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Sailing Greece - Santorini to Santorini image
Find trips›Greece›Sailing Greece - Santorini to Santorini
◆Save 50% off, auto-applied, ends 2026-06-10
GOperated by G Adventures

Sailing Greece - Santorini to Santorini

From
CAD 2,959
Duration
10 days
Countries
Greece
Activity
moderate
Group size
Max 10

The adventure

A yacht adventure is the ideal way to experience what many consider the world’s most beautiful islands in Greece. Sail aboard our all-new, state-of-the-art 57 ft yachts, with time for hiking, snorkelling, and relaxing. Explore ancient archaeological sites and taverna-lined harbours, dine on fresh seafood and don’t forget to try the Ouzo! This 10-day round trip from Santorini will give you the chance to explore some of the treasures of the Greek Islands.

◆Arrival day. Join the group at 11am for a welcome meeting and safety briefing before beginning the journey through the Cyclades.
◆Spend time in the Greek Isles with experienced skippers and a flexible schedule. The coming days will be tailored to meet the desires of the group and weather conditions. Stops might include Ios, the Small Cyclades and Naxos.
◆Spend time in the Greek Isles with experienced skippers and a flexible schedule. The coming days will be tailored to meet the desires of the group and weather conditions. Stops might include Ios, the Small Cyclades and Naxos.
◆Spend time in the Greek Isles with experienced skippers and a flexible schedule. The coming days will be tailored to meet the desires of the group and weather conditions. Stops might include Ios, the Small Cyclades and Naxos.
◆Arrive to Mykonos and opt to visit the local windmills and enjoy a cocktail on a veranda overlooking Little Venice. The beaches and nightlife add excitement to this picturesque island.
◆Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset.
◆Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset.
◆Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset.
◆Spend the next few days enjoying more of the Cyclades. Depending on where the wind will take us, stroll through the markets of Syros, uncover the beauty of the Venetian ruins in Paros and walk and hike through the trails and paths of Sifnos. Wander the breathtaking cliffside city of Hora or enjoy cocktails at sunset.
◆Depart after breakfast. Depending on weather conditions and access, the drop-off location may vary. A shuttle transfer will take you to Santorini, where you can explore or relax before your onward journey.

At a glance

Duration
10 days
Route
Santorini → Santorini
Countries
Greece
Activity level
moderate
Style
Beach & Islands, Culture & History, Cycling, Sailing & Marine, Trekking & Hiking
Group size
Max 10
Ages
16+
Flights
Not included
Solo travellers
Welcome

Where you'll go

Sailing Greece - Santorini to Santorini image

Day by day

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

Greece

Showing Days 1-7

10-day itinerary

Day 1Arrival daySantorini
A breathtaking sunset view of a cruise ship near the island of Santorini, Greece.Santorini
Arrival day. Join the group at 11am for a welcome meeting and safety briefing before beginning the journey through the Cyclades.
Map showing Santorini
Day 2Spend time in the Greek Isles with experienced…The islands of the Cyclades offer a range of different experiences on each island. While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb. Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.
The islands of the Cyclades offer a range of different experiences on each island. While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb. Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.
Day 3Spend time in the Greek Isles with experienced…The islands of the Cyclades offer a range of different experiences on each island. While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb. Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.
The islands of the Cyclades offer a range of different experiences on each island. While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb. Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.
Day 4Spend time in the Greek Isles with experienced…The islands of the Cyclades offer a range of different experiences on each island. While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb. Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.
The islands of the Cyclades offer a range of different experiences on each island. While on Ios, relax on famous Magganari beach and don't forget to visit Homer's tomb. Head out on an optional all-day adventure with your fellow yachtmates and skipper as you discover the best Naxos has to offer— the Temple of Dimitra, a microbrewery, views of Mt Zeus and a meal at a local tavern.
Day 5Arrive to Mykonos and opt to visit…
Arrive to Mykonos and opt to visit the local windmills and enjoy a cocktail on a veranda overlooking Little Venice. The beaches and nightlife add excitement to this picturesque island.
Day 6Spend the next few days enjoying more…Find countless treasures and must-grab deals while strolling through the markets of Syros. Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop. No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.
Find countless treasures and must-grab deals while strolling through the markets of Syros. Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop. No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.
Day 7Spend the next few days enjoying more…Find countless treasures and must-grab deals while strolling through the markets of Syros. Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop. No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.
Find countless treasures and must-grab deals while strolling through the markets of Syros. Explore the Venetian ruins in Paros. Walk and hike through the trails and paths of Sifnos before stopping at a local ceramic workshop. No trip is complete without wandering around the breathtaking cliffside city of Hora or enjoying cocktails at sunset over the whitewashed buildings that scatter the landscape.
1 / 2

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

Last Minute 50% off GVSS260611 · ends 2026-06-10 · auto-applied
DatesPrice / personAvailability
10 Aug – 19 Aug 2026
CAD 3,079Available
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20 Aug – 29 Aug 2026
CAD 3,079Available
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30 Aug – 8 Sep 2026
CAD 3,079Available
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Operated by G Adventures

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From
CAD 2,959 CAD / person
Twin share · prices may vary by departure
Next departures
Aug 10, 2026CAD 3,079 · available
Aug 20, 2026CAD 3,079 · available
Aug 30, 2026CAD 3,079 · available
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