Family Sailing Vacation in Greece

sailboat view of the aegean sea

Have you always wanted to visit Greece? Does your family like to travel together with a bit of adventure and excitement in the mix? A family sailing vacation in Greece is the way to go! We spent two weeks total in Greece and spent one week sailing in the Cyclades. We loved island hopping around to some of the lesser known destinations. I want to use this post to give you a good understanding of what a family sailing vacation in Greece is like and why it’s the best way to visit the islands in the Cyclades. I will also give you alternative ways to travel to the Greek islands to enjoy the beauty.

sweeping view of a beach on and island with while sand and turquoise waters and mountains in the background

Why Sailing in the Cyclades is So Incredible

The best way to vacation in Greece includes visiting the Cyclades islands in the Aegean Sea. Not only are the islands beautiful, but they each have their own personality. A family sailing vacation is the perfect way to experience Greece. The time on a sailboat while working together make it unforgettable. Your kids will get to be a part of another culture through food, they will talk to locals, and see the sights of each island.

A sailing trip in Greece will give your family a unique perspective and allow you to get off the beaten path to avoid the crowds. You can tailor your Cyclades sailing itinerary to fit the needs and desires of your family. Island hopping in the Cyclades will give you a taste of each individual island and you can stay as long or short as you prefer.

Cyclades sailing will also include incredible swimming spots and give you access to some of the best beaches in the Cyclades. Your family will see places that would be difficult to see any other way and the pace will be more relaxed while you choose your own adventure.

view of the Aegean Sea with rocks popping out of the water, taken from the deck of a sailboat

What to Expect While Sailing in Greece

You can expect real sailing in the Cyclades. This will not be like a cruise. Sailing around Greece in the Cyclades islands will be adventurous and thrilling at times. Your skipper will be using the sails and very little of the motor, which means there is a lot of action on the boat. Although you will be able to see land almost at all times, you will be crossing open waters that can be rough.

Sailing holidays in Greece are very popular among European families, but we crossed paths with only one other American family. This was really fun for our teens because it opened their eyes to other cultures and languages.

Another unexpected value in family sailing vacations is the applied physics lessons. It will be natural for your kids to be curious about how it all works to get from one place to another by wind and sails.

side view of a monohull sailboat with the sails down

Weather in the Cyclades

There is one specific reason that sailing during the summer in the Cyclades is so popular. The summer Meltemi brings a growing thermal wind as the land heats up from May to August. The winds can grow to over 30 knots, which makes for some awesome sailing. The islands also create channels for the winds to increase in speed. These winds also help to keep the temperatures well below what you would experience in Athens.

Greece has all four seasons, but the island climate is quite dry. Sailing weather in Greece is most optimal from May to September. Take advantage of the high winds and strong sunshine for the best Greece sailing vacation. Mornings and evenings will be cool, but the middle of the day will be filled with warm sun.

teenage girl holding her hair back from the wind with the turquoise waters of the Aegean in the background
a family and a skipper on a sailing on a sailboat

What you need to Sail in the Cyclades

I have a complete list of items to take with you for an optimal family sailing experience. Less is more. There is not a lot of space on a sailboat to store items so choose wisely. The islands are very casual and there is no need to get dressed up unless you want to snag a nice family photo. A few things I recommend especially for sailing the Cyclades are:

  • Waterproof lightweight jacket for splashes on board while sailing
  • Seasick meds-even if you think you won’t, you very well may get seasick
  • Great music playlists for your time at sea
  • Water bottle with filtration-most islands do not have clean drinking water unless you purchase bottled water
  • A pair of shoes dedicated for land use only so you don’t track sand and dirt onboard
sideview of a sailboat in the waters of the Aegean Sea, taken from the water

How to Get to the Cyclades

There are several ways you can get your family to the Cyclades islands in Greece. There are pros and cons to all of them. Several of the islands have small airports that offer both domestic and international flights to Cyclades. Mykonos tends to be the best for international flights, but there are also plenty that originate in Athens for a quick jaunt.

Another way to get yourself to the port of embarkation for your sailing vacation is to take a high speed ferry from Athens to Cyclades. There are a lot to choose from and some are direct. You can expect a high speed ferries to Cyclades to take about 3-5 hours depending on where you are headed. Ferries in Cyclades are much shorter routes, usually less than 2 hours between them.

One final option to start your charter sailing Greece adventure is to sail from Athens down to the Cyclades. This option would take out the hassle of catching a ferry and spending a night on an embarkation island. However, keep in mind that this means a very long first day of sailing (probably about 8-10 hours of sailing) that will eat into your sailing week.

three teenagers walking along a stone path on a Greek island with a view of the Aegean on the left and while Greek buildings on the right

Best Islands in the Cyclades

There are a host of islands in the cyclades to choose from that can more than fill up a week long sailing adventure. Take a look at the map of Cyclades below for a frame of reference.

Each island has its own personality. Some are big enough to offer many restaurants, hotels, beaches, and outdoor activity choices. Others have very few. What they lack in choice, they make up for in charm. You can have the experience you want without having someone dictate where you have to go.

We by no means visited every island, but would like to highlight a few. For a more thorough list, check out our full family adventure in Greece. The best Greek island for families is Paros, which has the best mix of beaches and activities without being too overrun with tourists. The largest island in the Cyclades is Naxos, which is another great family friendly Greek island. If you have teenagers, you won’t want to miss Ios where lots of young people hang out.

a white moon rock looking beach on the greek island of milos with the shades of blues of the aegean sea in the background

Charter a Sailing Boat in Greece

Charter sailing in Greece is the only way you will be able to sail in the Cyclades. If you have your own captain’s license with the required amount of sea hours, then you MAY be able to rent a boat. I truly believe the best way to enjoy charter sailing Greece is with a hired captain. We had an amazing experience with Blue Water Sailing and our captain, Rita, on a 51 foot monohull named Albatross.

Many people choose to do catamaran sailing in Greece as their family sailing vacation, but my opinion is that it is too windy to use a catamaran. You might feel more unstable in a monohull, but it will be able to withstand the winds much better and allow you out to sail more than the catamarans.

teenage boy laying on the deck of a sailboat looking out to the sea with yachts in the background

The majority of sailboat rentals embark from either Mykonos or Paros. From either of those locations you can get a full week of sailing in without having to sail for longer periods of the day to get from island to island.

You can expect to spend some nights at anchor in the bays and some nights docked up at the island’s marinas. Sailboats have a kitchen, so you may choose to cook food onboard or bring provisions for small meals. I suggest eating dinner on the islands to get the full experience of Greek island life.

Costs of Chartering a Sailboat

Of course the costs will depend on how long you sail for, how many people are in your party, and what type of boat you charter. In general there will be a fee for the boat rental itself, which covers the beds and bedding needed as well as basic needs on the boat such as water and fuel. A large part of your cost will be to pay your skipper/captain, but expect also to add extra to that for tip if you were pleased.

Your meals will not be covered unless agreed upon in advance with your charter company. If you require extra staff such as a hostess, your costs will also increase. Activities, transportation, shopping, and meals on land will all be on your own as well.

a view from a beach towel on the island of naxos, cyclades looking out to the turquoise sea

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