Original
Sailing
Greece Sailing Adventure: Cyclades Islands
4.9
Excellent
circle202 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 £2,030(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
Saturday Sep 19, 2026
Monday Sep 28, 2026
Trip size max: 11 - Sold Out
Wednesday Sep 23, 2026
Friday Oct 02, 2026
Trip size max: 11 - 2 spaces left
£2,239
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Tuesday Sep 29, 2026
Thursday Oct 08, 2026
Trip size max: 11 - 2 spaces left
£2,030
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Saturday May 01, 2027
Monday May 10, 2027
Trip size max: 11 - 11 spaces left
£2,102
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Tuesday May 11, 2027
Thursday May 20, 2027
Trip size max: 11 - 9 spaces left
£2,102
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Friday May 21, 2027
Sunday May 30, 2027
Trip size max: 11 - 11 spaces left
£2,102
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Tuesday May 25, 2027
Thursday Jun 03, 2027
Trip size max: 11 - 11 spaces left
£2,069
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Monday May 31, 2027
Wednesday Jun 09, 2027
Trip size max: 11 - 5 spaces left
£2,102
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Friday Jun 04, 2027
Sunday Jun 13, 2027
Trip size max: 11 - 11 spaces left
£2,047
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Thursday Jun 10, 2027
Saturday Jun 19, 2027
Trip size max: 11 - 9 spaces left
£2,047
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Monday Jun 14, 2027
Wednesday Jun 23, 2027
Trip size max: 11 - 11 spaces left
£2,047
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Sunday Jun 20, 2027
Tuesday Jun 29, 2027
Trip size max: 11 - 11 spaces left
£2,047
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Thursday Jun 24, 2027
Saturday Jul 03, 2027
Trip size max: 11 - 11 spaces left
£2,047
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Wednesday Jun 30, 2027
Friday Jul 09, 2027
Trip size max: 11 - 11 spaces left
£2,047
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Sunday Jul 04, 2027
Tuesday Jul 13, 2027
Trip size max: 11 - 9 spaces left
£2,047
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Important notes
Reviews (197)
5 stars
186
4 stars
10
3 stars
1
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Natalie
Sep 04, 2026
An unforgettable sailing experience filled with adventure, laughter and incredible memories. Travelling between the beautiful Greek islands by boat was such a unique way to experience Greece, from swimming in crystal-clear waters to exploring local towns and sharing meals together. I couldn’t recommend this trip enough — truly a once-in-a-lifetime experience!
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Jessica
Aug 29, 2026
I fully recommend this trip. You will get to experience the Greek Islands in a personal, intimate way.
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Spencer
Aug 29, 2026
Would definitely recommend these trips, i've just finished my first intrepid trip and came out with great friends and better memories
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Lauren
Aug 28, 2026
Had the most wonderful trip of my life! Every day was more magical than the one before, and we had an amazing group of people - our skipper Dimitris did the most amazing job. Highly recommend!!
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Angela
Aug 28, 2026
This trip was genuinely the best holiday I have ever taken. The islands we saw, the people we met, and the food we ate were all unforgettable. Our skipper Dimitris was an absolute blast, and managed to make every single day an absolute adventure. Cheeseries, dolphins, and cliff diving, this trip had something for everyone. Would do it again in a heartbeat 💜
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Jessica
Aug 20, 2026
This was such an amazing experience, and a great way to see the Greek Islands! Be prepared for tight living quarters, and itinerary changes are almost guaranteed. Due to high winds we had to stay 4 nights in Amorgos, and had to skip Mykonos to Folegandros. However, our skipper was great at organising other alternatives (Paros and Antiparos).
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Renata
Aug 20, 2026
Our island-hopping cycling trip was absolutely amazing from start to finish. Everything was perfectly organized, the islands were beautiful, and the activities were fantastic. Our skipper Stelios was exceptional—professional, friendly, knowledgeable, and incredibly accommodating. Travelling with our three teenagers, we felt safe, relaxed, and had an unforgettable family adventure together.
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Richard
Aug 20, 2026
Our Small Cyclades sailing trip with Intrepid Travel was absolutely wonderful! The islands were breathtaking, the sailing was unforgettable, and the whole experience was perfectly organized. Our skipper was professional, friendly, and made us feel safe throughout the journey. A fantastic family adventure filled with beautiful memories we’ll treasure forever!
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Sarah
Aug 19, 2026
Such a fun trip! Saw so many charming Greek islands (7), crystal clear water and had delicious food! Stelios our skipper was amazing! We only saw the lower Cyclades on our trip due to high winds; however the trip was still relaxing and we got to spend more time on quieter islands with less tourists! Pack light - it’s a small boat!
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Zara
Aug 13, 2026
I had a really great time on this trip. It was well organised and had a relaxed feel. We were well looked after by our skipper Dimitris, who did an excellent job. Highlights of the trip for me would be the friends I made, swimming spots we went to and dinners we shared.