Original
Sailing
Greece Sailing Adventure: Cyclades Islands
10 Days | Sunsets, seafood and seaside splendour in the Mediterranean
4.9
Excellent
151 reviews
10 days
Start
Santorini, Greece
Finish
Santorini, Greece
Trip Code
ZSRV
Min Age
15
Trip Size
1 - null
Physical Rating
Transport
Boat
Accommodation
Overnight boat (9 nights)
From £2,031(10 days)
Trip Informations
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.
Why you’ll love this trip
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.
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.
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.
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.
Itinerary
Inclusions
Transport
Boat
Accommodation
Overnight boat (9 nights)
Dates and availability
Starting
Ending
Remaining
Prices From
Important notes
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.
Reviews (146)
5 stars
134
4 stars
9
3 stars
2
2 stars
1
Jeff
Oct 21, 2024
An excellent way for sailors & non-sailors to experience the Greek Islands in a small group. Each island selected by Fotis had a unique offering. The experience was very well organised & even though I have done much sailing, I would not have enjoyed navigating the Greek Islands without the weather, port & island peculiarities knowledge Fotis had which made for a most enjoyable trip
Lisa
Oct 20, 2024
What a fantastic, immersive way to visit the Greek Cyclades islands! Fotis, our extremely skilled skipper, planned & navigated a wonderful route to make the best of otherwise very windy weather so that we could visit 7 islands - each so unique & interesting in its own special way. His recommendations as to what to see, eat & do on each island were spot on & enabled us to experience so much in relatively so little time. Delightful tavernas serving delicious Greek meze dishes, cheese & olive oil tastings in ancient buildings, watching Fotis reel in a large tuna & turn it into ceviche were just a few of the memorable experiences we enjoyed. Cannot thank Fotis enough or recommend this trip more highly (but make sure you thoroughly read the pre-briefing information & remember your accommodation is below deck on a yacht). Go with an open mind and a sense of humour, flexibility, inquiry & wonder - you won’t be disappointed. Thank you Fotis & Intrepid - we’re already booking our next Intrepid adventure!
Leah
Oct 20, 2024
Skipper Fotis was knowledgeable, passionate, and had a focus on safety. Due to winds our itinerary changed, only adding to the adventure. He gave excellent recommendations on food, things to do, with a desire for us to experience Greece as authentically as tourists can. Boat living isn’t for everyone but for the right people it is a hard trip to beat.
Thea
Oct 19, 2024
This trip was unforgettable. The greek islands are a breathtaking part of the world and our skipper navigated us safely and expertly. Prepare for close quarters, great food, summer evenings and new friendships! I have a new love of sailing and many new swimming spots to return to!
Hannah
Oct 12, 2024
Really excellent trip. Lovely professional skipper, exact itinerary adapted to optimise sailing conditions (winds), and knowledgeable re all the destinations. Helped set up good relationships between the travellers. Stopped at some truly beautiful places, some a bit off the beaten track. best time of year too - fewer tourists, good weather and warm sea! Couldn't be better
Shirley Ann
Oct 05, 2024
All you need is a love for sailing, and be flexible and adaptable and sit back and enjoy the experience. It was great to have jobs to do to assist the skipper. To be truly part of the sailing experience.
Carla
Oct 04, 2024
Highly recommend this trip!
Shirley Ann
Oct 03, 2024
Carla
Sep 30, 2024
This is an excellent trip, very relaxing and fun with sailing or exploring the many little villages on these tiny Cycladic islands. The food was fantastic a Lacto-Ovo- vegetarian cuisine delight
Kathryn
Sep 28, 2024
A fantastic way to experience the Cyclades. Sailing, swimming, and socialising.
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