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.

Start
Santorini, Greece
Finish
Santorini, Greece
Countries
Greece
Themes
Sailing
Code
ZSRV
Physical rating
Cultural rating
Ages
Min 15
Group size
Min 1 Max 11
Carbon offset
62kg pp per trip


Highlights

  • 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

Itinerary

Welcome to Greece. There will be an important 11 am group meeting today where you'll meet your skipper and shipmates. The first port of call is the local supermarket to buy supplies for your trip as a group. This '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 lovely Santorini and its awe-inspiring caldera. Check out the range of restaurants, shops and bars in the island's capital, Fira. 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, 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. The Orthodox Metropolitan Cathedral, Catholic Cathedral and Dominican Convent are worth a visit, as is Megaron Gyzi Museum. After the welcome meeting you'll set sail (approximately 5 hours) through Santorini’s caldera, cruising across the Aegean Sea to drop anchor at the island of Ios (the boat will stop at Manganari Beach along the way). Check out Hora's shops, restaurants and bars (a short walk from the harbour in Ios) which all come alive in the evenings. A visit to Panagia Gremiotissa (Church of the Virgin) offers beautiful sunset views from a hilltop.

Notes: 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. The itinerary 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.

Sail to the rugged island of Amorgos (approximately 4 hours). This is 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. The restaurants, cafes and bars along the waterfront are an excellent place to relax and enjoy 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 beautiful 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 and sail to the Small Cyclades this morning (approximately 4 hours). This group of islands boast quaint fishing villages, clear waters and beautiful beaches. While all of these 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 you'll 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 Hora.
Sail to the island of Syros (approximately 4 hours), 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 and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here). 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 cruise (approximately 3 hours) to an island packed with beauty and glamour, Mykonos. With a history of around 5,000 years, the island 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.

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 whitewashed 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.
Sail towards the tranquil island of Folegandros this morning. 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.
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.
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Inclusions

Meals
4 breakfasts, 3 lunches
Transport
Boat
Accommodation
Overnight boat (9 nights)

Dates

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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.

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Reviews

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