Guide to Sailing the Greek Isles on a Private Catamaran

How to sail the Greek Isles

Sail the Greek Isles

Picture yourself on a sailboat with sapphire-blue sea shimmering beneath in the hot Mediterranean sun. Surrounded by islands that portray scenes from an epic postcard. In Greece the eroded cliffs transition into inviting sandy beaches. Unlimited isolated coves that are more enchanting than the last. Can you picture yourself standing on the deck of your own boat, the scent of the salt air blowing through your hair? On a private charter sailboat, you’re in control. You can choose your own path, your own rhythm. In the Greek Isles you can charter your own private sailboat or catamaran. In the article below we steer through the process of researching, booking and enjoying a sailing trip in Greece.

Sailboat or a Catamaran? 

view of greece coastline from catamaran on the water

The first step in your journey is choosing the vessel that suits your needs and desires best. Sailboats and catamarans each offer unique experiences. A sailboat, with its slim profile and single hull, cuts through the water with grace. The intimacy of a sailboat, feeling every wave, hearing every splash, offers a more authentic and perhaps even romantic connection with the sea. 

On the other hand, catamarans, with their dual hulls, offer a greater degree of stability and comfort, especially for those who might be newer to the sailing experience. Their wider design provides more space for groups and families, with large living spaces and panoramic views. Whether you choose the authentic charm of a sailboat or the stability and comfort of a catamaran, both types of vessels come in different sizes and levels of luxury. Therefore, your choice will hinge on your personal preference, budget, and sailing experience.

Understanding Your Chartering Options

The next big decision on your checklist will be determining the type of charter that suits your level of experience and desire for adventure. There are three main boat charter options – bareboat, skippered, or crewed. 

Bareboat Charters

This is the most affordable option but is not for everyone. Bareboat chartering is the option for experienced sailors, those with a spirit of adventure who relish the freedom to chart their own course. The bareboat option gives you complete control of your vessel, allowing you to captain your ship and crew.  According to web research, a bareboat charter typically cost between 1,500 euros to 5,000 euros per week. 

Skippered Charters

This option is a more expensive option, but provides an element of safety. The skipper carries insurance, and is responsible for damage to the hull of the boat. So this is a good option for reducing potential financial liability should a chartered boat get damaged during rental. For those who prefer to sit back and relax, a skippered charter might be the better option. These charters come with an experienced captain, allowing you to enjoy the journey, while also learning the ropes if you wish. During our Croatia skippered charter, we paid the skipper approximately 1,500 Euros, plus approximately 5,000 euros to the boat charter company for a one week charter. 

When we booked our skippered charter in Greece, we used PlainSailing, a UK-based yacht & catamaran company. We had a very good experience with them when we booked our Croatia skippered charter, and recommend them if you are planning a Greek charter boat rental. Plain Sailing has a great website that makes it easy to search for boats by country and region. Additionally, we have found their customer service to be responsive, helpful, and accommodating for our special requests on the boat. 

Fully Crewed Charters

This is clearly the most expensive option, so if you have the pocketbook for an indulgent vacation, a fully crewed charter can’t be beaten. Offering the services of a captain, chef, and crew, you can sit back, enjoy the journey, and take in the stunning Greek Isles without a care in the world. A fully crewed charter includes your meals, travel itinerary, and required paperwork for the length of the charter. We have not been able to afford this approach, but this option may work for larger groups where budget is not a factor. According to web research, Luxury charters can range from 10,000 Euros to 50,000 Euros per week. 

Understanding your skill level, comfort on the water, and your vacation aspirations will help determine which chartering option is the best fit for you.

Top Islands to Cruise in Greece

No journey through the Greek Isles is complete without a tour of the main island regions. Each region offers unique experiences and a different slice of Greek life and culture.

The Cyclades Islands

fountaine pajot 40 foot catamaran on the water in greece

Known for their iconic whitewashed buildings with blue roofs, the Cyclades are the heart of the Aegean Sea. The Cyclades consist of more than 200 islands, the most famous among them being Santorini and Mykonos. Each island in this group has a unique character, ranging from the lively party atmosphere in Mykonos to the stunning caldera views in Santorini. 

There’s also the tranquil beauty of lesser-known islands like Amorgos or Serifos. The clear blue waters, golden sandy beaches, quaint villages, and vibrant nightlife make the Cyclades a must-visit on any sailing itinerary.

Mykonos and Santorini are all over social media and are the two most crowded and expensive islands in Greece. So, if you want a relaxing trip to Greece, avoid the crowds and higher costs in Mykonos and Santorini. 

The Ionian Islands

The Ionian Islands, on the west coast of Greece, are a world apart from the Cyclades. These islands are lush and green, offering a completely different landscape and an Italianate flavor, thanks to their history under Venetian rule. Corfu, with its rich cultural heritage and vibrant nightlife, and the idyllic beaches of Zakynthos are two of the more popular destinations. 

However, do not overlook the lesser-known Paxos and Anti-Paxos. Here you can find secluded coves, crystal clear waters, and the tranquility that perfectly complements the livelier islands.

The Dodecanese

This island chain is located near the Turkish coast. The Dodecanese islands are rich in history and culture. The largest of the islands is Rhodes which is the home to medieval architecture that takes you back in time. Rhodes also offers nightlife for those seeking a higher energy experience. 

Other islands like Kos, known for its sandy beaches, and the volcanic island of Nisyros, with its ancient monastery and picturesque villages, are also must-visits in this group. The Dodecanese offers a unique blend of Greek and Turkish influences, adding a distinct flavor to your island-hopping adventure.

The Saronic Gulf

Just a stone’s throw from Athens, the Saronic Gulf islands are ideal for those seeking short sails and a quick taste of island life. Aegina, known for its pistachio groves, Hydra, with its car-free cobblestone streets, and Poros, with its clock tower offering breathtaking views, each offer a slice of Greek life at a leisurely pace. These islands are perfect for those seeking a quieter, more traditional Greek island experience.

Preparing the Perfect Itinerary

With so many incredible islands to visit, crafting the perfect itinerary might seem daunting. When planning your itinerary make sure you consider the weather, season, and goals for the trip. 

Weather events and winds should be considered during the planning process. For example, the ‘Meltemi’ in the Aegean, which can be strong during the summer. If you conduct your due diligence, a well-planned route can allow you to explore the islands in your own way. You can build your perfect Greek islands itinerary around the discovery of hidden beaches, ancient ruins, tavernas, and markets. 

Also, remember to factor in some downtime. After all, this is your vacation, and there’s no better place to relax and unwind than on the deck of your private charter, watching the sun set over the Greek Isles.

Understanding Paperwork and Regulations

Before setting sail, it’s crucial to understand the legal aspects of chartering a boat in Greece. For bareboat charters, a valid sailing license is necessary, and having adequate insurance is always recommended. The Greek government may also require a transit log, a document detailing your journey, and a list of all passengers. For skippered charters and luxury cruises, the charter company typically acquires and processes the transit logs. But it is a good idea to ask about this during booking.  

Conclusion and Sailing Travel Tips

In conclusion, chartering a private sailboat or catamaran to explore the Greek Isles offers an unparalleled way to experience this majestic corner of the world. A well-planned itinerary can include adventure, relaxation, and a connection with a rich and ancient Greek culture. 

Sailing Greece Travel Tips: 

  1. How many groceries do I need to buy for the sailing trip? Don’t purchase all of your groceries on the first day of your sailing trip. You can buy small amounts of food and produce at each island you visit. 
  2. How do I purchase wine and alcohol for the sailing trip?  Don’t over do it on day one when you board the boat. You can purchase wine, beer, and alcohol on the islands you stop at on your trop. To learn more about Greek wines, review our Wines of Greece article to help you pick wines that match your tasting preferences.  

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