Sail and Explore Greek Islands
Sail the stunning and unspoilt Cyclades and discover its hidden hiking gems
3 days off work
Apr, Jul, Sep, Oct
Up to 10 people
You can take the hikes at your own pace, but being in reasonable physical condition will certainly help you make the most of your trip.
Embark on a 5-day adventure around the Cyclades islands, renowned for their rich history, culture and traditional cuisine
Live aboard a private yacht, docking each night in a different bay
Discover an undiscovered hiking paradise and trek to remote and pristine beaches
See the photos our community shared
All our reviews are verified
— Lisa, April 2022
This trip was fantastic! The perfect little getaway, sailing around some quieter islands off of the beaten track. We often had beaches to ourselves, it was sublime. The hours sailing everyday were delightful and we had the pleasure of seeing dolphins on a couple of the days! The trip itself was really well organised, a great pace with great people, including our skipper Costas.
— Sam Crichard, April 2022
It was great to see places you wouldn’t normally visit in Greece. Certainly a good introduction to what sailing and living on a boat is like. Our skipper was fantastic. A great guide but also a good addition to the group who came toghether.
— Mikael, September 2021
I Had the best time!! Our skipper, Zeo, ensured we had a great trip. My trip highlights were sailing into coves around the islands and bathing on secluded beaches. Every view off the boat included fantastic views of the Aegan Sea and surrounding islands. I would book this holiday again.
— Rebecca, September 2021
Lots of fun
— Marcus, September 2021
An amazing trip made even better by both the people in the group and the host "Zeo". The host was super flexible and accommodating with the itinerary. The group were super friendly and made my rather shy self feel very much included.
— Adel, April 2020
An absolutely must do trip. Something for everyone! Hikes for activity, sailing for those that want to join, sunbathing for those that don’t. Stunning islands with incredible food (if you pick the right restaurants) and super friendly people. 5 stars MBA - I only hope you get the same captain as we had 🥰 she was outstanding.
— Natasha, July 2020
Great experience with a fun group.
— Jake, September 2020
Superb trip. Heaps of fun, the local guides were great and the experience of sailing around the Greek islands in calm seas, blue skies and perfect sunshine was unforgettable. The port in Hydra is absolutely stunning and was the highlight for me.
— Ellen, October 2019
Andreas (skipper) really looked after us, the islands are beautiful and everything ran very smoothly.
— Jennifer, October 2019
Everything was great.
Experienced, English-speaking captain and guides
4 nights on a private yacht
All your breakfasts and lunches
To and from the airport and everything in-between
SUP boards always at the ready
Flights to and from the meeting point
Some meals as described
Athens International Airport
14:45 on Day 1
Athens International Airport
17:15 on Day 5
You’ll be picked up on arrival and dropped off in time for departure. Alternatively, you are free to arrive at any time and make your own way to Lavrio Marina. If you do so, please meet in Café Petrino at 15:15. Full directions will be provided before your trip departs.
There are regular flights to Athens from airports across the UK and Europe.
Boat · Twin share
Day 2 – Day 4
Boat · Twin share
What is the food like?
Both breakfast and lunch are provided on-board on a self-prepare basis. Your guide will try and use as many local, organic and Mediterranean ingredients as possible. For breakfast, you can expect yoghurt, fruit, cereals, juices, cheeses and bread and for lunch expect local salads, sandwiches, omelettes, pasta and fish.
Dinner will be taken on the islands, usually in small local tavernas with a range of seasonal dishes and fresh fish to try.
Vegetarian, vegan and most other dietary requirements can be provided for, just let your host know before the tour begins.
What is the accommodation like?
You’ll stay on a 51 or 56-foot sailing yacht with five cabins and five toilets. The boat has an indoor living room, kitchen and dining area, as well as an outdoor lounge and deck where you can relax when sailing. Cabins are double, twin-share, or triple share. All shared rooms are same gender.
For solo travellers looking for their own space, an optional private cabin can be booked for an extra charge, see Optional Extras for the price . Please request this at the time of booking (this is subject to availability)
Board your yacht in Lavrio Port and sail to the lush green island of Kea. Learn about life onboard from the skipper and arrive in time for a delicious local dinner in town.
Sail to a bay by the ancient Tetrapolis of Kea and see why its been attracting visitors since the 17th century. Take a dip in the sea, visit one of Kea’s most beautiful beaches and then set off for a relaxing afternoon’s sailing to the picturesque port of Loutra on Kythnos. The island is known for its natural warm springs, which you will have the chance to experience before heading out for dinner on the island.
Hike around the striking, arid countryside of Loutra, discover hidden castles and whitewashed churches and meet the farmers and shepherds who live off this dramatic landscape. Enjoy a swim and a light lunch before continuing on to Serifos island - an integral part of Greek mythology, associated with two of its most famous heroes: Ulysses and Perseus. If you're up for it, try a spot of paddle boarding off one of Serifos’ many secluded beaches.
Explore Chora’s narrow, whitewashed alleys, overflowing with green, pink and purple bougainvillea. Hike the steep trail to the lovely Ag. Konstantinos chapel and enjoy the amazing views of the Aegean Sea and the islands of Kimolos, Milos. Sifnos and your next destination, Kythnos, this time the western side. Enjoy the gold-sanded beaches of Apokrousi and Kolona which connect the main island to the islet of Agios Loukas and once you've freshened up, head to a local taverna for a home-cooked Mediterranean meal.
Lavrio Port and home
Take a spectacular loop-hike to Vryokastro, ancient capital of Kythnos and spend your last day swimming or paddle boarding around this beautiful island. Set sail for Lavrio Port in the early afternoon, where a transfer will be waiting to take you back to Athens and home
15% Off Outdoor Gear
What do I need to bring?
- A small rucksack
- One soft-suitcase per person as baggage to be kept in the cabin
- Hiking shoes
- Long walking socks
- Hiking trousers
- Long sleeve shirts
- Water-resistant jacket
- Sun cream
- A water bottle
- Trekking poles
- Bathing suit
- Basic First Aid Kit
Single Cabin Upgrade
Payable Before Departure
Single Cabin Upgrade
We've crunched the numbers to work out the total carbon footprint of this trip, and plant enough trees to suck 2x as much back out the atmosphere.
What's the number?
It works out on average at 199kg of CO2 emissions per person, including all local transport, accommodation, food, activities, guides, staff and office operations.
The only thing it doesn’t include right now is flights and travel to the destination. We do make an overall estimate across all our customers separately, but as we don’t book flights, have customers from all corners of the world, and no way of reliably knowing their travel plans, we simply can’t include an individual number in the figure on display here. We’ve got a goal for 2022 to fix that, so that when you book, there is a way to measure and mitigate the carbon emitted by your flight too.
But what does the number mean?
Yep, hard to picture eh? To give you an idea:
- Driving 1000miles/1609km would be approx. 281kg of CO2 in an average car (or 140.5kg per person if there was 2 of you in it).
- A return economy class flight London - New York would be approx. 1,619kg (1.66 tonnes) per person.
- 10 trees in a temperate forest are estimated to remove approx. 250kg of CO2 from the air in a period of 5-10 years.
What are we doing about it?
Our trips are relatively low-carbon by design, and we're working with all our hosts to develop long term carbon reduction plans. For every person booked with us since 2016 we’re planting enough trees to suck at least 2x more carbon out the atmosphere than is emitted by their trips. All native trees, as part of amazing projects that are re-foresting degraded land, tackling the biodiversity crisis and supporting local communities at the same time. We go further than that too, also funding re-wilding projects worldwide to help protect important keystone species from extinction. See the reforestation and re-wilding schemes we support. See our carbon action plan.
Want to know more?
Amazingly, no international travel company has ever publicly published their carbon measurements before, as far as we know. We believe that must change, quickly. So we’re openly sharing the method we used in the hope that other companies will be able to more easily follow suit and build on what we've done so far. You'll find it all here.
No prior knowledge is required and your captain will brief you about life on board and the basics of sailing.The boat's interior is designed to achieve maximum space efficiency and you will soon become accustomed to the few steep stairs to your cabin.
You do not need to be particularly fit, but being in reasonable condition will certainly help you make the most of your trip.
Sailing journeys are around 2-4 hours each day. On average the hike distances are approximately 8km. All hikes are optional and guests can relax on-board or at a nearby beach if they prefer. There are extended hiking routes possible for those who wish to go further and these are generally pretty straightforward.
Sure can! Over 50% of our travellers travel solo, it’s a great way to meet like-minded people.
The Cyclades has mild and moderately rainy winters and warm, sunny summers. Spring temperatures average 20°C. The wind blows frequently, cooling the heat of summer. July and August are the hottest months, with temperatures averaging 27°C. Autumn sees warm temperatures averaging 25°C.
Should adverse conditions prevail, your guide will have a back-up plan, such as alternative hikes or mooring in a different bay.
On very rare occasions, it is up to the judgement of the skipper to alter or cancel a sailing route and the hiking guide to do the same for a hike.
Very. Our skippers are qualified, native Greek seamen with vast experience navigating the local Aegean waters, the Mediterranean and beyond. The boats are also put under thorough monitoring during the winter in order to be in excellent condition when the sailing season starts.
Our hiking guides are year-round hikers themselves with a vast repertoire of paths hiked or trekked around Greece, including demanding gorge passages and high altitude routes. They are certified by the Hellenic Federation of Mountaineering & Climbing H.F.M.C.
Our recommended travel insurance provider is Campbell Irvine.
Travel insurance is compulsory on all of our adventures. Your insurance should include adequate protection for overseas medical treatment, evacuation/repatriation, your baggage and equipment and the specific activities involved on your adventure.
Your insurance policy should also include specific Covid-19 cover, including cancellation and curtailment cover if you, your travel companion or a close relative are diagnosed with Covid-19.
We fully endorse Campbell Irvine as their insurance offers all of the above, so get in touch with them or call on 020 7938 1734 to get your insurance sorted. We suggest that you book travel insurance as soon as you book your adventure, just to cover you for any last minute life changes. We know you’re an active lot and injuries do happen!
We automatically convert prices from the local currency that a host receives to your chosen currency. We update our exchange rates on a daily basis so this does mean that prices displayed on the site are subject to currency fluctuations, which is why you may see them change over time.
If you wish to change the currency you pay in, head to the bottom of the page.
All of our group adventures are specially designed for adults to enjoy (18+) as we want these adventures to bring together outdoorsy people who are truly like-minded. Children can be accommodated on some private departures.
Covid Refund Guarantee
If your trip is cancelled due to Covid choose from free date changes, account credit, or a full refund.
Full Financial Protection
Your money is safe. Every booking is fully financially protected.