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Greece Sailing Adventure: Cyclades Islands

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Operated by Intrepid Travel
Tripcode: ZSRV
Overview
Destination:
Greece
Start:Santorini, Greece
Finish:Santorini, Greece
Duration:10 days
Type:Group tour (max 11)
Style:
River/Small ship/Barge,
Sailing,
Travel Period
May 2025 - September 2026
Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places.

IMPORTANT INFORMATION

START TIME
This trip starts on Day 1 in Santorini at 1pm

ACCOMMODATION ON BOARD THE YACHT
This trip is accommodated entirely on board a yacht of between 54ft to 56ft. A typical yacht for 11 travellers is equipped with a mixture of 2 x double cabins, 2 x twin cabins and 1 x triple cabin. There are 5 shared bathrooms. Our boats are real yachts and this is a real sailing trip. Yachts are designed to keep sleeping areas to the absolute minimum of space, while maximising common areas as much as possible.

Rooms are allocated on arrival by our skipper according to group composition, which means it is not possible to reserve or guarantee any specific berth or cabin. Single passengers will be paired up with another passenger of the same gender, this may mean sharing a double cabin with a double mattress. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge. Everyone including the skipper shares the bathrooms on board.

While not everyone may feel entirely comfortable living in such close quarters, those who are looking to revel in the adventure and exhilaration of an authentic sailing trip usually find any discomfort from cramped living conditions is more than made up for by the whole experience.

HOT WEATHER:
Summer temperatures can reach up to 40°C, which can be uncomfortable for those not used to the heat. Please consider the time of the year you wish to travel and your suitability to that season.

PASSPORT DETAILS:
Please provide full passport details at time of booking including exact name as per passport, date of birth, nationality, issue and expiry dates as these are essential for booking services on this trip.

ADDITIONAL ACCOMMODATION:
Please note that the majority of our sailing trips start and/or finish at a marina or port. If you have pre-booked any additional accommodation through us, you will need to make your own way to the joining point on Day 1 and from the finish point on the final day. We do not provide transfers between hotels and the port/marina. Please check the Essential Trip Information for details. 

SNORKELLING
There are many opportunities for snorkelling during this trip. Diving masks, snorkels and fins are provided onboard the yacht and are for use by all passengers. They are disinfected prior to use. Some customers may prefer to bring their own diving mask and snorkel from home and just use the fins available on board.

TRIP KITTY:
On this trip it's compulsory to contribute to a kitty of EUR110 per person. The kitty is an on-ground payment put into a central fund managed by travellers. It helps fund for breakfast and lunch on the boat and other small items such as ice, water, snacks and drinks. Travellers are responsible for the preparation of these meals onboard and to shop at port where supermarkets are often very close to the mooring. Kitty amounts are subject to change to reflect local price increases. On day 1, the skipper will talk through the kitty and how it will be managed (by yourself or fellow travellers) The kitty will be collected when you arrive at the welcome meeting or in stages throughout your trip.

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Standard inclusions
  • Transport: Boat.
  • Accommodation: Overnight boat (9 nights).
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Itinerary
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Day 1: Santorini – Ios
Kalimera! Welcome to Greece. Your adventure begins in Santorini, where you’ll meet your skipper and fellow travellers at Cafe Spartakos at 1 pm at Athinios Port. If you’ve got time, consider arriving a couple of days early to see all that Santorini has to offer. There’s heaps of amazing restaurants, shops and bars in the island's capital, Thira, not to mention some of the most beautiful beaches and landscapes. Check out the volcanic beaches or take a walk along the caldera's rim to Firostefani, Imerovigli and Oia – this walk is also recommended at sunset, especially! After meeting your crew, you’ll board your yacht – your home for the next seven nights. You’ll sail to Ios’ port, where you’ll have some free time to explore the nearby beaches or check out Hora's shops, restaurants and bars – it’s all accessible within a short walk from the harbour.
Day 2: Amorgos
Sail to the rugged island of Amorgos. 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 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Maybe head to 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.
Day 3: Small Cyclades
Cast off and sail to the Small Cyclades this morning. This group of islands are home to some small fishing villages as well as beautifully clear waters and beaches. While all these islands once harboured communities, 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, maybe sample some fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.
Day 4: Naxos
Today you'll make your way to the largest Cycladic Island of Naxos. There’s the option of taking a daytrip 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. Maybe 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, 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 have lunch in the hills at a family tavern. Tonight, taste the local brew with a shot of Kitron (lemon liquor).
Days 5-6: Syros
Sail to the island of Syros, dropping by the Bay of Gaidharos 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. Over the next two days, maybe catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleys (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 town hall in the main square. At night, maybe immerse yourself in local island life with an optional group dinner at a neighbourhood family's home. Tuck into some homemade cuisine made with fresh, seasonal ingredients and enjoy the views from the seafront.
Day 7: Mykonos
Head to Mykonos today – with a history of around 5000 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 galleries and boutiques in town, see the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. Tonight, maybe wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – this is the ideal spot to sit back with a cocktail and enjoy the Aegean sunset. After, join the fun of Mykonos’ notorious nightlife.
Day 8: Sifnos
Set sail for the island of Sifnos, known for its production of high-quality ceramics. The island's bare hills contrast the 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 – the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland for panoramic ocean views and see the medieval architecture of the fortress of Kastro.
Day 9: Folegandros
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 waterfront tavernas 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, maybe wander up the hill to the Church of the Panagia – an excellent vantage point to view the sunset.
Day 10: Santorini
Bid farewell to the open water as you catch the ferry back from Ios to Santorini, arriving back at Athinios Port just before 12 pm. With no other activities planned, your adventure ends today in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport. If you would like to extend you stay, just get in touch with your booking agent ahead of time.
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Travellers

Operator
Intrepid Travel

Intrepid is a small group tour travel company with humble beginnings that now sends over 100,000 travellers a year on grassroots and responsible travel tours.

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Please note: We are proud to be an independent agent to travel providers of hotels, flights and other related services. We are not a tour operator. Details and information on the offer are provided by 3rd party businesses and although we do our best to verify the information, we cannot guarantee its accuracy on all occasions. These offers are not available in conjunction with any other offer unless otherwise stated. Pricing and availability are subject to change without notice. For more information, please see Terms of Use
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