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Athens: 5-day Sail the Cyclades Islands Tour

Tours Cruises & Boat Tours Water Sports Outdoor Sports Multi-day Tours Mythology Outdoor Activities Medium-risk activities High-risk activities

Embark on a 5-day sea and land adventure of a lifetime around the dazzling Cyclades islands. The islands are an undiscovered hiking paradise, renowned for their pristine beaches, rich history and culture, traditional cuisine, and friendly locals.


  • Sail to 3 islands of the Greek Cyclades
  • Swim in secluded beaches
  • Stand up paddle through the turquoise waters of the Cyclades
  • Meet like-minded travelers
  • Go where in-the-know locals go, and enjoy the best local cuisine


Day 1: Kea Your 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 with life-on-board, as well as all the operational aspects of the trip. You will then set sail to the lush green island of Kea, which is favored by hikers in the know. You should arrive at just about the perfect time for a delicious dinner, which will be based on local specialties. Day 2: Kythnos - Loutra After a hearty breakfast, you will sail towards Poles Bay in Kea, which overlooks Ancient Karthea. Your guide will take you to follow in the footsteps of travelers who have been visiting Kea since the 17th century. You will explore Karthea, including 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 to the picturesque port of Loutra on Kythnos. This port is known for its natural warm springs, which you will of course have the chance to experience. Day 3: Serifos After breakfast, your hike will take you around the striking, arid countryside of 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. Its name is associated with two of the most famous mythical heroes: Ulysses and Perseus, and 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 one of Serifos’ secluded beaches. Day 4: Kythnos (Kolona) In the morning, you will 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 then bring you to the Konstantinos Chapel. Up there, you will 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. Day 5: Kythnos - Lavrio In the morning, take a spectacular loop-hike which leads you to a hilltop from where you can admire this astonishing natural phenomenon. From up high, it seems to look much like a column standing out from a cobalt blue background. Today, you will have time to once again swim or go stand-up paddle boarding, before you set sail in the early afternoon back to Lavrio port. After arriving at 3.30PM, a single transfer will be scheduled to take you to Athens International Airport.


4 nights' accommodation 4 breakfasts onboard 4 lunches onboard 2 guided hikes with an expert hiking guide in Kythnos 2 SUPs onboard (stand-up paddle boards) 2 single timed transfers from/to Athens International Airport on day 1 and 5
Travel insurance (required) Entrance tickets to cultural places of interest Beverages Miscellaneous expenses Gratuities (optional)

Important Information

  • Your sailing yacht will be a 50-foot monohull yacht, beautifully shaped from surface finish to deep under the skin
  • The sailing yacht accommodation is in double or twin/bunk bed cabins with en-suite facilities, suitable both for couples and solo travelers (solo travelers of the same gender share a twin bed or a double bed cabin depending on availability) • Minimum group size is 2 people, with a maximum of 10 people

Easy cancellation

Cancel up to 24 hours in advance to receive a full refund
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