Greece Sailing Adventure: Cyclades Islands

Greece Sailing Adventure: Cyclades Islands

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10 Days
From

$2532

$1764

Greece Sailing Adventure: Cyclades Islands

10 Days Starting and ending in Santorini

Visiting: Santorini – Ios, Amorgos, Small Cyclades, Naxos, Syros, Mykonos, Sifnos, Folegandros, Santorini

Tour operator:

Intrepid Travel

Tour code:

ZSRV

Guide Type:

Fully Guided

Group size:

1 - 11

Physical rating:

Medium, Medium

Age range:

15-99 years

Tour operated in:
English
Trip Styles:

Adventure Tours, Sailing

Activities:

Swimming

From:
$2532
$1764 (USD) Operator discount: -$718 The Big ADVENTURE Sale: -$50 -30%
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Tour Overview

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.

Highlights

  • A Santorini sunset around the caldera is a sight to behold. Walk along the volcanic rim of the island past white villages that cling to plunging cliffs and watch as day turns to night in the most stunning of ways.

  • Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.

  • Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life. This is island living, Greek style.

  • Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village – a couple of the many experiences to be had around the Cyclades.

  • No Greek island adventure is complete without a stop in Mykonos. Embrace your hedonistic side with its boutique culture and nightlife or relax on one of the many beaches dotted along the coast.

Itinerary

Expand All
Day 1: Santorini – Ios
Location: Santorini – Ios
Accommodation: Overnight boat

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
Location: Amorgos
Accommodation: Overnight boat

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
Location: Small Cyclades
Accommodation: Overnight boat

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
Location: Naxos
Accommodation: Overnight boat

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.

Day 5-6: Syros
Location: Syros
Accommodation: Overnight boat

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
Location: Mykonos
Accommodation: Overnight boat

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
Location: Sifnos
Accommodation: Overnight boat

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
Location: Folegandros
Accommodation: Overnight boat

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
Location: 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.

What's Included

  • Accommodation

    Overnight boat (9 nights)

  • Transport

    Boat

What's Not Included

  • Tipping and Gratuities

  • International Travel

  • Meals

    No meals are included in this tour

Transport

  • This is a sailing adventure so our time is spent on board a monohull yacht. You may be asked to assist on-deck, particularly when coming into or leaving port. No experience is necessary, but getting to know some 'sailing language' might help to get you into the spirit of the adventure.
  • Bow - front of the boat
  • Stern - rear of the boat
  • Port - left
  • Starboard - right
  • Deck - outside, upper area of the boat
  • Hull - the main part or body of the boat
  • Keel - part of the boat under water that keeps the boat stable and stops it capsizing
  • Mainsail - the large sail attached to the mast and boom
  • Mast - the big vertical pole that supports the mainsail
  • Boom - the big horizontal pole attached to the mainsail, coming off the rear of the mast (swing from side to side)
  • Jib, headsail, genoa, foresail - smaller sail near the front of the boat
  • Sheet - ropes used to control the sails
  • Booty - another word for pirate treasure
  • Lines - other ropes on the boat (ropes are never called ropes on yachts)
  • Spinnaker - large extra sail
  • Trim the sails - adjust the position of the sails when the wind changes strength or direction
  • Tiller or wheel or helm - used to steer the boat
  • Helmsman - person steering the boat
  • Running - sailing with the wind
  • Tack - turning the bow of the boat when sailing through the wind
  • Jibe - turning the stern of the boat when sailing through the wind
  • Figure-eight knot - the stopper: often used at the end of lines to stop them getting away.
  • Bowline (knot) - strong and dependable knot that is commonly used
  • Clove Hitch (knot) - not as secure it is often used to attach an object to a line

Accommodation

  • 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. 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.
  • ADDITIONAL ACCOMMODATION:
  • Please note that the majority of our sailing trips start and/or finish at a marina or port. For most of our destinations, we can provide transfers between the airport/hotel and the port/marina. Please check the joining and finish point information in the trip notes for details.
  • ELECTRICITY:
  • While there should be electricity on board throughout your trip the voltage is likely to vary widely, from 12V to 220V, and when in port or moored we are dependent on the supply available. Please be aware that the supply may not be sufficient to power some electronic devices all the time and that you may need a voltage adapter or similar (such as portable inverter used in cars). On some trips it may be possible to charge devices ashore at restaurants or resorts, however this is not guaranteed.
  • WI-FI:
  • Please note that our sailing boats do not have Wi-Fi. You will be getting off the boat and visiting towns regularly so you will be able to connect with the outside world then.

Included Activities

    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.

    Check out our Q&As

    • Are all entrance fees included in the price?

      No

    • Are all the relevant entry visa’s included in the price of the tour?

      No

    • Are international flights included in this tour?

      No

    • Are airport transfers included in this tour?

      No

    • Are the local guides on the tour English speaking?

      Yes

    • Are children permitted to take part in the tour?

      Yes if aged 15+ and accompanied by an adult

    • Is this trip right for you

      As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. Most of our departures run in peak season, when the seas are calmer. The ship will experience some roll and pitch in choppy conditions, however all of our ships come equipped with stabilisers to minimise movement. There will be seasickness tablets on board and your crew will do all they can to minimise any discomfort.

      A Zodiac is used to transport passengers from the boat to the mainland, with landings taking place at piers (dry landings) as well as on beaches (wet landings). Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and can-do attitude is all you need.

      This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.

      Time on the water also means time in the sun. Remember to pack sun protection, such as sunscreen and a hat, and drink plenty of water to keep hydrated. See the Essential Trip Information below for a full packing list.

      Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if the weather becomes unfavourable. If any changes are made, you can trust in your knowledgeable skipper to choose an alternative route or activity.

      Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travellers. If you’re planning to have a late night, it’s a good idea to head into town and experience the local nightlife.

    • What policies are in place for Covid-19?

      Please contact us for latest COVID-19 policies

    • How long has the tour company been trading?

      Intrepid Travel has been taking travellers around the world for over 30 years

    • Will the accommodation included meet local health and safety regulations?

      Yes

    • What Ethical Travel credentials does the tour company have?

      Since 2002, The Intrepid Foundation has supported over 130 organisations across the world. We’re creating positive impact through the joy of travel, community and connection.

    • Do you operate a “single share” option and how does it work?

      Over 50% of traveller travel solo with Intrepid. You can choose to share a room with another solo travelle of the same sex for no additional charge, or choose to pay a single supplement if you’d like your own room. Please request this when booking, and we will secure you a single supplement wherever possible. Please note, if you are booking a last-minute trip, it may be harder for us to secure a single room

    Reviews from Travellers on this Tour

    Julie  

    Sailing the Greek Isles far exceeded my expectations

    03-Sep-2023

    Sailing the Greek Isles far exceeded my expectations. All of the places visited were stunning and it was a great way to tick off some of the smaller Greek Islands. George and Oreistis were amazing hosts and looked after the group very well.

    Mara  

    This was such a unique and incredible experience.

    17-Oct-2023

    This was such a unique and incredible experience. I would definitely say the a trip of a lifetime! What I'd like to pass onto anyone considering this trip is that you should pack an open mindset for adventure, cooperation and a can-do attitude. You are greatly rewarded with an incredibly rich experience of the Greek Islands. Our itinerary changed slightly due to weather, but we made the most of it with our knowledgeable skippers help. Georgie gave us so many great recommendations for every destination. He also organised many group dinners that were a total success. Not only did we see so much of Greece, we also made lifelong friends too! Highly recommend this trip. Hot tip: Pack an inflatable mattress if you can!

    David  

    Thoroughly recommend this trip

    27-Sep-2023

    Thoroughly recommend this trip. The boat was excellent, the sailing fantastic and we were under sail most of the time. Overnight destinations were lovely, with lovely restaurants/tavernas. Swimming opportunities most days. We found ourselves in a great group of like-minded people and came home with amazing memories and new friends.

    Paul  

    A fantastic trip sailing around some of the many Greek islands

    04-Sep-2023

    A fantastic trip sailing around some of the many Greek islands, most days included a swim stop in the pristine waters, the skipper offers information at each stopover to further enhance the island experience.

    Mallory  

    Lots of opportunities to swim in crystal clear water and explore the islands

    01-Oct-2023

    Our skipper, George was great! He was highly experienced and knowledgeable. He gave us briefings at every port so we would have local insight and history of the area. We had lots of opportunities to swim in crystal clear water and explore the islands. Great trip!

    Katie  

    Great experience sailing around the Cyclades Islands

    26-Sep-2023

    This was a great experience sailing around the Cyclades Islands. It's good to get a taste of each island (you don't get to stay at each one for long) and get a taste for boat life. Our itinerary had to change due to poor weather but we got to spend a night on anchor instead which was fun. The swim spots we went to were fantastic. The accommodation on the boat is basic and tight when at full capacity. Definitely pack light if you can. Best for the group when everyone pitches in to help with cleaning, shopping or food prep so be prepared to help out and don't be lazy as your group will notice!

    Read all 6 reviews

    Dates & Availability

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    Saturday - Monday

    May 04, 2024 - May 13, 2024
    $2722 $2396 (USD)

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    Jul 06, 2025 - Jul 15, 2025
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    Jul 22, 2025 - Jul 31, 2025
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    Aug 15, 2025 - Aug 24, 2025
    $2853 $2775 (USD)

    The Big ADVENTURE Sale: -$78 (USD)

    Instant Booking Available

    Thursday - Saturday

    Aug 21, 2025 - Aug 30, 2025
    $2853 $2775 (USD)

    The Big ADVENTURE Sale: -$78 (USD)

    Instant Booking Available

    Monday - Wednesday

    Aug 25, 2025 - Sep 03, 2025
    $2853 $2775 (USD)

    The Big ADVENTURE Sale: -$78 (USD)

    Instant Booking Available

    Sunday - Tuesday

    Aug 31, 2025 - Sep 09, 2025
    $2853 $2775 (USD)

    The Big ADVENTURE Sale: -$78 (USD)

    Instant Booking Available

    Thursday - Saturday

    Sep 04, 2025 - Sep 13, 2025
    $2853 $2775 (USD)

    The Big ADVENTURE Sale: -$78 (USD)

    Instant Booking Available

    Wednesday - Friday

    Sep 10, 2025 - Sep 19, 2025
    $2753 $2677 (USD)

    The Big ADVENTURE Sale: -$76 (USD)

    Instant Booking Available

    Sunday - Tuesday

    Sep 14, 2025 - Sep 23, 2025
    $2653 $2580 (USD)

    The Big ADVENTURE Sale: -$73 (USD)

    Instant Booking Available

    Saturday - Monday

    Sep 20, 2025 - Sep 29, 2025
    $2653 $2580 (USD)

    The Big ADVENTURE Sale: -$73 (USD)

    Book with Confidence

    • Free Date Changes

      Intrepid Travel allows you to make 10 free date changes, as long as the change is made at least 56 days before the start of the tour.

    • Transfer as credit to Future Tours

      Intrepid Travel allows you to transfer existing payments to a future tour to avoid cancellation fees if you can't travel and inform intrepid travel, 56 days before departure.

    • Low Deposit

      Intrepid Travel requires a minimum deposit of 400 USD per person or the full booking value, whichever is less, with the final balance not due until 56 days before departure.

    • Cancellation Policy

      We don't charge a cancellation fee, here is a summary of intrepid travel charges.

      Up to 56 days before tour starts: Forfeit 100% of deposit.

      At 55 days before tour starts: Forfeit 30% of booking price.

      At 30 days before tour starts: Forfeit 60% of booking price.

      At 14 days before tour starts: Forfeit 100% of booking price.

    • COVID Protection

      Trips from 1 January 2023 onwards
      From 1 January 2023, Intrepid will no longer require travellers to provide proof of vaccination against COVID-19.

      However, we continue to strongly recommend that all travellers and leaders get vaccinated to protect themselves and other Specific proof of testing or vaccination may still be required by your destination or airline. Please ensure you check travel and entry requirements carefully.

      This policy excludes all Polar trips and select adventure cruises, where testing and vaccination remains a requirement. Please refer to the Essential Trip Information of your chosen tour for more details.

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