Day 1: Mykonos
Kalimera! Welcome to Greece. Your adventure begins in cosmopolitan Mykonos – known for its beach bars, boutiques and nightlife. If you arrive early, maybe wander the laneways of Little Venice – a picturesque neighbourhood lined with old houses, shops and cafes. At 4 pm, you have a welcome meeting at a restaurant called De-Tox Café in Marina Tourlo, where you’ll meet your skipper and fellow travellers and find out what to expect over the next eight days on the water. Then, head to a supermarket to stock up on breakfast, lunch and snack supplies. Tonight, perhaps get to know everyone over dinner at a local taverna, then settle in for your first night aboard the yacht – your floating home for the week ahead!
Day 2: Mykonos - Rinia - Delos - Syros
Rise and shine for your first day on the water! First, stop at the uninhabited island of Rinia. There’s no noise here aside from a few grazing goats, so take the chance to relax on the crowd-free shores. Rinia was the necropolis during the Peloponnesian War in the fifth century BC, and you may stumble on remnants of temples and burial stones as you explore. Then, nip over to Delos – the legendary birthplace of Apollo (god of the sun) and Artemis (goddess of the moon). The entire island is a UNESCO World Heritage site with heaps of archaeological sites – including the Terrace of the Lions, Temple of Isis and Sanctuary of Apollo. Your final stop is Syros. Do a self-guided walk around the port town of Ermoupoli and the fortified village of Ano Syros – your skipper will suggest things to see and do. Then, regroup for a special dinner with a local family at their home in Finikas Bay.
Day 3: Syros - Kythnos (Loutra)
Set sail to Kythnos – a sleepy island dotted with bald hills, dry-stone walls and hundreds of white chapels. Dock in Loutra – a traditional fishing settlement named after the thermal springs (loutra means ‘bath’ in Greek) that flow into the bay – and enjoy a soak. These mineral-rich waters have been used for their healing properties since ancient times. This afternoon, get your blood pumping on a hike to the Castle of Oria – the former medieval capital of Kythnos. You'll wind past traditional stone farmhouses and rocky outcrops before arriving at the castle which sits on a 250 m-tall cliff. Soak in the views of the eastern Cyclades and learn about the castle’s history – it was part of a fortified town that housed hundreds of people, including the powerful Gozzadini family from the 14th to the 17th century. Return to Loutra, then perhaps refuel with some local specialities – like tangy kopanisti cheese or strapatsada (a local take on scrambled eggs).
Day 4: Kythnos (Loutra) - Serifos
Cruise to Serifos this morning, stopping off to swim or snorkel in the clear waters of Agios Stefanos Bay. In the afternoon, you’ll do a moderate hike from Livadi to the town of Chora which sits on a 230-m-tall hill. Follow a stony path past terraced fields, whitewashed houses and olive groves before arriving at Chora where you'll be rewarded with sweeping views across the Aegean Sea. Before returning to Livadi, take some time to wander the medieval alleyways – and maybe treat yourself to a local pastry. The rest of the evening is free to enjoy at your own pace. How about kicking back with a cocktail or feasting on meze along the seafront?
Day 5: Serifos - Kythnos (Apokrousi Bay)
Cruise back to Kythnos this morning – but this time, drop anchor in Apokrousi Bay, a peaceful cove hugged by low hills. The water here is ideal for swimming, or you could take in the scenery from a stand-up paddleboard. If you're feeling active in the afternoon, join an optional hike from Apokrousi Bay to Vryokastro – the ruins of the island’s ancient capital. Explore remnants of cisterns, homes and temples dedicated to Apollo, Artemis, Aphrodite and Demeter. Then, return to Apokrousi in time to eat dinner on deck while the sun dips below the horizon.
Day 6: Kythnos (Apokrousi Bay) - Kea
Next stop: Kea. This charming island is known for its vineyards, olive groves and laidback villages. On the way, make a stop at Karthaia Bay on the southeastern side of the island to swim or snorkel in the turquoise waters, then go ashore to discover the impressive ruins of the ancient city of Karthaia. Walk through weathered temple columns and the bones of a 6th-century BC theatre set against the sea. Eat lunch on deck, then dock in Kea village where you’ll spend the night. You could dig into local produce at a seaside taverna for dinner this evening.
Day 7: Kea - Lavrio, Athens
Take a private transfer to the village of Ioulida this morning for a scenic hike to Otzias Beach – a shaded downhill trail perfect for your final hike! Cool down with a dip at Otzias Bay, then refuel with an optional lunch at a nearby fishing village – it's a great chance to dig into some fresh seafood. Then, it’s time to jump back on the yacht to sail to Lavrio near Athens. As this is your last night as a group, you might like to go for a farewell dinner together and raise a toast to an unforgettable week in the Cyclades. Yiamas!
Day 8: Lavrio, Athens
Your sailing adventure comes to an end this morning. If you’d like to spend more time in Athens, just speak to your booking agent ahead of time.
