(What It’s Really Like — From People Who Lived It)
In the summer of 2022, we somehow found ourselves spending six unforgettable months in Greece as flotilla leaders in the Saronic Gulf.
“Somehow” is the keyword here.
We applied for what sounded like an interesting sailing opportunity, without really knowing much about flotillas at all (they don’t really exist around South Africa or Switzerland — our home countries). Thirteen days later, we were Athens-bound, slightly stunned, very excited, and quietly wondering what on earth we’d signed up for.
What followed was the experience of a lifetime.
It was exhilarating.
It was exhausting.
I cried (often).
We laughed even more.
I turned 60 during our time in Greece, which made us two of the more “mature” flotilla leaders — not quite as nimble as the younger crews, but armed with decades of sailing experience, life experience, and an impressive ability to pace ourselves.
That said… we still managed to party with the best of them.
One of our favourite guests? An 84-year-old skipper who out-sailed, out-laughed, and out-lived just about everyone.
This guide is written from that lived experience. We hope it answers some of the questions you might have about flotillas — and if not, our contact details are at the end. We’re always happy to chat.
So… What Is a Flotilla?
At its simplest, a flotilla is a group of yachts sailing together on a loosely planned route, supported by a lead crew.
You sail your own boat.
You’re the captain.
But you’re not alone.
Flotillas exist for many reasons — leisure, exploration, racing, humanitarian causes, even protest — but for most people reading this, a leisure flotilla holiday is the focus.
These are popular with:
- First-time charterers
- Less experienced sailors
- Families and mixed-ability crews
- Anyone who wants independence with backup
You get the joy of sailing your own yacht, plus the reassurance that someone knowledgeable is keeping an eye on weather, routes, and logistics.
Flotilla vs Bareboat Charter – What’s the Difference?
This is one of the most common questions we were asked.
Flotilla Sailing
- You sail in a group with a lead boat
- Routes and anchorages are suggested, not forced
- Help is available if things go sideways
- You can hire a local skipper if you’re unsure
It’s independent sailing with a safety net.
Bareboat Charter
- You’re on your own
- No crew, no guidance
- You plan everything
- You handle everything
Bareboat charters are wonderful — but they suit confident, experienced sailors who genuinely want full independence.
If you’re new, rusty, or just want a more social experience, flotillas can be a fantastic stepping stone.
The Good, the Great, and the Slightly Tricky Bits of Flotilla Life
The Upsides
The Social Side
Flotillas are wonderfully social. You meet people from all over the world, share stories, meals, and sundowners, and often end up with lifelong friendships.
Quick tip: if the social side matters to you, ask how many boats are booked for your week.
We once had a very flamboyant group of lads who were devastated to discover they were the only boat that week. We compensated with an aggressive tavern-based itinerary, and they left exhausted, happy, and declaring it “the best flotilla ever.”
Support & Safety
If something breaks, the weather turns, or nerves kick in — you’re not alone. That peace of mind is priceless, especially for newer crews.
Route Planning (Without the Headache)
The lead crew knows the area, the best anchorages, and which tavernas are actually worth walking to. You benefit from that knowledge without spending weeks researching.
Learning Curve
For newer sailors, flotillas are an incredible learning environment. You pick up skills, confidence, and knowledge simply by being around more experienced sailors.
The Downsides (Let’s Be Honest)
Less Privacy
You’re sailing with others. If total solitude is your dream, a flotilla may feel busy at times.
Less Control Over the Route
The route is flexible — but not infinite. Weather, numbers, and logistics all play a role.
Group Dynamics
Put different cultures, ages, expectations, and personalities together and… well… most of the time it’s fantastic. Occasionally, it’s not. That’s just people.
Busy Anchorages
In peak season, popular spots get crowded. That’s Mediterranean summer sailing — flotilla or not.
When Is the Best Time to Do a Flotilla in Greece?
Generally:
- May–June & September are magic
- July–August is hot, busy, and vibrant
- Shoulder seasons are calmer and often cheaper
If you’re flexible, shoulder season wins every time.
How to Choose a Flotilla Company
This matters.
Different companies offer very different experiences — levels of support, social activities, boat quality, and crew expertise vary hugely.
Recommendations from friends are gold.
Reviews on Trustpilot are more honest than cherry-picked testimonials.
If something feels off — trust that instinct.
Safety: What Actually Matters on a Flotilla
A good flotilla is obsessively weather-aware.
We checked forecasts four times a day and changed routes when needed. We stayed put when it was sensible. Nobody ever complained.
Good flotillas:
- Communicate clearly
- Use VHF properly
- Encourage sensible seamanship
- Respect that every skipper is captain of their own boat
And yes — safety briefings matter. Even on holiday.
What to Pack for a Flotilla (From Experience)
Space on boats is limited — soft bags only!
Bring:
- Lightweight clothing
- Good deck shoes
- Cheap swim booties (essential for Greece)
- A waterproof bag
- Sunscreen, hat, sunglasses
- Handheld VHF if you have one (hugely useful)
Ask what’s already onboard before overpacking — and remember, you’ll need to store those suitcases somewhere…
A Few Final Thoughts (This Bit Really Matters)
To have the best flotilla holiday of your life:
Be flexible.
Boats change.
Marinas change.
Routes change.
Weather changes everything.
You will see all the places you’re excited about — just maybe not in the order you imagined.
A flotilla is not a floating sorority. You don’t have to do everything together. Dinners are suggestions. Routes are suggestions. If you want a quiet anchorage one night, tell the lead crew and go for it.
Most of the time:
- The water is glorious
- The scenery is stunning
- The food is ridiculous
- And “Mamma Mia” music follows you everywhere
Which, honestly, is not a bad way to spend a holiday.
If you have any questions at all, feel free to get in touch — we’re always happy to help if we can.
📧 sailingandsunshine@gmail.com
🌍 www.sailingandsunshine.com
Captain Mike & First Mate Nikki ⚓☀️
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