Sail the Cyclades

Charter your Own Boat and Get Away from the Crowd

The Cyclades offer the quintessential Greek island holiday, and tourists by the thousands take the ferry from Athens each season. The group comprises some 220 islands with countless places to explore from a charter yacht and great sailing between. With so many stopover options to choose from in the Cyclades, it pays to do the research and get the best advice you can.

If sailing is your passion, the Cyclades is your place. Enjoying the freedom of travelling under sail across the sparkling Aegean to the next wonderful Greek island, is an experience that visitors by ferry can only imagine. Once there, glide past the breakwater for your place on the quay. Tie up, relax, explore and wait for the evening to come alive. Another great day of charter boat vacationing in Greece.

The best-known islands in the Cyclades group include Mykonos, Paros, Syros and Santorini. This is a compact group in the area of the Aegean Sea to the east of Athens, making these the most popular of Greek island sailing waters.

The voyage to and from Cyclades waters provides great sailing, as much a part of the adventure as the island-hopping itself. And with so many options to consider on arrival, each day you can do as much or as little sailing as you wish. 

Our client reviews about charter sailing in Greece

Rating: 5 / 5
The Lagoon 46 was the best catamaran we have chartered. There was plenty of deck and seating space and all the bedrooms/ensuites were a good size.

Preveza was a great starting point and we enjoyed travelling south to Ithaki and north to Paxi. Kalamos was a highlight we tied up to a pier next to a taverna for the night and it was a lovely spot.

We had very good service from Robert and Sue at Yachting Holidays and dealing with an NZ company gave us peace of mind. The service from Fyly in Greece was also excellent. We really appreciated being able to board the boat early and our skipper was also very friendly and easy to get along with.

Our skipper Adrian Dimitru was keen to get away on Saturday afternoon so we headed south and got a day ahead which was great. .he cruise was excellent and Adrian got us to some of his favourite spots so we were very lucky.

Ithaki not to be missed. Craig, New Zealand, Oct 18th, 2023
Rating: 5 / 5
Dear Sue, we would like to thank you and Robert for all the work you put in to make our charter run so smoothly from your end. We absolutely loved the Greek Islands, they were everything we had ever imagined. Jill and Pip, New Zealand , Oct 9th, 2019
Good breezes that provided just the right level of challenge. Not super crowded - no troubles berthing / mooring / eating / etc. Fairly chilled - at least compared to Croatia. Patmos was very good. John, Australia, Aug 17th, 2019
Had a great time. The wind was terrific - good fun, but nothing too hairy - exactly what we were looking for to take it up a notch or two from Croatia last year. And the Dodecanese were really good - nice ports, not too crowded (esp compared to Croatia) - just felt a bit more out of the way. DYC were fine - a little bit more on the 'smell of an oily rag' end of things compared to the very efficient German-run scene at Trogir, but it all worked and no real issues. Excellent recommendation Robert - boat and destination - you nailed it!

John, Australia, Jul 31st, 2019
The Lucky Clover was fantastic. We travelled around the Saronic Islands which were beautiful. A new adventure every day. One day we hired scooters and explored the islands. Great service thank you. 10 out of 10, a trip of a lifetime! Deborah, New Zealand, Aug 1st, 2017
For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

Related Blog Posts

  • Barcelona gets ready for the America’s Cup

    Barcelona gets ready for the America’s Cup

    As well as the competition for the Auld Mug itself, the 37th America’s Cup in Barcelona will incorporate the first ever Women’s and Youth America’s Cup regattas. Chartering Barcelona 2024 will be in demand!

  • Charter Sailing in Greece: It’s not just about the Islands

    Charter Sailing in Greece: It’s not just about the Islands

    Charter sailing tourism started in Greece. It’s still the place where first-time charterers want to go sailing, the place seasoned sailors return to year after year. And there’s plenty of Greece to go around

  • The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering

    The Sun Loft 47 Monocat: a Game Changer for Yacht Chartering

    A peak season cabin-share sailing holiday with skipper in glorious Croatia in August. Chartering a 2020-model 47 foot sailboat for just 175€ per person per day! This is the reality aboard the Sun Loft Monocat 47: a whole new concept in group charter with friends or extended family.

  • Charter a Gulet: Luxury Cruising in Classical Style

    Charter a Gulet: Luxury Cruising in Classical Style

    For your next sailing holiday, particularly in the eastern Mediterranean but in some other surprising places as well, consider chartering a gulet. Today's gulet is now a modern charter boat built for a unique vacation experience enjoyed in complete passenger comfort and luxury living aboard.

  • Lefkas to Athens: Boat Delivery on a Busman’s Holiday

    Lefkas to Athens: Boat Delivery on a Busman’s Holiday

    The Ionian Islands lie off the west coast of Greece. Reaching them is a little more complicated than getting to Greece's Aegean sailing holiday destinations that are accessible by ferry or charter directly out of Athens. The Ionians are worth the effort however, with the bonus Gulf of Corinth experience if time allows.

The Sail Connections Guarantee

One contact - every option - advice you can trust.


  • Matching any competitive offer
  • Sourcing boats with discounts available
  • Personalising our proposal just for you
  • Qualifying the operator as well as the boat
  • Advising without bias based on 25+ years of experience
  • We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

Get in Touch

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is jam-packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.