Greece Sailing Adventure: Cyclades Islands

10 Days | Sunsets, seafood and seaside splendour in the Mediterranean

4.9 out of 5 based on 90 reviews submitted.
Sailing
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EUR €2,060
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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.

Trip overview

Map of Greece Sailing Adventure: Cyclades Islands including Greece
Start
Santorini, Greece
Finish
Santorini, Greece
Theme
Sailing
Destinations
Greece
Physical rating
Indicates how physically exerting a trip is, and how fit you will need to be to enjoy it. More info on physical ratings
Style
Original
Ages
Min 15
Group size
Min 1 - Max 11
Trip code
ZSRV
This trip generates 16.3 kg of CO2-e per person per day.
We offset these emissions on your behalf. But we know that is not enough, so we also have a carbon reduction target.

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.
  • 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.

Boats

Ocean Star 56 Boat
Ocean Star 56
On this itinerary, you'll be travelling aboard the Ocean Star 56
Explore features

Itinerary

Map of Greece Sailing Adventure: Cyclades Islands including Greece

Inclusions

Transport

Boat

Accommodation

Overnight boat (9 nights)

Dates and availability

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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.

Essential Trip Information

Want an in-depth insight into this trip? Essential Trip Information provides a detailed itinerary, visa info, how to get to your hotel, what's included - pretty much everything you need to know about this adventure and more.

Read Essential Trip Information

Reviews

4.9 out of 5 based on 90 reviews submitted.
Reviews are from travellers who have completed their trip and want to share their experience. We show all reviews, but may remove any that include profanity or inappropriate content, are unrelated to the trip or reveal personal details.

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Mara · Traveled September 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!
Review submitted 17 Oct 2023

Mallory · Traveled September 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!
Review submitted 01 Oct 2023

Katie · Traveled September 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!
Review submitted 26 Sep 2023

David · Traveled September 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.
Review submitted 27 Sep 2023

Lesley · Traveled September 2023
I would not recommend this trip as there are 5 small cabins and a maximun of 11 people .You may be asked to share a very small double bed with a complete stranger or share a cabin with 3 very small bunks with standing room for one person . Contortionists would suit.
Review submitted 13 Sep 2023
Greece Sailing Adventure: Cyclades Islands
From
EUR €2,060