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.

  • Greece
  • March—May, October
  • Eleftherios Venizelos International Airport, Athens (ATH)

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.

Need To Know

You will not be provided with:
- Flights to/from Athens
- Travel insurance
- Entrance tickets to cultural places of interest
- Evening meals
- Breakfast and lunch on the arrival day - Beverages
- Tip for crew (optional)

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

Start point
Your guide will collect you from Athens International Airport at 14:45 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.

If you have made your own way to Lavrio Marino, please meet in Café Petrino at 15:15.

Finish point
You will end up returning to the Lavrio Port Marina, Athens, where you can continue your adventure or your guide will take you back to the airport. You’re free to book any flight that departs at 19:15 or later.

Getting there and away?
You will need to fly into Athens International Airport in Greece. 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.

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Location

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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
Your guide will collect you from Athens International Airport at 14:45 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.

If you have made your own way to Lavrio Marino, please meet in Café Petrino at 15:15.

Finish point
You will end up returning to the Lavrio Port Marina, Athens, where you can continue your adventure or your guide will take you back to the airport. You’re free to book any flight that departs at 19:15 or later.

Getting there and away?
You will need to fly into Athens International Airport in Greece. 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.

Start point

Arrive at Athens International Airport in the morning.

Finish point

Athens International Airport

What to Expect

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.

Accommodation

You will stay in a 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 front deck where you can relax when sailing.

If a solo traveller wishes to occupy a double cabin there is a supplementary charge.

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Dates & Prices

Prices include

  • Accommodation
  • Airport Transfers
  • Equipment
  • Guide
  • Local Transport
  • Meals As Described

Please note: Flights are NOT included and must be purchased separately.

Large group? Make a private booking
Special requirements? Get a quote for a custom trip

If you can't find a private trip that suits you, try a group trip or ask for a quote.

Optional Extras

Make your life easy. Once you have reserved your space, your host can help you arrange the extras you’ll need. Here are some guide prices which can be confirmed with you during booking.

Single Room Supplement Payable Before Departure
Single Room Supplement £300.00

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