flotilla - Oasis Sailing

Flotilla Sailing in Greece

Planning a group trip? We can arrange a private flotilla in the Ionian with multiple boats, a lead skipper, and a shared route — tailored to your group and dates from Lefkas Marina.

REVIEWS & TRUST

A Smooth Way to Coordinate Multiple Boats

We help groups sail together with clear planning, local guidance, and support — so everyone enjoys the week without the stress of organizing it alone.

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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.

WHAT IT IS

Multiple Yachts, One Shared Plan

A flotilla is a group of yachts that follow the same route together. Each crew keeps their own boat and privacy, but the group shares a plan, daily coordination, and optional lead support — making it easier to sail as a group in a new area.

IS THIS FOR YOU?

Ideal for Big Groups and Multi‑Boat Trips

Flotillas work best for groups who want to travel together but need more than one yacht — friends, extended families, clubs, or team trips. It’s also great when some crews want more guidance while others prefer more independence.

HOW IT WORKS

We Coordinate the Week — You Enjoy It

We help select the right boats, agree on a shared route, and set up simple daily coordination. Boats sail at their own pace, then meet in the same bay or harbour. If you want, a lead skipper can help with briefings and group coordination.

YOUR SETUP

Bareboat Crews, Skippered Crews — or a Mix

If your group includes licensed sailors, some boats can run bareboat. If others prefer to relax, we can add skippers. We’ll recommend the best mix based on your group’s experience and comfort level.

FAQ

Flotilla Sailing — Quick Answers

The most common questions about arranging a multi‑boat trip from Lefkas Marina.

Frequently Asked Questions

Can you arrange a flotilla for our group?

Yes — if you have a larger group and need multiple yachts, we can arrange a private flotilla on your dates, starting from Lefkas Marina.

What group size makes a flotilla worth it?

Usually when you need 2+ yachts (friends, extended families, clubs, team trips). Tell us your headcount and we’ll suggest the best setup.

Can some boats be bareboat and others skippered?

Yes. Many groups choose a mix — licensed sailors can go bareboat, while others sail with a skipper.

Where does the flotilla start?

Most trips start from Lefkas Marina. We’ll confirm the meeting plan and timing for the whole group.

Do we all follow the same itinerary?

We agree on a shared route and meeting points, but each boat can sail at its own pace. The goal is to stay coordinated without feeling rigid.

How far in advance should we plan a flotilla?

The earlier the better, especially in summer. Multi‑boat availability is limited, so early planning gives you the best choice of yachts and crew.

PLANNING A GROUP TRIP?

Ask About a Private Flotilla in the Ionian

Tell us your dates, approximate group size, and how many boats you think you’ll need — and we’ll come back with the best options and a simple plan.

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