Every week of the season somebody asks me the same question, usually from New York, Boston or Los Angeles, and usually with a map open on the other screen: which Greek islands should we charter to? The honest answer is that Greece is not one sailing ground but five, and they behave like five different countries. Choose the ground first and the islands choose themselves.
This is the broker's version for 2027, written for a fully crewed week, which is the only kind this house arranges. Every distance below comes from the sailing table we use to plan real weeks, every anchorage from our 48 island anchorage guides, and every rate from the Greek Charter Index, per yacht, per week, in euros.
Which Greek islands are best for a crewed yacht charter in 2027?
The Cyclades are the islands on the postcard, Mykonos, Paros, Naxos, Ios, Santorini, and the ground with real wind. The Ionian is green, sheltered and gentle, the region I put families on first. The Saronic Gulf starts where you land: Aegina is 18 nautical miles from Alimos Marina, Hydra a few hours from the airport. The Dodecanese from Rhodes and the Sporades from Skiathos are beautiful grounds and outside the ones this house works; more on that below.
Which Cyclades islands work best by yacht, and in what order?
Sail them south, so the meltemi is behind you. From Alimos it is 35 nautical miles to Kea and 15 more to Kythnos, the two stepping stones. Then Mykonos to Paros is 30 miles, Paros to Naxos 12, Naxos to Ios 30, Ios to Santorini 25. That is the classic seven-day Cyclades route, and it ends at Santorini's Vlychada Marina, alongside in 5 to 8 metres, for the flight home.
The anchorages are the detail that decides a good week. Ornos Bay on Mykonos holds in 6 to 12 metres of sand with excellent shelter from the north, which is why it fills by mid-morning in July. On Paros, Naoussa Bay is open to the meltemi while Parikia on the west side is protected from it; the captain chooses by the morning forecast, not by the brochure. Santorini has no anchorage at all: Ammoudi under Oia is mooring buoys over a caldera 80 to 180 metres deep. For the quiet islands, Milos and Folegandros, I wrote a separate piece on the Cyclades beyond Mykonos and Santorini.
One warning, given honestly. The meltemi blows in July and August, strongest from mid-July to late August, and reaches force 6 in the channels between the islands. A crewed catamaran flattens it, a motor yacht outruns it, and June or September removes it. If someone aboard is nervous about wind, do not book the Cyclades for the second week of August.
Why is the Ionian the best Greek island group for a family charter?
Because the legs are short and the water is flat. There is no meltemi on the west coast, only an afternoon thermal, and the islands sit close: from Lefkada it is 20 miles to Ithaca and 25 to Kefalonia; from Corfu it is 35 to Paxos. Children swim every afternoon, nobody is seasick, and the harbours, Fiskardo, Gaios, Vathy, Frikes, Kioni, are the prettiest villages in the country seen from the water. The seven-day Ionian route runs Lefkada, Meganisi, Ithaca, Kefalonia, Paxos and back, and the playbook for chartering with young children was written with these waters in mind.
Which islands can you reach in a short week from Athens?
The Saronic ones. Aegina is 18 nautical miles from Alimos, Hydra 25 beyond it, Spetses 25 beyond that, so a five-day crewed charter covers the lot without a single long passage. Hydra has no cars and a harbour you moor stern-to on chains laid by the port authority over a 30 to 40 metre bottom; when the quay is full the captain anchors at Vlychos in 8 to 15 metres and tenders you in. Spetses keeps the same scale. This is the ground for guests landing late in Athens, or for a first charter before committing to a full Cycladic week.
Are the Dodecanese and the Sporades part of a George Yachts week?
Honestly, no. This house charters from Athens, the Cyclades and the Saronic, and from Lefkada or Corfu for the Ionian; the crewed fleet is based there, and that is where I can vouch for every yacht and every crew. From Rhodes, Symi is 25 miles and Kos 45, and the seven-day Dodecanese itinerary adds Patmos; the Sporades are a different green altogether, with Skopelos 15 miles from Skiathos and the pine reaching the water. Our anchorage guides cover them for the sailor planning those waters, but I do not arrange weeks there. If your heart is set on Rhodes, I will tell you so on the first call rather than sell you a delivery.
Which yacht suits which islands?
A crewed catamaran draws little and opens the bays deep keels must skip, the Antiparos channel in 5 to 15 metres among them; it is the family answer in every ground. A motor yacht buys distance and timing, Athens to Mykonos in four to five hours on a planing hull, which matters when the meltemi opens and closes the good anchorages by the hour. Three honest examples from the live fleet, per yacht per week, net base: Summer Star, a 16 metre sailing catamaran for ten, at EUR 17,000 to 22,000; Majesty of Greece, a 20 metre power catamaran for ten, at EUR 34,000 to 48,000; and Imladris, a 24 metre sailing catamaran for eight, at EUR 65,000 to 85,000.
What does a crewed week to the Greek islands cost in 2027?
One price per yacht per week, never by the head. On the Greek Charter Index the weekly net base runs from EUR 17,000 to 22,000 for a crewed sailing catamaran of 12 to 16 metres, EUR 17,500 to 47,500 for a motor yacht of 18 to 25 metres, and EUR 56,000 to 90,000 for the 23 to 24 metre catamarans. Add VAT at the yacht's certified rate, 5.2, 6.5, 7.8 or 12 percent, with 13 the statutory ceiling; APA of 20 to 30 percent for sail and catamaran and 30 to 40 percent for motor yachts, spent by the captain against receipts; and a customary gratuity of 10 to 15 percent of the base. The cost calculator runs the whole line in one screen, and the complete cost breakdown explains every item.
How does an American family book a crewed charter to the Greek islands?
With a US company on their side of the Atlantic. Most of our guests are American, and every charter this house closed this season was booked by American guests. You contract with George Yachts Brokerage House LLC, a Wyoming company, under MYBA-standard charter terms, and you reach me on a Miami line, +1 786 798 8798, or in Athens. Athens is a direct flight from New York; the crewed fleet is based there, so you board at Alimos on the day you land or the next morning, on any day of the week. The page for American clients sets out the entity, the contract and the flights, the American's guide covers money and the door-to-deck day, and the 2027 lead times explain why the best July and August weeks commit by late winter.
When are the Greek islands NOT the right choice?
Three honest cases. If the party is wind-averse and the dates must be the second half of August, the Cyclades will argue with you every afternoon; take the Ionian, or a catamaran, or move the week to June or September, as the month-by-month guide sets out. If Santorini must be a night at anchor, it cannot be: the caldera is mooring buoys or the marina at Vlychada. And if you are more than twelve guests, Greek law caps every charter yacht at twelve sleeping passengers, so plan two yachts sailing in company.
The 2027 calendars are open. Tell me who is coming, how many, and what the sea needs to do for them, and I will answer with three named yachts and the ground that suits them. If you would rather start by playing, the island quiz takes ninety seconds.
