuit of victory at the battle of Troy.


Ithaca is a peaceful island, ideal for relaxing and enjoying a slower pace of life and some of the meals the local tavernas prepare stay true to the ancient recipes of an older time.  

On our way to Vathy, we'll stop off to explore the Blue Caves, so get your swimmers on and be ready.

Sail Greece Melisanni Caves
Sami (Kefalonia)

Whilst on your private yacht for the week, no trip is complete without stopping at Kefalonia, which is the largest island in the Ionian Sea and has so much to offer.


Famous for it’s exotic beaches, including Antisamos and Skala are stunningly beautiful beaches we’ll pass on the way to Sami, where you can make your way to the Melissani Cave, lounge on the glorious beaches or explore the island at your own pace.  

We arrive early in port today, which gives you the opportunity to see the Melisanni Caves, scooter to Myrtos Beach or take a wine tour. Whatever you do, you'll have the opportunity to see this beautiful Greek island.

Sail Greek Islands Catamaran
Fiskardo (Kefalonia)

Fiskardo must have THE BEST RESTAURANTS in the Ionian!  We almost need to stay a week to explore all the restaurants here.  This isn’t a secret and a lot of boats come to this special little place, so we need to get there early if we want to get a place on the town quay. No Greek sailing holiday is complete without stopping here for dinner.


Greek Island sailing holidays are about a unique experience and Fiscardo at night takes on an entirely different perspective. The lights, the old buildings, cafés, bars & restaurants all combine to provide a magical Mediterranean atmosphere. Of  all the villages on Kefalonia, Fiscardo stands out as having a unique ambience, especially on a summer evening.

Private Charter Greek Islands
Porto Katsiki/Sivota Bay

When you think about sailing the Greek Islands, you think about clear water, beautiful beaches and white cliffs.  This is it. We sail you to Porto Katsiki beach on Lefkada Island, which is one of the most beautiful Greek beaches.  It is also in the top of the list of best beaches in Europe each year. You will absolutely fall in love with the beach and won't want to leave, ever. We will stop for lunch and swim before heading to Sivota Bay.


Greece sailing holidays are know for protected harbours, and Sivota is one of the nicest natural harbours and one of the most picturesque fishing village in whole Ionion.  After parking the boat, you’ll stroll the streets soaking up the special atmosphere of the magical bay. 

Sail Greek Islands Porto Katsiki

We'll sail the catamaran to Papa Nicholas Caves where it’s said that it was a secret hideout during World War II for the submarine Papanikolis of the Italian armada. After a swim and exploration, we’ll sail to a final stop for the trip.

We have a day of smooth sailing, beaches, relaxing and soaking up the sun before heading to Kalamos.

Kalamos is a small town, which has small town charm for dinner on the water's edge.

Sailing Greece, beaches
Ormos Vrako/Lefkas

When we sail back to Lefkas, we’ll stop in the protected bay of Ormos Vrako on the mainland.


There is a cocktail beach bar, where you can enjoy the music, lap in the shallows of the water or grab your snorkel and explore the rocks and the surrounding bays.  Sometimes 'Sailing the Greek Islands' means laying on the beach with a cocktail.


What a superb way to end your week sailing the Greek islands, before heading back to the marina by 6pm. 

Sailing Holidays Greece
Check out

All good things must come to an end and it's time to say goodbye.

Check out and disembarkation is at 9:00

If you have the time, it's always nice to stay in town for a day or two to enjoy the island life. Perhaps a villa with an infinity pool, overlooking the sea speaks to you?


When you book a sailing holiday in the Greek Islands, it’s important that you factor in all the running costs of the trip, so you have an accurate quote, you have the most value and you’re not surprised with unknown charges on the day.


If you are booking at sailing holiday for your friends and family in the Greek islands, you might want to consider a private charter so your group have the exclusive use of the boat. This way you also have more control over your in inclusions and overall trip.

The alternative to booking a private charter is booking a cabin charter. This way you get all the benefit of a private charter for a fraction of the price. It’s advisable to look what is included in the price, as much as what is not.


It doesn’t matter if you’re booking a private charter or a cabin charter for your Greek sailing holiday, we include everything you could need on your trip. Because of this, at first glance our fully crewed sailing holidays may appear to be more expensive than the other operators, however you will discover that we offer more value for money, giving you more bang for your buck.



Greece Dates

Pricing is based on 2 people sharing a double cabin.

Please make an enquiry if your preferred dates aren't available.

Greece Book Now

Master Cabin

Forward Cabin

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