Sailing & Hiking in Cyclades 8 days

8 Days

Sailing & Hiking in Cyclades 8 days

Sail to the most unknown corners of stunning Cyclades Islands such as Kea

Sail to the most unknown corners of stunning Cyclades Islands such as Kea, Kythnos, Syros and Serifos and walk in the footsteps of the ancients along beautiful trails. Our top of the range boats are navigated by qualified skippers, who are eager to share their regional knowledge with you. Whether you’re an experienced sea and land adventurer or it’s your first time, you’ll enjoy a unique, multi-level experience in the Aegean Sea. Connect with like-minded travelers as you sail on our steadfast mono-hull boats, navigating yourself or simply kicking back to bask in the sun whilst enjoying the caresses of the Aegean winds.


Departure date  Return date Theme Price Per person Spaces on request
08/10/2022 16/10/2022 Sailing Adventure €1120 Spaces on request
29/04/2023 06/05/2023 Sailing Adventure €1290 Spaces on request
07/10/2023 14/10/2023 Sailing Adventure €1290 Spaces on request

Trip Highlights

  • Sail to 4 islands of the Cyclades
  • Hike 4 magnificent trails of the Cyclades
  • Swim in secluded beaches
  • Stand up paddle (SUP) through the turquoise waters of the Cyclades
  • Meet like-minded travelers
  • Go where in the know locals go and enjoy the best local cuisine

Photo Gallery

Day to Day Itinerary

Kea Welcome to this unique adventure to the Cyclades! Our team, will be waiting to greet you at Lavrio port and guide you to your sailing yacht. Upon arrival onboard you will receive a thorough briefing by your skipper covering all operational and life-on-board aspects of the trip. Let the wind guide you to the island of Kea. Fertile and green, Kea is hikers’ paradise, abundant with routes to beautiful, remote beaches. You should arrive just about the perfect time for a delectable dinner based on local specialties. Kali orexi!
Kalimera! After a hearty breakfast it’s time for an invigorating hike along ancient footpaths through flower-carpeted valleys and ancient ruins, walking in the footsteps of travelers who have been visiting Kea since the 17th century. After a dip at one of Kea’s most beautiful beaches, Aeolus, God of wind, will blow into the sails of your yacht as you set off for a relaxing afternoon sailing across to the picturesque port of Loutra on Kythnos, known for its natural warm springs, which you will have the chance to experience!
After breakfast and taking advantage of the cool morning air, your hike will take you around the striking, arid countryside around Loutra in Kythnos, where you will discover hidden centuries-old castles, quaint whitewashed churches and other sites while coming across farmers and shepherds who live off this dramatic landscape. After a refreshing dip and a light lunch the voyage continues to sophisticated Syros, to the stunning port of Foinikas. For those who wish, sailing becomes more hands on, testing out your skills against the elements.
Start the day in Syros with a sun salutation to gather your energy for the day’s events, as today you will explore the western part of Syros hiking. For those who prefer to stay and relax in Foinikas, our expert guides will be more than willing to suggest alternative ideas to spend your time creatively. 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 pedestrianized streets and its maze of stairways, then discuss the day’s highlights while savoring local cuisine in some of the finest restaurants in the Cyclades and enjoy a cocktail in one of the local bars.
First thing in the morning it’s off to Serifos island, an integral part of Greek mythology, since its name is associated with two of the most famous mythical heroes: Ulysses and Perseas. You can mull over this yarn and other local legends whilst sipping a traditional Greek coffee and enjoying a local sweet at the sparkling port of Livadi. Later on take a fascinating walk to Chora, the island’s capital, which is perched on a hill above the port, and discover its narrow whitewashed alleys colored with the lush green, pink and purple of overflowing bougainvillea.
The next stage of the trip takes you back to Kythnos, but this time on the western side to the gold-sanded beaches of Kolona, which are basically the edges of a narrow bar connecting the main island of Kythnos to the islet of Agios Loukas. The amazing loop hike here leads you to a hilltop from where you can admire this unique natural phenomenon, which from up high looks much like a column standing-out from a cobalt blue background. After this invigorating hike, breathing in the Aegean meltemi wind, head down to the beach for some serious relaxation! A local tavern is always the best way to conclude the trip and share the myths lived and future plans dreamed of with your co-sailors.
Good morning Kythnos! Today is your last swim with us on the Greek islands before you set sail on the last leg of your trip back to Lavrio port. Spending your final night on board offers a great opportunity to enjoy being on the water to the max while taking in the dreamlike experiences of the past week and enjoying dinner and no doubt a few glasses of wine!
Trip end A single timed transfer to the Athens International Airport is provided.


  • Accommodation (sailing boat in double or twin bed cabin with en-suite bathroom)
  • 7 breakfasts on-board
  • 6 lunches on-board
  • Guided hiking by expert hiking guide in Kea, Kythnos and Syros
  • 2 SUPs on-board (Stand up paddle boards)
  • 2 single timed transfers from/to Athens International Airport

Not included

  • Travel insurance (required)
  • Entrance tickets to cultural places of interest
  • Beverages
  • Miscellaneous expenses souvenirs etc.
  • Gratuities (optional)

Know before you go

Our yachts are fully sanitized after each charter with certified products based on COVID19 related cleaning protocols. The captain/skipper is wearing a mask at all times while being indoors, whereas our guests are advised to wear a mask (this is not mandatory). We will provide one mask and antiseptic gel per guest. All guests are requested to fill a COVID19 related health document before embarkation. Based on recent guidelines, entering Greece requires a negative Covid19 test taken three days before arrival. In minibus airport transfers, all the necessary measures are taken regarding sanitization after each minibus trip. The maximum size per van is 5 guests. The driver and all guests are required to wear a face mask for the duration of the ride.
By clicking the 'Book now' button above, you will be asked to pay a 20% deposit. This is to secure your booking with us. On receipt of your booking, we will send you full written confirmation of your booking, the trip file and trip notes, together with your trip invoice, which is usually due for payment 8 weeks prior to departure. The date payment is due will show on the invoice. Please call us at +30 2152151629 if you need more information.
Most flights from Europe arrive in Athens by 2:00 pm. Our driver will be at the Athens International Airport at 2:45 pm to drive you to Lavrio Port Marina A' (40km, 30-minute drive) where our yacht is docked. Our sailing trip departs at 4:00 pm. In case you have arrived on a previous day in Athens city, please arrange your own taxi transfer to Lavrio port Marina A' at 'Mikis Theodorakis' avenue. Our meeting point is at cafe 'Petrino' in Lavrio at 3.15pm
Our monohull sailing yachts are: Ocean Star 56.1 and 51.2, hand-built, beautifully shaped from surface finish to deep under the skin, top-quality, strong and reassuringly solid. Sailing yacht accommodation is in double or twin/bunk bed cabins with en-suite facilities, suitable both for couples and solo travelers. Solo travellers of the same gender share a twin bed or a double bed cabin depending on availability.
Minimum guests: 2 Maximum guests: 10
Our 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. Our hiking guides are year round hikers themselves and have a vast repertoire of paths trekked around Greece, including demanding gorge passages and high altitudes. They are trained in hiking schools which 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 us. Your captain will brief you in detail on moving around the sailing yacht and will teach you the basics of sailing during your holiday. You will easily get accustomed to the indoors of the boat which is designed in such a way to achieve maximum space efficiency.
Our daily distance covered hiking will be 8km on average. Since this is a vacation trip and not a race, we are flexible in a way to increase satisfaction. There will be extended hiking routes for those who want to hike further. Our sailing passages will be 2 to 4 hours long.
Both breakfast and lunch are provided on-board on a self-prepare basis. We try to use as much as possible local, organic goods, adding to the local character of the trip. Examples of breakfast: - Milk & yogurt - Honey - Fruits (bananas, peaches, grapes, apples, oranges) - Cereals (oats, cornflakes) - Orange, lemon juice - Organic bread (slices) - Yellow cheese (slices) Examples of lunch: - Greek salad (tomatoes, feta cheese, cucumber, onions, caper, olive oil, oregano) - Dakos salad (specialty from Crete island) - Sandwiches (organic loaf, salami, yellow cheese, lettuce) - Eggs – Omelettes - Spaggetti/Pesto - Pasta/Tortellini - Salmon - Tuna - Quinoa
We go at our own pace. We hike in normal rhythms and whenever we feel like it we 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. In order though to better appreciate the uniqueness of your holiday, we advise you to be in good physical condition. On your last two weeks before the trip, it is a good idea to take several walks in hilly terrain.
We require our participants to be above 18 years old. In the case of families we offer private sailing/hiking trips with no age limitation.
During your week long adventure, you will have the opportunity to paddle along the turquoise waters of the Cyclades. Our inflatable boards are ideal for beginners and our skipper will be more than happy to show you the basics of stand up paddling.
The weather conditions during spring and autumn are on average ideal for sailing and hiking: moderate breezes combined with pleasantly warm temperatures. Air temperature in spring is 16-23 degrees and in autumn 19-26 degrees. All sailing routes are designed based on statistically most probable wind speed and direction in the Cyclades islands. However, should adverse conditions prevail (too strong winds or opposite direction winds that prevent us from anchoring in specific bays, we have plan B scenarios already available meaning alternative hikes if necessary or alternative mooring locations/ports in the island in concern. In such 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.
The hiking paths are selected to ensure that you can fully take in the magnificence of the landscapes, while discovering their flora and fauna. The selected paths are easy and safe.
Small day-pack, hiking shoes & long walking socks, sandals, a pair of shoes that may get wet, hiking (comfortable) trousers, long sleeve shirts, water-resist jacket & trousers, sunglasses, hat, sun cream, water can, trekking poles, bathing suit, beach towel, head-torch, toiletries, basic First Aid Kit including: antiseptic cream, throat lozenges, diarrhoea treatment (Imodium), painkillers, plasters and blister treatment, insect repellent. We would ask you to bring 1 soft-suitcase per person. On a sailing boat there is no luggage storage space - all passengers keep their luggage in their cabins.
There are always alternatives we can suggest if you don’t want to participate in a hike. From resting at the sailing yacht deck to strolling around the streets of the villages we visit, we encourage you to do whatever feels right to you.
Our aim is to reduce as much as possible the negative and increase the positive impacts our operational practices have on the social and physical environment within the areas of our operation. During briefing, our team will inform you of how we try to achieve this in practice.
Our scheduled Sailing & Hiking trips have guaranteed departures.
We require that all our travellers are insured while travelling. In case you need assistance in order to choose your travel insurance please contact us. Personality Journeys is a World Nomads partner, Lonely Planet's trusted travel insurance provider.
The single supplement is an extra charge of 600€ for solo travellers who wish to book a double bed cabin on their own. In the occasion of two solo travellers of the same gender sharing a twin bed or a double bed cabin there is no single supplement charge.

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Exceeded all Expectations!

We had the most exceptional travel experience with Personality Journeys. Both our travel agent and out travel guide (“skipper”) were fantastic! Dimitris was everything we could have looked for in a travel agent....


10th Anniversary and Honey Moon!

This was our first overseas trip ever and it turned out amazing! Dimitris planned our trip out within our budget and the lodging was fantastic. Our favorite hotel was the Corfos Bay Hotel in Mykonos for its genuine beauty and true Island architecture. All of our ferry…

Jacky Merianos

Sail the Cyclades islands 5 days

Dimitris was everything we could have looked for in a travel agent. Following the parameters we laid out for him, he provided us with the absolute best options for our travels. He was both honest and patient with us, and made sure we took as much time as we needed to finalize a trip that...


perfect week!

Dimitris organized a private sail and hike trip for us. Everything was perfectly planned. Dimitris made us feel safe at all time as he was always in contact. He met us for one of the hikes , which was wonderful. Socrates, our captain and Savy his assistant, were so kind to us...


Amazing experience

Amazing experience! absolutely recommend it!


5 stars

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Sailing & Hiking in Cyclades 8 days

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