Skippered Boat Charter in Greece: Private Sailing Holidays from Paros
Your own sailboat and skipper in the Cyclades
Owner-Operated Sailing Holidays in the Greek Islands
Discover the islands at your own pace with a team treating your Greek islands sailing vacations as their own. We provide a meticulously maintained skippered yacht in Greece and local insights-
the perfect choice for a private sailing holiday even if you have never stepped on a boat before. With a professional captain handling every detail of the navigation, you are free to simply relax and enjoy the Aegean.
Don't just take our word for it - listen to our guests. With
190 5-star reviews on TripAdvisor, we take
immense pride in our reputation. Because we are a small,
family-owned company, we treat every skippered yacht charter as if it were for our own family. Our goal is not just a "good" trip; it is the best sailing vacation
vacation of your life. Please check
Blue Water Sailing Greece TripAdvisor page
The Ultimate Convenience: Everything Taken Care Of
Unpack once and let the beauty of the Aegean unfold around
you.
Once on board your private boat in Greece, there is nothing for you to organize or worry about. At each destination, we, Adriana and Radu, share local insights on what to explore, how to get around, and where to find the most authentic island flavors.
Whether you want an active day of exploring or a quiet afternoon in a bay, we tailor the rhythm to your group's wishes. No planning, no research, no hassle — just the freedom to relax and enjoy the journey. Can you imagine a more seamless way to experience the Greek islands than your own private sailing vacations in Greece?
From your very first inquiry, you speak directly with us -
Adriana and Radu, the owners of the company. We personally manage every booking, itinerary plan, and preparation, ensuring you know exactly what to expect before you even land in Greece for your yacht sailing vacation.
When it is time to set sail, you will be in the hands of the people you already trust. On board Freedom, you sail with us, Radu as your skipper and Adriana as co-skipper: the same people who planned your trip with you, for a truly personal skippered yacht charter Greece service.
A Bespoke Sailing Vacation: Tailored to Your Group
We transform your time in the Cyclades into a personalized adventure designed specifically for your partner, family and friends.
We do not believe in "one size fits all" tourism; instead, we focus on creating a rhythm that suits your group. Your tailor-made sailing vacations Greek islands experience will be exactly what you hoped for: a unique, authentic, and personal experience that reflects your style of travel.
We believe a sailing vacation in Greece should be about relaxation, not unexpected calculations. While some charter companies add surprise costs for captain, fuel, final cleaning, and other fees, we offer total price transparency.
You simply pay a one-time, flat-rate "Skipper + Boat Essentials" fee that covers your private captain, fuel, and final cleaning for your private boat charter Greece.
No hidden extras, no end-of-trip surprises - just straightforward planning so you can focus on the journey ahead.
Authentic Cyclades Experiences
Your Dream Vacation Begins Now
Step away from the crowds and discover the Cyclades at your own pace with a team that treats your sailing vacation in Greece as if it were their own.
We provide a meticulously maintained yacht and local insights that go beyond the route, ensuring your time in the Greek islands is authentic and effortless.
Our Story: 14 Years of Sailing the Cyclades
If you are seeking a Greek island sailing vacation with a truly personal touch, you have found your home on the water. Blue Water Sailing Greece is a
small, family-owned company and
our boutique size is our greatest strength.
With just one yacht, Freedom, we are able to provide a level of care that larger fleets simply cannot match for a skippered yacht charter in Greece.
There are no intermediaries or sales agents here. From your first email to the moment you step on board, you deal directly with us, Adriana and Radu: the owners, your skipper and co-skipper, and your planning team. For over 14 years,
our goal has been to provide
authentic skippered sailing Greek islands experiences that feel less like a tour and more like a journey with friends. Based in the Cyclades, in Paros, we combine professional maritime expertise with the genuine warmth of a family business.
Your ultimate Greek islands private boat charter awaits! Skip the logistical chaos of ferry-hopping and sail straight to the heart of the Cyclades on a premium, 'unpack once' sailing vacation in Greece.
From secret swimming spots to sunset dinners in quiet hamlets, our family-owned tours offer a level of flexibility and local insight
you will not find anywhere else on a 7 days skippered yacht charter in Greece.
Perfect for a curated escape, our shorter trips fit seamlessly into your travel plans. If you are looking for a private sailing trip but have limited time, these boutique 3-5 day options are the ideal choice.
Experience the beauty of the Aegean on our skippered yacht in Greece without the commitment of a full week. We specialize in making your trip feel personal, authentic and completely effortless.
The best day of your vacation starts here. Rent our private sailboat with a captain for an
exclusive private day trip. Explore hidden coves and crystal-clear waters on a special day
charter designed for relaxation and fun.
The best day of your vacation starts here. Rent our sailboat with a captain for those looking to explore Paros in style.
Finding the right skippered charter yacht Greece is about more than just cabin count; it’s about the soul of the vessel and the care of the owners.
FREEDOM: Classic Charm & Owner-Operated Care. Set sail on Freedom, a beautiful Beneteau 53, a 53-foot sailing yacht known for
her classic silhouette and reliable performance. At 53 feet, she was designed with a specific philosophy: comfort over capacity.
While many charter boats of this size are designed to fit as many cabins as possible, Freedom was built to prioritize better living space for 6 guests (+ crew) for a more relaxed environment for your sailing vacations on
a skippered yacht charter in Greece.
While nautical spaces are naturally more compact than a home on land, this layout offers a more
relaxed and less crowded environment than a typical charter vessel. As our personal yacht,
Freedom is maintained with a level of care you can feel the
moment you step on board. Her interior features traditional high-end wood finishes, creating a warm, cozy, and inviting atmosphere - perfect for families
looking for an authentic, intimate Greek islands sailing vacation.
Adventure with Comfort: Life on Board. We believe that a sailing vacation in Greece should be fun, not "roughing it." Freedom is equipped with modern essentials: electric toilets, pressurized hot water,
and a well-stocked galley with a reliable electric fridge. Between island stops, you can relax in the shaded cockpit, or explore hidden coves with our complimentary paddleboard and snorkeling gear.
For a detailed list of equipment and layout, please visit our
your yacht
page.
Meet Your Crew: The Faces Behind Your Journey
When you book a skippered yacht charter Greece with us, you are not just renting a boat; you are joining a family. We believe that the right team makes the difference between a simple trip and a life-changing experience.
Adriana & Radu: Founders, Owners & Your Personal Hosts
With over 14 years spent navigating the Cyclades, these islands are where we feel most at home. We’ve spent many seasons at sea, and we simply enjoy sharing the local warmth and the authentic side of the Greek islands with our guests.
Adriana is the heartbeat of your planning. From your first inquiry to the moment you step off the yacht, her attention to detail ensures your Greece sailing vacation is seamless.
When you email us, you speak directly
to her - ensuring total transparency and a personal touch from start to finish.
Radu is a dedicated captain focused on the perfect balance of safety and adventure. He enjoys sharing the quiet spots he’s discovered over the years, ensuring you experience the islands
at a relaxed pace.
With Radu at the helm, you can fully trust his expertise to shape the ideal route
for your journey - expertly balancing the day’s winds with hidden gems and crystal-clear bays.
The Key to Escape: Sailing Holidays with Your Own Skipper
Explore, Relax, and Feel Free
Experience the freedom of the Aegean without any of the stress. On board your own sailboat with a captain, you can unwind completely while we handle the navigation.
The Magic of the Cyclades from Your Own Boat
Discover the soul of the islands from the deck of your own boat. A skippered sailing trip in the Greek islands offers a level of intimacy and adventure that simply cannot be found on a ferry or a large cruise ship.
It is about the quiet mornings in hidden bays and the sunset dinners in authentic coastal villages.
See What Your Sailing Holiday Looks Like
Step inside the experience. This is more than just a boat rental with captain; it's your floating home. See the crystal-clear waters that become your backyard for the duration of your sailing vacation.
Why Our Guests Love Their Sailing Vacations
Some of the spoken testimonials from Greece
5.0/5 on TripAdvisor191 guest reviews
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.
Incredible way to see the Cyclades!
Our family had an incredible experience sailing the Aegean aboard the Freedom during the first week of October! We sailed from Paros to Koufonisi, Amorgos, Schinoussa, and Ios before returning to Paros, with a quick stay in Athens before heading home. We loved the flexibility of the itinerary, which allowed us to enjoy each island at our own pace. Traveling in the offseason was great as well. We had more privacy on the beaches and plenty of room to explore, and although some places were closed, we never had trouble finding beautiful walks, interesting things to see, or great places to eat and drink. My wife and I are vegan and our our family isn’t. Finding food options for all was never an issue. Additionally, our hosts were happy to point us toward plant based options, and we found fantastic vegan friendly spots on every island! Greece truly is a very vegan-friendly country!
Our sailboat, the Freedom, was fantastic! Well appointed, comfortable, and spacious enough for our group of six to really settle in. Having the boat as our home base meant our accommodations traveled with us from island to island, without constantly packing and unpacking. Honestly, I can't imagine a better way to experience the Cyclades and get a real feel for the islands. Swimming off secluded beaches and jumping into the Aegean right from the boat were highlights we'll remember for a long time. A huge thank you to our hosts Adriana and Radu for making the experience so special, helping us feel at home aboard the Freedom, and making the trip so enjoyable for our whole family! We left with wonderful memories and would absolutely recommend them to anyone looking to explore the Greek islands in a more personal and memorable way.
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
Highly Recommended Sailing Adventure
Two friends and I chartered the Freedom for a week in June. It was a wonderful experience. Adriana and Radu were great hosts and excellent sailors – very accommodating, considerate and fun. Their knowledge of the Greek Islands was amazing. Adriana sent loads of valuable information prior to our departure for Greece and then she gave us great recommendations for what to do at each anchorage. Radu was tireless and very helpful in dropping us off and picking us up in the dingy. The Freedom is a beautiful boat with ensuite cabins and plenty of space. Overall a fabulous trip! I highly recommend Blue Water Sailing!
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.
"Proudly rated 5.0/5 with 191 reviews on TripAdvisor."
What you will experience
David M, who sailed with us in October, wrote:
"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 after a hassle free, relaxing yet
exciting adventure that is exactly what you will
get:
Visiting Greece on board a private boat charter Greece with captain allows you to unpack
your bag once and visit as much as possible in a week. Rent a sailboat with a captain and you will be visiting 5-6 different destinationsx in the same week.
A skippered boat charter is the guarantee for a 100% hassle-free sailing vacation while exploring a multitude of destinations.
The chance to experience the amazing life of living on a Greek islands hopping private boat:
relax and unwind each day for several hours on the water, then gear up and explore the various islands, then wind down at night with a drink on the boat!
A unique experience and perfect way to explore the islands!
A maximum of variety - you will have the opportunity to mix exploring off-the-beaten-path islands
(hamlets and quiet villages untouched by tourism), as well as cosmopolitan destinations.
Sample
delicious Greek cuisine at water front taverns
(many of them right on the beach).
Everyone in your family/group will get to do
things they enjoy best, from seeing historical sites to nature
hikes to partying at clubs.
Each day of our
skippered yacht charter Greece will be a perfect combination of sailing, snorkeling and island exploration.
Upon arriving at each destination, we will provide information about the island and not-to-miss experiences,
points of interest, modes of transportation, and of course, restaurant recommendations.
We will make it so easy you will not have to spend hours reading travel guides.
On board you will also find maps of each place.
An incredible experience for everybody from teenagers to grandparents wanting to explore the Greek islands as a real traveler,
away from the crowds and with the possibility to explore off-the-beaten-path places unspoiled by tourism.
A personalized adventure tailor made for your family and
friends.
A dream come true - a yacht charter in Greece for memories of a lifetime.
Sailing in Greece: Frequently Asked Questions
Which company provides private sailing trips in the Greek islands?
Blue Water Sailing Greece is a family-owned company offering private, owner-operated sailing holidays in Greece. We depart from Paros and sail with small private groups across the Cyclades islands.
Owners Adriana & Radu provide an authentic local experience for every private group on their own yacht, Freedom, with Radu as skipper and Adriana as co-skipper.
Do I need sailing experience to book a trip?
No, you do not need any sailing experience to book a private yacht charter in Greece with us. We specialize in sailing vacations for non-sailors, beginners, and families.
Every trip is a professional skippered charter where Radu, owner and captain of Freedom, handles all navigation and technical operations, with Adriana as co-skipper, ensuring a safe, accessible, and completely stress-free experience for
any private group enjoying a yacht for the first time.
Start Your Adventure: Check Dates and Book
Ready to trade the crowds for the open sea? Secure your skippered boat charter Greece with a family-owned team that treats your holiday as their own.
Whether you are looking for a “once in a life time” experience on board a private boat or a reliable skippered charter, we are here to help you navigate the perfect route.
Don't leave your holiday to chance. Contact us today to discuss your vision for a private Greek islands getaway. From the first email to the final sunset, we ensure every detail of your skippered yacht charter in Greece is handled with professional care and local expertise.
Owner-Operated Excellence Since 2012
Blue Water Sailing Greece: Your premier choice for an owner-operated skippered charter yacht Greece
Blue Water Sailing Greece is a boutique charter company founded and managed directly by owners Adriana and Radu. With over 14 years of professional sailing experience in the Cyclades, we provide expert skippered vacations on our private yacht,
Freedom, sailed by us: Radu as skipper and Adriana as co-skipper. Based in Paros, we specialize in authentic private boat charter Greek islands experiences throughout the Cyclades. Our deep local knowledge and owner-direct service ensure safe, authentic, and personalized Greek island adventures for families, couples, and groups of friends seeking a private getaway.
