Custom Sailing Holidays in Greece: Tailored Just for You

Your Dream Greek Sailing Journey, Tailored Just for You!

From secluded bays to authentic Greek villages, we'll design your perfect sailing journey. Choose your ideal vessel - from elegant monohulls to spacious catamarans - and let us create your personalized Mediterranean escape.

Voices from Our Sailing Family

Perfect Reviews from Happy Sailors Who Trusted Us with Their Dream Holiday

Oasis Sailing

5.0

Based on 40 reviews

Brett Trelfa

08:57 01 Oct 24

Mike expertly led our flotilla from Lefkada around the various islands and back. His local knowledge and connections made it easy to obtain beautiful mornings as well as locating some of the best food. He helped organize shuttles and sightseeing excursions.We really appreciated Mike’s low-key no stress approach. We never felt rushed and his communication was excellent.Highly recommend choosing Mike as your flotilla leader or for a sail.Yamaaaaas!

Ken Bostock

06:51 23 Sep 24

We had a wonderful time sailing with the Oasis flotilla. Mike and his team were terrific help and provided great tips for anchoring and med mooring. Thanks for helping make such fun memories.

Woody Glover

10:36 22 Sep 24

Mike is an incredible captain who has a vast knowledge of the Ionian sea. He and Sofia made our sailing journey one that we will never forget. They both speak excellent English. Sofia is an amazing hostess. She is an excellent chef that makes you feel totally at ease while also a deck hand that can perform any task on the boat.

Sylvain DERWEL

18:33 11 Aug 24

We’ve had an incredible time during this trip with oasis.We saw some magnificent spots, the pace was perfect, the boat was in excellent condition, and Mike, our skipper, was both super friendly and professional.We recommend 100%.

Beth Almeda

19:12 19 Jun 24

The only way to see Greece! Everything was perfect to include the sailing, stops in small towns, swimming at the best private beaches and the restaurants Captain Mike suggested. The experience of sailing with a friendly and knowledgeable captain makes your trip the best. Your next adventure should be with Oasis Sailing for sure. Captain Mike, we are forever grateful for our time with you in Greece!

virginie serviere

16:58 10 Dec 23

the trip we did end of April was amaizing! one of the best vacations we had! we had great weather with good wing and could sail 70 Nautical miles in 4 days across several islands. We had lots of fun with Mike and really relaxed! we look forward coming back another time!

Vladimir Bolin

16:02 11 Nov 23

Our two-week sailing adventure with Oasis in Greece was nothing short of spectacular! My father-in-law and I embarked on a journey through the Ionian Sea with Captain Mike in September, and it turned out to be the trip of a lifetime.From the moment we stepped aboard, Captain Mike's warm and polite demeanor set the tone for an incredible experience. His passion for sailing was evident, and it was contagious. Mike not only ensured our safety at all times but also took the time to patiently teach us the art of sailing. His expert guidance made us feel confident and capable, even as beginners.What truly set Oasis apart was Captain Mike's ability to balance professionalism with a sense of fun and adventure. Whether expertly maneuvering the boat or sharing stories about the beautiful Greek islands, Mike's enthusiasm was infectious. His knack for finding the perfect balance between education and entertainment made every moment on the water memorable.One of the highlights was Mike's impressive skill in parking the boat. Watching him artfully navigate tight spots in picturesque harbors was a testament to his years of experience and expertise. It added an extra layer of excitement and admiration for the art of sailing.Beyond the sailing itself, Captain Mike went above and beyond to enhance our experience. He took us to some of the best restaurants in the region, allowing us to savor local cuisine and immerse ourselves in the Greek culture. His recommendations were spot-on, showcasing not only his knowledge of the sea but also his familiarity with the hidden gems along the coast.In summary, our sailing adventure with Oasis was made extraordinary by Captain Mike's professionalism, friendliness, and genuine love for sailing. If you're looking for a charter that combines safety, education, and a whole lot of fun, look no further than Oasis. Our heartfelt thanks to Captain Mike for making our Greek sailing experience truly unforgettable.

Ruth Taylor

17:53 13 Jul 23

We shared the most amazing week with Mike on the Ionian Sea. He planned the perfect itinerary for our group and did a great job advising us on what to do and see, where to eat, and even set up a fantastic massage overlooking the water. He’s a really wonderful guy to hang out with and an absolutely incredible instructor. We can’t wait to go back next year!

Aileen Reyes Fulgar

19:27 06 Jul 23

Amazing experience 10/10!

Balázs Siegler

17:59 04 Jul 23

We had a great holiday, I can only recommend sailing with Mike!

Expert Local Knowledge

Tailor-Made Routes to Suit Your Preferences

Authentic Experiences

Safety Excellence

Local Connections

Crafted with Expertise

Where Local Knowledge Meets Your Personal Preferences

In the heart of the Ionian Sea, our expert local skippers transform your sailing dreams into reality. With intimate knowledge of every hidden cove and authentic taverna, we craft journeys that go beyond the ordinary tourist routes. From selecting your ideal yacht to discovering the secrets of the Ionian archipelago, we design your perfect Greek sailing adventure with meticulous attention to detail.

Why Choose Custom Sailing Holidays in Greece?

Experience the Freedom of a Truly Personalized Journey

Flexible Freedom

Your Journey, Your Pace...

Whether you prefer long swims in crystal-clear waters or exploring charming villages, each day adapts to your mood and desires. Our experienced skippers ensure your journey flows naturally, balancing activities and relaxation exactly as you wish.

Complete Care

Hassle-Free Planning

Leave the complexities of sailing logistics to us while you simply enjoy the journey. From weather routing to dinner reservations at the best local spots, we handle every detail to ensure your holiday flows smoothly from start to finish.

Personal Space

Private & Intimate Experience

Create precious moments with your loved ones in your floating sanctuary. While our crew handles navigation and logistics, you focus on what matters most – quality time together in the stunning backdrop of the Ionian Sea.

Hidden Treasures

Discover Beyond the Ordinary

Step away from crowded tourist spots into a world of secret coves and authentic Greek life. Our local knowledge opens doors to exclusive experiences – from secluded beaches perfect for snorkeling to family-run tavernas serving generations-old recipes.

What Makes Our Custom Sailing Holidays in Greece Special

Every Detail Crafted for Your Perfect Mediterranean Escape

Expert Guidance

Professional Skippers

Our experienced skippers bring deep local knowledge and professional certifications, ensuring both safety and enriching experiences. They’re skilled at finding the perfect balance between adventure and comfort, always adapting to your preferences.

Complete Package

Equipment & Comfort

Your sailing holiday comes fully equipped with everything needed for adventure and relaxation – from safety equipment and navigation tools to water sports gear for added fun. Every vessel in our selection is maintained to the highest standards.

Smart Navigation

Route Planning

Each itinerary is thoughtfully designed around weather conditions, your interests, and local events. From sheltered bays during windy days to vibrant harbors during local festivals, we optimize your journey for the best possible experience.

Authentic Connections

Local Experiences

Access our network of trusted local partners – from family-run tavernas serving traditional dishes to expert guides for special activities. We connect you with the authentic heart of the Ionian islands, away from mass tourism.”

FAQ

Got Questions? We've Got Answers!

How do you create custom sailing holidays in Greece

We start by understanding your preferences, group dynamics, and dream destinations. Based on this, we craft a personalized itinerary that combines your interests with our local knowledge, while staying flexible to adapt to weather conditions and your daily wishes.

What's included in a typical sailing holiday?

What’s included in a typical sailing holiday?” “Your holiday includes a professional skipper, fully equipped yacht, marina fees, fuel, and final cleaning. We can also arrange additional services like provisioning, transfers, and special activities based on your preferences.

What's the best time to sail in the Ionian Sea?

The sailing season runs from April to October, with peak conditions from June to September. Each period offers unique advantages – from mild spring weather to warm summer waters.

What about meals and provisions?

You can choose to prepare meals in the fully equipped galley, dine at our recommended local tavernas, or mix both. We can assist with provisioning and recommend the best local restaurants.

Do we need sailing experience?

Not at all! Our professional skippers handle all navigation and sailing aspects. You can choose to learn basic sailing skills during your holiday or simply relax and enjoy the journey.

How long is a typical sailing holiday?

Our sailing holidays operate on a strict weekly schedule, starting every Saturday at 17:00 and ending the following Saturday morning. For extended adventures, you can book multiple consecutive weeks. The weekly format ensures the best possible experience for all our guests.

How do we plan our daily routes?

Your skipper will suggest daily routes based on weather conditions, your interests, and local events. Each morning, you’ll discuss the day’s plan over breakfast, with the flexibility to adjust as you wish.

Adventure Awaits

Ready to Create Your Perfect Escape?

Ready to craft your custom sailing holidays in Greece? We are here to help design your perfect Mediterranean escape. With 100% guest satisfaction and a decade of experience in the Ionian Sea, we’re ready to make your sailing dreams come true.