Team Building Sailing Retreats That Inspire Collaboration!

Strengthen bonds, boost morale, and build trust with tailored team-building sailing experiences in the Ionian Sea.

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Sailing Journeys Loved by Guests, Rated by Smiles

Whether for families, adventurers, or teams, our personalized sailing experiences create lasting memories.

Oasis Sailing place picture
Oasis Sailing
5.0
Based on 54 reviews
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Jose Ortiz profile pictureJose 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.
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Amy McCoy profile pictureAmy 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 profile pictureKelsey 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 profile pictureBrittany 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 profile pictureRebekah 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!
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Jill Henly profile pictureJill 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!
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Tatyana Smirnov profile pictureTatyana 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.
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Rick Stearns profile pictureRick 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 profile picturenikosgeopaok43
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.
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Despoina Papadopoulou profile pictureDespoina 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.
Our Reviews

Strengthen Bonds with Unforgettable Team Experiences

Crafted with Expertise

Tailored Sailing Adventures to Empower Collaboration and Connection

At Oasis Sailing, we specialize in creating team-building retreats that go beyond the ordinary. With expert local skippers, personalized itineraries, and a focus on safety and comfort, we craft journeys that inspire teamwork and lasting connections. Let the stunning Ionian Sea set the stage for your team’s transformation.

Expert Local Knowledge

Discover hidden Ionian gems with guidance from experienced skippers.

Personalized Planning

Every retreat is tailored to meet your team’s unique goals and dynamics.

Authentic Experiences

Immerse your team in local culture, from hidden coves to traditional tavernas.

Safety Excellence

Fully equipped yachts ensure a safe and worry-free retreat.

Team-Focused Activities

Strengthen collaboration and trust through shared adventures.

Why Teams Love Our Sailing Retreats

Unforgettable Adventures Designed to Inspire and Unite

Strengthen Team Collaboration

Foster trust and teamwork through shared sailing adventures and activities.

Tailored Retreats for Your Goals

Custom itineraries designed to meet your team’s unique objectives.

Discover Hidden Ionian Gems

Explore secluded coves, secret beaches, and authentic Greek villages.

Relax in Comfort and Safety

Fully equipped yachts with top-notch safety features for a worry-free experience.

Create Lasting Memories

Bond over unforgettable moments, from sunset dinners to group adventures.

What Makes Our Sailing Holidays 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!

What is included in the team-building sailing retreat package?

Our retreats include the yacht rental, an experienced skipper, safety equipment, and personalized itineraries. Upon request, a hostess is also available to prepare meals tailored to your team’s preferences and dietary needs. Additional activities like snorkeling, wine tasting, or team challenges can also be arranged upon request.

Do we need prior sailing experience?

Not at all! Our expert skippers handle all sailing, allowing your team to relax and enjoy the experience. If interested, team members can also learn basic sailing skills during the retreat.

How many people can join the retreat?

There’s no limit to how many people can join! We can arrange yachts of various sizes, including larger vessels, to accommodate your team. For even bigger groups, we can organize a flotilla with multiple yachts, creating a seamless and connected experience for everyone.

Can the itinerary be customized to our team’s goals?

Absolutely! We work with you to create a tailored itinerary that aligns with your team’s objectives, whether it’s collaboration, leadership training, or relaxation.

What safety measures are in place?

Safety is our top priority. Our yachts are equipped with life jackets, emergency kits, VHF radios, and more. Our skippers are highly trained and experienced in handling all situations.

What should we bring for the retreat?

Comfortable clothing, sunscreen, swimwear, and any personal items. We’ll provide a detailed packing list after booking to ensure your team is fully prepared.

Can we include additional team-building activities?

Yes! We can arrange activities such as hiking, yoga, cooking classes, or even team challenges to make your retreat more engaging and memorable.

What happens in case of bad weather?

Our skippers monitor weather conditions closely. If needed, we’ll adjust the itinerary to ensure your team’s safety and comfort without compromising the experience.

Got more questions?

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Team-Building Redefined

Chart a New Course for Your Team Today!

Don’t miss the chance to transform your team with a tailored sailing retreat in the Ionian Sea. Let’s start planning your unforgettable adventure!

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

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