Start and finish in Mykonos and spend the week in the heart of the Cyclades: Naxos, Amorgos, Santorini, Ios and Paros, with a full day on the Santorini caldera in the middle. Flying into Mykonos means you can be on board within an hour of landing — no ferry, no repositioning day — and the route runs about 180 nautical miles with no leg longer than ~47nm.
The week runs Saturday to Saturday: board Saturday afternoon at Mykonos, hand back the following Saturday morning, seven nights aboard. Mid-summer meltemi is strongest in this stretch of the Cyclades, so your captain may reverse the loop or reorder days — the shape below assumes normal conditions.
The route at a glance
- Day 1: Board in Mykonos — old town evening
- Day 2: Mykonos to Naxos (~20nm)
- Day 3: Naxos to Amorgos (~30nm)
- Day 4: Amorgos to Santorini (~45nm)
- Day 5: Santorini — the caldera day
- Day 6: Santorini to Ios (~20nm)
- Day 7: Ios to Paros and Mykonos (~47nm)
Day 1 – Board in Mykonos
Embarkation is Saturday afternoon at Mykonos — most guests land at the airport and are aboard within the hour. Spend the first evening the way Mykonos does best: the windmills and Little Venice at sunset, dinner in the old town’s lanes, and as much nightlife as your group has appetite for. We book restaurant tables ahead in July and August; walk-ins are genuinely difficult in season.
Day 2 – Mykonos to Naxos (~20nm)
A short morning hop south to the largest island of the Cyclades. Naxos harbor sits directly beneath the Portara — the huge marble doorway of the unfinished Temple of Apollo — and the old town behind it is a maze of Venetian arcades that mass tourism has largely missed. Mount Zas, the highest peak in the Cyclades, dominates the skyline inland. Swim stop options on the southwest coast beaches are excellent in meltemi weather; your captain will pick the sheltered side.
Day 3 – Naxos to Amorgos (~30nm)
East to the wildest island of the week. Amorgos is steep, quiet, and dramatic — its Panagia Hozoviotissa monastery is plastered against a sheer cliff 300 meters above the sea, and the visit (dress modestly, accept the offered loukoumi) is one of the most memorable hours in the Cyclades. Katapola and Aegiali are both good overnight harbors with honest tavernas; the bay swimming along the way is the deep-blue kind the island is famous for.
Day 4 – Amorgos to Santorini (~45nm)
The longest leg of the week, run in the morning so you arrive at the caldera with the afternoon ahead. Entering Santorini by sea — cliffs banded red and black, villages like snow on the rim — is the way this island is meant to be seen. Go up to Oia or Fira late in the day as the cruise crowds leave, or hold the sunset for the deck. The caldera anchorages are exposed, so where you spend the night is the captain’s call.
Day 5 – Santorini
A full day for the week’s headliner, and it earns it. Morning at the Nea Kameni hot springs in the middle of the flooded crater, a swim off the volcanic islets, then time ashore: the caldera-rim walk between Fira and Oia if your group likes to move, or a winery visit — Santorini’s volcanic assyrtiko is a genuinely distinctive white — if it prefers to sit still with a view. Dinner ashore tonight is the one we most often book in advance.
Day 6 – Santorini to Ios (~20nm)
A short run north puts you on Ios by lunch. The island wears two faces: the party beaches around Mylopotas, and quiet coves like Agia Theodoti and Manganari that most visitors never reach — tell us which face your group wants and the day is planned around it. The hilltop Chora is far prettier than Ios’ reputation suggests, and evenings in its lanes are lively without Mykonos prices.
Day 7 – Ios to Paros and Mykonos (~47nm)
The run home, broken at Paros: a swim and long lunch off the Antiparos channel or Kolymbithres’ sculpted granite coves in Naoussa bay. From there it is an afternoon leg back to Mykonos for a final evening in the old town — and if the group missed Delos earlier in the week, the sacred island sits right on the approach and a late pass is often possible. Disembarkation is Saturday morning after breakfast.
How to make this week work
This is the best-value way to combine Mykonos and Santorini in one week: you fly into and out of the same airport, skip the long Athens crossings, and still get a full caldera day. It suits catamarans and motor yachts equally — the two ~45nm legs are the only real distances. In strong meltemi your captain may run the loop in reverse so the long legs go downwind; the islands stay the same either way.
Coming from Athens instead? See the Athens to Santorini round trip, or start closer to the middle of the chain with the Paros catamaran itinerary.
Talk to a Yacht Charter Expert
Finding the right yacht is one of the most important parts of the whole charter process, and one of the easiest places to go wrong without the right guidance.
That is where our experience matters. We know how to look beyond the listing, spot the differences that matter, and shortlist yachts that are a strong fit for the group, the budget, and the kind of trip you actually want to have.
If you are planning a charter in Greece, we would be happy to help you find the right yacht.
