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 adventure
- 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.
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This trip can be tailor made for your perfect travel dates. Please make a booking enquiry for more information.
This trip includes an action packed itinerary! Please make an enquiry and we'll send you the full itinerary for each day including meals, activities, travel and accommodation.
- 0 breakfasts, 0 dinners and 0 lunches
- Overnight boat (9 nights)
Overnight boat (9 nights)
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.
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.
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.
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.
0 breakfasts, 0 dinners and 0 lunches
Food and dietary requirements
The amazing food on offer is one of the highlights of any trip in Europe. To make the most of this we’ve structured our meal arrangements to provide both flexibility and variety.
For most dinners and some lunches we will moored in a port or marina near meaning that the group will have a choice of on-land eating options available. We find our group often eat together however you have the freedom to go off and do your own thing. Our skippers can recommend options for restaurants and on many occasions will dine with the group.
While your skipper will co-ordinate the shopping for and preparation of these meals we’ve found that the best trips are those where everyone pitches in together to help with the meal preparation.
If you have dietary requirements and/or food allergies please notify us at the time of booking so we can determine the extent to which your dietary requirements can be met. There are many vegetarian options available in Greece, Croatia, Italy and France though vegans might find their choice less varied especially away from the bigger cities. Travellers that require a gluten free diet may also find their choices limited. Most of our trips start in a larger towns where you will find greater choice of supermarkets and markets however they do not stock the range of gluten free products that you may be used to at home.
Who is this trip for?
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.
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.
Port – left
Starboard – right
Bow – front of the boat
Stern – rear of the boat
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
Your fellow travellers
As you travel on a group trip you will be exposed to all the pleasures and maybe some of the frustrations of travelling in a group. Your fellow travellers will probably come from all corners of the world and likely a range of age groups too. We ask you to be understanding of the various needs and preferences of your group – patience with your fellow travellers is sometimes required for the benefit of everyone’s travel experience. Remember too that you have responsibilities to the group. If you are requested to be at a place at a certain time, ensure that you don’t keep the rest of the group waiting. We have found time and time again that the very best trips we operate are those where the dynamics within the group work well – this takes just a little effort on your part. Due to privacy reasons, we are unable to provide you with contact details and any personal information about your fellow travellers booked on your trip prior to departure.
The bonus of our sailing adventures are that they are small groups, a maximum of 8 – 11 travellers (with the average number of travellers 7). However when you add in a Skipper and the fact you will be eating, sleeping and lounging about together for up to 9 days in the confines of a monohull you may need to call on some patience, maybe some headphones but above all a sense of humour.
Most travellers come away from our sailing adventures saying it was a the trip of a lifetime and that they have made lifelong friends…………..we’re sure you will too!
If you wish to have a single cabin on our sailing trips, please advise at the time of booking. You will be required to pay double to guarantee a cabin to yourself.
You don’t need to hold a recreational skippers ticket or any sailing experience at all to join this trip however you may be called on to help around the boat, help keep the bathrooms and galley clean by emptying the bins and overall keeping the communal areas free and available for your fellow travellers. You will also be asked to chip in at meal time, either helping with food preparation, cooking, setting or clearing the table and washing up dishes.
This operator has a policy in place for COVID-19 and their adventures. Please request full details so we can share the most up to date information with you. Thanks!
We love this operator for the freedom and flexibility they give travellers to get off the tourist trails and really experience local cultures. Their style of small group travel is perfect for solo travellers, couples or small groups of friends and their grassroots style of travel seeks to have a positive impact on the communities they visit.
They use local leaders, local accommodation & transport and support local community projects, ensuring sustainability is at the centre of everything they do.
In addition, they expect their staff and travellers to demonstrate the principles of responsible travel – respecting people, cultures and local environments; in the distribution of wealth; in good will and cross-cultural sharing; and in contributing to sustainable development.
A most helpful, friendly and knowledgeable travel company!Very helpful and provided lots of research material and excellent personal perspectives on the tall ship sailing trip I was interested in taking.
Excellent thoughtful service.They were prompt and friendly, and so thorough and helpful in connecting me with my adventure.
One of a Kind Service!From the very beginning of reaching out to AWA, they were super helpful, enthusiastic and informative.
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