Sail the Cyclades

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 Mykinos, 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 highlight destination was Capri where because of unsettled weather we stayed in the marina. We found a brilliant restaurant in Ana-capri and enjoyed strolling the narrow streets. San Michelle villa was delightful. Peter, New Zealand, Oct 24th, 2018
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
Receive a personalized proposal with boat, cost and extra options as applicable.

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

Related Blog Posts

  • 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.

  • Sailing Bareboat in the Ionian Islands, 30 Years on

    Sailing Bareboat in the Ionian Islands, 30 Years on

    After many enjoyable years in the charter business and experiencing other great sailing destinations, it was time in 2017 to return to Greece. Back to where it the very idea of the Mediterranean charter boating began: a bareboat sailing holiday around the Ionian Islands.

  • Chartering a Boat in Greece: The Dodecanese

    Chartering a Boat in Greece: The Dodecanese

    Just offshore southwestern Turkey, the Dodecanese are nevertheless very much Greek islands. From charter bases in Kos and Rhodes, explore this historic, diverse group of islands that straddle east and west.

  • Chartering a Boat in Greece: the Cyclades Group

    Chartering a Boat in Greece: the Cyclades Group

    The Cyclades group of islands offers some of the best charter boat sailing on the Aegean Sea, with unforgettable experiences of Greek life in every port

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...

Receive a personalised proposal with boat suggestions, pricing and optional extras as applicable.