Much Better Adventures

Adventures / Adventure Tapas

Sail and Explore Greek Islands

Sail the stunning and unspoilt Cyclades and discover its hidden hiking gems


Trip Ref #9042

Adventures / Adventure Tapas

Sail and Explore Greek Islands

Sail the stunning and unspoilt Cyclades and discover its hidden hiking gems


4 nights




3 days off work


Apr, Jul, Sep, Oct


Up to 8 people


Athens Airport





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



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

Not Included

Flights to and from the meeting point

Travel insurance

Some meals as described

The Area



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.

Travel options

There are regular flights to Athens from airports across the UK and Europe.

What about all the carbon?

We mitigate 4x the carbon generated by all our customer flights annually through our partnership with Cool Earth.

Day 1

Boat · Twin share




Day 2 – Day 4

Boat · Twin share




Day 5

Departure day




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?

The Cyclades

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)

Day 1

Set sail

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.

Day 2


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.

Day 3


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.

Day 4


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.

Day 5

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

Please Note

All our adventures take place in wild places. Things can go wrong in wild places. Your perfectly planned itinerary may change a bit (or a lot) if the weather turns, someone gets hurt, or a volcano erupts. Usually though, changes make it all the better.

15% Off Outdoor Gear

In need of a few more items? All bookings receive a 15% discount on us to use at Cotswold Outdoor, Snow + Rock, Runner's Need, and Cycle Surgery.

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
  • Sandals
  • Hiking trousers
  • Long sleeve shirts
  • Water-resistant jacket


  • Sunglasses
  • Hat
  • Sun cream
  • A water bottle
  • Trekking poles
  • Bathing suit
  • Head-torch
  • Toiletries
  • Basic First Aid Kit

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.

If you are travelling with excess luggage that you do not wish to bring on the boat, there are two options:

At Athens airport or In Athens city

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.

We’ve teamed up with the guys at World Nomads to offer insurance designed for adventurous travellers across 140 countries that includes overseas medical, evacuation, baggage and a range of adventure sports and activities. To get yours sorted, click here.

We suggest that you book travel insurance as soon as you book the trip, just to cover you for any last minute life changes. We know you’re an active lot and injuries do happen!

All of our group adventures are especially designed for adults to enjoy (18+) as we want these adventures to bring together outdoorsy people who are truly like-minded.

"I cannot recommend this highly enough! The people on the trip were amazing. Easily the best trip I've ever been on!" Charlotte, 2019, Trustpilot.

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.

From …

Transferrable Deposits

Cancel up to 60 days before departure and we'll transfer your deposit into credit for a future booking.

Free Date Changes

Free date changes up to 60 days before departure.

Similar Trips



All our adventures get you out of the city to explore the wilder side of our world


Get places you wouldn’t yourself. Our guides know where to go, what to do and how to stay safe


Route planning? Transport? Accommodation? Equipment? It’s all taken care of


Join a diverse global community, bound by a shared love of the outdoors