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REF: #08528

8-Days Sailing and Hiking the Cyclades Islands

Spend a week navigating picture-perfect Greek islands.

Jump aboard a classic sailing boat with 7 to 10 co-sailors and cruise between azure bays and white-washed villages. Your idyllic summer adventure includes:

  • 8 days, 7 nights aboard your private yacht
  • Overnight stops at Kea, Loutra Kythnos, Syros, Serifos, Kolona Kythnos
  • Guided hikes on Kea, Kythnos, Syros and Serifos
  • Experienced local captain and expert hiking guides
  • Return transfers from Athens Airport to Lavrio Port Marina
  • 7 breakfasts and 6 lunches onboard
  • —Lávrio > Lávrio
  • Activity Type
    • With skipper
    • Sail place to place
  • Groups up to 10


The Plan

Under the expert guidance of your local captain, navigate your private boat between Greece’s stunning Cyclades Islands. Moor up, take a dip off the boat and head to shore to explore the rugged landscapes, remote beaches and whitewashed villages of your new base. Spending each night docked in another pristine bay, and enjoy the local bars and restaurants ashore.

Day 1, Lavrio - Kea

You will be greeted upon arrival at Athens International Airport for the 30-minute drive to Lavrio Port Marina, where your yacht and captain await. Settle in while the captain briefs you life onboard, then let the wind catch your sails and guide you to the lush green island of Kea. You should arrive in time for a sunset swim and delicious evening meal ashore.

Day 2, Kea – Loutra, Kythnos

After a hearty breakfast on board, enjoy an invigorating hike along ancient footpaths through flower-carpeted valleys and ancient ruins. Fertile and green, Kea is hikers’s paradise, abundant with routes to beautiful, remote beaches.

There is time for a swim at one of Kea’s most beautiful beaches, before a relaxing lunch and afternoon sail to the picturesque port of Loutra on the isle of Kythnos, known for it’s natural warm springs (which we’ll have to try)!

Day 3, Loutra, Kythnos - Syros

After breakfast, we’ll take a hike through the striking arid countryside surrounding Loutra, where you will discover centuries-old castles, quaint white-washed churches, and other sites while meeting farmers and shepherds who live off this dramatic landscape.

After a refreshing dip and a light lunch on board, the voyage continues to Syros and the beautiful port of Foinikas. By now you’ll be finding your sea legs, so perhaps it’s time to get a bit more hands on and test your sailing skills!

Day 4, Syros

Salute the morning sunshine from the deck, before breakfast and the chance to explore the the western side of Syros by foot. If you want to relax and explore Foinikas your host will have plenty of options to suggest.

Known as the duchess of the Aegean, Syros’ main port of Ermoupolis, with its grandiose 19th century architecture, is buzzing with life year-round. Explore the quaint pedestrianised streets and its maze of stairways, then discuss the day’s highlights while savouring local cuisine in some of the finest restaurants in the Cyclades and enjoy a cocktail in one of the local bars.

Day 5, Syros - Serifos

First thing this morning, set sail for mythical Serifos, famous for its association with Ulysses and Perseus. Mull over these legends with a coffee in the sparkling port of Livadi.

Later on take a fascinating hike with your tour leader to Chora, the island’s capital, which is perched on a hill above the port, starting from Kallitsos Village, which as you will discover aptly translates as ‘the most beautiful’. For the rest of the evening amble around Chora’s narrow whitewashed alleys, coloured with the lush green, pink and purple of overflowing bougainvillea.

Day 6, Serifos – Kolona, Kythnos

Sail back to Kythnos, but this time to the western side and the golden sandy beaches of Kolona which connect the main island to the islet of Agios Loukas.

A great loop hike here leads you to a hilltop from where you can get a birds-eye view of this beautiful column of sand laid down in the cobalt blue waters.

Wind down the evening in a local tavern, discovering the lives, stories and dreams of your co-sailors.

Day 7, Kolona, Kythnos - Lavrio

Enjoy a final morning swim before leaving Kythnos and your final day at sea. With the wind in your sails, you’ll arrive at Lavrio at sunset. Spend your last night onboard reliving the adventures of the week and no doubt enjoying a few glasses of wine.

Day 8, Lavrio

After breakfast, your transfer will return you to Athens International Airport for your flight home, with a pocketful of amazing photos.


The sailing boat running the trips in April is 56 feet with 5 cabins (2 double and 3 twin bed) all with en-suite bathrooms + 1 cabin for skipper and hiking guide. Maximum 10 people.

The boat running the trips in September is 51 feet with 4 cabins (2 double and 2 twin bed) all with en-suite bathrooms + 1 cabin for skipper. Max 7 people.

On both boats there are communal areas to hangout - cockpit and deck outside, and inside galley and living room.

Alternative boats may be used as required. Both boat are of the same builder/brand and same structure.

Solo travellers of the same gender may be asked to share a double cabin or can request a private double cabin for an extra of £275.

Twin Rooms will always be sold first, unless you are booking as a couple. We’ll confirm your cabin at the time of booking.


The iconic Cyclades Islands are a must do for anyone considering an island-hopping break. From the ancient ruins of Kea to the bougainvillea-clad white-washed alleys of Serifos, sit back and enjoy as your captain unveils 6 different destinations filled with a combination of quiet beaches, traditional architecture and amazing hikes with stunning views; or simply enjoy the comforts of your own private yacht!

Please note all routes are subject to weather conditions and may be slightly modified based on the captain’s assessment of guests’ safety and comfort.

Start point

Lavrio Port Marina, Athens.

Finish point

Lavrio Port Marina, Athens.

Getting there and away?

All sailing trips run from Saturday to Saturday. Most flights from Europe arrive in Athens by 2:00pm. Alternatively, you will need an additional night in Athens on Friday before the trip.

Your guide will be at Athens International Airport on Saturday at 2:45pm to drive you to Lavrio Port Marina (40km, 30-minute drive) where our yacht is docked. Our sailing trip departs at 4:00pm.

If you are already in Athens please arrange your own transportation to Lavrio Port. We will provide you with exact details (address and contact number) of our meeting point in Lavrio Marina.


What extra costs are there?

If a solo traveller wishes to occupy a double cabin there is a supplementary charge of £275. Breakfasts and lunches are included, but you will buy your own evening meals and drinks onshore.

Can I book on my own?

Sure can! A lot of people do, it’s a great way to meet like-minded people.

Are departures guaranteed?

Yes, our scheduled trips have guaranteed departures. If you can’t make this dates enquire for a private trip instead.

What is the food like?

Local Mediterranean food. Light, fresh breakfast and lunch ingredients are provided and guests prepare for themselves.

Can my dietary requirements be catered to?

Absolutely. Just let the host before your tour begins.

How long are the daily sailing journeys and hikes?

Sailing journeys are 2-4 hours each day. On average the hike distances are approximately 8km. All hikes are optional and guests can relax onboard or at a nearby beach. There are extended hiking routes possible for those who wish to hike farther. The selected paths are generally easy.

How fit do I need to be?

We go at our own pace. We hike in normal rhythms and whenever we feel like it, stop to take pictures of the stunning scenery and enjoy the views of the horizon. We will always adjust the pace to keep everyone happy.

What if I don't want to hike?

There are always alternatives we can suggest if you don’t want to participate in a hike. From relaxing on the yacht deck to sunbathing on a quiet beach or strolling around the streets of the village we encourage you to do whatever you feel like doing.

What's the weather like?

The Cyclades have 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.

What do I need to bring?

A small rucksack, hiking shoes and long walking socks, sandals, hiking trousers, long sleeve shirts, water-resistant jacket, sunglasses, hat, sun cream, water bottle, trekking poles, bathing suit, head-torch, toiletries, basic First Aid Kit. One soft-suitcase per person as baggage is kept in the cabin.

How experienced are the guides?

Skippers are qualified, native Greek seamen with vast experience navigating their local Aegean waters, the Mediterranean and beyond. Our boats are put under thorough monitoring during the winter in order to be in excellent condition when the sailing season starts.

Hiking guides are year-round hikers themselves and have a vast repertoire of paths hiked or trekked around Greece including demanding gorge passages and high altitudes. They are certified by the Hellenic Federation of Mountaineering & Climbing H.F.M.C.

I have never gone sailing before, what should I know?

No prior knowledge is required to participate in a sailing trip with our team. Your captain will brief you in detail on moving around the yacht and will teach you the basics of sailing during your holiday. Life on a sailing boat is an experience of a lifetime. It is important to respect the rules of seafarers. The itinerary route or the duration of stay on each island may alter in case weather conditions are not favourable. The final decision on this issue is always made by the captain. There are always alternatives to enjoy your stay no matter the potential route rescheduling. The boat’s interior is designed in such a way to achieve maximum space efficiency. You will easily become accustomed to the few steep stairs to your cabins.

Do I need travel insurance?

Yes. We require that all our guests are insured while travelling. In case you need assistance in order to choose your travel insurance please contact us.