Much Better Adventures

Adventures / Adventure Tapas

Sail and Explore Greek Islands

Sail to the most unspoiled corners of the stunning Cyclades Islands, discovering its hidden hiking gems. 3 days off work.


Trip Ref #9042

Adventures / Adventure Tapas

Sail and Explore Greek Islands

Sail to the most unspoiled corners of the stunning Cyclades Islands, discovering its hidden hiking gems. 3 days off work.

4 nights
Eleftherios Venizelos International Airport

Embark on a 5-day adventure around the dazzling Cyclades islands; an undiscovered hiking paradise which is renowned for its rich history, culture and traditional cuisine. Each night you will be docked in a different bay, where you can enjoy the local bars and restaurants ashore. No prior experience is required as your local captain will guide you between Greece’s stunning Cyclades Islands, before a hiking expert will take you to some of the undiscovered and pristine beaches. Your idyllic summer adventure includes:

  • 5 days sailing on a private yacht
  • 3 days of walking around Kythnos and Serifos
  • 4 nights accommodation on board
  • Local, professional English-speaking captain
  • Local, professional English-speaking hiking guide
  • Learning the basics of sailing (optional)
  • 2 SUP boards (available at all times)
  • Breakfasts and lunches throughout trip
  • Airport transfers

Perfect for: Anyone who wants a taste of the yacht life while hiking around some of the most picturesque islands Greece has to offer.



Airport Transfers



Local transport

Meals as described

Day 1: Kea

As you fly into Athens International Airport, your guide will be waiting to greet you and take you to Lavrio port, where the real adventure will begin.

The yacht will leave the harbour at 16:00 and set sail to the lush green island of Kea, but before this, the skipper will give you a briefing on life-on-board and the operational aspects of the trip.

You should arrive at just about the perfect time for a delicious local dinner in town.

Day 2: Kea - Kythnos

Tuck into breakfast aboard the ship before heading off sailing to a bay overlooking ancient Karthea. Your guide will take you footsteps of travellers who have been visiting Kea since the 17th century exploring Karthea, the most important of the ancient Tetrapolis of Kea in the antiquity.

After a dip in the sea at one of Kea’s most beautiful beaches, set off for a relaxing afternoon sailing across to the picturesque port of Loutra on Kythnos. This island is known for its natural warm springs, which you will have the chance to experience before heading on for dinner on the island.

Day 3: Kythnos - Serifos

After breakfast, hike around the striking, arid countryside of Loutra and discover the hidden castles and whitewashed churches, meeting farmers and shepherds who live off this dramatic landscape along the way.

Enjoy a swim on one of the beaches and a light lunch before the voyage continues to Serifos island. Serifos is an integral part of Greek mythology since its name is associated with two of the most famous mythical heroes: Ulysses and Perseus.

If you're up for it, you can try your balance at paddle boarding in of Serifos’ secluded beaches.

Day 4: Serifos - Kythnos

This morning after breakfast, explore Serifos Chora’s narrow whitewashed alleys, coloured with the lush green, pink and purple of overflowing bougainvillea. A steep walk up to the peak will bring you to Ag. Konstantinos chapel. Enjoy amazing views of the Aegean Sea islands of Kythnos, Kimolos, Milos and Sifnos.

The next stage of the trip takes you back to Kythnos, but this time, to the western side. Here, there are gold-sanded beaches of Apokrousi and Kolona which connect the main island of Kythnos to the islet of Agios Loukas.

Once you've freshened up, head to a local tavern where you can enjoy a home-cooked Mediterranean meal.

Da 5: Kythnos - Lavrio port

In the morning your guide will take you on the spectacular loop hike to the ancient capital of Kythnos ‘Vryokastro’, which goes from a hilltop with astonishing views all the way back to your yacht in the mooring. Spend your last day swimming or paddle boarding around the beautiful Greek island, before setting sail back to Lavrio Port in the early afternoon.

You will arrive back by 15:30 where a transfer will be waiting to take you back to Athens International Airport.

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.

You will stay in a 56 sailing yacht with five cabins and five toilets. For July and September departures we use a Beneteau Cyclades 51-foot yacht with five cabins and three toilets. Both boats have an indoor living room, kitchen and dining area, as well as an outdoor lounge and front deck where you can relax when sailing.

Cabins are either twin or triple share, same gender. If you are a solo traveller and would like a cabin to yourself, a €300 upgrade is possible (depending on availability). Please request this 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, the combination of quiet beaches, traditional architecture and amazing hikes with stunning views makes this trip the perfect summer adventure.

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

Athens International Airport - 14:45

Your adventure begins at guide Athens International Airport (ATH) at 14:45. Please ensure you flight is scheduled to arrive at least 30 minutes before this time. Your host will be waiting for you in the arrivals area, and take you to the boat in the Lavrio Port Marino, Athens. The sailing boat will depart at 16:00 from the port of Lavrio. It takes approx 30 mins to get from the Airport to the Marina.

Alternatively, you are free to arrive any time and make your own way to Lavrio Marina. If you do this - please meet in Café Petrino at 15:15. Full directions will be provided by your host before your trip departs.

Finish Point

Athens International Airport - 17:15

Your adventure ends at the Lavrio Port Marina, Athens and from there your guide will take you back to the airport. You're free to book any flight that departs after 19:15. Alternatively, you can stay on in Athens and continue your adventure.

You will not be provided with:

  • Flights to/from Athens
  • Travel insurance
  • Entrance tickets to cultural places of interest
  • Evening meals: roughly 15-25€ pp
  • Drinks during the trip
  • Tip for crew (optional). Approx 20-30€ per person

If you are travelling with excess luggage which you do not wish to bring on the boat, there are two options for leaving luggage during the trip:

At Athens airport In Athens city

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

Both breakfast and lunch are provided on-board on a self-prepare basis. Your guide will try to use as much as possible local, organic and Mediterranean food.

For breakfast, you can expect yoghurt, fruit, cereals, juices, cheeses and bread.

For lunch, you can expect local salads, sandwiches, omelettes, pasta and fish.

Absolutely. Just let the host before your tour begins.

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 further and the trails are generally pretty straightforward.

You do not need to be particularly fit as you can take the hike at your own pace, but being in good physical condition will help you make the most of your trip. Your guide will take you in normal rhythms and stop whenever you feel like it.

There are always alternatives your guide can suggest if you don’t want to participate in a hike. From relaxing on the yacht deck, over SUP boarding to sunbathing on a quiet beach or strolling around the streets of the village, this is your trip, so spend it however you want!

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.

Should adverse conditions prevail - too strong winds or opposite direction winds that prevent us from anchoring in specific bays - your guide will have back-up plans such as alternative hikes or mooring in different bays.

In very rare occasions, it is up to the judgement of the skipper to alter or cancel a sailing route and up to the judgement of the hiking guide to alter or cancel a hike.

Skippers are qualified, native Greek seamen with vast experience navigating their local Aegean waters, the Mediterranean and beyond. The 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.

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.

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.

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.

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 your local host.

Your guide recommends that you bring:

  • A small rucksack
  • 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
  • One soft-suitcase per person as baggage is kept in the cabin

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.

This trip will go ahead with a minimum group size of 4 people.

Money Back Guarantee

We're so sure your holiday will be the best yet, we guarantee it

Pay 25% now to secure your spot

Spread the cost with as many payments as you need

Similar Trips


Why Us?

Here’s why we’re rated the UK’s ‘Best for Experiences’


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