Aerial view of the Ocean Star 56 yacht in the Ionian Sea in Greece
Operated by Intrepid Travel

Sail & Hike Greece: Mykonos to Athens

From
CAD 2,487
Duration
8 days
Countries
Greece
Activity
moderate
Group size
Max 11
Rating
5.0 · 6 reviewsvia Intrepid Travel

The adventure

Spend eight salty-skinned days sailing, hiking and swimming your way through some of the lesser-known Cyclades. Starting in lively Mykonos, you’ll cruise the sparkling Aegean Sea aboard a private yacht and drop anchor at islands that seem unchanged by time. Hike to a clifftop castle in Kythnos, share a homemade dinner with a local family in Syros and unearth the stories of legendary gods and ancient civilisations on the UNESCO-listed Delos. With a passionate skipper at the helm, daily swims and plenty of free time to enjoy the Cyclades’ laidback pace, this is Greek island hopping done right.

At a glance

Duration
8 days
Route
Mykonos → Lavrio
Countries
Greece
Activity level
moderate
Style
Beach & Islands, Culture & History, Cycling, Sailing & Marine, Trekking & Hiking
Group size
Max 11
Ages
15+
Flights
Not included
Solo travellers
Welcome

Day by day

Charming coastal town with hills and sea under a cloudy sky.
Your journey through

Greece

Day 1MykonosKalimera! 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!
Charming white buildings and vibrant boats in Mykonos harbor on a sunny summer day.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!
Map showing Mykonos
Day 2Mykonos - Rinia - Delos - SyrosRise 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.
Explore the picturesque Agios Nikolaos Church by the sea on a sunny day in Mykonos, Greece.Mykonos
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.
Map showing Mykonos
Day 3Syros - 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).
Beautiful pastel-colored buildings on Syros island coastline at dusk.Syros
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).
Map showing Syros
Day 4Kythnos (Loutra) - SerifosCruise 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?
A stunning aerial view of Kythnos, Greece, showcasing a sandy beach, turquoise waters, and anchored boats.Kythnos (Loutra)
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?
Map showing Kythnos (Loutra)
Day 5Serifos - 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 a refreshing dip, or you could simply take in the scenery from the deck with a good book or drink in hand. 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.
Discover the charming white buildings of Serifos, Greece, by the sea.Serifos
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 a refreshing dip, or you could simply take in the scenery from the deck with a good book or drink in hand. 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.
Map showing Serifos
Day 6Kythnos (Apokrousi Bay) - KeaNext 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.
A stunning aerial view of Kythnos, Greece, showcasing a sandy beach, turquoise waters, and anchored boats.Kythnos (Apokrousi Bay)
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.
Map showing Kythnos (Apokrousi Bay)
Day 7Kea - Lavrio, AthensTake 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!
Vibrant Greek architecture along the coast in Mandrakia, Milos, Greece.Kea
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!
Map showing Kea
Day 8Lavrio, AthensYour 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.
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.

Traveller reviews

5.0

Based on 6 reviews · via Intrepid Travel

Discover Greece

A glimpse of the destination you'll explore.

Breathtaking aerial view of Kerkyra's lush landscape with hills, valleys, and ancient structures under a clear sky.
Breathtaking coastal landscape of Agios Stefanos, Greece featuring rocky hills and a tranquil sea.
Breathtaking view of a Greek island coastline with clear blue waters and vibrant nature.
Scenic view of Athens cityscape from a hilltop with clear skies.
Picturesque coastal scene with clear skies, azure waters, and distant mountains.

Upcoming departures

DatesPrice / personAvailability
4 Oct 202611 Oct 2026CAD 2,487On requestBook my trip
4 Oct 202611 Oct 2026CAD 2,722On requestBook my trip
4 Oct 202611 Oct 2026CAD 2,722On requestBook my trip
18 Oct 202625 Oct 2026CAD 2,487Only a few spotsBook my trip
18 Oct 202625 Oct 2026CAD 2,722On requestBook my trip
18 Oct 202625 Oct 2026CAD 2,722On requestBook my trip
Operated by Intrepid Travel

A TripFinder-trusted operator. We compare the trip and handle your booking with a real advisor — you travel under the operator's terms.

Book my trip →

More Europe adventures

Zagreb to Santorini: 35 Unforgettable Days image
G Adventures
Save 20%

Zagreb to Santorini: 35 Unforgettable Days

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 35 days · Easy

fromCAD 7,679
Next: 21 Jun
Zagreb to Athens: Monasteries & The Mediterranean image
G Adventures
Save 20%

Zagreb to Athens: Monasteries & The Mediterranean

Bosnia and Herzegovina, Albania, Greece, Montenegro, Croatia · 29 days · Easy

fromCAD 5,839
Next: 21 Jun
Intrepid Travel Montenegro Kotor
Intrepid Travel
Deal

Vienna to Dubrovnik

Austria, Bosnia and Herzegovina, Croatia, Czechia, Hungary, Montenegro, Poland, Serbia, Slovakia · 29 days · Easy4.9(9)

fromCAD 6,923
Next: 20 Jun