Sailing Greece - Santorini to Santorini - 10 Days
Who is this trip for
Genders
- Female50%
- Male50%
Average age
Start / End
- Firá
- Firá
Physical rating
Group size
1 - 10Meals included
0Highlights
- Embark on an unforgettable 10-day yacht adventure from the iconic island of Santorini, sailing aboard a state-of-the-art 57 ft vessel through the dazzling azure waters of the Greek Cyclades.
- Discover the diverse beauty of the Cycladic islands, including tranquil Ios with its famous Magganari beach and ancient sites like Homer's tomb, alongside Naxos, offering optional excursions to the historic Temple of Dimitra, a local microbrewery, and stunning views of Mount Zeus.
- Immerse yourself in the cosmopolitan charm of Mykonos, where you can admire picturesque windmills, enjoy a refreshing cocktail with panoramic views over Little Venice, and experience the island's vibrant beaches and thrilling nightlife.
- Explore a tapestry of other Cycladic gems, from strolling through the bustling markets of Syros to wandering amidst the atmospheric Venetian ruins on Paros, each island offering a unique glimpse into Greek culture and history.
- Engage with local traditions and breathtaking landscapes on Sifnos, where you can hike scenic trails and visit artisan ceramic workshops, before being captivated by Folegandros' dramatic cliffside city of Hora, the perfect spot for sunset cocktails.
- Indulge in the authentic flavours of Greece, dining on fresh seafood at charming local tavernas and sampling traditional Ouzo, with ample opportunities for enriching activities like snorkelling in crystal-clear bays and participating in a meaningful Naxos Wildlife and Conservation Awareness Experience.
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Summary
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.
Itinerary
Day 1
Santorini
Arrival day. Join the group at 11am for a welcome meeting and safety briefing before beginning the journey through the Cyclades. We highly recommend booking pre-tour accommodation in order to have time to explore the island of Santorini.
Day 2
Cyclades - Ios/Small Cyclades/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. 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 3
Cyclades - Ios/Small Cyclades/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. 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 4
Cyclades - Ios/Small Cyclades/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. 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 5
Mykonos
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 6
Cyclades - Syros/Paros/Sifnos/Folegandros
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. 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 7
Cyclades - Syros/Paros/Sifnos/Folegandros
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. 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 8
Cyclades - Syros/Paros/Sifnos/Folegandros
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. 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 9
Cyclades - Syros/Paros/Sifnos/Folegandros
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. 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 10
Santorini
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. We highly recommend booking post-tour accommodation on the island.
What's Included
Accommodation
5 twin/double bed cabins with en suite or shared facilities.
Meals
Breakfasts: 0, Lunches: 0, Dinners: 0
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
GuidedThis adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.
Wifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
Apr 2026
from £1,413May 2026
from £1,413Jun 2026
from £1,564Jul 2026
from £1,564Aug 2026
from £1,840Sep 2026
from £1,781Apr 2027
from £1,662May 2027
from £1,662Jun 2027
from £1,662Jul 2027
from £1,662Aug 2027
from £1,662Sep 2027
from £1,662
- Save 16%Sat 2 May 2026 > Mon 11 May 2026Guaranteed Departure4 spaces of 10 left£1,679Best offer£1,413
- Save 16%Tue 12 May 2026 > Thu 21 May 2026Guaranteed Departure🔥2 spaces of 10 left£1,679Best offer£1,413
- Save 1%Fri 22 May 2026 > Sun 31 May 2026Guaranteed Departure🔥2 spaces of 10 left£1,679£1,662Book for£250 today, pay the rest later
Customer reviews & ratings
Amazing! For me this was a magical experience! It was an amazing unique adventure!
Arlene Oct, 2024 VerifiedIt was a magical experience. An opportunity to do things and see things that are amazing. Wonderful experience. A chance to see and do things you never expected
Frances Oct, 2024 Verified
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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