7-Day Western Cyclades Crewed Catamaran Itinerary | Greece 2026-2027
Discover the highlights of the Western Cyclades Island on a 7-day Luxury Crewed Catamaran Itinerary for Summer 2026 and 2027
Day 1: Cape Sounio and Kythnos| Day 2: Sifnos | Day 3: Milos | Day 4: Poliegos and Kimolos | Day 5: Serifos | Day 6: Kea | Day 7: Vouliagmeni | Day 8: Disembark in Athens
The Western Cyclades are a unique cluster of Greek islands where ancient villages tumble down gentle island hills into beautiful bays of turquoise water. These islands are hidden and preserved from mass tourism, they hold history, colorful coastal villages to wonder through and delicious local food to discover. This is the perfect itinerary to discover the authentic Greece whilst enjoying stunning views and pristine beaches. Chartering a crewed Catamaran is the ideal way to explore this other side of the cyclades, allowing you to swim in crystal blue waters along stiff cliffs and make the most of water toys.
To ensure that you experience the best Greece has to offer, our Boatbookings Charter Experts have created this sample itinerary to help you plan the perfect getaway. Explore below to see where a luxury Crewed Catamaran can take you.
Map of the Western Cyclades Crewed Catamaran Itinerary:
Day 1: Cape Sounio and Kythnos
Embark your Greece luxury crewed catamaran in Athens and settle in with a welcome Aegean Spritz as you cruise to Cape Sounio, anchoring beneath the historical Temple of Poseidon for a refreshing swim and lunch onboard featuring grilled chicken souvlaki with lemon potatoes, and your first of many, greek salad. Continue to the stunning Kolona Beach in Kythnos, where turquoise twin bays invite paddleboarding and beachcombing before a relaxed aperitivo watching the sunset. Your private chef will then serve an amazing BBQ seafood dinner onboard showcasing charcoal-grilled sea bream, grilled calamari and octopus, accompanied by vegetables. A perfect end to your first day aboard your crewed catamaran.
Day 2: Sifnos
Cruise to the quaint island of Sifnos and anchor off Kamares. Step on land in the morning to walk around the small village, brows ceramics and artisan shops in Apollina before heading to Platis Gialos for beach time. Indulge in a slow roasted lamb with oregano and thyme with a fresh glass of Assyrtiko, a dry and mineral white wine made in Santorini, perfect to pair with the traditional dish. Enjoy a nap in the sun with a swim in secluded bays before going to Sifnos Citrus Paloma to watch the sunset over the water, followed by dinner at Omega3 or Yahoos, where local chickpea stew (revithada) is a beloved island speciality.
Day 3: Milos
In the morning sail to the lovely Milos, stopping at Kleftiko’s dramatic sea caves for snorkeling and dinghy exploration in crystal blue waters. Milos is a small yet authentic island overlooking the cyclades, although it is popular it somehow remains untouched and preserved from tourism, keeping all of its charm. Discover the unique seaside of Milos and its colorful beach cabanas, the white cliffs, and hidden bays as you cruise past them sitting at the front of your crewed catamaran. After your water activities, have lunch onboard just off Gerakas with a fresh tsatsiki, some fried calamari, and finish with a board of cut watermelon. Let the crew take you to land so you can explore the fisherman's village, small shops and a delicious gelato in Adamas, then sip on a tasteful Aperol Spritz at sunset with dinner onboard, or ashore at Makris, known for its tender lamb kleftiko slow-cooked in parchment.
Day 4: Poliegos and Kimolos
Take one last look at Milos as you cruise to the uninhabited island of Poliegos for paddleboarding and snorkeling in its pristine coves. Enjoy the peaceful atmosphere the wild coasts offer with some water toys available aboard your crewed catamaran. Later on, continue to nearby Kimolos. Indulge in a delicious meal in a taverna in town before wandering the small white and blue village, and finish your day of relaxation with a dinner onboard of fava purée, lamb meatballs in a tomato sauce flavoured with anise, oregnao and feta, paired with a Greek Martini.
Day 5: Serifos
Sail to the stunning Serifos, an island completely preserved from toursim and yet extremely welcoming. This island is stunning with its clifftop Chora (old town) made of white walls and ocean blue domes, walk along the narrow streets, up and down the hill to explore every nook and crany, and to enjoy the scenic view from atop the village. Find the hidden century old churches in the village and amble along the coast to enjoy a freshly squeezed orange juice facing the bay of Serifos. Make sure you stop at the village square and sit at one of the sunbathed tavernas for a quick break from your adventure. As evening falls, enjoy a Serifos Rosemary Spritz and dinner at Rizes or Metalleio, sampling fresh grilled calamari.
Day 6: Kea
After a delicious and fresh breakfast aboard, cruise to Kea. This small island is home to a rich history dating back to 3500 BC in the cycladic era. The best way to fully explore the island is to head to Stavvroudhaki, and start following the ancient paths throughout the island that will eventually lead you to two temples: The Doric temple of Athena and the Temple of Pythion Apollo. Kea's ancient village and capital, Loulida, is also well worth a casual walk through to discover some of the local traditional artistry. Kea is the perfect stop for a crewed catamaran itinerary as it is known for its Underwater History Marine Park, a unique part of the island that hide three shipwrecks, notable the HMHS Britannic, sank in 1916, and considered the sister ship of the RMS Titanic. So if you enjoy diving this is the time to experience somethein extraoridnary. Throughout your exploration of the island make sure to sit at a local taverna to enjoy some delicious fresh greek food or choose to have lunch onboard before heading to one of Kea's private little bays.
Day 7: Vouliagmeni, Athens
Spend the morning in Kea, enjoying the turquoise waters and natural sea breeze before starting your journey back towards Athens. Your crew will anchor in a lovely bay facing the the Four Seasons and therefore giving you access to its luxury beach club for lunch, or head to our favorite, Krabo. This last stop is perfect as its the ideal playground for you to use the watertoys one last time! Finally, toast the journey with a farewell Aegean 75 at sunset, followed by a celebration dinner aboard showcasing all you favorite local specialties.
Day 8: Disembark in Athens
Enjoy your last breakfast onboard before sailing to Athens for disembarkation and onward travel, departing with sun-warmed skin, shared memories, and a longing to return.
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