Original
Sailing
Greece Sailing Adventure: Cyclades Islands
4.9
Excellent
circle195 reviews
location_on 10 days
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Start
Santorini, Greece
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Finish
Santorini, Greece
tour
Trip Code
ZSRV
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Min Age
15
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Trip Size
1 - 11
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Physical Rating
airport_shuttle
Transport
Boat
bed
Accommodation
Overnight boat (9 nights)
From £1,254(10 days)
Trip Informations
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.
Why you’ll love this trip
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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.
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Walk along the volcanic rim of Santorini, past white villages that cling to cliffs and watch as day turns to night during sunset at the caldera – this is a memory you’ll bring home!
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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.
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Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village.
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Visit Mykonos for the quintessential Greek Islands experience. Embrace your hedonistic side with the boutique culture and nightlife or relax on one of the many beaches dotted along the coast.
Is this trip right for you?
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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 – it's recommended that you bring sea sickness medication just in case.
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Our yachts have a small Zodiac on board, which is used to transport travellers to shore if we need to anchor in the bay. However, we will most often overnight in the small marinas on each island we visit, so the Zodiacs aren’t used. Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and a can-do attitude are all you need.
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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.
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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.
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On your trip, the skipper will move the boat using the sails and motor; occasionally, they will need to use the motor for the whole trip. This choice is weather-dependent, so is unpredictable, but our expert skippers will keep you updated on any necessary itinerary changes. They love to sail and will raise the sails at every opportunity.
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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.
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If you’re travelling with your own group of friends or family and would like to book a private departure on this sailing trip, our Tailor-Made team will be happy to help: https://www.tuuur.com/tailor-made https://www.tuuur.com/tailor-made (https://www.tuuur.com/tailor-made)
Itinerary
Sunsets, seafood and seaside views on this sailing trip in the Mediterranean
- DAY 1Day 1 • Santorini – Ios
- DAY 2Day 2 • Amorgos
- DAY 3Day 3 • Small Cyclades
- DAY 4Day 4 • Naxos
- DAY 5Day 5-6 • Syros
- DAY 6Day 7 • Mykonos
- DAY 7Day 8 • Sifnos
- DAY 8Day 9 • Folegandros
- DAY 9Day 10 • Santorini
Inclusions
airport_shuttle Transport
Boat
bed Accommodation
Overnight boat (9 nights)
Dates and availability
Starting
Ending
Remaining
Prices From
Sunday Jun 21, 2026
Tuesday Jun 30, 2026
Trip size max: 11 - Sold Out
Thursday Jun 25, 2026
Saturday Jul 04, 2026
Trip size max: 11 - 4 spaces left
£1,920£1,376
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Wednesday Jul 01, 2026
Friday Jul 10, 2026
Trip size max: 11 - Sold Out
Sunday Jul 05, 2026
Tuesday Jul 14, 2026
Trip size max: 11 - 3 spaces left
£1,915
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Saturday Jul 11, 2026
Monday Jul 20, 2026
Trip size max: 11 - 7 spaces left
£1,739£1,330
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Wednesday Jul 15, 2026
Friday Jul 24, 2026
Trip size max: 11 - 2 spaces left
£1,739£1,575
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Tuesday Jul 21, 2026
Thursday Jul 30, 2026
Trip size max: 11 - 10 spaces left
£2,019£1,254
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Saturday Jul 25, 2026
Monday Aug 03, 2026
Trip size max: 11 - 10 spaces left
£1,832£1,314
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Friday Jul 31, 2026
Sunday Aug 09, 2026
Trip size max: 11 - 3 spaces left
£1,981£1,793
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Tuesday Aug 04, 2026
Thursday Aug 13, 2026
Trip size max: 11 - 7 spaces left
£1,832£1,401
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Monday Aug 10, 2026
Wednesday Aug 19, 2026
Trip size max: 11 - Sold Out
Friday Aug 14, 2026
Sunday Aug 23, 2026
Trip size max: 11 - 7 spaces left
£1,920£1,648
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Thursday Aug 20, 2026
Saturday Aug 29, 2026
Trip size max: 11 - 8 spaces left
£1,832£1,401
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Monday Aug 24, 2026
Wednesday Sep 02, 2026
Trip size max: 11 - 4 spaces left
£2,118£1,816
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Sunday Aug 30, 2026
Tuesday Sep 08, 2026
Trip size max: 11 - 5 spaces left
£2,030£1,838
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Important notes
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START TIME
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This trip starts on Day 1 in Santorini at 1pm
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ACCOMMODATION ON BOARD THE YACHT
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This trip is accommodated entirely on board a yacht of between 54ft to 56ft. The yacht can accommodate up to 11 traveller's in the following cabin types:
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double bed cabins (x2)
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twin bunk bed cabins (x2)
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triple bunk bed cabin (x1)
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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. Everyone including the skipper shares the bathrooms on board.
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Solo customers can choose to book either a twin bunk bed cabin or a triple bunk bed cabin and will be matched up with other solo customers of the same gender. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge when booking either a twin or double cabin.
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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. If you are booking a bunk bed cabin you must be willing to sleep on the top bunk.
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Double bed cabins can only be booked by 2 people travelling together or a solo customer who pays for a single supplement.
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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.
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HOT WEATHER:
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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.
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PASSPORT DETAILS:
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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.
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ADDITIONAL ACCOMMODATION:
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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.
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TRIP KITTY:
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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 the group. The kitty will be collected when you arrive at the welcome meeting or in stages throughout your trip.
Reviews (189)
5 stars
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2 stars
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Alan
Jun 06, 2026
This sailing trip takes you to idyllic places you can’t access any other way. Be prepared for basic accomodation and to be independent with meals (cooperating with the other guests for lunches). The surprise here was the skippers knowledge of culture, history and cuisine. This included lessons on the right way to make a Greek salad, how to pick and preserve fresh Capers, and the fish, cheeses and local dishes around the islands. A most amazing trip!
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Christopher
Jun 04, 2026
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Jack
Jun 04, 2026
Wonderful trip for people who like to sail and see the Greek islands. Our skipper Fortis made the trip fantastic.
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Steve
Jun 03, 2026
This was an amazing trip that combined sailing in the Mediterranean sea, living aboard a sailboat, swimming and visiting Greek cultural and historical sites. It was peaceful and relaxing, and also challenging and engaging. I loved sailing between small islands on a small boat, with few people. The captain was knowledgable, skilled, thoughtful and fun. I would definitely take this trip again - especially if I could be assured that Dimitris would be my captain again!
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Andrea
May 31, 2026
Our skipper Dimitris was outstanding, sharing his love of Greece. I loved sailing, eating, swimming, repeat!
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Emma
May 11, 2026
The 10 day sailing tour was the perfect length to see the islands and our skipper Fotis made it an incredible experience for us. We had such a great time and would recommend this trip!
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Ebony
May 11, 2026
I would definitely recommend this sailing trip as a unique way to get a taste of the Cyclades, both the popular and lesser known islands. We had an amazing skipper in Fotis, who provided a great sailing experience as well as brilliant local knowledge and food + activity recommendations. Family dinners at local tavernas was a highlight of the trip. Would recommend this trip for other solo travellers!
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Isabel
May 11, 2026
The experience was exciting and our skipper was very helpful and knowledgeable. Fotis, our skipper, made our days enjoyable and memorable with his expertise. We became like a small family, and I would recommend this trip to others for the unique experience of the Greek islands!
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Claire
Oct 26, 2025
What an adventure! Awesome trip with lots of laughs. Jorg our skipper is a legend. Super informative and has a great sense of humour
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Mike
Oct 24, 2025
I would fully recommend this trip our Captain was excellent and made us feel.special trip of a lifetime