Sail & Hike Greece: Mykonos to Athens

Say ahoy! to ancient ruins, fishing villages and bright blue swimming coves

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.

Start: Mykonos, Greece

End: Lavrio, Greece


Duration
8 days
Group size
1 to 11
Minimum age
15 years old
Style
Original
Theme

Our themes categorise trips based on a common interest or activity, while showcasing the highlights of a destination.

Sailing, Walking & trekking
Physical rating

Indicates how physically exerting a trip is, and how fit you will need to be to enjoy it. More info on physical ratings


From
CAD $2,487
CAD $2,022
Trip code: ZSRY

Where you’ll stay

Ocean Star 56
11 passengers

The Ocean Star 56  is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, the Ocean Star 56 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins, 2 twin cabins and 1 triple cabin,  the Ocean Star 56 is the perfect yacht for novices to learn the ‘ropes’.

Explore yacht

Why you'll love this trip

  • Experience life at sea with a local skipper and a crew of adventure-keen travellers aboard a private yacht. Wake up to ocean views, soak up the sun on deck and snorkel in peaceful bays far from the crowds.
  • Join a local family for a home-cooked dinner at their home in Syros to get an authentic taste of Greek hospitality.
  • Step back in time on Delos – one of Greece’s most significant archaeological sites. Wander the Avenue of Lions, visit the House of Cleopatra and imagine ancient crowds at a 5000-seat theatre.
  • Hike trails that take you into the heart of the Cyclades. Walk past grazing goats and whitewashed chapels, say kalimera (hello) to farmers and climb to the medieval Castle of Oria for amazing Aegean views.
  • Watch the Cyclades’ famous tangerine sunsets from the deck of your yacht, cold drink in hand, while the waves lap against the hull.

Itinerary

Map of Sail & Hike Greece: Mykonos To Athens including Greece

We’re in the process of figuring out how much CO2-e this trip generates. In the meantime, learn more about our climate commitment.

Inclusions and activities

Transport

Boat

Accommodation

Overnight boat (7 nights)

Included activities

  • Delos - Archaeological Site
  • Syros – Traditional Greek dinner in family home
  • Kythnos – Castle of Oria guided walk
  • Serifos – Chora Village hilltop guided walk
  • Kea - Ioulida Village to Otzias Beach guided walk

Optional activities

  • Kythnos - Vryokastro self- guided walk - Free

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Before you book you should know

Dates and prices

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Prices can change anytime
Our prices drop or increase based on demand, seasonality, availability and market conditions.
Learn more about pricing
Prices can change anytime
Our prices drop or increase based on demand, seasonality, availability and market conditions.
Learn more about pricing
Loading trip dates and availabilities...

Reviews

5 . 6 reviews
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Jan
Traveled May 2026
Leonie
Traveled May 2026
Gabriella
Traveled April 2026
Karin
Traveled April 2026
Michaela
Traveled April 2026