If we’re describing what a true perfect circle looks like, there’s no need to look much further than the Cyclades, or “Circular Islands.” Go where the weather (and your skipper) takes you aboard our all-new, state-of-the-art 57 ft yacht, whether that’s exploring ruins, stopping by a microbrewery for a taste, or relaxing on golden sands. See the famous windmills of Mykonos and sail through Santorini's caldera, all while enjoying the view from aboard our yacht along the way.
Day 1Arrival dayMykonosWe highly recommend booking pre-tour accommodation in order to have time to explore the island of Mykonos. You may also have time to explore Mykonos island on the last day of the trip.
Mykonos
We highly recommend booking pre-tour accommodation in order to have time to explore the island of Mykonos. You may also have time to explore Mykonos island on the last day of the trip.
Day 2Spend time in the Greek Isles…SantoriniExplore the Venetian ruins in Paros. Walk and hike through the main port and discover the Church of a Hundred Doors. Hike to the top of the stunning cliffs on Folegandros, overlooking the beautiful village and views over to Santorini and western cyclades
Santorini
Explore the Venetian ruins in Paros. Walk and hike through the main port and discover the Church of a Hundred Doors. Hike to the top of the stunning cliffs on Folegandros, overlooking the beautiful village and views over to Santorini and western cyclades
Day 3Spend time in the Greek Isles…SantoriniExplore the Venetian ruins in Paros. Walk and hike through the main port and discover the Church of a Hundred Doors. Hike to the top of the stunning cliffs on Folegandros, overlooking the beautiful village and views over to Santorini and western cyclades
Santorini
Explore the Venetian ruins in Paros. Walk and hike through the main port and discover the Church of a Hundred Doors. Hike to the top of the stunning cliffs on Folegandros, overlooking the beautiful village and views over to Santorini and western cyclades
Day 4Spend time in the Greek Isles…SantoriniExplore the Venetian ruins in Paros. Walk and hike through the main port and discover the Church of a Hundred Doors. Hike to the top of the stunning cliffs on Folegandros, overlooking the beautiful village and views over to Santorini and western cyclades
Santorini
Explore the Venetian ruins in Paros. Walk and hike through the main port and discover the Church of a Hundred Doors. Hike to the top of the stunning cliffs on Folegandros, overlooking the beautiful village and views over to Santorini and western cyclades
Day 5While on IosSantoriniWhile a visit to Santorini's main island is not a core part of the sailing itinerary, there may be an opportunity to take a short ferry across from nearby Ios for those especially interested. The skipper will lead a group discussion to assess interest and feasibility.
Santorini
While a visit to Santorini's main island is not a core part of the sailing itinerary, there may be an opportunity to take a short ferry across from nearby Ios for those especially interested. The skipper will lead a group discussion to assess interest and feasibility.
Day 6Spend the next few days enjoying more…The islands of the Cyclades offer a range of different experiences on each island. Settle in for a deeper dive into the magical culture of the Cyclades, with a highlight being a two-night stay on the vibrant island of Naxos. Rich in culture, history, and local flavour, Naxos offers something for every traveller, from the sweeping views of Mt Zeus and golden beaches, to the charming artisan shops and some of the best cuisine in the Aegean. Join the highlight and an unforgettable full-day tour led by a G Adventures approved local guide and ecologist, including a visit to the Temple of Dimitra, a local Microbrewery, Olive Oil press and secret island discoveries. This immersive experience, including transport, is around 70-80EUR, well worth it for the insights and access you'll gain. With time to also explore Syros or nearby hidden gems of the Small Cyclades, this stretch of the journey balances relaxed island living with rich, meaningful exploration. Find countless treasures and must-grab deals while strolling through the markets of Syros, and it's lovely, lively towns. Do the 3 church challenge!
The islands of the Cyclades offer a range of different experiences on each island. Settle in for a deeper dive into the magical culture of the Cyclades, with a highlight being a two-night stay on the vibrant island of Naxos. Rich in culture, history, and local flavour, Naxos offers something for every traveller, from the sweeping views of Mt Zeus and golden beaches, to the charming artisan shops and some of the best cuisine in the Aegean. Join the highlight and an unforgettable full-day tour led by a G Adventures approved local guide and ecologist, including a visit to the Temple of Dimitra, a local Microbrewery, Olive Oil press and secret island discoveries. This immersive experience, including transport, is around 70-80EUR, well worth it for the insights and access you'll gain. With time to also explore Syros or nearby hidden gems of the Small Cyclades, this stretch of the journey balances relaxed island living with rich, meaningful exploration. Find countless treasures and must-grab deals while strolling through the markets of Syros, and it's lovely, lively towns. Do the 3 church challenge!
Day 7Spend the next few days enjoying more…The islands of the Cyclades offer a range of different experiences on each island. Settle in for a deeper dive into the magical culture of the Cyclades, with a highlight being a two-night stay on the vibrant island of Naxos. Rich in culture, history, and local flavour, Naxos offers something for every traveller, from the sweeping views of Mt Zeus and golden beaches, to the charming artisan shops and some of the best cuisine in the Aegean. Join the highlight and an unforgettable full-day tour led by a G Adventures approved local guide and ecologist, including a visit to the Temple of Dimitra, a local Microbrewery, Olive Oil press and secret island discoveries. This immersive experience, including transport, is around 70-80EUR, well worth it for the insights and access you'll gain. With time to also explore Syros or nearby hidden gems of the Small Cyclades, this stretch of the journey balances relaxed island living with rich, meaningful exploration. Find countless treasures and must-grab deals while strolling through the markets of Syros, and it's lovely, lively towns. Do the 3 church challenge!
The islands of the Cyclades offer a range of different experiences on each island. Settle in for a deeper dive into the magical culture of the Cyclades, with a highlight being a two-night stay on the vibrant island of Naxos. Rich in culture, history, and local flavour, Naxos offers something for every traveller, from the sweeping views of Mt Zeus and golden beaches, to the charming artisan shops and some of the best cuisine in the Aegean. Join the highlight and an unforgettable full-day tour led by a G Adventures approved local guide and ecologist, including a visit to the Temple of Dimitra, a local Microbrewery, Olive Oil press and secret island discoveries. This immersive experience, including transport, is around 70-80EUR, well worth it for the insights and access you'll gain. With time to also explore Syros or nearby hidden gems of the Small Cyclades, this stretch of the journey balances relaxed island living with rich, meaningful exploration. Find countless treasures and must-grab deals while strolling through the markets of Syros, and it's lovely, lively towns. Do the 3 church challenge!
Day 8Spend the next few days enjoying more…The islands of the Cyclades offer a range of different experiences on each island. Settle in for a deeper dive into the magical culture of the Cyclades, with a highlight being a two-night stay on the vibrant island of Naxos. Rich in culture, history, and local flavour, Naxos offers something for every traveller, from the sweeping views of Mt Zeus and golden beaches, to the charming artisan shops and some of the best cuisine in the Aegean. Join the highlight and an unforgettable full-day tour led by a G Adventures approved local guide and ecologist, including a visit to the Temple of Dimitra, a local Microbrewery, Olive Oil press and secret island discoveries. This immersive experience, including transport, is around 70-80EUR, well worth it for the insights and access you'll gain. With time to also explore Syros or nearby hidden gems of the Small Cyclades, this stretch of the journey balances relaxed island living with rich, meaningful exploration. Find countless treasures and must-grab deals while strolling through the markets of Syros, and it's lovely, lively towns. Do the 3 church challenge!
The islands of the Cyclades offer a range of different experiences on each island. Settle in for a deeper dive into the magical culture of the Cyclades, with a highlight being a two-night stay on the vibrant island of Naxos. Rich in culture, history, and local flavour, Naxos offers something for every traveller, from the sweeping views of Mt Zeus and golden beaches, to the charming artisan shops and some of the best cuisine in the Aegean. Join the highlight and an unforgettable full-day tour led by a G Adventures approved local guide and ecologist, including a visit to the Temple of Dimitra, a local Microbrewery, Olive Oil press and secret island discoveries. This immersive experience, including transport, is around 70-80EUR, well worth it for the insights and access you'll gain. With time to also explore Syros or nearby hidden gems of the Small Cyclades, this stretch of the journey balances relaxed island living with rich, meaningful exploration. Find countless treasures and must-grab deals while strolling through the markets of Syros, and it's lovely, lively towns. Do the 3 church challenge!
Day 9Arrive to Mykonos and opt to visit…
Mykonos
Arrive to Mykonos and opt to visit the local windmills and enjoy a cocktail on a veranda overlooking Little Venice.
Day 10Depart after breakfastWe highly recommend booking post-tour accommodation on the island.
We highly recommend booking post-tour accommodation on the island.
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Upcoming departures
Last Minute 50% off GVMM260621 · ends 2026-06-20 · auto-applied
DatesPrice / personAvailability
21 Jun 2026 – 30 Jun 2026CAD 1,500AvailableBook my trip
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