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• The Boats & Your Skipper • Exploring the Cyclades • Dining & Meal Options
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Whether you are a seasoned explorer or a non-sailor seeking your first true experience at sea, our private boat tours offer the rare freedom to explore the Cyclades at your own pace. Your journey is guided by our permanent skipper who handles every technical detail, leaving you free to immerse yourself in the scenery. While most guests find their perfect rhythm in a 1-week sailing holiday, we specialize in bespoke 9 or 10-day adventures for those who wish to dive deeper into the hidden corners of the Aegean. It is the ultimate ‘unpack once’ sailing vacation in the Cyclades - a premium, private experience where the only schedule is the one we create together. The Personal Touch: 14 Years of Owner-Operated Excellence We are a small, family-owned sailing company with just two boats—and that is our greatest strength. From your first email to the moment you step on board, you deal directly with us: the owners. On board Freedom you sail with the owners themselves; on boat Albatross, with our trusted long-term captain. By removing intermediaries and sales agents, we ensure a seamless skippered sailing experience with no last-minute surprises. For over 14 years, our goal has remained simple: to turn your Greek Islands sailing holiday with skipper into an authentic, stress-free reality. Why Choose a Sailing Holiday with Skipper in Greece? Imagine a Greek islands sailing vacation where time slows down. Mornings begin with a swim in clear blue water, days unfold at your own pace, and every decision is guided by the sea, the wind, and your curiosity. A sailing holiday with skipper aboard Albatross or Freedom adapts effortlessly to the way you like to travel — whether that means relaxed days at anchor or island-hopping filled with discovery. A private boat tour in the Cyclades offers a completely different experience from the classic “ferry + hotel” approach. You unpack once, yet visit a new Greek island almost every day. Weather permitting, if a place captures your heart, you stay longer. This level of freedom and flexibility is something land-based travel can’t offer. Instead of fixed routes and tight schedules, you enjoy a private skippered sailing experience shaped around your interests and the conditions of the Aegean. Skippered sailing in Greece allows you to slow down and truly connect with the places you visit — away from busy ports and crowded beaches, discovering the islands as they are meant to be seen: calm, beautiful, and unhurried. |
Greece is one of the world’s most inspiring sailing destinations — not just for its turquoise waters and dramatic coastlines, but for the feeling of freedom it offers. Waking up to a new horizon, swimming straight from the boat, enjoying long dinners by the sea, and ending the day beneath a sky full of stars creates moments that stay with you long after the trip ends.
We don’t simply sail from island to island. Each day of your sailing with skipper in the Greek islands is planned together, allowing you to discover quiet bays, authentic villages, and the islands that best match your mood. With no strangers onboard and no rush to follow an itinerary, your Cyclades sailing holiday unfolds naturally, offering a more genuine way to experience the archipelago.
If this way of traveling speaks to you, we’d be happy to help you bring it to life. Get in touch, and let’s start shaping a sailing experience with skipper that feels effortless, authentic, and entirely yours.
What you will experience |
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David M, that sailed with us in October was writing: "If you only visit Greece once, sail. Sail into the harbors of the old villages and truly experience their breathtaking beauty. Imagine what it was like hundreds or thousands of years ago ... So much history and beauty awaits!" If you are looking for a hassle-free, relaxing, yet exciting adventure, this is exactly what you will experience: ⚓ Local Knowledge, Zero Stress: At every stop on your private boat tour starting from Paros, we provide insider tips on the best sights, transport, and restaurants. We provide the maps and the secrets; you just provide the curiosity. No guidebooks required. ⚓ Something for Everyone: From historical sites and nature hikes to snorkeling and nightlife, we tailor our private sailing tours with skipper so that every member of your group—from teenagers to grandparents—finds their own version of paradise in the Cyclades. ⚓ The Ultimate Efficiency: Unlike the classic "ferry and hotel" shuffle where you might spend half your time in transit, our boutique sailing holidays with skipper allow you to unpack your bag once. You’ll visit 5–6 different Greek islands in a single week, enjoying a new horizon every day without ever lifting a piece of luggage. ⚓ Life at Sea: Experience the unique rhythm of boat life—balancing hours of sailing with active exploration. Relax on deck as we glide between islands, then gear up to explore hidden coves and picturesque villages, finishing the day with an incredible dinner on shore. ⚓ The Perfect Mix: We offer the best of both worlds—the chance to discover off-the-beaten-path hamlets untouched by tourism, alongside the vibrant energy of Greece’s most cosmopolitan destinations. ⚓ Authentic Flavors: Sample world-class Greek cuisine at waterfront taverns, where the ingredients are fresh and the view is unmatched. ⚓ A Personalized Adventure: This isn't a "one size fits all" cruise. This is a bespoke sailing experience for your family and friends—a dream holiday designed to create memories for a lifetime. |
This is more than just a boat rental; it’s a glimpse into the skippered sailing experience we’ve spent 14 years perfecting to ensure your time on the water is as comfortable as it is unforgettable.
We are a boutique yacht charter company devoted to creating deeply personal sailing experiences. We started this journey 14 years ago with a simple mission: to offer the kind of voyage we would want ourselves—relaxed, welcoming, and thoughtfully tailored to every guest. Because our boats are not just our business but our passion, every skippered sailing holiday we host is a reflection of our reputation.
Meet Edouard: Captain of AlbatrossA passionate sailor who began his career as a sailing instructor in Northern France, Edouard spent years navigating the Mediterranean—from Spain to Italy—before the magic of Greece captured his heart.  Today, he brings that technical "French school" precision and a deep love for the Cyclades to every trip. Having sailed with his father since childhood, the sea is in his blood. For Edouard, every day on the water is an opportunity to share the joy of navigation and the breathtaking landscapes of the Aegean, ensuring a safe, serene, and soulful private boat tour with skipper. Every outing at sea is an opportunity for Edouard to pass on this passion and create unforgettable memories! |
Meet Adriana & Radu: Owners & Your Local ExpertsAs boat owners and lifelong adventurers, we have spent 14 years exploring the Greek islands we now proudly call home. Having sailed thousands of miles across the Aegean, we’ve mastered the rhythms of the winds and the hidden gems of the archipelago. Our approach is simple: we create private sailing experiences that feel effortless and authentic.  Adriana – Planning & Guest Experience: Adriana is the architect of your journey. From your first inquiry to the fine details of life on board, she ensures every aspect of your trip is thoughtfully planned. Her focus is on clear, direct communication and a detail-oriented approach to avoid any on-board surprise. Radu – Skipper & Navigator: Radu is a highly experienced skipper with an intimate, "insider" knowledge of the Greek seas. While safety is his top priority, his passion is finding the magic in every mile. Radu’s expertise ensures you experience the absolute best of the Greek islands, from secret coves to the most authentic local spots. |
We have carefully chosen and maintained our two yachts to ensure they offer the perfect balance of sailing performance and onboard comfort. Both are fully equipped to be your private home on the water in the Cyclades.
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Albatross: The Authentic Aegean Specialist : Albatross is our sturdy and reliable "expert" yacht, perfect for travelers seeking a genuine sailing adventure. It is a high-performance boat built in Greece specifically to handle the local conditions with grace.
Freedom: The Boutique Space & Design : Freedom is a 52-foot sailing yacht designed with a focus on classic lines and a more spacious interior layout. Unlike many modern yachts designed to fit as many cabins as possible, Freedom prioritizes a more open and comfortable environment.
For a detailed list of the amenities please check your yacht page. |
When planning your sailing holidays with skipper in the Greek islands, it’s important to understand how our pricing works. Unlike a cabin charter, our rates are for the exclusive use of the entire yacht. This ensures the boat is yours alone - a private and uncrowded way to explore the Cyclades.
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Use the buttons below to select your trip duration and view the charter rates for your selected period :
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ALBATROSS sailboat
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Included in the charter rate (a) Your sailing yacht - accommodation on board Snorkeling equipment (mask, snorkel and short fins) Floats for non swimmers (6 noodles) All amenities as described at your yacht(hot water shower, fridge, etc) Linens & Towels (1 set / week) Flexibility: customized itinerary, flexible start date (other than the tipical Saturday) and duration. charter rate VAT Use of 1 stand up paddle board (SUP) -150 €/week FREE |
Skipper and boat expensesb) "All costs included" combo - 350 euro / day / boat. Includes: b1) Essentials pack : . Fuel for any of the routes listed, end cleaning, cooking gas, dish-washing liquid, two dishcloths, one sponge, trash bags, toilet paper. b2) Skipper pack : . VAT not included - recommended to be paid on board directly to the captain.The above packs will make it super easy to plan and budget for your sailing vacation. No hidden costs and a flat rate for the extra expenses associated with hiring a boat.
... read more |
We offer our guests the advantage to pay a flat rate prior to setting sail, and that’s it!
After surfing the web and looking at different options for your sailing vacation, you might have noticed most of the other charter companies structure their yacht rental similarly to renting a car. Their charter rate covers the price of hiring the yacht itself (just like the car rental price covers the car itself). Excluding all other aspects/costs involved for example; fuel, toll rates, parking fees, these are costs that you are expected to cover as you go.
With similar structure, when you are budgeting for your sailing holiday, with most charter companies you will have to add on top of the charter rate, the other expenses involved as they appear. The trouble with this approach, is that for a yacht the total/ final price including the extras is considerably higher than the base rate. This makes it difficult for the charterer to figure out the total price he will end up paying (an aspect that will naturally make him worried or anxious).
For example, the rate applied for skipper services is pretty much standard for all companies (200 - 260 euro/day),however, all the other costs will vary according to many factors. For example; fuel consumption depends how long the engine will be running - more specifically on the wind conditions and distances to your favorite destinations. You might be wondering - "But won't we be sailing most of the time-why are we discussing fuel?' Please read below the paragraph marked with **
So we are taking a different approach. In order to avoid all the variables and uncertainties, we are offering the : "All costs included" combo of 350 euro/day. Our bundle includes ALL expenses associated with chartering the sailing yacht (fuel, skipper, final cleaning, etc) that will guarantee you a worry free vacation. You won't have to keep an expense account. You simply pay a one-time flat rate (350 Euro/day/boat - divided between the members of your group) prior to setting sail, and that’s it! Much easier to plan and budget for! No hidden costs, no surprises at the end of the trip.
** How much will we be sailing / motoring?Well...it all depends on the wind conditions and the distance to the next destination. So let's take for example a sail from Mykonos to the port of Paroikia in Paros; a distance of 28 nautical miles (a good average).
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FREEDOM sailboat
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The total cost of your skippered boat charter is composed of two straightforward parts: the Charter Rate (found in the table below) and a flat-rate "All Costs Included" combo of €350 per day.
The €350/day Daily Pack covers:
To calculate the final cost per person for your private sailing tour with skipper, simply add these two amounts together and divide by the number of people in your party. This model offers an honest value for a meticulously maintained sailboat and a flexible itinerary, managed with the personal care that only a family-owned company can provide.
Many guests find their perfect rhythm in a one-week sailing holiday, but your sailing holiday in the Cyclades doesn’t have to follow a fixed template.
Custom Trip Lengths : While many guests choose a one-week sailing holiday, your trip doesn’t need to fit a standard format. If you’re considering a duration not listed in our rates (such as 9 or 10 days sailing tours), simply contact us and we’ll prepare a custom quote tailored to your schedule.
Why Starting & Ending in Paros Matters : Paros is centrally located in the Cyclades, giving your skipper the freedom to adapt the route daily based on wind and sea conditions. This means smoother sailing, shorter passages, and more time spent enjoying islands and anchorages — not battling the elements. For guests new to sailing, this flexibility is especially important. Rather than following a fixed plan, your skipper can always choose the most comfortable and enjoyable direction, ensuring a relaxed and stress-free experience.
About One-Way Trips (Important to Know)
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One-way sailing itineraries between islands can sometimes be arranged upon request, but they significantly limit flexibility and are not ideal for most guests.
With a fixed end destination, the skipper must sail toward that point regardless of changing winds, which can result in rougher crossings and longer days at sea. Additionally, a one-way fee (€800–€1,450) applies to cover the yacht’s return to base.
For comfort, safety, and enjoyment — particularly if this is your first sailing holiday — a round-trip from Paros is by far the best choice and the experience we confidently recommend.
Real Stories from the AegeanThere is a reason why so many of our guests return to the Cyclades. A skippered boat charter in Greece offers a rare blend of total freedom and complete relaxation. It’s about more than just the destinations; it’s about the feeling of the wind, the quiet of a morning swim, and the local secrets you only discover when you sail with an expert. Watch this short film to see the rhythm of life on board Freedom and Albatross—where the only schedule is the one you create with the sea. | |
Why a Private Skippered Sailing Holiday is the Ultimate Bucket List Experience |
Click on the photos below to read the full experiences of those who have sailed with us  Our best family vacation ever!
Our experience on the Freedom with Adriana and Radu was magical. We had an amazing family vacation. We spent quality time with each other while Adriana and Radu sailed the boat expertly. We cooked, laughed, stared in awe almost every moment with the beauty of the water and islands. We snorkeled, swam, sun bathed, hiked up to castles and old villages and began to experience a few Greek Islands. The schedule and timing was ours and what worked for us. We were never rushed or hurried along. We fell in love with life on the sea! Thank you, Freedom and Adriana and Radu for the best vacation ever! TripAdvisor member GlacierClimber Awesome way to experience the Cyclades!
We had a great experience with Radu and Adriana on the Freedom. Even during our research and planning months before the prompt and details of communication were spot on. They were willing to work with our plans and flexible where they could and plenty options if not. By the time we got to the boat, everything was clear and set so it was short briefing and we were off to enjoy the beautiful waters and the quiet little islands around. Radu and Adriana had great knowledge of the area and had good recommendations at start of every day and it was just down to us to enjoy everything the area had to offer. We didn't need much but the boat was clean and well equipped with toilet and showers for each cabin. For 6 of us it was plenty of room to eat and drink and hang out during travel between the islands. Very much recommended. TripAdvisor member jyoon59. Fabulous, relaxed, exhilarating, and a truly memorable experience
What a fantastic week we had, making up a group of 6 on board of the Albatross, brilliantly skippered by Edouard. Edouard is a hugely accomplished skipper, and we all felt immensely safe and secure on the seas under his calm and controlled lead. We found ourselves doing exhilarating sailing and mooring up in the most beautiful & tranquil bays. Edouard made the experience truly enjoyable – calm, polite, accommodating and great company, making the trip most relaxing, full of good laughs and above all unforgettable. We can highly recommend sailing with Edouard & Blue Water. Dorothee & Justin TripAdvisor member D G Outperformed our expectations, would recommend and would return !!
We spent 4 nights on board with Adriana and Radu on the Freedom. They provided meticulous detail and information about getting ready for the trip and what to expect in the lead up. Their suggestions for our sailing route exceeded all of our expectations and more !! We had an excellent holiday where we felt extremely relaxed with nothing to worry about. We were taken to locations we otherwise would not have known or picked, and there was always something unique and enjoyable at each spot. We just had to explore on land when we docked and get our bellies filled with the local specialties, they took care of everything else. The boat was fabulous, and we felt very at home. Their attention to detail was great ! Double thumbs up ! TripAdvisor member C N Great trip, excellent captain
Eduardo was an outstanding captain who made everything effortless. He focused on the bays and islands we wanted to see, and in high winds he smartly adjusted our route to the Small Cyclades for relaxed swimming and paddle boarding. Always social, fun to have around, and full of great restaurant tips, he made the whole trip truly enjoyable. Couldn’t ask for a better skipper – we’ll be requesting him again on our next voyage. TripAdvisor member Tom Dwyer Sailing trip with Adriana and Radu
We spontaneously booked the trip with Adriana and Radu on the Freedom. From the first contact with Adriana, we felt very well informed, looked after and safe. Adriana was particularly helpful in planning the trip with her experience and professional manner and made it easy for us to get an idea of the cruise, as it was our first time on a sailing boat. The tour itself was incredible and we experienced magical moments. Adriana and Radu, as experienced sailors, sailed us safely around the Cycladic islands and were also able to give us helpful recommendations for the time on land. We particularly liked Adriana and Radu's spontaneous, uncomplicated manner. The sailing boat was very well maintained, which underlined their passion for what they do. The two of them responded to our individual wishes and needs and gave us a unique experience. We would like to thank Adriana and Radu again and recommend them to everyone! TripAdvisor member Anja A A trip of a Lifetime
We were so fortunate to have sailed with Adrianna and Radu in our most recent adventure. They were truly amazing and the vessel was spectacular in every way. Thier teamwork and professionalism were foremost in all aspects of the trip. From managing the sails, shuttling us back and forth on the dingy, and suggesting the best places to eat and visit, they were absolutely the best. It was a trip of a lifetime; and at 71 years of age, that is a remarkable feat. TripAdvisor member Tom W Read more of our reviews on our TripAdvisor page. |
The culinary experience is a central part of any sailing holiday in the Greek islands. We believe the best way to enjoy the Cyclades is a blend of simple, relaxed moments on the water and authentic flavors on shore.
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Dining Ashore (The Highlight of the Trip). We highly recommend dining at the traditional waterfront tavernas found at every overnight place.
Dining Onboard (Lunch & Snacks). Our yachts are fully equipped with a cooker, oven, fridge, and galley for your use.
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What About Hiring a Hostess?
We specialize in private skippered cruises and purposefully do not include a hostess as standard.
Where do we embark? | |
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The Cyclades are the islands most people picture when they dream of Greece: whitewashed villages, blue-domed churches, and crystal-clear turquoise waters. To truly experience the best of this iconic archipelago within a one-week journey, your starting point is everything. Paros: The Heart of the Cyclades While many charters depart from Athens, those trips often spend long days at sea just to reach the first Cycladic island. By contrast, our private sailing tours in the Cyclades begin right where the magic is. By contrast, Paros sits at the very heart of the Cyclades, archipelago, making it the ultimate gateway for island hopping. Because of its central location, we can reach a wide variety of destinations within comfortable distances. Whether you want to see the cosmopolitan sights of Santorini or the untouched beauty of Amorgos, Sifnos, and the Small Cyclades, sailing with a skipper from Paros means more time exploring and less time on long, exhausting passages. (Note: Depending on the week and availability, a Mykonos start may occasionally be accommodated.) |
Simple & Convenient Access. Reaching Paros is easy and fits perfectly into any Greek travel itinerary:
With its perfect balance of accessibility and central location, Paros is the most efficient and enjoyable way to explore the very best of the Aegean. Contact us and we’ll be happy to help you plan the best way to reach Paros and begin your journey. |
Ready to Start Your Sailing Adventure in the Cyclades?Taking the next step is simple. Whether you have your dates finalized or are just beginning to dream about your skippered sailing holiday, we are here to help you guide the process.
Without the pressure of someone else taking your dates, you can plan with peace of mind and focus on the excitement of your upcoming private boat tour. | |
Which are the Best Greek Islands to Visit?>This is the question we are asked most often. While world-famous landmarks need no introduction, the true magic of a sailing tour in Greece with skipper is discovering the hidden gems you haven’t heard of yet—the quiet bays and authentic villages that aren't on the typical tourist map. Rather than sticking to a rigid list of famous names, we focus on the experience you want to have:
Your Bespoke Cyclades Sailing Itinerary from Paros.Because we start in the heart of the archipelago, Greek island hopping by boat is incredibly diverse. Whether you are looking for a 7-day, 10-day, or 14-day journey, we help you find the best route based on the reality of the sea. View Sample Itineraries : 7 days, 14 days. The Benefit of a Flexible Route. One of the greatest advantages of skippered sailing in Greece is the ability to "follow the weather." We strongly recommend staying flexible rather than having your heart set on one specific island. Before we set sail, we will discuss your interests and the current forecast. Whether you prefer short hops with more time for snorkeling or longer, active sailing passages, your skipper will tailor the journey to the conditions of the week. By letting the Aegean surprise you, we ensure a relaxed, safe, and stress-free holiday that feels like your own personal discovery. |
How Long Should I Plan My Sailing Holiday?The ideal duration for your sailing holiday in the Greek islands depends on your pace and how deeply you want to explore. Each day brings a new island with a completely different personality—from lively, cobbled villages to quiet, untouched bays. Naturally, more days on board allow for a more varied and relaxed Cyclades sailing itinerary. However, your starting point changes the math entirely. While a two-week trip is often required to reach the heart of the archipelago when departing from Athens, starting from Paros is a game-changer. Because we are located in the center of the Cyclades, iconic destinations like Santorini, Amorgos, or the Small Cyclades are within easy reach of a 7-day sailing trip. This allows even travelers with limited time to enjoy a rich, diverse experience without the "marathon" sailing days required from other ports. |
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Chartering a yacht in Greece comes with so much more besides sailing; exploring, sightseeing, archaeology, cooking classes, culture, biking and trekking. Essentially in a 1-2 week sailing holiday with skipper to the Greek islands, each day will feel like a full vacation thanks to the mix of so many activities:
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Looking forward to seeing you soon.
Notes:
You do not need any yachting qualifications or experience in order to participate on this sailing trip. Skippered yacht charter is perfect for everybody from young, fun-loving groups to families with children wanting to experience a boating holiday in Greece without the pressure of looking after the boat. Choosing a sailing holiday with a skipper is the best option if you are searching for a relaxing holiday and want to discover the Greek islands. Sailing the Cyclades starting at Paros or Mykonos without having to worry about anything at all. Just relax and enjoy the trip.
Contact usBy email at: info@sailboatchartergreece.com or sailboatchartergreece@gmail.com By phone at: 0030 6933 218 799. |
