Greece
Crewed sailing expeditions
Sail beyond the ordinary
Amazing adventures await you! Come join us as we explore the world on land and water — aboard a comfortable catamaran in the planet's most beautiful waters.
Why Sail & Road
Real sailing, zero hassle
We charter beautiful yachts in unique corners of the world, handle every detail, and take you somewhere you'll never forget. No experience required — just show up.
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Captain-led
Sail with licensed international captains who know these waters intimately.
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No experience needed
Learn the ropes if you want to, or simply relax and enjoy the ride.
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Small groups
Intimate trips with hidden coves, secluded swims, and room to breathe.
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Curated routes
Hand-planned itineraries balancing adventure, culture, and pure relaxation.
Upcoming voyages
Choose your adventure
Greece
French Polynesia
The experience
Wake up somewhere new
Crystal-clear water off the stern, breakfast on deck, and a fresh horizon every morning. Our days mix easy sailing, snorkeling in secluded bays, island wandering, and slow sunset evenings at anchor.
- Daily swim stops
- Snorkel & paddleboard
- Island harbors
- Sunset anchorages
- Fresh local food
Your crew
Meet the captains
Iryna Kochubiei — founder and international sailboat captain. Iryna has logged thousands of miles across the world's oceans and leads every Sail & Road expedition.
Matt Barker — co-skipper and captain of his own 45-foot sailboat, Matt joins many of the adventures and keeps every voyage running smoothly.
More about us
Ready to cast off?
Spots on each voyage are limited. Reserve yours and start counting down.