When to Book a Skippered Charter in Greece for 2027: Deposits, Deadlines and the Weeks That Go First
Written by Gediminas Vengrauskas, licensed Coastal Skipper · ICC · VHF. Updated October 2026
The short answer
For a July or August week in Greece in 2027, book between now and the end of January; for May, June or September you can wait until spring, but not much later. That advice rests on three published facts rather than a feeling. Sunsail's booking search already offers departures as far ahead as April 2028, so 2027 boats are on sale today. The Greek fleet Ionian Charter ran its 2026 early-booking discount of 10% only until 31 January 2026. And the summer weeks are the ones that fill: on my own calendar, July and August go first.
What most guides skip is the money side of booking early. You usually pay half the boat on the day you book, and what you lose if plans change depends far more on which fleet you book with than on how early you book. Below are the real terms from two operators' own published conditions, the dates they put on your calendar, and the order I would do things in.
Key takeaways
2027 is already bookable at Sunsail, whose booking search runs to April 2028; Ionian Charter's site still showed only its 2026 price list on 19 October 2026.
The early-booking discount at Ionian Charter was 10% for 2026 and closed on 31 January 2026. It did not apply to its Bali 4.4, 4.6 and 4.8 catamarans.
Both fleets I checked take 50% of the charter fee to confirm a booking. The balance is due 4 weeks before the start at Ionian Charter, and 120 days before departure under Sunsail and The Moorings' UK terms.
Cancellation costs are where they really differ. More than 90 days out, Ionian Charter keeps €250; Sunsail and The Moorings keep the 50% deposit.
The booking payment is not the security deposit. That is a separate sum, covered in my guide to charter security deposits.
When can you book a 2027 skippered charter in Greece?
You can book 2027 now. When I checked Sunsail's site on 19 October 2026, its booking search offered departure months from October 2026 through to April 2028, so 2027 departures are already on sale.
Smaller Greek fleets move at their own pace. On the same day, Ionian Charter's price list page still covered only the 2026 season, with its own season periods and discounts for that year and nothing yet for 2027. That is normal for a local company, and it is the one thing to watch for this winter: when a fleet publishes next year's list, it usually publishes next year's early-booking deadline with it.
If you already know your week, you do not have to wait for the price list to start. A skipper can hold dates before a boat is chosen, and a fleet can often tell you whether a particular boat is still free for your week before its new prices are online.
Is there an early-booking discount, and how big is it?
At Ionian Charter, the 2026 early-booking discount was 10%, available until 31 January 2026. Its price list states that this discount did not apply to the Bali 4.8, Bali 4.4 and Bali 4.6 catamarans: five- and six-cabin boats that cost €13,100 to €17,500 a week at the 2026 peak, among the most expensive on its list.
The same list publishes the other discounts, and how far they stack:
Early booking: 10%, until 31 January (2026 season)
Boat show or repeat customer: 5%
Two-week charter: 5%
Three weeks or more: 10%
Maximum combined discount: 15%
On a boat listed at €4,000 for the week, an example figure rather than a quote, 10% is €400, or about €67 each for a crew of six. That is real money, but it is not the main reason to book early. The main reason is choice: in January you are picking from the whole fleet, and in May you are picking from what is left.
There is no guarantee that the 2027 deadline will be 31 January again. Treat it as the pattern to check for, not a promise, and ask the fleet directly when you enquire.
How much do you pay when you book, and when is the rest due?
Expect to pay half the charter fee to confirm the boat. Both operators I checked say exactly that, but they collect the second half at very different times.
Ionian Charter (Greece): 50% of the charter fee on confirmation; the other 50% 4 weeks before embarkation. If no payment arrives after confirmation, the charter is treated as cancelled.
Sunsail and The Moorings (UK terms): 50% of the total holiday cost at booking; the balance at least 120 days before departure. A missed payment cancels the booking.
Four weeks against 120 days is a big gap. For a charter starting on Saturday 24 July 2027, the balance at Ionian Charter falls due around 26 June. Under Sunsail and The Moorings' UK terms it is due by 26 March, four months before you sail.
My own fee works on the same principle, just smaller. A skipper week booked directly with me is a separate written agreement from the boat: a deposit locks the dates, and the balance is due 30 days before boarding, as my FAQ sets out. The weekly fee and what it covers are on my Hire a Captain page, and the wider question of what a skipper costs and why is in my guide to hiring a freelance skipper.
What does it cost to cancel a booked charter?
It depends almost entirely on the fleet. Early booking is only cheap if cancelling early is cheap, and the two sets of terms I read could hardly be further apart.
Ionian Charter's published cancellation scale:
More than 90 days before embarkation: a €250 cancellation fee
40 to 90 days before: the 50% down payment is kept
Less than 40 days before: the full 100% is kept
If the yacht is chartered again for the same period on the same conditions, the 50% down payment is refunded
Sunsail and The Moorings' UK conditions (March 2025):
91 days or more before departure: you lose the deposit, 50% of the total holiday cost
90 days or less: 100% of the total holiday cost
Put the same €4,000 example boat through both, 100 days before departure. At Ionian Charter, cancelling costs €250. Under the Sunsail and Moorings UK terms it costs €2,000, because 100 days is still more than 91 and the deposit goes. At 60 days out it is €2,000 at Ionian Charter and €4,000 at the other two.
None of this makes one fleet better than another; prices and inclusions differ in other ways too, and I compared the two big operators in detail in Sunsail Flotilla vs The Moorings. It does mean that the date you book and the fleet you book with are one decision, not two. If there is any real chance your plans change, read the cancellation table before you pay the first half, and check what your travel insurance would cover.
Which weeks go first?
July and August, and that is true on my calendar as well as the fleets'. As of October 2026, every week of my 2027 season is still open except 15 to 22 May, with the last week of August confirmed on request.
The fleets price that demand openly. Ionian Charter's most expensive period for 2026 ran from 25 July to 22 August, with its middle period from 9 May to 25 July and from 22 August to 3 October. I worked through what the shoulder weeks actually save in Sailing Greece in the shoulder season, so I will not repeat the arithmetic here.
One more signal is worth noticing. Ionian Charter excluded three of its biggest, most expensive catamarans from the early-booking discount. A fleet has little reason to discount boats it expects to sell anyway. Read that as a hint, not a statistic, but if you want a large catamaran in August, I would treat the winter as your booking window, not the spring.
Should you book the skipper or the boat first?
Talk to the skipper first, then confirm the boat. The boat is where the 50% payment and the cancellation scale sit, so it makes sense to know your skipper is free before you commit that money.
That is how I work. You tell me your dates, waters and crew; within 24 hours you have a straight answer on whether I am free, a suggestion for the route or the boat, and one written quote. I do not own a fleet, so the yacht comes from a licensed partner charter company and I help you choose a good one. Once the dates are agreed in writing, you book the boat knowing the skipper is already in place.
Doing it the other way round is not a disaster, but it can leave you with a confirmed July boat, half of it paid, and a search for a skipper in the busiest weeks of the year.
What does a sensible 2027 booking calendar look like?
For a summer week, it looks like this.
October to December 2026. Settle the week, the waters and the size of the crew. Ask a skipper to hold the dates. If you are choosing between Athens and the Ionian, read my 7-day Ionian itinerary from Lefkada and the Greece charters page now, while every boat is still free.
By the end of January 2027. Confirm the boat, if your fleet repeats a 31 January early-booking deadline. Pay the 50%.
Late March. Balance due if you booked under Sunsail and The Moorings' UK terms (120 days before a 24 July start).
Late April. At both fleets, cancelling now costs at least half the charter fee.
Mid June. At Ionian Charter, cancelling now costs the full fee.
Late June. Skipper balance (30 days before) and the Ionian Charter balance (4 weeks before).
For a May, June or September week you can slide the first two steps a couple of months later. I would still confirm by the end of March: the earlier you book, the more of the fleet you are choosing from.
Is it worth waiting for a last-minute deal?
For a summer week with children, no. Last-minute discounts exist, but by definition they are for weeks that have not sold.
The Moorings' current Mediterranean offer is a good example: 20% off charters in Croatia, Italy and Greece departing up to 30 November 2026, booked by 2 November 2026, for its US bookings. That is a late-autumn sale on this year's remaining weeks. Ionian Charter's 2026 list publishes an early-booking discount and length discounts, but no last-minute one at all.
If your dates are flexible and you are happy with whatever boat is free, waiting can work. If you are tied to school holidays, you are betting that the one boat you want in the busiest fortnight of the year will still be empty in June. I would not take that bet with a family.
How does a skippered booking differ from a bareboat one?
The boat side is the same; you simply add a second, smaller agreement. You still charter the yacht from the fleet on the fleet's terms, with the same 50% to confirm, the same balance date and the same cancellation scale. The skipper's fee is separate and paid to the skipper.
The practical differences are on the boat: a skipper needs their own cabin, and their meals normally come from the crew's provisioning. Both are explained in my guide to what having a skipper on board is like. And the refundable security deposit that the fleet holds against damage is a separate thing again from any of the booking payments above; it has its own rules, which I set out in charter security deposits in Greece and Croatia.
FAQ
When should I book a skippered charter in Greece for July or August 2027?
Between now and the end of January 2027. Big fleets such as Sunsail are already taking 2027 bookings, the summer weeks fill first, and at least one Greek fleet ran its 2026 early-booking discount only until 31 January.
How much deposit do I pay to book a charter yacht in Greece?
Typically half the charter fee to confirm. Ionian Charter asks for 50% on confirmation and the rest 4 weeks before embarkation; Sunsail and The Moorings' UK terms ask for 50% at booking and the balance at least 120 days before departure.
Is there an early-booking discount for 2027?
For the 2026 season, Ionian Charter offered 10% until 31 January 2026, excluding its Bali 4.4, 4.6 and 4.8 catamarans. Its 2027 list was not yet published on 19 October 2026, so ask the fleet for the current deadline.
What happens if I cancel my charter?
It depends on the fleet. At Ionian Charter you pay €250 more than 90 days out, lose the 50% down payment from 40 to 90 days, and lose everything inside 40 days. Under Sunsail and The Moorings' UK terms you lose the 50% deposit 91 days or more out and 100% at 90 days or less.
Is the booking deposit the same as the security deposit?
No. The booking payment is part of the charter price. The security deposit is a separate, refundable sum the fleet holds against damage.
Which weeks of 2027 are still available with you?
As of October 2026, every week except 15 to 22 May; the last week of August I confirm on request. July and August go first.
Should I book the skipper or the boat first?
Ask the skipper first. Once your skipper has confirmed the dates in writing, book the boat and pay its first 50% knowing the week is complete.
Are last-minute charter deals worth waiting for?
Only if your dates and boat are flexible. Last-minute offers are for weeks that have not sold, which rarely include the school-holiday weeks families need.
About the author
I am Gediminas Vengrauskas, a Lithuanian captain with six years of sailing and about 1,000 nautical miles logged. I hold a Coastal Skipper licence for sail and motor vessels up to 24 metres, day and night, up to 12 miles offshore, plus an ICC, a VHF radio certificate and a 2026 first-aid certificate. The boats I have skippered are the Bali Catspace and Lagoon 42 catamarans and the Beneteau Oceanis 46 and Jeanneau Sun Odyssey 42 monohulls, and I have sailed the Ionian, the Saronic and the Cyclades in Greece, Dalmatia in Croatia, and the Baltic. I do not own a fleet; your boat comes from a licensed partner charter company, and I skipper it.
Planning a week in 2027?
Send me your preferred week, your crew and the waters you have in mind through the contact form, and I will tell you honestly whether the dates work. I reply within 24 hours.
Sources checked 19 October 2026: Ionian Charter's 2026 price list and terms; Sunsail and The Moorings UK booking terms and conditions (March 2025); Sunsail's booking search and The Moorings' Mediterranean offer page.
