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 54 reviews

Jose Ortiz

18:06 09 Oct 25

We just had a fantastic sailing experience with Oasis. Mike is a exceptional, laid back captain, who is very knowledgeable and an amazing host. Sophia was also great to have along, and kept things in order. The both of them were like family, and made our passage very special. The Ionians are simply spectacular. Captain Mike's knowledge of secluded private coves made our voyage unique. The food on the islands was delicious and the people are very welcoming. We definitely recommend sailing with Oasis. Our crew will certainly be back again.

Amy McCoy

00:37 30 Sep 25

Absolutely incredible! They made our trip safe, comfortable, and unforgettable. Whether the day went according to plan or had to be adjusted because of rough waters, they were chill, communicative, and made sure we got to beautiful and fun locations that cannot be accessed by big boats and cruise ships. The food was amazing and always so fresh. They know the area so they gave great recommendations for when we were off the boat too.
Thank you Mike and Sofia for making my first boat vacation amazing! I can't recommend you enough!

Kelsey De Pree

19:36 29 Sep 25

I just finished a trip with Oasis. I can’t recommend Mike and Sofia enough. They were so friendly, knowledgeable, and knew how to make each day special. They really took into account the interests of our group and curated our experiences, and island stops, to match. Everything Sofia made, for food, was delicious and she was so carful to pay attention to what we liked even going so far as to get special drinks she heard us mention in passing. Mike checked the weather and adjusted to smooth oceans for swimming and other excursions and talked to locals to get us the best deals on shore. 10/10 would recommend this company and hope to be back on another boat with Oasis before long.

Brittany Hayes

19:16 29 Sep 25

Sailed with Mike and Sofia, they were both fantastic! I felt very safe traveling with them. Sofia made delicious meals and regularly reminded us to stay hydrated. Very relaxing and comfortable trip.

Rebekah Ueland

17:26 29 Sep 25

Mike and Sofia were beyond exceptional at every level! I had the privilege of spending a week with them and 5 of my friends sailing the South Ionian islands. Every stop was incredible. Sofia provided breakfasts, lunches, and snacks on the boat, and every meal was incredible--light but filling and a complete tour of Greek cuisine.

This was my first time doing any sort of sailing holiday, and I ran the trip as an experiment for a travel business of my own--hosting fellow travelers for a once in a lifetime adventure. Mike was an exceptional partner and wonderfully patient as I asked questions and learned the ins and outs of planning a sailing vacation. He and Sofia helped me understand all aspects of planning the itinerary, budgeting for the boat and associated expenses, and more. I felt support and encouraged the whole way. They even provided ideas and coordination for shore excursions uniquely suited to our interests.

All five of my fellow guests agreed that we would happily sail with Oasis again. I can't wait for another adventure with Oasis Sailing!

Jill Henly

16:29 24 Sep 25

Oasis Sailing was a top 10 experience! Mike and Sophia made our vacation and sailing experience absolutely outstanding. Highly recommend them to both experienced and less experienced sailors. Big love!

Tatyana Smirnov

07:34 07 Sep 25

We just finished our sailing vacation with Mike and Pit from Lefkada. We had a great time and saw a lot of gems. If you are looking to have a relaxing and worry free sailing experience, Oasis sailing is the company to go with. You will not regret it.

Rick Stearns

15:56 20 Jul 25

Our captain Mike and his hostess Sophia were outstanding. We had 6 people traveling (parents and kids aged 11-25). They attended to everyone with great care and thoughtfulness. The ports amd swimming bays we visited were outstanding. The crew was relaxed and yet extremely attentive to whatever anyone needed. We would HIGHLY recommend this sailing trip in general (cute towns, fun tavernas, amazing water) and would recommend this crew without hesitation. They thought of everything. We couldn’t have been happier.

nikosgeopaok43

17:37 14 Jul 25

Great experience at sea and excellent knowledge of the Ionian islands, Professional and throughout the trip you had a sense of safety. He was always there to show us all the places and answer any questions we have and the children had. Captain Pit, thank you and we will definitely see you again.

Despoina Papadopoulou

08:54 14 Jul 25

PROFESSIONALS. We spent a week and everything was perfect. Captain Pit was always there to explain anything you asked and that gave you a sense of security on the boat. Keep it up and we will definitely be back. Thank you Captain Pit.

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.

Our mission is to create unforgettable experiences for our clients, whether they are seeking adventure, relaxation, or a combination of both.