Greece Sailing Adventure: Cyclades Islands
From $3075 per person twin share | 8 Days
Sunsets, seafood and seaside views on this sailing trip in the Mediterranean
Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places.
Travel period: May 2026 - Oct 2027
Why you'll love this trip
- Sail the Aegean Sea on your small group yacht and island-hop through the Cyclades, taking regular stops to swim off the side of your boat and letting the pitch and roll of the ocean help you sleep at night.
- Walk along the volcanic rim of Santorini, past white villages that cling to cliffs and watch as day turns to night during sunset at the caldera – this is a memory you’ll bring home!
- Feast on fresh seafood at a sleepy waterfront taverna in the Small Cyclades islands – far away from tourist crowds and deep in the local way of life.
- Step back in time among the Venetian architecture of Naxos and consider learning about rural life with a daytrip to a country village.
- Visit Mykonos for the quintessential Greek Islands experience. Embrace your hedonistic side with the boutique culture and nightlife or relax on one of the many beaches dotted along the coast.
Start: Santorini, Greece
End: Santorini, Greece
Destinations: Greece
Group size: 1 to 11
Ages: 15 years old
Theme: Sailing
Style: Original
Physical rating: 3/5
Greece Sailing Adventure: Cyclades Islands
Day 1 • Santorini – Ios
Day 2 • Amorgos
Day 3 • Small Cyclades
Day 4 • Naxos
Day 5-6 • Syros
Day 7 • Mykonos
Day 8 • Sifnos
Day 9 • Folegandros
Day 10 • Santorini






































