SHORTLIST

Greece Sailing Adventure: Cyclades Islands

Fulfil your dreams of sailing the Greek Islands on a ten-day seafaring adventure around the renowned Cyclades. Setting off from Santorini, 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 the Aegean’s turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places. Trust us – it’s all smooth sailing from here.

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.

Tour details
Tour Provider Intrepid Travel
Price From
$3,772
Number of Days
10
Start Location
Santorini, Greece
End Location
Santorini, Greece
Age Range
Avg. 30+
Group Size
1 to 11
Tour Style
Standard
Tour Themes
River/Small ship/Barge
Physical Rating
Moderate
Itinerary Open all
Day 1: Santorini – Ios
Welcome to Greece! Meet your skipper and shipmates at Cafe Spartakos at 1pm at Athinios Port, Santorini and take a ferry to Ios where you will board your yacht. If you’ve got time, why not consider arriving a couple of days early to enjoy Santorini. Check out the range of restaurants, shops and bars in the island's capital, Thira. 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.

After your welcome meeting, unpack and get settled into your new home away from home a real sailing yacht. You will have some free time today to enjoy everything that Ios as to offer, including the beautiful nearby sandy beaches or check out Hora's shops, restaurants and bars – it’s all accessible within a short walk from the harbour in Ios – which all come alive in the evenings.
Day 2: Amorgos
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.
Day 3: Small Cyclades
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.
Day 4: Naxos
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.
Days 5-6: Syros
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.
Day 7: Mykonos
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 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 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.
Day 8: Sifnos
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.
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 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.
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 12pm midday. With no other activities planned for today, your adventure ends on arrival in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport.
Inclusions
  • Transport: Boat.
  • Accommodation: Overnight boat (9 nights).
Departure dates
All pp pricing is based on twin share occupancy. Single supplements will apply
Start End Availability Price NZD
03 May 2025 12 May 2025 6 $3,957
13 May 2025 22 May 2025 2 $4,182
23 May 2025 01 Jun 2025 3 $3,957
27 May 2025 05 Jun 2025 10 $3,772
02 Jun 2025 11 Jun 2025 11 $3,772
06 Jun 2025 15 Jun 2025 8 $3,772
12 Jun 2025 21 Jun 2025 8 $3,772
16 Jun 2025 25 Jun 2025 9 $3,772
22 Jun 2025 01 Jul 2025 8 $3,772
26 Jun 2025 05 Jul 2025 7 $3,812
02 Jul 2025 11 Jul 2025 10 $3,917
06 Jul 2025 15 Jul 2025 4 $4,032
12 Jul 2025 21 Jul 2025 10 $3,917
16 Jul 2025 25 Jul 2025 11 $3,917
22 Jul 2025 31 Jul 2025 9 $3,962
26 Jul 2025 04 Aug 2025 9 $3,962
01 Aug 2025 10 Aug 2025 11 $3,917
05 Aug 2025 14 Aug 2025 9 $3,962
11 Aug 2025 20 Aug 2025 8 $3,917
15 Aug 2025 24 Aug 2025 9 $4,097
21 Aug 2025 30 Aug 2025 10 $4,057
25 Aug 2025 03 Sep 2025 11 $4,057
31 Aug 2025 09 Sep 2025 8 $4,097
04 Sep 2025 13 Sep 2025 8 $4,097
10 Sep 2025 19 Sep 2025 5 $4,177
14 Sep 2025 23 Sep 2025 9 $4,097
20 Sep 2025 29 Sep 2025 9 $4,097
30 Sep 2025 09 Oct 2025 10 $4,057
10 Oct 2025 19 Oct 2025 8 $3,927
15 Oct 2025 24 Oct 2025 10 $3,882
02 May 2026 11 May 2026 11 $3,952
12 May 2026 21 May 2026 11 $3,952
22 May 2026 31 May 2026 11 $3,952
26 May 2026 04 Jun 2026 11 $3,952
01 Jun 2026 10 Jun 2026 11 $3,952
05 Jun 2026 14 Jun 2026 11 $3,952
11 Jun 2026 20 Jun 2026 11 $3,952
15 Jun 2026 24 Jun 2026 11 $3,952
21 Jun 2026 30 Jun 2026 11 $3,952
25 Jun 2026 04 Jul 2026 11 $4,102
01 Jul 2026 10 Jul 2026 11 $4,102
05 Jul 2026 14 Jul 2026 11 $4,102
11 Jul 2026 20 Jul 2026 11 $4,102
15 Jul 2026 24 Jul 2026 11 $4,102
21 Jul 2026 30 Jul 2026 11 $4,102
25 Jul 2026 03 Aug 2026 11 $4,102
31 Jul 2026 09 Aug 2026 11 $4,102
04 Aug 2026 13 Aug 2026 11 $4,102
10 Aug 2026 19 Aug 2026 11 $4,102
14 Aug 2026 23 Aug 2026 11 $4,252
20 Aug 2026 29 Aug 2026 11 $4,252
24 Aug 2026 02 Sep 2026 11 $4,252
30 Aug 2026 08 Sep 2026 11 $4,252
03 Sep 2026 12 Sep 2026 11 $4,252
09 Sep 2026 18 Sep 2026 11 $4,252
13 Sep 2026 22 Sep 2026 11 $4,252
19 Sep 2026 28 Sep 2026 11 $4,252
23 Sep 2026 02 Oct 2026 11 $4,252
29 Sep 2026 08 Oct 2026 11 $4,252