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Yacht Charter in Greece | First-Timer’s Guide to a Sailing Holiday

Whether it’s during a holiday, retirement, or as a new hobby, many folks have fantasies of sailing off to beautiful destinations around the world. Always intrigued with the idea to charter a yacht in Greece, we jumped on the chance to sail with Seafarer Cruising and Sailing Holidays, the best yacht charter in Greece. As first time sailors, we knew this would grant us the perfect opportunity to see what yacht life truly entailed.

Yacht Charter in Greece | First-Timer’s Guide to a Sailing Holiday

For two weeks, we sailed around the Cyclades Islands aboard the Malama. During this time, we documented our sailing adventure through daily vlogs. Our goal was to share everything that we learned to help others who are interested in sailing (especially first-time sailors), get the most from their holiday.

Standing at the helm, while navigating the sea was sexy, adventurous, and freeing. | Yacht Charter in Greece

Why Sail Greece | Best Yacht Charter in Greece

Greece has approximately 6,000 islands and more than 10,000 miles of coastline! Sailing offered us a great opportunity to see more than just one or two major islands. In two weeks, we explored secluded bays and visited over ten different marinas.

Some of our favorite spots were the off the beaten path destinations, such as the Little Cyclades and Serifos. You will miss so much of what Greece has to offer if you don’t get out onto the water.

Although Santorini was memorable, our favorite part of touring Greece was sailing the Cyclades where few other tourists venture. | Yacht Charter in Greece

Benefits of Chartering

Want to know a dirty little secret? Sailing is a lot of responsibility! During our charter, anchor lines got crossed with other yachts. High winds often influenced mooring and unmooring. Every day, intensive planning was done by the skipper to ensure the safe passage of both the passengers and the yacht.

There was paperwork, responsibilities such as getting shore power, and interactions with harbormasters that all needed to be handled at every marina. Behind the scenes, the crew was working hard! As first time sailors, we were happy to sit back and let the highly-trained experts take care of all the dirty details.

Opportunity to Get Involved in the Sailing

Another benefit of chartering is that guests have the opportunity to get involved in sailing. This was our first time staying aboard a yacht and experiencing what life was like out on the sea. Some days we were actively involved, other days we relaxed and just watched the world go by.

Finally, chartering a yacht is a great way for couples, friends, and families to explore together. It is extremely affordable and offers great value for groups looking to share a unique holiday experience.

Cyclades vs. Ionian – What’s the Difference?

One of the first steps when planning your sailing tour in Greece is to decide what region to explore. There are two main island chains to chose from; the Ionian, which lies in the north, and the Cyclades to the south. It’s important to know that these two island groups offer completely different sailing experiences.

We sailed in the Cyclades during mid-May. Due to the unprotected layout of the islands, and the frequent windy conditions, this area offered more of an adventurous sailing tour. If the goal is to maximize sailing time, this may be the preferred itinerary.

Yacht Rental Greece

The lumpy waters tend to keep many of the tourists away. There were days we’d only see one or two other yachts out on the water. It was wonderfully underpopulated and quiet. Without mass tourism, the Cyclades are known to provide a more authentic Greek island experience.

Southern Greece, in the Cyclades, is known for the Meltemi winds. When sailing the Cyclades, expect windier conditions and lumpier waters. It’s important to mention these winds because they can have a dramatic impact on your sailing holiday.

The Ionian region, in northwest Greece, has a completely different vibe and sailing experience. The islands are more sheltered by land which typically lends itself to calmer waters. However, this makes the region more touristy, populated, and a bigger party scene. For these reasons, the majority of the flotillas will sail around these islands.

What’s the Typical Day Like

Depending on the course of the day, mornings typically started around 7-8 am. We began each day with a light breakfast, which consisted of cereals, yogurts, fruit, bread, jams, and coffee or tea. Depending on the wind conditions, we sailed for around 5-6 hours, with a lunch stop en route to the next marina.

Throughout the day there are opportunities to swim if desired.  Upon arrival, we were free to explore the island. At sunset, we’d enjoy wine and appetizers purchased from the local island shops.

Serifos was our favorite island stop in the Cyclades. | Yacht Charter in Greece

Dinner is not part of the package price. However, there were many tavernas (a small Greek restaurant or cafe) at every marina we visited. We even had the option to prepare meals on-board. Purchasing some appetizers and drinks and eating them aboard the yacht before dinner was a great way to save money!

Motion Sickness

We enjoyed experiencing all the faces of the Aegean Sea, from calm and flat to unpredictable and bumpy. But the reality was, the sea was unpredictable and rough. Seasickness came with the territory.

Being prepared and knowing our bodies, really helped us work through any motion sickness. For example, a lighter breakfast with tea instead of coffee was always better. We discovered that muesli and yogurt were harder for us to digest and weighed heavy in our stomachs after departing.

During lumpy segments, we opted to avoid eating lunch all together and simply enjoyed lunch when we arrived at the next marina. It’s okay to wait! At times, we munched on salty snacks like chips or pretzels.

Every morning we set course for yet another beautiful location, feeling the sense of freedom with the wind in our hair and our sail. In the afternoon, we arrived at a new island, each having its character and dramatic scenery to enjoy and explore. | Yacht Charter in Greece

The motion sickness medication typically lasted between 4-6 hours. Often during longer journeys, when the medicine started to wear off, I would lie down in our cabin to rest or read until we reached the marina.

What If You Don’t Like Seasickness Pills?

Harry, on the other hand, did not like the drowsiness he felt when taking the motion sickness pills and therefore, he refrained. Harry would rather vomit than be sleepy and drowsy. If he started feeling that his equilibrium was off, he opted to lie down in our cabin.

A postcard-perfect view in Ios, Greece. | Yacht Charter in Greece

Cabins below the helm of the yacht experience less movement than cabins towards the bow. We never felt ashamed to relax or retire to our cabin if we weren’t feeling well. It’s normal. It’s acceptable. No one judged us if we weren’t feeling ill and needed some time to lay down while riding out the waves. The crew wanted us to enjoy ourselves and of course, not throw up.

Reflections On Our Yacht Charter

Reflecting on our time aboard the Malama, I crave to be back on the yacht, sitting on deck riding the waves and watching the world go by. For us, it wasn’t always smooth sailing, but we are travelers who crave an adventure with a story to tell at the end of our journey.

This was the island of Folegandros. Check out this amazing coastline! | Yacht Charter in Greece

If given the opportunity, we would jump on the chance to sail the Cyclades with Seafarer Cruising and Sailing again. We loved the feeling of looking out at the Aegean Sea, often without another soul in sight. We preferred the authenticity of these islands, with many still untouched by cruise ships and mass tourism. For that reason, we were happy with our decision to sail the Cyclades.

We documented life aboard a 52-foot sailing yacht as first-time sailors. It was an adventure of a lifetime. We invite you to watch our two-week documentary series, Rapture of the Deep, to learn more about what chartering a sailing yacht is all about.

What to Bring On Yacht Charter in Greece

Before our departure, Seafarer Cruising and Sailing provided a great packing list to help us prepare for our time on the Malama. The following are some insider packing tips to ensure a great trip.

  • Beach towels were provided so no need to bring them.
  • There are no outlets in the cabins on the Malama, but the galley has a few outlets and a great (fast) USB charging station. Bring necessary cords and European plug adapters.
  • Bring shampoo, conditioner, body soap, and lots of sunscreen.
  • We packed super light and only brought two small backpacks. Less stuff means more room in the cabin.
  • Yacht etiquette calls for no shoes aboard. If you have sensory issues like me, consider packing cloth slippers or cozy socks.
  • Pharmacies were not common in some of the marinas. Bring any medicine and toiletries needed, especially motion sickness medication if desired.
Liz and Martin were amazing, professional hosts. We arrived as guests but departed as friends. | Yacht Charter in Greece

Interested in going on the best yacht charter in Greece? Check out Seafarer Cruising and Sailing Holidays. If sailing on a small boat is just not your thing, be sure to check out CruiseDirect for the best prices on traditional cruises.

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5 thoughts on “Yacht Charter in Greece | First-Timer’s Guide to a Sailing Holiday
  1. Your blog is really nice and inspiring. It sounds really good to be able to travel the world like you two. I’ve spent about three hours reading your blog. Thanks for sharing this with us. Keep up the interesting and informative writing.

  2. Hey, really nice pictures & videos you shared the blog you post it is really interesting to read. I am also planning for the trip on the charter I really wish this blog will help me a lot while choosing place and charter. Thanks for sharing this blog. Have a good day…. 🙂

    1. Thank you so much for stopping by and for your kind comments. You will be chartering with Seafarer Cruising and Sailing Holidays? They have such a great, high quality sailing tour for such a great cost. Great value. If you have any questions, we’d be happy to help!

  3. I have so very thoroughly enjoyed this mini series of yours!! So entertaining, and the best part? My husband and i often talk about returning to Santorini, but now we are excitedly looking into this sailing company for an adventure like yours! Thanks for all your private messages to me to discuss the details and letting me know first hand why this is the location and company to go with! Much appreciated!

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