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8 day Western Cyclades Sailing Experience

The Western Cyclades Sailing Experience is the best way to start planning your holiday.

Sail through one of the most famous archipelagos in the world: the Cyclades. With way more to offer than pristine beaches, crystal clear waters and amazing sailing experiences. They are the cradle of over ten millennia of rich history, boast extreme geographical diversity, abundant marine wildlife and feature the best of traditional Aegean architecture and Mediterranean cuisine. This sailing adventure goes far beyond island hopping, giving you a chance to explore way beyond each island’s marina, as well as immerse in local culture, savor the local flavors and learn a thing or two about the history of this immensely beautiful part of the world. And did we mention that it provides you with the opportunity to actively engage yourself in sailing, whether you have done it before or not? The Aegean archipelago, with its clear deep blue waters is the ideal place to get acquainted with the basics of sailing and our skippers are always happy to show you the ropes!

Tour Highlights

  • Immerse in the rich culture, delicious cuisine and millennia spanning history of Athens
  • Explore over a dozen different beautiful sailing destinations, visiting six islands in the process
  • Spend a night on the deck, under the Temple of Poseidon at Cape Sounion
  • Have a BBQ under the stars on a quiet island beach
  • Go swimming or snorkelling in crystal clear waters
  • Enjoy the laid back atmosphere on the quiet island of Kythnos
  • Savor amazing Aegean seafood on the ‘iron island’ of Serifos
  • See unique geological formations and swim in turquoise waters on the volcanic island of Milos
  • Hike on the uninhabited tiny island of Polyaigos and, if you are lucky, spot a Mediterranean seal hunting for fish
  • Experience the nightlife on the island of Poros

 Day to Day Itinerary

Day 1: Athens – Cape Sounion

Our day starts with a short stroll around the historic center of Athens, before we head to the marina and board the sailing boat that is going to be our home for the next week. Late afternoon we leave the marina, enjoying views of the southern suburbs of Athens. We head east, towards one of the most iconic landmarks or both the ancient and the modern world. The Temple of Poseidon, built high on a cliff over the dark blue waters at Cape Sounion, is the place where the Aegean archipelagos gets its name from. We spend the night anchored near the cliffs, where you get a chance to relax and swim. The short climb up the hill to the Temple at sunset is an unforgettable experience we cannot recommend enough.

Overnight: Cabin aboard the sailing boat

Meals Included: Light lunch onboard

Day 2: Cape Sounion – Kythnos

Early in the morning, after breakfast and a swim, we leave the Temple behind us as we set sails for open seas. The quiet island of Kythnos, with its traditional Aegean architecture, superb beaches and array of food taverns that specialize in regional Mediterranean cuisine, is our final destination for the day. You get a chance to explore the old town on foot. Don’t be afraid to let yourselves get lost in the back alleys of the old town. It is an important cultural experience and will allow you to witness island life at its most authentic. Visit the local bakeries and traditional coffee houses, while we get supplies. As the sun sets, we prepare a delicious BBQ on a quiet beach.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast, Light lunch on board, BBQ Dinner

Day 3: Kythnos – Serifos

In the morning you have time for a quick swim, while we prepare the sailing boat for yet another amazing sailing experience. This time our destination is the ‘iron island’ of Serifos, home of Perseus and the Cyclops according to Greek mythology. We set course through the straits of Serifos, towards the island itself, stop for a midday day swim before we arrive to the marina late afternoon. We drop anchor in the protected bay by the port and we strongly advise you start exploring the harbor area with its array of tavernas, grocery shops and coffee houses, before you move on to the Chora, overlooking the port, with its narrow streets, white houses and tiny churches scattered all around. Swimming is a real treat in Serifos, so you don’t want to miss out on that as well!

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast, Light lunch on board

Day 4: Serifos –Polyaigos – Milos

After breakfast you have a chance to unwind, have a swim or explore the island some more. Serifos is renowned for its hospitality so don’t miss out on interacting with the locals. Late morning we leave the island behind us, sailing south towards the island of Milos, our base for the next two days. Before we reach the island, we pass near the island of Kimolos and have a nice mid-day stop at the uninhabited island of Polyaigos. Polyaigos is tiny, barren and home to a dwindling population of Mediterranean seals, usually hunting for fish near the sea caverns they call home. The highlight of any visit to Polyaigos Island, besides marine wildlife lucky viewings, is swimming. The island’s south side boasts some of Europe’s most terrific beaches, ideal for swimming and snorkelling. We leave the island early evening and sail towards its bigger neighbour, the island of Milos, where we get before sunset.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast, Light lunch on board

Day 5: Milos – Kleftiko – Sarakiniko

Milos is a volcanic island, which is evident by the bizarre geological formations one sees around the island. After breakfast we get a chance to sail to two stunningly beautiful swimming spots, starting with the Kleftiko beach, in the southern tip of the island. Kleftiko used to be a pirate’s cove and a visit there is one of highlights to any trip to the Cyclades. Crystal clear waters, sea caverns and rocks pointing towards the sky, all contribute to an amazing, unique landscape. On the northern tip of the island lies the world famous Sarakiniko beach, a lunarlike landscape of white rocks and sand. It is the most photographed landscape in the Aegean, so don’t forget to have your cameras charged and ready! Late evening we drop anchor in the marina and you have plenty of time to savor the local food, experience the nightlife and explore the old town some more.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast, Light lunch on board

Day 6: Milos – Poros

After breakfast it’s time to leave Milos behind us, as the island of Poros awaits, and this is where we head next. We hit the open seas, sailing towards the Peloponnesian coast. Poros is tiny compared to Milos, and easy to explore on foot. It’s a place of rich history that spans over two millennia and one of the most important islands in the Gulf of Saronikos. We arrive in the evening and you can walk through the old town, have a swim, unwind on deck and taste some of the best seafood in this part of Greece.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast, Light lunch on board

Day 7: Poros – Aegina – Athens

We have breakfast onboard and have plenty of time for another swim. Late morning or early afternoon, we bid farewell to Poros and set sails north towards the island of Aegina. Our destination for the day is the seaside settlement of Agia Marina on the northeast tip of the island, a perfect place for yet another traditional taverna meal. As the sun sets, we head back towards Athens.

Overnight: Cabin aboard the sailing boat

Meals Included: Breakfast, Light lunch on board

Day 8: Athens

In the morning we pack our bags and bid farewell to the sailing boat that’s been our home for the past week and our adventure ends.

Meals Included: Breakfast

Important Tips

  • Travel Bite date and/or time might be modified or cancelled due to weather conditions and in this event the option of an alternative date or full refund will be given.
  • Being as light as possible is always important on an adventure tour plus space is limited on board a sailing boat so, our travellers are expected to bring with them a backpack or suitcase as well as a daypack for personal items and valuables.
  • We strongly advise you to have a valid Personal Travel & Health Insurance and bring your personal medication, sunscreen, insect repellent, travel sickness tablets, sunglasses, insect bite gel.
  • We would recommend you for Clothing/walking/swimming gear to bring with you fleece/softshell, jacket, waterproof & windproof jacket, sun, hat, long trousers (wearing shorts is not permitted in monasteries and churches), shorts, swimming costume, extra towel for swimming, t-shirts, hooded tops, trainers/walking shoes, waterproof hiking shoes/boots, personal mattress or a sleeping bag (should you choose to sleep on the yacht’s sundeck), torch, umbrella, snorkelling mask and fins.

Tips & Useful Info

Starting point: Athens International Airport, Attiki Odos, Spata-Artemida, Greece
Languages: English, Greek
Included Amenities: Accommodation: 7 nights sailing yacht double cabin, Meals: 7 Breakfasts, 7 Light lunches on board the sailing yacht (Days 1-7), 1 BBQ Dinner (Day 2), Transport: Fuel costs, toll costs, sailing boat rental costs, all electricity and water port costs, Tour Staff: English speaking tour leaders, professional skipper, local guides where needed, Outdoor Activities: Sailing, swimming and snorkeling in the Cyclades
Excluded Amenities: Airline tickets, Travel and activity insurance, Personal expenses, Transfers where needed
Minimum number of guests needed: 5
Maximum number of guests: 6
Physical Level: Moderate difficulty. Previous experience is not required. Average level of fitness is needed for travel bite enjoyment.

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