Cyclades · Santorini, Paros and Syros, Greece
In the Cyclades, our stops begin as daylight fades
A Cyclades sailing trip from 17 to 28 October 2025, from Santorini to Paros and Syros, between anchorages, illuminated villages and late-season sailing.
The route, stop by stop
Traced from the positions of our photos.
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01 / 07 · 17 to 21 October
Spato-Loutsa
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02 / 07 · 21 to 22 October
Oia
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03 / 07 · 22 October
Thira
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04 / 07 · 22 to 24 October
Nisida Nea Kammeni
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05 / 07 · 24 to 25 October
Náoussa
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06 / 07 · 25 to 28 October
Ormos Foinika
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07 / 07 · 28 October
Spato-Loutsa
Base map: Natural Earth
In 30 seconds
Place The Cyclades in late October, from Santorini to Paros and Syros: Oia illuminated on its cliff, a Naoussa church gilded by the evening sun and Foinikas Bay beneath a crescent moon.
People What matters in the Cyclades is the group on board: friends, family and Florent as our skipper, free to set our own pace.
Activity Sailing from island to island at the very end of the season, and finishing 25 October almost level with the water in Foinikas Bay.
- When
- 17 to 28 October 2025, the final month of a sailing season that runs from May to October.
- Route
- Attica, Santorini, Paros, Syros, then northwest and back to Attica.
- Boat
- probably a charter catamaran with a skipper; our memory of the model is uncertain.
- Weather
- October averages 20°C in the air and 22°C in the water, after the Meltemi peaks in July and August.
- Best for
- crews who prefer the end of the season to the height of summer.
Why we came
During these 12 days in the Cyclades, several of our photographs are taken as the light drops. At Santorini, Oia lights up at the top of the cliff while we lie at anchor. On Paros, the evening sun colours the walls of a church in Naoussa. On Syros, Foinikas Bay is photographed from the tender beneath a crescent moon.
We travel from 17 to 28 October 2025, in the final days of the sailing season. The boat leaves Paros, heads south to Santorini, then returns north through Paros and Syros before Attica. In late October, days are shorter and warmth is less dependable than in summer.
The stay, hour by hour
Eight days, ten moments
Day 1 · Attica, late at night
23:30
We land in the evening at Athens International Airport in Spata, then take a taxi. The yacht is waiting for us on Paros.
Day 4 · Meals on board
18:00
Two silver fish lie in a cardboard box on the boat's table. The photo introduces another part of the sailing trip: meals on board. At lunchtime, we cook something quick. In the evening, the two cooks in our crew often take over, and we eat extremely well. On shore, our default choice remains gyros.
Day 5 · Oia lights up above us
19:50
Night has already fallen when we anchor below Oia, at the northwestern tip of Santorini. High on the cliff, the white houses glow yellow, blue and purple around a small bell tower. From the yacht, the village appears suspended above a mass of black rock. Large pale clouds cross the sky, but the lights remain visible deep into the caldera.
Day 6 · At the centre of Santorini's caldera
12:07
At noon, we reach Néa Kaméni (Nea Kameni), the volcanic island at the centre of Santorini's caldera. It is the still-active part of the volcano that shaped the archipelago.
12:49
We anchor beside the island, then continue on foot across the volcano. The smell of sulphur follows us.
Day 8 · Naoussa in the evening sun
18:04
We moor in the small harbour at Naoussa, on northern Paros. The evening sun falls directly onto a white church with two bell towers, red doors and green domes. We stay for dinner in the village. We find Naoussa especially appealing.
Day 9 · Moonlight over Foinikas Bay
19:26
After a day at sea from Naoussa, we enter Foinikas Bay on southwestern Syros. From the tender, our viewpoint is almost level with the water. A strip of orange remains on the horizon as a crescent moon rises into the dark blue. Its reflection reaches towards us across the rippled sea. To the right, the red light of an islet trembles beside the moonlight.
Day 10 · Heading northwest
12:45
We leave Syros and head northwest. By noon, the boat is already west of the island.
19:59
By nightfall, we have made further progress northwest.
Day 12 · Back to Attica
We return the yacht to its home port on Paros, then reach Attica before our flight home.
15:15
In the afternoon, we are back in Spata, near Athens International Airport. The sailing trip ends here.
Sailing in the Cyclades: the options and the boat
There are three ways to sail the Cyclades: book a cabin on a shared boat, charter a private yacht with a skipper or rent without a skipper, which requires a licence. We had booked a monohull, but an accident involving the operator changes the boat shortly before departure. We eventually sail on what we believe is a charter catamaran, with Florent as skipper.
The room: a cabin on board
We sleep on board every night, in one of the boat's four cabins. They are simple and make use of every inch, but do exactly what we need them to do.
Things to do during the stops
What to do on a Cyclades sailing trip, based on our route:
- Oia, Santorini: watch the village light up after dark from below the cliff.
- Nea Kameni: walk on the volcanic island at the centre of Santorini's caldera.
- Naoussa, Paros: climb to the twin-bell church in the evening sun.
- Foinikas, Syros: finish the day at water level beneath the moon.
Eat
On shore, we eat plenty of gyros. Lunch on board is quick; in the evening, two cooks in our crew often take charge of dinner.
The vibe as daylight fades
In late October, much of the journey happens at the end of the day: golden light on Naoussa, the deep blue of Foinikas Bay, then Oia illuminated above the anchorage. Between the main stops, we pause in several small anchorages.
That's why
At 19:26 on 25 October 2025, in Foinikas Bay on Syros, the reflection of a crescent moon and the red light of an islet lie side by side on the rippled sea, almost level with the water. That is the moment our photographs keep from this trip.
You'll love it if
- you prefer the end of the day to midday beaches: our stops unfold at sunset and after dark
- you want to sail the Cyclades after the Meltemi peak in July and August
- you enjoy islands that feel distinct from one another: Santorini's volcanic caldera, Naoussa Bay on Paros and a bay on Syros
Skip it if
- you are looking for summer heat: October averages about 20°C in the Cyclades
- you want long evenings on the beach: by 19:50 on 21 October, Oia is in complete darkness
- you prefer to unpack in one hotel: a sailing trip changes anchorage
Our take
We would sail the Cyclades again, though not under exactly the same conditions. The route between Santorini, Paros and Syros produces very different stops: a volcanic caldera, Naoussa harbour and then a Syros bay beneath the moon. By late October, the peak of the Meltemi has passed.
The trade-off is clear. With average air temperatures around 20°C, days are shorter and the weather no longer feels like summer. Our itinerary also involves a great deal of sailing compared with time ashore. It therefore suits crews who genuinely enjoy life at sea, more than travellers imagining a sequence of long beach days.
We would leave earlier in the year next time, for a few extra degrees and more hours of daylight, and choose a shorter route. To charter without a skipper, you need a coastal licence or equivalent and a VHF radio certificate. With a skipper or on a cabin charter, no licence is required.
Your questions
Where do Cyclades sailing trips start?
Most Cyclades sailing trips leave from ports near Athens, such as Lavrio or Piraeus, 30 to 45 minutes from Athens International Airport. Some itineraries start directly on an island. Our journey begins near the airport, but the boat leaves from Paros.
When is the best time to sail the Cyclades?
The Cyclades sailing season runs from May to October. For calmer conditions and fewer people, May to June and September are the strongest windows. July and August are the peak of the Meltemi, a northerly wind that generally reaches force 5 to 7 on the Beaufort scale, with gusts above force 8 in channels between islands. October closes the season, averaging 20°C in the air and 22°C in the water.
Do you need a licence to sail in the Cyclades?
Yes, if you charter without a skipper. The skipper must hold a coastal licence or equivalent certificate of competence, along with a restricted VHF radio certificate, and there must be a second experienced crew member. No licence or sailing experience is required for a skippered or cabin charter.
How many miles and hours do you sail?
The positions recorded by our photographs represent about 126 nautical miles in straight lines between Santorini's caldera and our return to Attica, across five days at sea. The calculation gives 43.5 miles from Nea Kameni to Naoussa over two days; 23.8 from Naoussa to Foinikas Bay in one day; 20.7 and 8.6 on 26 October; then 29.9 to Attica. The route actually sailed is longer because these calculations do not follow tacks or course changes.
How much does a Cyclades sailing trip cost?
In October 2026, published prices for a catamaran in the Cyclades ranged from €2,700 to €12,000 per week, depending on the boat and arrangement. The shared onboard kitty, used for trip expenses, comes on top of that price.
The essentials
A late-October Cyclades sailing trip uses the final window of the season: our route over 12 days takes in Santorini, Paros and Syros.
| Detail | What we know |
|---|---|
| Dates | 12 days, from 17 to 28 October 2025 |
| Route | Attica, Santorini (Oia, Nea Kameni), Paros (Naoussa), Syros (Foinikas), then back to Attica; about 126 nautical miles in straight lines between photo positions |
| October averages | 20°C in the air, 22°C in the water |
| Access | Athens International Airport in Spata; nearby ports are 30 to 45 minutes away |
| Departure port | Paros, boarding on the evening of 17 October |
| Boat and arrangement | probably a charter catamaran with a skipper; model not confirmed |
| Catamaran price from one operator, 7 nights | €2,700 to €3,700 depending on model, Cyclades Sailing's 2027 rates, checked in October 2026 |
| Price by arrangement from one broker | €3,000 to €6,000 per week bareboat, €2,000 to €4,000 for a monohull, €5,500 to €12,000 crewed, according to Wiyachts, checked in October 2026 |
| Additional budget | 40 to 70% above the base price for the total budget, according to Wiyachts, checked in October 2026 |
We paid for this stay ourselves in October 2025.
Adapted from the original French article.
The address
Cyclades
Archipelago · Cyclades, Mer Égée, Greece
- Dates
- 12 days, from 17 to 28 October 2025
- Route
- Attica, Santorini (Oia, Nea Kameni), Paros (Naoussa), Syros (Foinikas), then back to Attica; about 126 nautical miles in straight lines between photo positions
- October averages
- 20°C in the air, 22°C in the water
- Access
- Athens International Airport in Spata; nearby ports are 30 to 45 minutes away
- Departure port
- Paros, boarding on the evening of 17 October
- Boat and arrangement
- probably a charter catamaran with a skipper; model not confirmed
- Catamaran price from one operator, 7 nights
- €2,700 to €3,700 depending on model, Cyclades Sailing's 2027 rates, checked in October 2026
- Price by arrangement from one broker
- €3,000 to €6,000 per week bareboat, €2,000 to €4,000 for a monohull, €5,500 to €12,000 crewed, according to Wiyachts, checked in October 2026
- Additional budget
- 40 to 70% above the base price for the total budget, according to Wiyachts, checked in October 2026
- Getting there
- Athens International Airport in Spata; nearby ports are 30 to 45 minutes away
- Coordinates
- 37.0000° N, 25.0000° E
37.0000° N, 25.0000° E
How this story was made
Stay paid for by us in October 2025.
We have nothing to sell you. We are simply here to share the incredible experiences we are lucky enough to live.
Tom and Julie
