Greece is one of the most beautiful places in Europe and no wonder it’s on many people’s bucket list. Crystal clear waters, great food, beautiful beaches, kind locals and one of the best places to experience the perfect European summer dream. If you want to take this dream even further, I highly recommend island-hopping Greece by private Catamaran. You will experience the best of Greece while tasting the maximum form of freedom with family and friends. 

Keep reading as I will be sharing all the insights, tips and tricks to make the best out of your Greek island-hopping sailing experience. 

Prepare for your Ultimate Island-hopping Sailing Experience in Greece 

When we planned our trip, we were in full lock-down during the Covid Pandemic dreaming about our next gateway. We had insider information that Greece and Portugal would be the first European countries to open for the summer. So, we took a calculated risk and decided to book a Catamaran from Mykonos with the plan to sail the Cyclades in July 2021. What better way to stay away from the crowds and experience the full summer dream!

Catamaran island-hopping Mykonos
Catamaran Mykonos

Tip: You can choose between many island-hopping itineraries in Greece. However, if you only have a week, I would strongly suggest to choose the Greek Cyclades islands. These islands are well situated and close to one another, leaving you plenty of room and time to visit many local islands and make the most out of your trip. 

We booked our Catamaran through Zeilnet Vakantie Reizen, they are an experienced Dutch Travel Agency who are specialized in sailing trips, charters, and boat rentals across Europe. They have a large sailing network with many types of boats available. My dad is ex-military and used to be captain, so we rented a Catamaran for a week from Mykonos with him as our captain. However, if you do not know anyone who is a captain or don’t know how to sail, don’t worry, there are plenty of options to rent boats with captains as well. 

OMG which Boat Type to Choose for your Island-hopping Adventure in Greece?

So many options available! The most important thing is to know with how many people you are traveling. Our Catamaran had 4 bedrooms with each having a private bathroom, suitable for up to 8 people. Make sure you have enough space to equip everyone. We choose a catamaran because we like to stay on the trampoline like structure while sailing. On top the Catamaran is more spacious with a big back terrace, which is the perfect place to enjoy a nice aperitif during sunset at sea. 

How to Create your Perfect Island-hopping Greece Itinerary

If you rent a captain to come with you, you will choose prior to your departure a specific Itinerary. However, my dad made one himself studying the weather and winds. Our goal was to sail the Cyclades from Mykonos to Santorini while stopping in Naxos, Paros, and Syros along the way. 

Tip: It’s extremely important to study the Meltemi winds. These are strong winds that turn around at sea. If the winds suddenly take a turn, you might get stuck at sea, or you won’t be able to even depart. Keep this in mind. We had to adapt our itinerary in the middle of our journey, or we would have never been able to make it back to Mykonos to deliver the boat back on time. 

Budget and Port Fees 

You won’t believe it, but renting a Catamaran or Sailing yacht is not that expensive! We spent around 2100 Euros for a week which is around 350 euros per person (we were 6). Looking at the hotel prices in high season, this is extremely affordable. On top you will have to pay small port fees if you decide to stay overnight at a port or must fill up your water tank and electricity. You can also decide to anchor in a bay and not pay any port fees. You can just take out your small boat to reach the shore and go for dinner. 

Additionally, you will have to pay some insurance fee to ensure your boat is all-risk insured. You never know what can happen out at sea, so it is better to be safe than sorry. 

Things to do while Island-hopping Greece

There is plenty to do on a boat while you are sailing at sea. Make yourself a lovely cocktail and soak in the sunshine, bring a rod and fish directly from the boat or just have a good time with family and friends. 

Ermoupoli
Ermoupoli, Syros
Parikia, Paros Port
Parikia, Paros Port

If you choose to sail the Cyclades, you have plenty of time to discover the local islands as sailing time isn’t that long. Have a lovely Greek lunch, rent a buggy or scooter and go explore the hidden beaches or stroll around the authentic villages buying souvenirs. The Greek local ports are centrally located, alive and vibrant with lots of local restaurants, pubs, cocktail bars and ice cream shops. There is plenty to do!

The Best of the Cyclades, our Island-hopping Itinerary to Mykonos, Naxos, Paros, Syros and Santorini

Chora, Naxos
Chora, Naxos

First Stop, Mykonos

Also knows as one of the most popular tourist destinations in Greece. It’s well known for the beautiful beaches, summer parties, luxury resorts and wild nightlife. We spent a weekend exploring Mykonos before to hop on the boat and sail the Greek Cyclades for 7 days. Also read 2 days in Mykonos – A Complete Guide for the Party Pooper and get the complete guide on where to stay, where eat and what to do in comfort and in style. Please note that this guide is dedicated to those who want to explore the island beyond its crazy nightlife. 

Mykonos Little Venice island-hopping
Mykonos Little Venice
Mykonos Little Venice
Mykonos Little Venice

Next Stop, Naxos 

Our first stop was Naxos and we fell in love with the place. Mykonos is very touristic, but if you are looking for the authentic Greek experience, Naxos is your place to be. Naxos is the largest island of the Cyclades group with lots of activities. Spend your day on the beautiful beaches, visit some historical sites or stroll around Chora (Naxos main town) with many vibrant Greek tavernas, bars and shops. 

Naxos, Chora
Naxos, Chora
The Temple of Apollo, island-hopping Greece
The Temple of Apollo

Second Stop, Paros

In Paros, we arrived in port Parikia, not your average Greek port. Parikia is filled with oceanfront restaurants, incredible history, and an town to completely get lost in. 

If you are planning a day to Parikia, ensure you pre-book restaurant Stou Fred, to have the best culinary experience of a lifetime. This place is one of my best restaurant experiences from around the world. For more details, also read Paros Ultimate Eats – A Unique Hidden Culinary Gem  

Parikia, Paros
Parikia, Paros
Stou Fred
Stou Fred Restaurant

Third Stop, Syros

When arriving at Syros, you will dock at Ermoupoli, the administrative center of the Cyclades islands. Ermoupoli is much more Cosmopolitan, European looking than the other islands with more color tones of peach, yellow and red. There is a lot to do in Ermoupoli itself, the city is quite big, there are lots of shops, popular restaurants and bars to enjoy. 

Ermoupoli, Syros
Ermoupoli, Syros
Church of St. Nikolas
Church of St. Nikolas

Last Stop, Santorini 

Unfortunately, the Catamaran didn’t make it to Santorini because the Maltemi winds changed, but Santorini had been on my bucket list for years. So, I decided with my boyfriend to take the ferry from Ermoupoli, Syros, to Santorini and leave my family behind on the boat. Oops! But they understood 🙂 They continued their journey to another Greek island close to Mykonos.

Santorini Greece
Santorini Greece
The Divine Cave Experience
The Divine Cave Experience

Since Santorini was a bucket list item, I knew it need to be the full authentic Greek experience. So why not sleep in a cave! Also read Santorini – The Divine Cave Experience and Oia Santorini – Instagram vs Reality + better alternatives

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