“Worth it if you want hands-on sailing with exceptional local guides in stunning islands. Think twice if you need land-based comfort or prefer minimal sea time.”
- About £153/day across 10 days
- ~£1,627 all-in with a typical £102 flight from London (£163/day)
- We only rate a price against this trip's own history once we've tracked it for 21 days — no guessing before that.
- About average per day vs 4 similar trips (~£150/day)
- 4.6★ from 21 traveller reviews
Price movement, fill and the all-in cost come from our own daily tracking— not the operator’s feed. You book on TourRadar; the live price always applies there.
About this trip
Ten days sailing around the Cyclades, starting in Santorini and following the wind toward Mykonos and other islands, mixing ancient towns with quiet coves.
Days are shaped by the boat and the weather — swimming stops in clear water, fresh seafood and local wine on shore, and a skipper who raises the sails whenever conditions allow.
You'll mostly overnight in small island marinas rather than at anchor, with a local leader steering you toward the right spots on land.
What you'll do
- Sail the Aegean between Santorini, Mykonos and smaller Cycladic islands
- Swim and cool off in turquoise coves along the route
- Eat freshly caught seafood and try local wines ashore
- Overnight in small island marinas most nights
- Explore ancient towns and laid-back island life on foot
- You live and sleep on a real yacht, so cabins, bathrooms and living space are shared and can feel compact
- You need to be comfortable moving around the boat, including stairs — sea sickness medication is worth packing
- Sound carries easily on board, so late nights are best spent ashore rather than on the yacht
Day by day
Exactly what you do each day, where you sleep, and how it flows — written by us, from the real itinerary.
What's included
- Guide: On this trip you will be accompanied by one of our skippers. Your skipper's role involves taking charge of the sailing, the safety of the vessel and safety for all passengers on board. Skippers all hold a Yacht Master Offshore license or higher and have completed an intense training and review process before sailing with us. They are also fully qualified in CPR : and First Aid. The aim of the skipper is also to take the hassle out of your travels by organizing the overall operation and smooth-running of the trip, managing trip logistics and coordinating the kitty (where applicable). Your skipper will provide information on the places you are travelling through, offer suggestions for things to do and see, recommend great local eating venues and introduce you to our local friends. While not being guides in the traditional sense you can expect skippers to have a broad general knowledge of the places visited on the trip, including historical, cultural, religious and social aspects.
- Transport: 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. Bow - front of the boat Stern - rear of the boat Port - left Starboard - right 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 Boat
- Accommodation: ACCOMMODATION ON BOARD THE YACHT: 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: double bed cabins (x2) twin bunk bed cabins (x2) triple bunk bed cabin (x1) 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. 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. 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. Double bed cabins can only be booked by 2 people travelling together or a solo customer who pays for a single supplement. 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. , ADDITIONAL ACCOMMODATION: 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., ELECTRICITY: 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., WI-FI: 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. Overnight boat (9 nights)
- Meals: Meals are not included in this tour
- Activities: Other activities and services not included
- Flights: International flights not included.
- Optional: Other activities and services not included
- Insurance: Insurance is not included. Travel insurance is required for this tour. Please make sure you are adequately covered. If you require travel insurance, TourRadar has partnered up with Cover Genius to provide a hassle-free experience. More information can be found here (https://www.tourradar.com/travel-insurance).
How travellers rate it
Cheapest live departure per day, in £, recorded by our tracker since 18 Jul. Never a brochure “was” price.
Your free day in Santorini
Landing early, staying on, or filling free time? The best-rated day experiences in Santorini — you book on Viator (we may earn a commission).
Worth it if you want hands-on sailing with exceptional local guides in stunning islands. Think twice if you need land-based comfort or prefer minimal sea time.
- Skippers George and Orestis were genuinely knowledgeable, safety-focused, and made the trip fun with Greek history insights.
- Afternoons and evenings exploring different islands while mornings spent sailing gives real variety across ten days.
- Budget two days minimum to adjust to constant boat life; this isn't a resort experience.
- Daily briefings with island info and dining recommendations help maximise time ashore at each stop.
Distilled from real traveller reviews on TourRadar — we don't edit out the bad bits.
The same-vibe trips, side by side — price, value per day, and how each is moving. Only we can lay two operators' trips out honestly.
Sorted by fit — never by who paid. Price moves and availability come from our own daily tracking.
Departing in Aug is cheapest — from £1,525, about 30% below the priciest month (May).
Getting there
One-way so you can book your return whenever. Prices & booking shown on Trip.com.
Hotels in Santorini
View more accommodationLive prices via Booking.com & partners, booked on their site — separate from your tour. We may earn a commission; it never changes your price.
On a budget?
Hostels in Santorini for the night before your tour · 19 Aug – 20 Aug
Booked on Hostelworld, separate from your tour. We may earn a commission — it never changes your price.
Common questions
How long is Greece Sailing Adventure: Cyclades Islands?
It's a 10-day trip. It starts and ends in Santorini.
How much does Greece Sailing Adventure: Cyclades Islands cost?
The land price starts from £1,525 per person for the 10-day trip. You book on TourRadar, where the live price always applies.
What will Greece Sailing Adventure: Cyclades Islands really cost me all-in?
On top of the £1,525 land price, budget roughly £102 for a return flight from the UK — about £1,627 all-in before spending money. Most day-to-day meals out and optional activities are extra.
What's included in the price?
The price covers all your accommodation, transport during the trip, a group leader/guide. Anything the operator lists as optional or not included — see the full breakdown on this page.
What's not included?
international flights and travel insurance (required) are not included, so factor them into your budget. We show typical flight costs and can point you to insurance on this page.
How big is the group?
Groups are capped at around 11 travellers — a small-group trip, mostly solo 18–35s travelling to meet people, not a coach tour.
When does Greece Sailing Adventure: Cyclades Islands run?
It runs across roughly 7 months of the year, so there's usually a departure to fit your dates. Check live availability and prices in the dates section above.
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