7-Day Cyclades Crewed Sailing Yacht Itinerary | Greece 2025-2026
Discover Athens, Kythnos, Mykonos, Paros, Ios, Sifnos & Serifos on a Luxury Crewed Sailing Yacht Itinerary
Overview | Map | Athens | Kythnos | Mykonos | Paros | Ios | Sifnos | Serifos
Athens is a city of history, culture, and beauty, with everything from archaeological sites to some of the liveliest beach clubs in the Mediterranean. It is the perfect place to charter a crewed sailing yacht or catamaran for the ultimate holiday in the Greek Islands. The city and the rest of Greece are absolutely beautiful, and you can experience every aspect of this varied and colorful landscape whether you prefer the tranquillity of empty bays and quaint fishing villages or scintillating nightlife and fabulous cuisine.
This itinerary is perfect for those looking to venture beyond the Saronic Gulf to see some of Greece's most iconic islands like Mykonos and Sifnos. Our Boatbookings Charter Experts can answer any questions you have about this itinerary or help you plan your personalized itinerary in Greece.
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Day 1: Athens to Kythnos
Start your crewed sailing yacht charter in the heart of Greece’s charter scene, the capital city of Athens. Explore this ancient and enchanting city before you set sail for the rest of the enchanting Greek islands. Sail through the clear blue waters, along the mainland coast on your way to Kythnos, an island of undulating hills and beautiful beaches.
You can anchor in a bay, enjoy a picnic on the beach, and spend your afternoon floating on the azure waters or snorkeling down below. In the evening, why not enjoy the port town of Merihas with its lively restaurants and bars?
Day 2: Kythnos to Mykonos
For those who enjoy an exhilarating nightlife, stunning beaches, and great shopping, Mykonos is a must-visit. Set sail for this enticing island and spend the day anchored in a beautiful bay before heading into the port for the evening. Once in town, this is a perfect place to get off the boat and enjoy a delectable meal at a local restaurant.
Mykonos is home to the all-day beach club Alemagou where you can get a taste of some fast-paced seaside fun, or a more refined dinner, book a table at Krama, a fantastic seasonal restaurant. Mykonos has something for everyone, making it a truly memorable charter destination.
Day 3: Mykonos to Paros
Sail south in this gorgeous Greek weather for the island of Paros. Spend some time on the beach, or swim in one of the lovely bays, before heading inland to explore the breathtaking natural splendor of the footpaths and villages of the island.
Some of the finest restaurants of the Cyclades can be found here for dinner this evening, including Marios in the old Venetian port of Naoussa, and Barbarossa, a wonderful seafood restaurant that is not to be missed! Another great restaurant is Levantis, with a vine-covered courtyard and exciting menu, this is sure to be a memorable meal.
Day 4: Paros to Ios
Spend your morning enjoying a leisurely breakfast in the sunshine while your crew sails on to Ios and stops off in the port of Ormos harbor. From the harbor, you can walk or take the bus up to the beautifully picturesque village of Chora, a stunning place to walk around as it is inaccessible for any kind of vehicle.
Be sure to take the time to try out some of the best restaurants on the island, including Ios Club Restaurant which offers a wonderfully romantic ambiance as well as tantalizing Greek cuisine and delicious cocktails. Whether you choose to explore the island or to stay on board your sailing yacht, Ios is the perfect place to relax and sip some cocktails during a truly fantastic sunset.
Day 5: Ios to Sifnos
Anchor off the beautiful island of Sifnos after a morning sail with your crew. This island is home to three quaint fishing towns and breathtaking vistas from every angle. It is an unforgettable landscape full of perfect beaches and impossibly turquoise waters where you can enjoy snorkeling or paddle boarding around the coves surrounding the island.
If you wish to explore inland, you can venture through the towns and enjoy the abundant fragrance of olive groves, almond trees, oleander, and herbs that fill the air here. Walk the quiet streets, and explore the waters and the stunning coastline before an evening meal in a local taverna that will not disappoint.
Day 6: Sifnos to Serifos
Set sail early, and make way for the stunning island of Serifos. With a selection of fantastic restaurants, and boutique shops, it is the perfect destination for your final night on board your luxury sailing yacht charter. Once you reach the island, anchor in a quiet bay and get ready to explore to your heart's content.
Walk the streets of this elegant circular town and look down over the rest of the island from the top of the hill. Enjoy the atmosphere and food at the quaint bars, restaurants, and tavernas that line the narrow streets, or walk up to the 15th-century Venetian castle for a fantastic view of the sunset over the azure Greek waters. With so much to offer, Serifos is a delight for everyone to explore and experience.
Day 7: Serifos to Athens
Spend your final day swimming and enjoying the quiet bays of Serifos before sailing back to Athens, your final destination. Once you arrive in the historical city, enjoy a beautiful meal by the harbourside before you say farewell to your wonderful crew and unforgettable yacht as you disembark.
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