☰ Menu
Sample itinerary · Greece · 7 nights
One Week by Yacht in the Cyclades
A sample seven-night crewed yacht itinerary from Mykonos to Santorini, by way of sacred Delos, Paros and Antiparos, the sea caves of Milos and quiet Folegandros.
White villages spilling down to the water, blue-domed chapels, volcanic cliffs and some of the clearest sea in the Mediterranean: the Cyclades are what most people picture when they think of a Greek island summer. A yacht lets you see the famous names at their best, early in the morning or after the ferries have gone, and then slip away to islands most visitors never reach.
This sample week is a starting point for a crewed charter in 2027. Your captain will adjust it around the wind, the yacht and your group. For the bigger picture, see our yacht charter in Greece page.
Why the Cyclades work so well by yacht
The Cyclades are a ring of islands in the central Aegean, and the hops between them are mostly a few hours. Mykonos and Santorini both have international airports, so this route runs one way, with no need to retrace your steps.
The one thing to plan around is the meltemi, the dry northerly wind that blows through the Aegean in summer and is usually strongest in July and August. It keeps the islands fresh, but it can make some crossings lively. Sailing broadly north to south, as this itinerary does, keeps most of the wind behind you, and many groups choose a motor yacht or a stable catamaran for comfort. Your captain will read the forecast each day and reorder stops if needed.
The week, day by day
Day 1 · Mykonos – board and settle in
Meet the yacht in Mykonos, settle in and go through the plan with the captain and chef. In the evening, the tender can take you ashore to Little Venice, where the old captains’ houses sit right on the water, and up to the windmills for sunset.
Day 2 · Delos, then on to Paros
Start with a morning visit to Delos, a short hop from Mykonos. In myth it was the birthplace of Apollo and Artemis, and the whole island is a UNESCO World Heritage archaeological site, with the Terrace of the Lions, temples and mosaic-floored houses. Visitors can’t stay overnight, so go early, then cruise south to Paros in the afternoon.
Day 3 · Paros and Naoussa
Anchor in the bay off Naoussa on Paros’s north coast. The little harbour of fishing boats is lined with tavernas and bars, and the lanes behind are among the prettiest in the Cyclades. The beaches around the bay, such as Kolymbithres with its sculpted granite rocks, are good for swimming.
Day 4 · Antiparos and Despotiko
Cross the narrow channel to Antiparos, Paros’s quieter neighbour. Anchor in the clear, shallow water near the uninhabited island of Despotiko, where archaeologists have been uncovering an ancient sanctuary of Apollo. Ashore on Antiparos, the great cave in the hills is worth the short trip.
Day 5 · Milos and Kleftiko
A longer run south-west brings you to Milos, a volcanic island of coloured cliffs and coves. The highlight is Kleftiko on the south-west coast, a cluster of white rock arches and sea caves once used by pirates, which is best reached by boat. Anchor nearby, swim through the arches and explore by tender or paddleboard.
Day 6 · Milos – Sarakiniko and Plaka
Spend a second day on Milos. On the north coast, Sarakiniko’s smooth, white volcanic rock looks like a moonscape. Later, head up to the hilltop village of Plaka for sunset, or visit Klima, where the brightly painted boathouses sit right at the water’s edge.
Day 7 · Folegandros, then Santorini
Stop at Folegandros, one of the most unspoilt islands in the group, whose clifftop Chora is one of the most beautiful villages in Greece. Then cruise on to Santorini. Arriving inside the caldera, the flooded crater of the ancient volcano, with the white towns lining the rim above you, is unforgettable. Anchor below Oia for the famous sunset from the water, without the crowds.
Day 8 · Disembark in Santorini
After breakfast, disembark in Santorini for your flight home or a few extra nights on the island.
Tell us your dates and group size. Jake will send a free shortlist of crewed yachts for the Cyclades, with availability and rates.
When to go and how to book
The Greek charter season runs from May to October. June and September are often ideal, with warm water, lighter winds than midsummer and fewer crowds. July and August are the busiest and windiest months in the Cyclades, so choose your yacht with that in mind. If you’d like a calmer, shorter-hop week close to Athens, our sample Saronic Islands itinerary is a good alternative.
Crewed charters are usually quoted as a weekly charter fee, plus an Advance Provisioning Allowance (APA) for fuel, food, drinks and berthing, and VAT and local taxes where they apply. Our plain-English guide to yacht charter costs explains each element before you commit.
The best yachts and weeks go early, especially for the peak summer. Our guide to booking a Mediterranean charter for 2027 early explains how contracts and deposits work.
Keep planning
More Greece guides
Plan your Cyclades charter
Tell us your dates, group size and the kind of yacht you have in mind, whether that’s a sleek motor yacht, a spacious catamaran or a classic sailing yacht. We’ll come back with a shortlist of crewed yachts, with photos, crew details, availability and rates. Contact us or message Jake on WhatsApp to start planning your 2027 week in the Greek islands.
Plan your charter
Your free yacht shortlist in 30 seconds
Tap your answers and send them to Jake on WhatsApp. You’ll get yachts, crews, availability and rates, usually within one working day. Free, with no obligation.