RELAX & DISCOVER
Sail The Greek Islands with Heart!
Welcome aboard SailTheGreekIslands.com —Your Gateway to an Unforgettable Sailing Holiday through the Aegean and Ionian Seas.
Led by Captain Yiannis, a seasoned skipper with over 24 years of experience, we offer Tailor-Made Yacht Charters that blend adventure, comfort, and heartfelt hospitality. Your 2026 Greek Island Dream Starts Here Now!
TRAVEL CARE-FREE
A Journey Beyond the Horizon!
This isn’t just a sailing holiday — it’s a soulful escape into the heart of Greece.
Each voyage is a tapestry of turquoise waters, ancient legends, and spontaneous joy.
Whether you're anchoring beneath a starlit sky or sharing stories over fresh seafood in a hidden taverna.
You'll feel the rhythm of the islands and the warmth of true Greek hospitality.
UNPACK ONLY ONCE
Meet Your Guide & Captain!
Captain Yiannis is more than a Skipper — he’s a Storyteller, a Guide, and a Passionate Ambassador of the Sea.
With decades of experience and a poetic spirit, he brings a rare blend of professionalism and heart to every charter: Guests often say that Sailing with Yiannis feels like reconnecting with something timeless — a sense of freedom, wonder, and belonging.
Did you Know?
THE WHOLE TRIP CAN COST LESS THAN JUST BOOKING A HOTEL WOULD.
When you organize your family and friends to share in the trip with you,
a yacht charter will cost less than booking a hotel would,
and your transportation from port to port is included.
Our yachts can accommodate from two up to twelve persons.
TWENTY-FOUR YEARS OF
5-Star Reviews!
From the moment of initial contact with Captain Yiannis, everything was seamless.
Our experience has been nothing short of exceptional.
From the moment of initial contact with Captain Yiannis, everything was seamless. This company and the entire team could not have been more helpful! We live in the USA and never had a problem with communication. The Catamaran we selected was the Lagoon 450F. It was beautiful, spacious, clean, and easy to live on for a week as we sailed to beautiful beaches.
The Ionian Islands we visited were breathtaking, especially Kefalonia – it was our favorite! Above all, the feeling of safety that Captain George ensured throughout our trip made our journey even more memorable. We can’t wait to experience it again.
So, if you’re looking for an unforgettable sailing experience around the Greek Islands with a professional company and a knowledgeable and friendly guide, look no further!
Caroline Groeneveld
July 7, 2023
The Great Greek Adventure
We have seen many islands thanks to Yannis, who has an unsurpassed knowledge of the, and we might add amazing docking skills! Matoula has been an amazing hostess, a wonderful cook and always gracious with a beautiful attitude. We will never forget our Great Adventure!
Danny and Karen
June 7th 2019
A safe pair of hands, experience and unlimited knowledge.
We’ve just spent a week sailing the Greek islands with Captain Yiannis. If your looking for a safe pair of hands, experience and unlimited knowledge of the Greek islands then Yiannis is the captain you need.
Jeff Brown
May 10th 2019
Great knowledge of the area and its history.
Excellent week of sailing in the Greek Islands with Yiannis. He has great knowledge of the area and its history. He showed us unique beaches and key sites on the islands. A memorable week of adventure, drama, and weather. A great first visit to the country of Greece and its islands. Recommend Yiannis as a skipper and guide for your trip.
David and Suzanne Kelly
September 25, 2021
The kids enjoyed jumping off the boat and even steering.
We made it back safely and happily to Paros today. Yianni showed us secluded beaches, surprising chortas and agreed to take us to santorini even though he hates sailing there! The kids enjoyed jumping off the boat and even steering it on occasion. It’s a beautiful part of the world and we’d definitely recommend exploring it.
Christine
August 22, 2021
Yannis is a superb captain
First and foremost, Yannis is a superb captain. He is a true professional and puts the comfort and safety of the guests first. We had a superb week and thanks to the knowledge of Yannis we visited hidden beaches and places that were sublime. Yannis is passionate about sailing, and we all improved our sailing skills and learned about sailing this magical part of the world.
We cannot wait to return and know that Captain Yannis is our go-to Greek master of the seas.”
Kim Cornwall and friends
October 14, 2021
The best tavernas for dining and the most interesting places to visit.
My friends and I had a terrific sailing trip with Cpt. Yiannis. We sailed islands from Athens to Milos for a week. [...] Captain Yiannis was not only an outstanding skipper, but he also is a very knowledgeable tour guide. [...] Also, he had tremendous knowledge of any island we stopped on the way and recommended the best tavernas for dining and the most interesting places to visit.
The captain was very professional and sailed extremely safe and responsible. Great guy, a great captain, thank you, Captain Yiannis!
Remis – Boston, USA
June 26, 2021
Yannis gave us the ideal family yacht
We had a wonderful week of sailing in the Saronic Gulf end of August. Yannis gave us the ideal family yacht for this bareboat charter trip . Together with the charter company we felt us in very good hands, for all questions we had. Except in this year 2020, with these special conditions!
Thanks Yiannis.
Marc Schwarz
September 6, 2020
WHY SAIL WITH US?
Expert Navigation & Local Insight! - Captain Yiannis knows the islands like the lines of a well-worn chart — guiding you to secret beaches, authentic tavernas, and breathtaking sunsets.
Tailored Itineraries! Every journey is personalized. Whether you seek serenity, celebration, or cultural immersion, we design your route to reflect your spirit.
Warm Hospitality & Professionalism: From the first email to the final farewell, we treat you like family — with respect, care, and joy.
Safety & Comfort at Sea! Our yachts are meticulously maintained, and our crew is trained to ensure smooth sailing and peace of mind.
Your Journey Begins Here!
Choose your dream route:
Cyclades Magic — Santorini, Paros, Naxos & more
Ionian Serenity — Lefkas, Ithaca, Kefalonia
Custom Voyages — Tell us your vision, and we’ll chart the course
Reach out for availability, pricing, and itinerary ideas — we’re here to help you plan every detail.
We Expertly Organize Charters of: Bareboat, Skippered and Fully Crewed Luxury Yachts and Catamarans.
- Your Number One Choice for VALUE Yacht Charters around the Greek Islands!
- PERSONALIZED - TOP-QUALITY - SERVICE
- With Our Local Knowledge... YOU WILL GET... The Best Yacht for Your Requirements and Budget.
- Wide Choice of Top-Quality Yachts on 15 Bases for the Greek Islands.
- Over 2,000 Top of the Line Monohulls and Catamarans.
- Damage Waiver Insurance with Low Security Deposits.
- Easy Booking and Payments.
- Well-Equipped And Maintained Fleets.
- Fully Trained and Experienced Teams.
Ready to Sail?
Let’s make your sailing dream a reality.
- Plan Your Voyage - Get a Quote - Secure Your Yacht Charter -
The Best Yachts and Offers Are Reserved Early—Secure Your 2026 Charter NOW and Take Advantage of Premium Value and Early Booking Benefits!
We'll get back to you with offers to choose from within a few hours.
This Summer Discover
- The Crystal Clear Waters
- The Herb and Salt-Scented Winds
- The Secluded Beaches & Swimming Spots
- The Temperate Climate
- The Bright Sun
- The Fabled Mountains
- The Cycladian White Architecture
- The Picturesque Ports
- The Ancient Cultural Heritage
- The Welcoming People