Sail the Mediterranean waters around Greece's Cyclades Islands

Give in to dreams of sailing the Greek Islands on this seafaring adventure around the renowned Cyclades Islands. Bliss out on Mediterranean waters, swim in turquoise seas, explore ancient towns and delight in fresh Greek food and culture. From laidback non-touristy islands like Small Cyclades to the vibrant holiday mecca of Mykonos, all holiday bases are covered on this eight-day sailing odyssey.

Santorini, Greece
Santorini, Greece
Physical rating
Cultural rating
Min 15
Group size
Min 1, Max 11
Carbon offset
62kg pp per trip


  • Jump into Ios’s vibrant nightlife
  • Visit ancient ruins on Amorgos
  • Take an optional tour into the countryside on Naxos
  • Float atop the blue waters off Kamares’s port
  • Admire cascading bougainvilleas


This itinerary is valid for departures from 01 January 2016 to 31 December 2016. View the itinerary for departures between 01 January 2015 - 31 December 2015

Welcome to Greece. There will be an 11 am group meeting this morning, where you'll meet your skipper and shipmates. Insurance details and next of kin information will be collected at this meeting, so ensure you bring these details to provide to your leader. The first port of call is the local supermarket to buy supplies for your trip as a group (we call this a ‘starter park’). The starter pack will include provisions for breakfast, lunch and/or snacks for the whole trip. If you have any special dietary requirements, please make sure you notify us at the time of booking so we can accommodate your requests. Consider arriving a couple of days early in order to enjoy breathtaking Santorini. In 1500 BC a volcanic eruption sank the centre of the island, forming one of the most significant geological formations on the planet - the awe-inspiring caldera. Check out the range of restaurants, shops and bars in the island's capital of Fira. The Orthodox Metropolitan Cathedral, Catholic Cathedral and Dominican Convent are also worth a visit. Megaron Gyzi Museum has an interesting display of photographs showing Fira before and after the quake. An absolute must is to take a walk along the caldera's rim to Firostefani, Imerovigli and Oia. This is a particularly memorable experience at sunset (Santorini's sunsets are famous), but make sure you leave plenty of time so you aren't walking in darkness. Santorini's volcanic beaches are another must-see. Check out Red Beach or the black beaches of Perissa, Vlhada, Perivolos and Agios Georgios. After the welcome meeting today set sail through Santorini’s caldera, cruising for five hours across the Aegean Sea to drop anchor at the island of Ios. The boat will stop at Manganari Beach along the way. Ios proudly claims to be the burial place of epic Greek poet Homer. While there is no proof of this, the myth has become firmly etched into the local psyche. Despite its party island reputation, Ios has managed to retain some allure, due to its abundance of beaches and the preservation of its classic cube houses in the laneways of Hora. A short walk from the harbour in Ios, Hora's shops, restaurants and bars all come alive in the evenings. Enjoy sunset views from the hilltop Panagia Gremiotissa (Church of the Virgin). Notes: The marina in Santorini is currently closed for dredging. Until further notice, you’ll be met at the existing meeting point and transferred to the yacht by vehicle or water taxi. Please be at the meeting point 15 minutes before departure time. If you can't arrange a flight that will arrive in time, you may wish to arrive a day early so you're able to attend. We'll be happy to book additional accommodation for you (subject to availability). ***The beauty of sailing is that each day is unique and, while we have a destination to reach, if the weather changes or something takes the group’s fancy, we are flexible on the day's itinerary***
Today, sail for around four hours and reach the rugged island of Amorgos, known as the stunning location of Luc Bresson's film, 'The Big Blue'. Stop for a swim at Paradisi Beach before continuing along the coast to the port of Katapola. Ravaged by piracy in the late middle ages, Amorgos was ruled by the Venetians, Byzantines and Ottomans until the Greek Revolution. The restaurants, cafes and bars along the waterfront are an excellent place to relax, while enjoying views of classic Cycladic windmills and an old Venetian castle. You might like to explore the ancient Minoan Settlement or drive up to the spectacular 11th-century monastery, Moni Hozoviotissis, for breathtaking views of the Aegean Sea. Also worth a visit is the village of Hora, sitting high up in the rocky mountainside. Stroll through the labyrinth of stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower.
Cast off this morning for the four-hour sail to the Small Cyclades. This group of islands boast quaint fishing villages, clear waters and great beaches. While all of the islands once harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Schinoussa and Donousa have permanent residents, with the largest population said to be around 300. In the evening, perhaps sample fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.
Today, make your way to the largest Cycladic island of Naxos. There’s the option of taking a day trip around the island, but you can always stay behind and relax. The island’s best beaches are to the south, where water sports are also on offer. Perhaps hike up to the old Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches all retain a medieval feel. While here, stop by the Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. Take an optional trip to the countryside to observe rural life, see one of the oldest temples in Greece and enjoy lunch in the hills at a family tavern. Get a taste of the local brew with a shot of Kitron, best described as a lemon liquor. In the evenings, indulge in the vibrant nightlife of the island’s capital, Hora.
Sail for around four hours to the island of Syros, dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek revolution made it a safe-haven for the persecuted. Perhaps catch a bus up the hill to the fortress-like village of Ano Syros, exploring the town’s stone archways, narrow alleyways and stunning views of the Aegean. Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the magnificent town hall in the main square.
In the morning, raise anchor and set off on a short three-hour cruise to an island packed with beauty and glamour, Mykonos. Mykonos has a history of around 5,000 years and is said to be named after Apollo's grandson. It was also the mythological base for a deadly battle between Zeus and the Titans, their giant petrified bodies forming the rocks of the island. Browse the chic galleries and boutiques in town, examine the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. In the evening, perhaps wander down to Little Venice, where colourful, wooden balconies hang precariously over the sea - the ideal spot to sit back with a cocktail and enjoy an Aegean sunset. Afterwards, join in the fun of Mykonos’ notorious nightlife.
Today set sail for the island of Sifnos, known for its production of high quality ceramics. The island's bare hills belie fertile valleys of wild juniper, terraced olive groves and almond trees. The beach in the main port of Kamares is one of the best on the island and the ideal place to swim. Wander among the white-washed houses, churches and chapels of the village of Apollonia, which is the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland to enjoy panoramic ocean views and see the medieval architecture of the fortress of Kastro.
This morning, cast off towards the tranquil island of Folegandros. Named after the son of a former King of Crete, Folegandros has suffered a long history of colonisation and occupation like many of the surrounding islands. In the port of Karavostasis, the pebbly beach or a waterfront taverna are nice places to relax. Take a stroll through the island’s capital of Hora, one of the oldest villages in the Cyclades. The area in and around the Kastro is the most striking. In the evening wander up the hill to the pretty Church of the Panagia, an excellent vantage point to view the sunset.
First thing this morning, bid farewell to the open water as you sail back through the caldera and drop anchor in Santorini. You should arrive by approximately 11 am, after which time you are free to go. If you plan to depart today, please don’t book a flight earlier than 4 pm in case the boat’s arrival is delayed due to weather conditions. Note: The Itinerary above may be subject to change depending on weather or berth availability. Your skipper will make the final call to ensure your safety at all times.
View trip notes to read full itinerary


4 breakfasts, 3 lunches
Overnight boat (9 nights)


There are currently no departures for this trip.

If you can’t find the dates you’re after here, click on the button below to find options for the next season. Please bear in mind that some of our itineraries can change from year to year, so this trip may differ slightly next season to the information shown on this page.

Previous Season Dates
{{departure_day.departure_date | date:'EEE d MMMM yyyy'}} {{departure_day.arrival_date | date:'EEE d MMMM yyyy'}}

Style: {{}}

Boat/Ship: {{departure.vehicle_name}}
On sale Hot deal Departure guaranteed On request
{{product.currency_code}} {{room.base_price | noFractionCurrency:product.currency_symbol}}
{{product.currency_code}} {{room.discount_price | noFractionCurrency:product.currency_symbol}}
Fully booked Bookings closed

Total price per person {{room.room_type | lowercase}}
Includes {{departure.kitty_currency_code}} {{departure.kitty | noFractionCurrency:departure.kitty_currency_symbol}} kitty
Includes {{extra.extras_code}} {{extra.extras_symbol}}{{extra.extras_value}} in local payments Single supplement available from {{product.currency_code}} {{departure.single_supp | noFractionCurrency:product.currency_symbol}}

Contact us to arrange an alternative departure for you

Book {{departure.places_left}} spaces left! space left!

Important notes

This trip starts on Day 1 in Santorini at 11am.

Trip notes

Want an in-depth insight into this trip? Your trip notes provide a detailed itinerary, visa info, how to get to your hotel, what’s included - pretty much everything you need to know about this adventure and more.

View trip notes


Our Greece Sailing Adventure - Cyclades Islands trips score an average of 4.81 out of 5 based on 47 reviews in the last year.

Greece Sailing Adventure - Cyclades Islands , September 2015

Greece Sailing Adventure - Cyclades Islands , September 2015