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Picture-Perfect Greece
Cyclades Sailing Holidays

Two weeks sailing in the Cyclades islands, where whitewashed villages meet the crystal blue mediterranean sea, will enchant you. Set-sail from Lavrion, near Athens, and explore the Greek islands that make up this incredible part of the world. A 14-day itinerary is simply the best way to explore and enjoy the Cyclades, in-depth.

Dance the night away in Mykonos, relax on the sandy beaches of Kythnos and become acquainted with traditional Greek life in Paros. The Cyclades ensures there is something for everyone to enjoy whether you’re a food lover, thrill-seeker, budding historian or simply just want two weeks of sun, sea and sailing!

Contact The Big Sail for your quote for the perfect family sailing holiday or group yacht charter.




Day 1


Fly to Athens & arrive and check-in in Lavrion

Lavrion is the gateway to the Cyclades islands. Situated on the southern tip of mainland Greece, it is only 45 minutes drive from Athens International Airport. Lavrion has several supermarkets – making it the perfect place to stock up and set sail from, and we can also arrange a supermarket delivery directly to your yacht. If you arrive early, head into Athens by taxi (just under 1hr) and explore some of the city’s historic sights. If you book an early check-in and are able to set sail by mid-afternoon, head to the Temple of Poseidon around the corner in Cape Sounion Bay or sail to the nearby island of Kea for the night if you have time.


Day 2


Vourkari, Kea Island

Vourkari is situated to the north of Kea island. Well protected from the Meltemi wind, Vourkari has the feel of a small fishing town with lots of small fishing boats in its harbour. The island is home to some very good local restaurants specialising in fresh fish, lobster and other traditional dishes. If you’re looking for a quieter island destination for a night, then Kea is a great sailing destination, and for a really peaceful spot – try anchoring in the bay 100m away from the main port.


Day 3



With the most famously beautiful beaches in the Cyclades, Andros is a must-see for swimming, snorkelling and sunbathing lovers. The highlight of this island is definitely its natural beauty! The stunning beaches are accompanied by beautiful nature walks and incredible views. This stop off is the perfect opportunity to enjoy dinner and drinks onboard and make the most of the sunset.


Day 4


Mykonos town, Mykonos

On day four, enjoy a long relaxing sail from Andros to Mykonos. Mykonos is perhaps the most famous of the Cyclades islands and is known for its glamour, beautiful beaches and summer party atmosphere. Take your time getting here as you’ll have a full day on land tomorrow to take in all that Myknonos has to offer.


Day 5


Full Day Mykonos

Located in the heart of the Cyclades, Mykonos offers something for everyone with golden beaches, diving, windsurfing and endless nightlife options for those who crave it. Little Venice is the place to be for beautiful waterfront dining, complete with sunset views.


Day 6



After you’ve worn yourself out in buzzing and vibrant Mykonos, it’s time to get back to the peaceful side of a sailing holiday, with a dose of nature in Naoussa Bay on the island of Paros. Here you’ll find beautiful nature walking trails, quaint tavernas and a lighthouse with incredible views. This village is famous for its traditional Greek way of life so make the most of the opportunity to enjoy a bit of old Greece!


Day 7



Ios will be a stand out stop-off for your entire group! Ios is known for its great food, historic sites, hiking trails and amazing views – there is something for everyone here! Hike up (or take a taxi!) to the town of Chora for dinner. Situated on the hilltop, high above the main town of Ios, Chora is the perfect spot to cast your gaze across the entire Cyclades islands and enjoy a bite to eat from one of the town’s many small restaurants.


Day 8



It’s time to take a slightly longer sail south, to the famous island of Santorini! Known locally as ‘Thira’, this Cycladic island is best-known for its postcard-perfect whitewashed buildings with blue rooves and stunning cliff-top views across the volcanic caldera and towards the other Cyclades islands to the north. As the marina is a long way from the main town of Thira, we sometimes recommend staying on land for a night to fully experience Santorini.


Day 9


Santorini Full Day

Enjoy a day exploring the iconic hills of Santorini! Fill your day with sightseeing, shopping, wine tasting and exploring the amazing architecture and history of this great island! End the day on a high with dinner on a candle-lit terrace whilst watching a spectacular sunset over the sea to the west of Thira.


Day 10


Return to Ios

Santorini is the furthest south of the Cyclades islands, so from here you’ll need to retrace your path a little and head back north to the island of Ios. From windsurfing to exploring historic architecture, there’s something for everyone on Ios! If you didn’t visit Chora last time around, take a 10-minute taxi up there for dinner – it’s worth it for the view!


Day 11



The largest island of the Cyclades, Naxos has an incredible amount to offer! The whitewashed village is cut into the lush green hillside and is teeming with restaurants, tavernas, shops and museums. Once you tire of the stunning beach, you’ll have plenty to do onshore!


Day 12



There is more to Syros than just its beauty – it has a vibrant culture and is well known for its history and art – visitors should make time to explore the museums and galleries in Ermoupolis as well as the islands stunning beaches, caves and winding streets. Syros is generally known for its family beaches and quiet nights and is a great contrast to Mykonos and Ios.


Day 13



Your final stop before returning to Lavrion will be the picturesque anchorage of Fikiadha Bay on the island of Kythnos. The bay is divided by a sandy spit, making this an excellent spot for protected swimming in the shallow water and taking the dinghy for some sundowners on the beach. Cook dinner onboard and enjoy watching the sunset in this stunning bay.


Day 14


Return to Lavrion

It’s time to return your yacht back to base and sail to Lavrion. Take this opportunity to sail to Cape Sounion Bay (just south of Lavrion) and spend your final afternoon hiking up to the ancient Temple of Poseidon which sits impressively up on the hill above the bay. Or alternatively, make the most of your time onboard by simply enjoying the sheltered bay by sunbathing and paddleboarding for the afternoon before making the final 1-hour sail north, back to Lavrion. Spend a little time getting ready for your departure tomorrow, then head to a traditional Greek taverna for dinner in Lavrion.


Check-out is at 9am Saturday morning – depart the marina, head to Athens airport or begin your next adventure.


Get your tailor-made charter quote today

  • Choose any destination worldwide.
  • Yachts available to meet every budget, and any group size.
  • No experience required – we’ll provide a skipper if you don’t have sailing certification.
  • We’ll create a tailor-made itinerary for your group including restaurant recommendations and anchorage tips.

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