Sail the Cyclades islands in 5 days

Embark on a 5 day sea and land adventure of a lifetime around the dazzling Cyclades islands, an undiscovered hiking paradise, renowned for its pristine beaches, rich history and culture, traditional cuisine and friendly locals. No prior sailing experience is required in this multi-level experience in the Aegean Sea. Along with like-minded travellers, you will have the opportunity to learn navigating our steadfast sailing boats, hike scenic trails, try SUP (stand up paddle boarding), and connect with local communities, whilst enjoying the caresses of the Aegean winds.


Departure date
Return date
Price Per person
Sailing Adventure
Fully Booked
Sailing Adventure
Fully Booked
Sailing Adventure
Fully Booked
Sailing Adventure
Fully Booked
Sailing Adventure
Sailing Adventure
Sailing Adventure



Welcome to this unique adventure to the Cyclades! Our team will be waiting to greet you at  Athens International Airport for your transfer to Lavrio port, where your captain will guide you to your sailing yacht. Settle in while your skipper briefs you life-on-board and all operational aspects of the trip.

Set sails to the lush green island of Kea, which is favoured by hikers in the know. You should arrive just about the perfect time for a delicious dinner based on local specialties. Kali orexi!


Kalimera! After a hearty breakfast, head off sailing to Poles bay in Kea, overlooking ancient Karthea. Your guide will take you to follow in the footsteps of travelers 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 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, your hike will take you around the striking, arid countryside around Loutra in Kythnos, where you will discover hidden centuries-old castles and whitewashed churches while coming across farmers and shepherds who live off this dramatic landscape.

After a refreshing dip and a light lunch, the voyage continues to Serifos island, an integral part of Greek mythology, since its name is associated with two of the most famous mythical heroes: Ulysses and Perseus. 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. If you’re up for it, you can try your balance at paddleboarding in of Serifos’ secluded beaches.

Kythnos (Kolona)

In the morning explore Serifos Chora’s narrow whitewashed alleys, colored 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 on the western side to the gold-sanded beaches of Apokrousi and Kolona, which are basically the edges of a narrow bar connecting the main island of Kythnos to the islet of Agios Loukas.

A local tavern is always the best way to conclude the day and share the myths lived and future plans dreamed of with your co-sailors.

Kythnos - Trip end

Good morning Kythnos! Take a spectacular loop hike which leads you to a hilltop from where you can admire this astonishing natural phenomenon, which from up high looks much like a column standing-out from a cobalt blue background. Today, we will swim or go stand up paddleboarding, before we set sail in the early afternoon, back to Lavrio port.  A single timed transfer is scheduled to the Athens International Airport.


Accommodation (4 nights, sailing boat in double or twin cabin with en-suite bathroom)4 breakfasts on-board4 lunches on-board
2 guided hikes by expert hiking guide in Kythnos and Serifos2 SUPs on-board (Stand up paddle boards)2 single timed transfers from/to Athens International Airport


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


COVID19 Related measures

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.

How to book

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.

Arriving in Athens

Our meeting at the Athens airport on Day 1, is adjusted to our travelers’ flight arriving last. This is usually between 12:00pm and 2:00pm Greek time. We strongly recommend booking a flight that arrives in Athens on Day 1 by 2:00pm or earlier. Please meet your guide at the arrival’s hall B/Exit5. In case your flight's exit is the arrivals hall A, this is a 5' walk from arrivals Hall B/Exit5. He will be holding a sign ' Personality Journeys'. About a week before departure when we will have all travelers’ arrival schedules, you will receive an email with detailed information on our airport meeting.

In case you have arrived in Athens on the previous day, you are welcome to join this scheduled departure from Athens airport. Alternatively, please make your own transfer arrangements to Lavrio port and meet us at Cafe Petrino at 3:15 pm. Café ‘Petrino’ (‘The Stone’) is located just in front of the harbor and serves both coffee, tea and Greek homemade food.

Yacht accommodation

Our monohull sailing yachts are: Ocean Star 56.1 or 51.2 or Cyclades 50.5. Beautifully shaped from surface finish to deep under the skin, top-quality, strong and reassuringly solid. They have 5 guest cabins and one crew cabin & 5 or 3 toilets.

Solo travelers of the same gender share a twin bed or a double bed cabin depending on availability.

Departure flight

Regarding your departure flight on Monday we recommend booking flights with take off time at 6:00pm or later.

Group size

Minimum guests: 2
Maximum guests: 10

Personality Journeys sailing & hiking team experience

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.

I have never gone sailing before what should I know?

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.

Hike & sail daily plan

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

Fitness level

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.

Minimum and maximum age limit

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.

SUP (stand up paddle board)

During your 5 day 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, early summer 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 early summer & 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 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.

How safe is it to hike in the Greek islands?

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.

What do I need to bring?

Small day-pack, hiking shoes & long walking socks, sandals, a pair of shoes that may get wet, hiking (comfortable) long 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.

Alternatives for less active companions

There are always alternatives we can suggest if you don’t want to participate in a hike. From stand up paddle boarding to 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.

Responsible travel policy

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.

Guaranteed departures

Our scheduled sailing trips have guaranteed departures.

Travel Insurance

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.

Single supplement

The single supplement is an extra charge of 450€ 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.

Make this trip private

Adjust this itinerary to suit your preferences. Choose your preferred dates and we will plan a custom sailing adventure for you.

Hellenic Association of Travel & Tourist Agencies
Adventure Travel Trade Association Member
Greek National Tourism Organisation
Hellenic Yacht Brokers Association
Hikers Friendly