Sail in Greece
Explore Greek islands on a luxurious catamaran or an adventurous sailboat.
The Magic of Sailing in Greece: A Journey of Sun, Sea, and Flavor
Experience a vacation Greece in a completely different way-choosing to sail with HoliSail. We offer a variety of sailing adventures for couples, families, and small groups. Indulge in a holiday on the water while savoring Greece’s exquisite cuisine, doing yoga and meditating, looking for long lost treasures, and more. Wake up each morning to stunning views of the Greek coastline, explore charming islands, or enjoy the serenity of the Aegean and Ionian seas. Set sail and experience the world in a whole new way.
Book a Cruise
CRUISE DESTINATIONS

Ionian Islands

Sporades

Dodecanes
We've got you covered
Explore Top Destinations
We know all of the hidden gems on the Ionian and Aegean sea. Just sit back, relax, and let our experienced skipper show you all of Greece’s secrets.
Itinerary to and from the Ship
Having trouble deciding what’s the best way to get to your ship? Let us know your departure place and we will find options for you.
Connections with Other Travelers
If you don’t have a large party and still want to experience sailing in Greece, we can provide contacts with other interested parties to minimize costs.
Travel Insurance
Travel with peace of mind, knowing you're prepared for the unexpected. Having travel insurance is always a wise choice for a worry-free journey.
Support When You Need It
While cruising with us, we are always available to you for any further necessities. Feel free to contact us with any questions you may have.
Scenic Sailing Retreats
HoliBreeze Newsletter
HoliBreeze brings you exclusive sailing adventures, hidden gems, and special offers—let the HoliBreeze guide your next journey!

Personalize Your Cruise
Want to make your sailing adventure truly your own? With our personalized options, simply share your vision, and we’ll do our best to make it happen, based on what we can offer.
Why Choose HoliSail?
Born from our love for adventure and the open sea, HoliSail is here to revolutionize nautical tourism. Our goal is simple: to offer the best sailing experience, with no hidden fees.
Innovation drives us. With seamless online bookings, all-inclusive packages, and custom sailing routes, we ensure every moment on the water is unforgettable.

All in One
While others take care of you once you board the ship, our support starts even before you set sail with HoliSail. Feel free to ask us to tell you the best way to get to one of our base marinas, book insurance, and more.
Connections with Other Travelers
Why not get in touch with other sailing enthusiasts even before your adventure starts? We’ll get you in touch with other participants to plan your trip, minimize the costs, and more.
No Variable Costs
Other agencies charge you for sailing with them and variable costs. These include fuel, docking and marina fees, cleaning fee, etc. With HoliSail, everything is already included in the price.*
*The price does not include personal costs, and, depending on the package of your choice, provisions.