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Embark on a sun-drenched sailing adventure through the heart of the Cyclades, where iconic whitewashed villages, sapphire waters, and golden beaches await at every turn. Over seven unforgettable days aboard a comfortable catamaran, you'll explore some of the Aegean’s most enchanting islands—each with its own unique charm and rhythm. Start in Paros and glide into the chic harbor of Naoussa, then head to the vibrant island of Naxos, known for its ancient ruins and long sandy beaches. From the laid-back allure of Koufonisia to the quiet beauty of Schinoussa, every stop promises crystal-clear waters and authentic Greek island life. Discover the hidden coves of Ios, and stroll the quaint streets of Antiparos before returning to Paros, where the journey concludes in serene Piso Livadi Bay. With daily swims, seaside tavernas, and starry nights at anchor, this voyage offers the perfect blend of relaxation, exploration, and Cycladic charm.
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Day 1
Board boat in Paros, sail to Naoussa
Known for its laid-back atmosphere, Paros offers an authentic taste of Greek Island living, with traditional Greek hospitality and stunning local architecture around every corner. Take a stroll amongst the cobbled streets, boutique shops, and windmills before meeting your crew at the marina. Departing Paros in the afternoon, we'll have a short sail North to the picturesque fishing village of Naoussa. Enjoy strolling what is considered to be one of the prettiest and most photographed villages in the Cyclades. Full of Greek authenticity and traditional character, with its whitewashed houses and churches. Enjoy some delicious local cuisine by the water, and raise a glass to an incredible week ahead.
Meals: Nil
Day 2
Naxos
Enjoy a sunrise sail as we head to the largest island of the Cyclades. According to mythology, Naxos is where the god Dionysus taught the inhabitants to make wine, so be sure to sample the local varieties, or take a wine tour. With its mountain villages, ancient ruins and long stretches of beach, the island is perfect for exploring.
Meals: B,L
Day 3
Koufonisia
Enjoy a scenic sail as we head over to the crystal clear waters of Koufonisia. Making the most of the day, we’ll sail around the small Cyclades at a leisurely pace, looking out for hidden wrecks and stunning bays along the way. Spend your afternoon swimming and exploring the town, before enjoying a meal ashore in a local taverna and settling in for a quiet night under the stars.
Day 4
Schinoussa
Often referred to as the jewel of the Cyclades, experience traditional island life in Schinoussa. With a charming old town and terraced hills sweeping down to sandy beaches, you'll have ample opportunities for swimming, hiking or just relaxing onboard. Dotted with traditional tavernas the cuisine is exquisite, offering some of the finest dining in the islands.
Day 5
Ios
After a morning swim we’ll sail across to the beautiful island of Ios. Enjoy the peaceful side of this island discovering secluded beaches, ancient ruins and charming bays or make your way to the hilltop church of Panagia Gremiotissa for an outstanding view over the bay. Ios is well known for its lively bars and watersports, so is a great choice to enjoy a few sunset cocktails.
Day 6
Antiparos
Heading North, our week ends on a high as we set sail to Antiparos. Enjoy a swim at the blue caves before strolling around the cobbled and peaceful walkways of this charming town. In the evening, sit down to a delicious traditional feast whilst reminiscing about the beautiful islands, and admiring another stunning Greek sunset.
Day 7
Trip concludes in Paros at 5pm
Enjoy your final sail as we head back to Paros, stopping at your skippers favourite secluded bays along the way. You'll have plenty of time to enjoy a delicious brunch onboard the yacht, swim, paddleboard, and soak up the Greek sunshine before saying your goodbyes and raising a glass to an unforgettable holiday. Take some time to savour the last moments on board before disembarking at 5pm. NB* The itinerary and sailing route is subject to change dependent on weather and prevailing conditions. Guests under the age of 18 are only permitted on whole yacht bookings or our Private Yacht Charters.
What's included
What's not included
Our voyages are designed for curious travellers — not just passengers. While our itineraries offer a range of activities, from gentle hikes, snorkelling and swimming, it’s important to understand the nature of this experience before you join us. These adventures are suitable for most travellers with an adventurous spirit, good health, and the ability to move confidently around a vessel — especially in variable weather and sea conditions. Some shore landings and excursions may involve uneven terrain, wet landings, or light scrambling. Navigating the boat may require balance and agility, though our experienced team is always on hand to assist. Each trip may include a variety of optional activities, most of which require no prior experience. Of course, all activities are optional — you’re always welcome to stay aboard and enjoy the boat at your own pace. Not sure if this trip is right for you?
Get in touch with our team — we’re here to help you choose the experience that best suits your interests, comfort, and curiosity.
The superior catamarans accommodate 8 guests over 4 double ensuite cabins. A skipper and a host are on every voyage.
Double Ensuite
The catamaran has 4 double ensuite cabins all the same size.
Per Person, Twin Share
Children are welcome on private charters and family cruises. Unfortunately, any guests under the age of 18 will not be permitted on shared cabin cruises.
We suggest packing casual summer attire, swimwear, beach towel and appropriate footwear. We advise against hard-cased, wheelie suitcases. The less you pack, the more room on board and in your cabin, making for a more comfortable sailing holiday! We also recommend packing a portable charger, any medication needed and your own reusable water bottle. If you are travelling in May or September, we recommend bringing a lightweight jacket and long trousers.
Yes. Our Hosts are well-equipped to cater for any specialist dietary requirements. We also recommend supplementing your meals with suitable specialist foods, as the variety in smaller towns can be quite limited.
Yes, all our cruises are 'bring your own' snacks and alcohol. There are supermarkets or local stores at the majority of our destinations, so you can replenish your supplies throughout the week. Guests are allowed to stock the yacht with whatever drinks and snacks they choose.
For dinner, you can choose from the range of restaurants and bars on offer at each of our destinations. Your crew will be happy to help with recommendations.
Rating: ☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆
Explore places the big ships can’t with the widest selection of genuine small-ship, activity-first cruising. On Water Expeditions offers exceptional value, quality services, no hidden costs, and plenty of inclusions.
Don't watch the action sail past your window, dive into it! Designed for active travellers, these itineraries give you more time to adventure off the boat.
Activity is built into every journey. From paddling to hiking, enjoy a basecamp-style experience that injects fun, meaningful connections and thrilling adventure into it.
Each voyage is thoughtfully selected for low-impact exploration, supporting genuine conservation and sustainability while respecting local communities and environments.