Sailing in the Cyclades is one of the great yacht charter experiences in Greece, but it is also one of the most misunderstood.
Every summer, crews arrive expecting gentle island hops, only to discover that the Meltemi wind dictates far more than personal preference. This guide focuses on what is, in practice, the most reliable and commonly sailed Cyclades route: one that keeps you in the islands even during strong wind periods, without committing you to long, exposed passages that can turn a holiday into a delivery.
This is not a “no-wind” itinerary. It is a wind-aware Cyclades route designed for crews who want flexibility, protected anchorages, and a stress-free return to base.
Why This Sailing Route Exists
During July and August, there are many weeks when:
- The Meltemi blows 25–35 knots for several consecutive days
- Southern crossings become uncomfortable or impractical
- Beating back north late in the week becomes the biggest risk
In these conditions, most experienced skippers do not push deeper south into the central Cyclades. Instead, they sail the western island chain, staying within reach of sheltered anchorages and multiple bail-out options.
This route is:
- Suitable for beginner to intermediate crews
- Ideal for families or mixed-experience groups
- The default choice when conditions are uncertain
- The safest way to remain in the Cyclades rather than diverting immediately to the Saronic Gulf
The Core Cyclades Route from Lavrion
Lavrion → Kythnos → Serifos → Sifnos → Kea → Lavrion
This western Cyclades loop benefits from:
- Partial lee from the Greek mainland
- Shorter daily legs (typically 15–25 NM)
- Excellent protection from the northerly Meltemi
- Frequent ports and water stops
- Flexible sequencing based on the forecast
It is the route most charter skippers end up sailing, regardless of original plans.
Do Not Sail This Route in a Fixed Order
The single biggest mistake crews make is following an itinerary blindly.This route works because it can be re-ordered around the wind.
If Strong Winds Are Forecast at the Start of the Week
- Sail south early while conditions allow
- Reach Serifos or Sifnos as soon as possible
- Spend the rest of the week working slowly north with shorter, protected hops
If Strong Winds Are Forecast at the End of the Week
- Stay closer to Lavrion and Kea initially
- Avoid committing too far south
- Position yourself north early so you are not forced into an upwind return
The islands do not change. The order does.
Why These Islands Work in Meltemi Conditions
Kythnos
Kythnos offers some of the best all-round protection in the western Cyclades.
- Kolona Bay provides shelter depending on wind angle
- Loutra offers a secure harbour with water, fuel access, and tavernas
- Multiple fallback anchorages on both coasts
Kythnos is often where crews wait out the first strong Meltemi pulse.
Serifos
Serifos combines rugged scenery with practical sailing.
- Livadi Harbour offers reliable shelter
- Easy access to the hilltop Chora
- Good holding and protection for northerly winds
It is far enough south to feel like “proper Cyclades” without committing to exposed crossings.
Sifnos
Sifnos is one of the most forgiving islands in strong winds.
- Kamares Bay is well protected
- Multiple nearby anchorages for varying conditions
- Excellent provisioning and road access inland
It is also a natural turning point if conditions deteriorate.
Kea
Kea is your safety net.
- Vourkari Bay is one of the most secure anchorages near Lavrion
- Ideal staging point before returning to base
- Excellent shelter if northerlies peak late in the week
Many skippers plan to finish here regardless of route.
Typical Daily Sailing Distances
- Lavrion → Kythnos: 20–25 NM
- Kythnos → Serifos: 20 NM
- Serifos → Sifnos: 18–22 NM
- Sifnos → Kea (split over two days if needed): 25–30 NM total
- Kea → Lavrion: 10–12 NM
These distances allow:
- Early departures before wind builds
- Arrival before afternoon gusts
- Time for swimming, exploring, and rest
What If the Wind Is Too Strong?
If forecasts show prolonged 35–40 knot conditions and crew comfort is a concern, the sensible alternative is not pushing deeper into the Cyclades.
At that point, the Saronic Gulf becomes the better choice, offering:
- Shorter distances
- More consistent shelter
- Excellent cruising grounds around Poros, Hydra, and Spetses
This is not a failure or downgrade. It is good seamanship.
Who This Route Is For
This Cyclades route is ideal if:
- You want to stay in the Cyclades without committing to long crossings
- You are sailing in July or August
- Your crew prioritises comfort and flexibility
- You want options if the forecast changes mid-week
If you have two weeks and a settled forecast, a deeper southern route may make sense. For most one-week charters, this is the smart default.
Suggested Reading: Sailing in the Cyclades 2026: Everything You Need to Know
Final Advice: Sail the Wind, Not the Map
The Cyclades reward crews who adapt.
This route works not because it avoids the Meltemi, but because it respects it. With protected anchorages, frequent ports, and flexible sequencing, it allows you to enjoy the Cyclades even when conditions are challenging.
If you plan with the wind in mind, reef early, and stay flexible, this itinerary delivers exactly what most crews are looking for: real Cyclades sailing, without unnecessary risk.
