Cyclades Sailing Cabin Charter: A 9-Night Island Hopping Cruise from Santorini and Ios
19 August 2027 - 28 August 2027
Ios, GR
9 days trip
11 places avaliable
Sailboat
Shared cruises may require a minimum number of guests.
Price may vary depending on the cabin type, occupancy and cruise date.
Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
Nine nights of cabin charter sailing around the Cyclades, from Santorini and Ios to Amorgos, the Small Cyclades, Naxos, Syros, Mykonos, Sifnos and Folegandros, with swim stops in clear Aegean water.
This nine-night cruise explores the Cyclades from Santorini and Ios, linking the wild south of the archipelago with famous Mykonos and the quieter islands in between. The islands differ from one another in harbour, beach and pace.
On the days with a planned sailing time, the legs take about three to four hours, which leaves time for swimming, walking and exploring ashore. The exact route and the overnight stops follow the wind, the sea state and the harbour space available.
The islands change character as the week goes on: the cliffs of Amorgos, the clear, shallow bays of the Small Cyclades, the long beaches of Naxos, the neoclassical elegance of Syros, the whitewashed lanes of Mykonos and the unspoilt hilltop villages of Sifnos and Folegandros. Swim stops and anchorages are chosen for calm water and good views.
Ashore there is plenty to discover: the windmills and the monastery of Amorgos, fresh seafood in waterfront tavernas in the Small Cyclades, the Venetian Kastro of Naxos, the town hall square of Ermoupoli on Syros, Little Venice in Mykonos and the sunset from the Church of the Panagia on Folegandros.
Life on board is relaxed and sociable. The group shares the boat, the swims and the evenings in port, and the voyage ends with the return to Ios and the ferry back to Santorini, with its volcanic caldera and famous sunsets.
Itinerary
Day1
Santorini to Ios: Boarding and First Evening
The adventure begins in Santorini, where the group meets the skipper and the fellow travellers before continuing to Ios, usually by ferry, to board the yacht. When the ferry is not running, a private transfer by sea is arranged. After settling into the cabins there is free time for the beaches near the harbour and for the shops, restaurants and bars of Ios Hora, an easy walk away.
Day2
Ios to Amorgos
A sail of about four hours leads to the rugged island of Amorgos, the setting of the film The Big Blue. A swim stop at Paradisi Beach comes before the port of Katapola, where windmills and an old Venetian castle overlook the waterfront. Within reach are the ancient Minoan settlement, the village of Hora in the rocky hillside and the cliffside monastery of Hozoviotissa.
Day3
Amorgos to the Small Cyclades
A sail of about four hours leads to the Small Cyclades, a scattering of islands with small fishing villages, beautifully clear water and quiet beaches. Koufonisia, Iraklia, Schinoussa and Donousa are the inhabited ones. The evening is made for fresh seafood in a waterfront taverna and the peace of the Aegean.
Day4
The Small Cyclades to Naxos
The route continues to Naxos, the largest of the Cyclades, whose best beaches lie along the south coast. In the old town, the hilltop Kastro keeps its medieval lanes, mansions and churches, and the cathedral and the archaeological museum are close by. Those who wish can head inland to see village life and one of the oldest temples in Greece.
Day5
Naxos to Syros
A sail of about four hours leads to Syros, with a swim stop in the Bay of Gaidaros along the way. Known for its relaxed atmosphere and neoclassical architecture, Syros is the home of Ermoupoli, the capital of the island and of the Cyclades, which is the base for the next two nights.
Day6
Syros: Ermoupoli and Ano Syros
A day to enjoy Syros at an easy pace. Ermoupoli has a grand town hall on its main square and plenty of places to sample authentic Greek food. A bus climbs to the fortress-like village of Ano Syros, with its stone archways, narrow alleys and wide views over the Aegean. In the evening, a home-cooked dinner with a local family can be arranged as an option.
Day7
Syros to Mykonos
A sail of about three hours leads to Mykonos, the quintessential Greek island. Galleries and boutiques fill the old town, the church of Panagia Paraportiani stands by the sea and the colourful balconies of Little Venice are the classic place for a sunset drink. The white beaches and the lively nightlife complete the picture.
Day8
Mykonos to Sifnos
The route continues to Sifnos, known for its ceramics, terraced olive groves and almond trees. The beach at the port of Kamares is one of the best on the island for a swim. Apollonia, the capital, is a maze of whitewashed houses and chapels, and the headland of the medieval Kastro rewards the climb with panoramic views.
Day9
Sifnos to Folegandros and Return to Santorini
A morning sail leads to tranquil Folegandros. At the port of Karavostasis the pebble beach and the waterfront tavernas are easy places to relax, and the hilltop Hora, one of the oldest villages in the Cyclades, has a striking Kastro and the Church of the Panagia, a fine viewpoint for the sunset. After the last night, the yacht returns to Ios and the group continues by ferry to Santorini, arriving at Athinios port in the late morning. When the ferry is not running, a private transfer by sea is arranged.
Important Note
This itinerary may vary depending on weather conditions, sea state and operational requirements. The captain may adjust the route, anchorages and overnight stops to ensure safety, comfort and the best possible sailing experience.
Cruise price details
Price per person
€ 2140
Accomodation on selected shared cabin, check out single use and details
Cabin type
Stern Cabin
cabin capacity
double bed
Price/person
€ 2140/
Bunk Bed Cabin
2
cabin capacity
bunk bed
Price/person
€ 2140/
Triple Cabin
cabin capacity
Price/person
€ 2140/
Included in the price
Shared cabin accommodation on board for 9 nights
Skipper, Yacht Master Offshore qualified, trained in CPR and first aid
Zodiac tender
Basic boat equipment, including snorkelling masks, snorkels and fins
Navigation insurance
Not included € 110 / person
Trip cash box: about €110 per person (indicative amount, subject to change), compulsory, paid on the spot into a group fund managed by the travellers for breakfast, lunch, ice, water, snacks and drinks on board
Travel insurance: compulsory, to be arranged by the traveller
Extra services
Single cabin supplement: available at an additional charge when booking a twin or double cabin, price on request
Optional group dinner at a local family home on Syros
Optional day trip to the countryside on Naxos
Meals ashore: suggested budget €340 per person
Tips for the skipper: suggested €8 to €10 per person per day
Flights, airport transfers and extra nights before or after the trip
What to pack for a sailing holiday?
Pack smart for your yacht charter: choose a soft bag instead of a hard suitcase, bring lightweight layers, reef-safe sunscreen, and non-slip shoes for onboard use. A couple of swimsuits and motion sickness remedies can also make a big difference. Each boat has limited storage, so pack light but wisely! Need help building the perfect list? Read our full guide: What to pack in a suitcase for a yacht charter
What’s a Typical Day Like on a Yacht Charter?
Days on this route combine sailing between the islands, with sailing times of about three to four hours on some legs, swim stops in quiet bays when conditions allow and time ashore in small harbours and villages. The route and pace follow the wind and the sea. Curious about the full experience? Discover more in our guide: What’s a typical day like on a sailing holiday?
Who Handles Cooking and Cleaning on a Yacht Charter?
On this cabin charter the skipper sails the boat, while breakfast and lunch on board are prepared by the travellers themselves, who share the cooking and tidying. Think salads, pasta, and good teamwork. It is a casual, collaborative vibe. On fully crewed yachts, by contrast, a chef and crew manage everything. Want to know what’s included in your setup? Read the full guide: Who takes care of cooking and cleaning on a sailing charter?
Shared cruises may require a minimum number of guests.
Price may vary depending on the cabin type, occupancy and cruise date.
Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
