Sailing

Sailing in Greece is how fell I in love with Greece on my first trip. Taking a sailing holiday in Greece is a great way to see several Greek islands and even some of the mainland in one trip. Not only do you get to see many places in one trip, but you can find spots that you want to revisit on your next Greece trip.

You sail from one beautiful Greek island to the next. Each will have a wonderful beach with clear turquoise or blue waters that practically beg you to swim in them. Then each night you will dock under the glowing harbor lights of a Greek village harbor and get to know the warmth of Greek hospitality.

There are several options for taking a sailing trip in Greece that can fit all types of vacations. Except for a few options, anyone can go on one of these sailing trips.

Sailing Charters in Greece

A sailing charter in Greece is probably the most common kind of sailing trip. On a sailing charter, you rent the boat, get crew, and the boat is provisioned for you. Usually, the crew and provisioning are included. Sometimes a hostess or cook is also included or can be added to the rental.

If you want a luxury sailing holiday in Greece, this is the way to go! You and your friends can rent the sailboat or yacht together to split the cost.

The other good thing about this option is that you usually have much more say in the itinerary so you can visit the Greek islands that you want or make a change if you decide to stay longer in one place. Dietary issues may also be more manageable since they will provision the boat as requested.

You can opt to have all your meals onboard or visit one of the many tavernas or restaurants in the places you visit.

Cabin Charters in Greece

A cabin charter is how I did my first sailing vacation in Greece. The cabin charter allows you to book a cabin on a charter with others. It can be a cheaper option if you can’t find enough people to charter a whole boat.

On a charter like this, the itinerary is set with mostly set in advance. Although, all sailing trips are dependent on the weather. The nice thing about this is that the captain usually knows the islands or towns very well, so you get top tips for each place.

I have done this type of sailing trip in Greece twice. Most recently, with Sailing Jollies. Although we were also doing a boat delivery and there was no hostess, and there was more responsibility. What I like about the cabin charter that usually you can learn a bit about sailing if you want.

Bareboat Charter in Greece

If you have your skipper’s license, you might be able to charter a yacht in Greece. Usually, this means there is no crew, and you provision the boat. This is a great option if you have a large family or group of friends already ready to go on the trip. You can make the food you want.

You also get to set your own itinerary so you can see the places you want without compromise. The only thing is having the yacht or sailboat back to the agreed-upon marina by the end date.

A bareboat charter in Greece is probably only a good idea if you have sailed in Greece before since the winds can be strong at certain times of the year. Another option is to join a flotilla of boats that may be a combination of bareboat or charter sailboats. Going on a flotilla is useful if you are confident in your sailing ability but unsure of the sailing waters. 

Day Sails in Greece

Almost every island has an option for a day sail around that island or to another island nearby. A day sail in Greece may also be possible from Athens and other major ports on the mainland. 

A day sail means that you will leave early in the morning and sail to points during the day. It usually consists of sailing to a swim stop, having lunch, and then sailing to another swim stop before returning to the port. Many times these swim stops are in spots on islands that may be unreachable by car or walking. 

Going on a day sail in Greece means that you might get to see parts of the country you may not have seen on your island vacation only.

Boat Delivery

Maybe you have some sailing experience and would like to build miles, then going on a boat delivery is a great option. The only drawback to these is that sometimes the delivery is on a schedule, and you cannot stop much for leisurely days in the ports. You may only have a few days to make the delivery.

As with some cabin charters, the trip is not going to be round trip, so you will need to find your way back to the starting point if that is where your flight leaves from. Of course, you might be able to pick up another boat delivery or enjoy the place you are in for longer.

Most boat deliveries need people with sailing experience, so this might not be an option for the casual sailor. It depends on the skipper that sail with.

Sunset Sails on the Greek Islands

By far, the most popular option for sailing in Greece is to take a sunset sail. Greek sunsets are out of this world, and unless a cloud blocks it, I have never seen a bad Greek sunset.

A sunset sail will usually leave in the late afternoon or early evening, depending on the activities involved. Some are quick for about two hours just to get out to watch the sail, usually with a drink. Others include swimming and a light meal. The boat will head back to the harbor as soon as the sun sets to avoid getting back too late in the dark, usually.

Keep in mind that the time of the sail may vary during the year for the sunset sail since the sunset changes times.

Greek Island Hopping Itineraries

Now, where should you go on one of these fantastic sailing trips in Greece? There are so many options. Of course, if you are going on a cabin charter, flotilla, or boat delivery, you may not have much choice in your sailing itinerary.

However, if you have booked the entire boat, you get to choose! If you depart from Athens, you can choose from the Saronic islands, the Peloponnese, or the Cycladic islands. For example, my first sailing trip was Athens, Aegina, Poros, Hydra, Sifnos, and Ios. The return was Ios, Paros, Syros, Delos, Kea, and Kythnos. This trip was great since we got to see both the Saronic and Cycladic islands.

If you have less time, you could leave Athens and head to Aegina, Poros, Hydra, Spetes, and return to Athens. My second trip was from Athens to Corfu. This trip was great as we saw lots of mainland villages and sailed through the Corinth Canal.

Another area to consider is the Dodecanese islands in eastern Greece. These islands are closer to Turkey so your itinerary could include Turkey as well as Kos, Kalimos, Leros, and Patmos.

Each of these areas of Greece offers something different, so you will want to do your research and see what kind of experience you would like to have.

Types of Boats

There are many options for types of boats to charter in Greece. If you know what kind of boat you want, you have already narrowed down your choices of charter companies. Some companies only do monohull sailboats and some do a mix of monohulls and catamarans. If you are only looking for motor yachts, then you can look for those as well.

Going on a monohull sailboat is my top choice. If you are unfamiliar, a monohull is a single hulled boat with sails. Many sailing enthusiasts prefer this as you get the real feel of sailing this way. When underway with higher speeds the boat will keel to one side. This is when one side of the sailboat is lower than the other. The wind whips through your hair and occasionally you will get a light spray of seawater!

Another type is a catamaran. These usually have two hulls that are connected. These offer more stability than a monohull. The cabins tend to be larger as is the saloon. These are a great option for people new to sailing or those traveling with young children.

Then there are motor yachts. There are many different kinds of these and I won’t go into them all. The ones you charter will have cabins for sleeping and it will vary on where the helm is. This may or may not matter to you if you are the skipper or not. If you are skippering your own boat, you will know what you prefer. If you going with a skipper, make sure the yacht has the features you desire.

Wondering what to pack for you Greek island sailing trip? Check out my post all about it by clicking here!

Have you been sailing in Greece? Share your experience in the comments!

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Since my objective was to be on a boat, I wasn’t focused on what islands we were on the itinerary. I just wanted to be on the water. I knew I want to go to Santorini and that was what prompted me to book two weeks as it allowed two days in Santorini. The guide I had purchased didn’t do most of the island’s justice and eventually, I decided just to learn on board the boat. That was part of the appeal of the charter company I chose; they provided information every day about the places we were going to visit. Several islands will get an individual post, but I want to give you an idea of each island.

Week One

The first stop was the small island of Aegina. Sailing to Aegina doesn’t take very long, and the captain said that this was because they hope to let passengers get their sea legs, so they don’t get seasick.

Aegina is known for the Temple of Aphaea as it is one of the best-preserved temples of ancient Greece. The temple is located at the top of the island, and you have to hike up to the top. I opted not to climb to the temple because I woke up with a migraine and it was still hot in Greece in September and would have made my migraine miserable. Since the island is also known for their pistachios, I went on a pistachio hunt! Later I decided to bring these back to Qatar for my coworkers, but they were some of the best pistachios I have ever had.

After lunch and swim, we headed to Poros, which isn’t far from Aegina. We docked at the town of Poros (I discovered there are many duplications of names in Greece). This was to be our sleeping spot for the evening. First thing on everyone’s mind was a shower. The local beer pub offered showers for €3! So, yes, I showered in a bar. It wasn’t the nicest shower I have ever had, but it certainly wasn’t the worst. And I definitely think it was part of the experience.

The next island was Hydra. Hydra was a happening place! The port was full, and we had a hard time finding a place to dock. There are no cars allowed on the island, and it is full of cats!

The captain wanted to head to Milos, but the weather wasn’t going to cooperate. Instead, we headed to Kythnos. Kythnos was one of my favorites. We slept in two nights in Kythnos in different places. (There will be more on Kythnos later.)

Next, we headed to Serifos for a short swim stop. The tricky part here is there is no harbor. We were given the option to swim to the beach or take the dingy. I was sure I could make it to shore, but I wasn’t sure I would be able to make it back the boat. I opted to take the dingy. The water was so clear here. It reminded me of the Caribbean.

The next and final stop for the first week was Ios. By this point, I was really tired and decided to stay on the boat that day knowing I still had to do Santorini and another week!  This turned out to be a good thing as I was struck down by the opposite of seasickness, land sickness (?) and was dizzy for several days. There are lots sights to see here, though, including Homer’s Tomb. We had dinner the last evening together at an amazing hotel overlooking the harbor and were treated to a spectacular sunset.

Week Two

After two nights in Santorini, I returned by ferry to Ios to begin week two! The land sickness went away for a bit on Santorini but was totally gone once I was back on the boat. Schinoussa was the next island and had the smallest population of all the Greek Islands we visited. As of 2011, 256 people lived there, but it seemed like less than that. There wasn’t anything at the port, but the walk up to the town was magical as they have made a great stone path that is lit at night. I wish we had more time on this tiny island.

Next, we sailed to Paros. Paros was much larger than Schinoussa and some of the other islands we visited. I decided to strike out on my own for the day and the evening meal. The island had great shopping and restaurants. You could wander the streets for hours. My only regret was that I didn’t have more room in my suitcase. The harbor was not protected, and we had a rough night on the boat and eventually, I went to sleep in the lounge area to try to escape the noise of the water hitting the stern where my cabin was located.

The ancient site of Delos was the next island. Delos is not an inhabited island due to the whole island being an archeological site. It is believed to have been inhabited since the 3rd millennium BC. If you aren’t on a sailing cruise, you can get here by ferry from Mykonos. Bring your hiking shoes and some water as there is lots to see and the only snack shop on the island is a bit of a walk from the port as are the bathrooms!

Another big island was up next with Syros. Syros is very modern and looks a little Italian. It had a nice mix of sites to see and shopping. We had a wonderful dinner here in a building that wasn’t fully restored, and the ceiling was made of vines that hung down into the dining room. The food was modern Greek.

Last, but not least was Kea. Kea was another favorite of mine. The harbor was small and quaint. The beach was a short walk from there. We slept at Kea and in the morning went to the hilltop Chora (village) to see the Lion of Kea. Kea has a wonderful museum in the village as well.

Are you tired yet? I was by this point and was glad and sad to be heading back to Athens. While I think I would have needed some serious naps, I would have loved to stay on the boat for the next two-week journey.

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