Skippered vs Bareboat vs Flotilla vs Cabin Charter: Which Is Right for You?
Written by Gediminas Vengrauskas, licensed Coastal Skipper · ICC · VHF · Updated July 2026
Bareboat, skippered, flotilla, cabin charter — four words used as if they were interchangeable, describing four genuinely different holidays that happen to use the same islands and the same boats. Picking the wrong one is the most common way a week that should have been the best of the year ends up a disappointment.
I sell one of these four, so weigh what follows accordingly. Here is the honest version, including where I'd send you elsewhere.
Key takeaways
Bareboat — you sail it yourself. Cheapest per boat, needs a recognised licence and recent experience.
Skippered — the same private yacht with a professional captain aboard. No licence, same route freedom.
Flotilla — you skipper your own boat but travel with a group and a lead crew.
Cabin charter — you book a berth, not a boat. Cheapest per person, shared with strangers on a fixed route.
Published 2026 “from” prices in Greece: bareboat £1,269 a week, flotilla £1,869, cabin charter €949 per person.
Only one of the four legally requires a licence — and it isn't the one most people assume.
The short answer
Take a bareboat if you hold a recognised offshore licence and want the boat entirely to yourself. Take a skippered charter if you want a private yacht without the licence, the paperwork or the 3 a.m. weather worry. Take a flotilla if you can already sail but would like company and a safety net. Take a cabin charter if you are travelling solo or as a couple and care more about price and people than privacy.
What is the actual difference between the four?
Bareboat charter. You charter the yacht alone. The contract is in your name, the boat is your responsibility, and you are the skipper: navigation, mooring, weather calls, all of it.
Skippered charter. Identical boat, identical freedom of route, with a licensed captain aboard. You choose where the week goes; I decide whether the forecast allows it.
Flotilla. You skipper your own yacht but sail with a group — typically six to twelve boats — behind a lead yacht and professional crew. Morning briefings, a shared destination most nights, help on the radio if the anchor drags.
Cabin charter. You buy a berth on a boat you don't control, alongside guests you haven't met. A professional skipper sails it, route and dates are fixed months ahead, and the price is per person rather than per boat.
The short way to hold it in your head: bareboat and skippered give you a private boat, flotilla gives you a private boat with company, cabin charter gives you a shared boat at a shared price.
What does each one cost in 2026?
Real numbers, published by the people who charge them.
My own skippered pricing (Greece, per week, for the whole group — not per person): the yacht runs €2,500–€4,500 depending on age, size and month, my day rate is €180–€220, fuel and harbours €200–€400, end cleaning €150–€250. Croatia is similar on the boat (€2,300–€4,500) but dearer on the water — €300–€500 a week, plus tourist tax of roughly €1.50 per person per day. I own no fleet; the boats come from licensed Greek and Croatian charter companies.
Bareboat and flotilla, from Sunsail's own published Greek figures (7 days, two people, page last updated April 2026): bareboat from £1,269 in low season and up to £9,199 in high; flotilla from £1,869 low, £3,719 high. Adding one of their skippers costs £280 per night.
Cabin charter: MedSailors lists 7-day skippered trips in Croatia and Greece from €949 per person on 2026 early-bird pricing, and premium catamaran cruises from about €1,997 per person.
Now the part those “from” prices leave out: they describe the smallest boat in the quietest week. Sunsail's own advice is to budget an extra 25–50% for living and operational costs, and its published extras show why — Greek mooring fees run €10–€202 a night, catamarans pay a 50–60% mooring supplement, the damage waiver is £60–£130 a day, and provisioning lands around £30–£50 per person per day. A bareboat quote is a boat, not a holiday budget.
For what a full skippered week actually totals, here is the line-by-line breakdown: what a skippered sailing holiday in Greece really costs.
Who should choose a bareboat charter?
Sailors — people with a recognised offshore licence, recent miles, and the confidence to berth stern-to in a crosswind while a Greek harbour watches.
If that's you, bareboat is unbeatable value: total privacy, no skipper's fee, nobody to answer to. The trade-offs are real — you carry the damage deposit or daily waiver, you make the weather calls, and in Greece you also need a second competent crew member on the paperwork, a rule that surprises couples every season. Full requirements here: do you need a licence to charter a boat in Greece?
One warning: a licence earned in sheltered water eight years ago is not the same as being current. The Ionian in June will forgive you. The Cyclades in a strong Meltemi will not.
Who should choose a skippered charter?
Groups who want the private boat but not the job. Families, friends celebrating something, two couples travelling together — and very often one competent sailor who is tired of being the only person aboard who can't switch off.
This is what I do, so weigh it accordingly. The day rate buys route planning around your wishes and the forecast, all the sailing and manoeuvring, harbour formalities, safety briefings, and the local knowledge of which taverna is worth the walk.
The part nobody advertises is the freedom to change your mind: if the wind turns north and everyone would rather have a quiet bay than a harbour town, we go to the quiet bay. See how that works on the Greece charters page or the Croatia charters page.If you are wondering what that actually looks like day to day, from where the skipper sleeps to who buys their food and what counts as a fair tip, I wrote a separate guide on what it is like having a skipper on board.
What is a flotilla holiday actually like?
Bareboat sailing with the training wheels within reach. You helm your own yacht, but a lead boat with a professional crew is somewhere ahead and the group converges on the same harbour most evenings.
For the right crew it's excellent — newly qualified skippers make their own decisions with help one radio call away, and the social side is part of the product. For the wrong crew it grates: you're on the flotilla's schedule, and if it would annoy you that everyone leaves at nine and eats in the same taverna, it will annoy you by Wednesday. It still needs a licence — the lead crew supervise, they don't take responsibility for your boat.
What is a cabin charter — and what's the catch?
You book a bed. The boat, route, dates and fellow guests are decided for you, which is exactly the appeal if you're travelling alone and don't have five friends who can take the same week off.
Two catches. Unless you pay for a private cabin you may be sharing one, and you'll certainly share the saloon, heads and cockpit with people you met at check-in. And the demographic is often deliberate — MedSailors states plainly that its island-hopping trips are for 18–35 year olds, while its premium catamaran cruises are open to all ages at roughly double the price. Honest segmentation, but worth reading before you book.
Do you need a licence for any of them?
Only bareboat — and flotilla, since you're still the skipper of your own yacht. Skippered and cabin charters both come with a qualified captain, so the requirement is met by the professional rather than by you. This is the misconception I'm asked about most, and it's why people rule out a holiday they were perfectly entitled to take. The full licence rules for Greece are here.
Which suits families, and which suits people who want to learn?
For families with young children: skippered first, flotilla second. A captain aboard means someone experienced watches the water while you watch the children, and the route can be rebuilt around a nap or a swimming obsession. Cabin charter is usually wrong here — the cheaper trips tend to be age-restricted or aimed at a social adult crowd.
For learning: flotilla if you already hold a licence, skippered if you're starting from zero — I include lessons along the way at no extra charge. The honest sequence is a skippered week, then a course, then a flotilla, then bareboat.
Which gives you the most privacy per euro?
A skippered charter, once your group reaches five or six — and it isn't close. A cabin charter is priced per person; a skippered week is priced per boat and then divided. In my worked example from the costs article, six friends on a 3-cabin yacht out of Athens in late June came to roughly €105 per person per day, all-in before dinner. Below five people the maths flips and cabin charter wins.
So how do I actually decide?
Run these in order and stop at the first yes.
Hold a current, recognised licence and want total independence? Bareboat.
Hold a licence but would rather not be out there alone? Flotilla.
Four or more people who want a private boat without the licence or the responsibility? Skippered.
One or two people who care more about price and meeting people than privacy? Cabin charter.
If two still look right, the tiebreaker is almost always this: how much of your holiday are you willing to spend being responsible for something?
FAQ
Is a skippered charter much more expensive than bareboat?
Less than people expect. The skipper adds €180–€220 a day to a boat already costing €2,500–€4,500 a week — for six people, roughly €20–€25 each per day.
Can I steer the boat on a skippered charter?
As much as you like. Most guests helm a good part of the week and I teach anyone who asks. The difference is that you're steering by choice rather than obligation.
Do I need sailing experience for a flotilla?
Yes. The lead crew supervise and assist, but you're the skipper of your own yacht and still need a licence the charter company accepts.
Will I have to share a cabin on a cabin charter?
Often, unless you pay the supplement for a private one. You'll certainly share the saloon, cockpit and heads with the other guests.
Which format is cheapest per person?
For one or two travellers, cabin charter — from around €949 per person for a week on 2026 early-bird pricing. For five or more, a skippered or bareboat charter split across the group beats it comfortably.
Can I switch from bareboat to skippered if I lose confidence?
Usually, if you ask early. Fleets can add a skipper to an existing booking subject to availability. Ask before the balance payment falls due, not the week before you fly.
Are catamarans available in all four formats?
Yes. Be aware they cost meaningfully more to charter and attract a mooring supplement of roughly 50–60% in Greek marinas — real comfort, real cost.
How far ahead should I book for 2027?
For peak July and August, the good boats and free skipper weeks go six to nine months out. My remaining 2026 availability is August–October; 2027 is open. June and September stay bookable later and are honestly the better sailing.
Which one is right for you?
Tell me your dates, your group size and roughly what you want from the week, and I'll tell you which of the four fits — including when the honest answer isn't the one I sell.
Tell me your dates or message me on WhatsApp. I reply within 24 hours, every time — one captain, one inbox, no call centre.
Written by Gediminas Vengrauskas, licensed Coastal Skipper (sail and motor vessels up to 24 m LOA, day and night, up to 12 NM offshore), ICC and VHF certified. I skipper charter weeks in the Greek islands and the Croatian Adriatic, run private day sails from Athens, and take on coastal deliveries worldwide. I own no fleet, which is why I can tell you honestly when a different boat or charter type suits you better. More about hiring me as a captain.
Sources checked 27 July 2026:Sunsail's published Greece charter pricing and MedSailors' published 2026 pricing. SailCurrent rates as published on this site.
