Greek Islands sailing holiday, Santorini to Mykonos

Our only 8 day sailing holiday, travelling in a small group from Santorini to Mykonos, where fun is more the focus than frills.
Santorini Island hill walking Ios island Naxos Amorgos Mykonos Small Cyclades
£1286To£1471excluding flights
8 Days
Small group
More info
In addition to the listed price, this trip also requires payment in counrty of a compulsory Trip Kitty of approx.
EUR 60
Last minute
Late availability on these dates: 25 Jun, 01 Jul, 18 Jul, 12 Aug, 26 Aug
Make enquiry

Description of Greek Islands sailing holiday, Santorini to Mykonos

When it comes to Greek Islands sailing holidays, the Cyclades really are a place of dreams, and starting off in the stunner that is Santorini, you'll be thinking, can it possibly get better than this? But the Cylcades keep on giving, especially when you get to sail through the famously sapphire waters, under forever blue skies through the joys of islands such as Ios, Amorgos, Naxos and ending up in Mykonos.

You will have plenty of time on land too, to explore either the vibrant port towns or a hike up into the hills, or along a coast path for tranquillity within minutes. On Ios, for example, you can wander through the traditional old town or seek out beach bliss at Valmas. Swimming is a must on Amorgos, especially if you have seen the iconic Luc Besson film, The Big Blue, which was shot here. On Naxos, the largest of the chain, you may want to hike up to the Cyclades’ highest peak, Mount Zas at just over 1000m., or just wander through ancient village peppered with archaeological gems.

Your last couple of days are on Mykonos, which is famously more of a party island, although it is easy to get off the beaten path if that is a bit much after a week on tranquil waters. Many of our guests enjoy taking a day trip to the sacred island of Delos, birthplace of Apollo and Artemis.

Sailing specifics

This is a real sailing adventure on a monohull yacht between 54-56 ft. We may opt for a smaller one if group size is best suited to that. Sleeping eleven travellers, there are 2 double cabins, 2 twin cabins and one triple cabin. All bathrooms are shared, with five in total. Rooms are allocated on arrival by the skipper and can’t be booked in advance, and solo travellers will be allocated a cabin with a fellow traveller of the same gender. In some cases, this may mean sharing a double mattress, so be prepared for close quarters, as is typical on a real sailing boat.
Similarly, there is an ‘all hands on deck’ approach to our sailing trips, although beginners are more than welcome, just swot up on your knots and terminology a little before heading off. There is minimal electricity, so this is not a hairdryer type holiday (the wind is free) and there is no Wi-Fi on board.


Price information

£1286To£1471excluding flights
In addition to the listed price, this trip also requires payment in counrty of a compulsory Trip Kitty of approx.
EUR 60
Make enquiry

Check dates, prices & availability

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Holiday information

Our top tip:
Buy the day’s catch from local fishermen, so when you help prepare lunch you can go all Rick Stein.
Trip type:
Small group holiday, max. 9 people.
Solos welcome but twin/double cabins only.
4 twin/double cabins, shared bathrooms.
Accommodation, skipper, crew (although tips are expected).
Breakfasts and lunches funded by communal kitty of €60 pp. Shopping and cooking a team effort. Tavernas and cafes for dinner.


1 Reviews of Greek Islands sailing holiday, Santorini to Mykonos

5 out of 5 stars

Reviewed on 29 May 2018 by

1. What was the most memorable or exciting part of your holiday?

Weather conditions were ideal for most days of our week of sailing, from fair to rough, but always safe and secure in the hands of our master mariner, Antonio

2. What tips would you give other travellers booking this holiday?

Be prepared for slight changes in your sailing itinerary - the wind blows where it wants to. You'll pack too many clothes - think sun - casual - a woolly for the wind. With time on your hands on board think of what you might do - read, write, converse. You're part of a crew/team not just an individual - our age range was 21 - 89. Sailing is a great leveller - there's one boss on board - the Skipper

3. Did you feel that your holiday benefited local people, reduced environmental impacts or supported conservation?

On shore try to use local amenities for food and drink. Make eye contact and keep smiling. I had the advantage of wearing the kilt which drew attention and invited comment of a cross cultural nature. Our skipper encouraged recycling, and water conservation is more and more important, yet you must drink plenty of it. There is a stark contrast between the 'green' of the UK and the apparent barrenness of the islands, yet these islands have sustained ancient civilisations for centuries producing hardy survivors - not to be patronised.

4. Finally, how would you rate your holiday overall?

One of the best holidays of a very long lifetime. Life on board and life ashore can be very precious if you're prepared for both. Enjoy the swimming!

Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


As a global tour operator, we are committed to operating every one of our trips in a way that respects and benefits local people, their culture and economy, while minimising our impact on the natural environment.

On this small group sailing adventure, we travel with a maximum of eight passengers on board a 50ft yacht, but if there are fewer passengers then we will use a smaller yacht. Bathrooms are shared and although there is hot water, we encourage passengers to use it carefully. Toilets are usually operated by hand-pumps and we have recycling arrangements on-board.

Weather permitting, your skipper will use the power of the wind to sail the boat as much as possible which means that we have less impact on the environment than if travelling by other modes of transport. When on land, you will mostly hike or walk although you may choose to take an excursion by car when we are on the island of Naxos.

As a tour company, our responsibilities don’t stop when our tours end. In 2002, we established a charitable foundation so that our passengers and staff could support grassroots community projects around the world. To date, it has raised over £2million for over 75 projects involved with health care, education, human rights, child welfare, sustainable development, and environmental and wildlife protection. We match every donation made by passengers and pay the administration costs, so every penny that is donated goes to a good cause.


We travel in small groups and wherever possible we use local transport, stay in locally-owned accommodation or homestays, eat at authentic local restaurants, support traditional artisans and small-scale businesses, and provide opportunities for travellers to interact with local people.

This excursion gives valuable employment to a local driver and also allows us to get a glimpse of rural life. We visit a local family-run tavern out in the hills and round our meal off with a shot of Kitron, a local liquor made from lemons.

Your boat will be skippered by an experienced sailor, who will also be your tour leader. One of our crew in Greece is local skipper, Georgios who loves to introduce travellers to the Cyclades Islands, in particular the less-visited islands of Amorgos and the Small Cyclades where he will introduce you to the rugged scenery, welcoming locals and delicious seafood, well off the beaten track.

During the trip, we shop for local produce for our breakfasts and lunches, which the whole group will prepare and eat together on board the boat. In the evenings, we go onshore to dine at small, often family-run restaurants and bars.

As well as a Responsible Travel Code of Conduct which we adhere to as a company, we expect our staff and travellers to demonstrate the principles of responsible travel and provide a number of responsible travel tips to facilitate this, for example advice on what clothing is appropriate and respectful. If you choose to visit any religious buildings on this trip, such as the cathedrals on Santorini, then we will request that you cover your shoulders.

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