Sailing the Cyclades

Nature
The wow factor for nature - does it show nature at its best? Doesn't need to be the wildebeest migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
8
Culture
How much does this experience showcase some of the better and finer things that us humans can offer? Sure, it can be ancient ruins and renaissance churches, but it can also be festivals or soaking up some of the great modern cities of the world
8
Fun factor/activity
Very simple - was it fun? This is usually linked in with doing some kind of activity - i mean, walking along some cliffs is nice, but paragliding from them, now that is fun. Its a vastly underrated factor in a truly great experience
8
Avoid the crowds
Big tour groups and being surrounded by loud fellow tourists can sap the life out of even the greatest of travel experiences. This score is to reflect just how much you can avoid this. But. . . The score also takes into account if the crowds actually add to the experience, such as with a party town or a bustling local market
4
World famous
How world famous is the experience?
7
unique
How hard is it to have a similar experience in other places round the world?
7
Overall TE Score
The overall travel experiences score:  fun factor + avoid the crowds + (best of nature or culture) + (best of world famous or unique). Then convert into a score out of 100
67 *What the scores mean and where do they come from
RANKING
How this travel experience ranks compared to all the other experiences on this site, based on the travel experience (te) score
195th/461
Top 40%
continent
Europe
country
Greece
Length of time
1-2 weeks
Typical daily price
This gives you a rough idea of the daily price based on 2 people travelling where they can split costs like accommodation. It excludes travel there and back, and factors in inflation the numbers in brackets show the price range for the full time of the experience (so not necessarily daily). It is a range to reflect different budget vs higher end
$210 (typically $130 - $290)
Time of year visited
September
All Tags
Wow Factor
Two scores: first is the wow factor which ranges from ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️, and a separate category for the truly "gash". The second is the more analytical travel experience score, which considers 6 varied criteria to give an overall score out of 100.
⭐⭐⭐⭐

Sailing the Cyclades

The Cyclades are the absolute epitome of azure Mediterranean seas, perfect white atmospheric villages straight from a movie set, heaps of ancient history and enough variety for a wonderful trip. Sounds delightful, and it really is. Arguably one of the best sailing destinations in the world and fully deserves the high wow rating.

I’ve been there a few times now, both sailing and taking the ferries. For anyone thinking about the adventure, I’d be thinking about which is the best . . . what are the real highlights . . . what’s the best route . . . and I’ve structured this post in the same way.

In a nutshell:

  • There isn’t a bad option. Both sailing and ferries are amazing.
  • Sailing gives you the wind-in-the-hair magic and the freedom to pull into little coves.
  • The ferries make the whole thing much simpler and, for most travellers, cheaper.
  • Santorini is far more than that famous photo spot. It is a mega wow.
  • Driving Naxos, lash in Mykonos, history in Athens are wows, but the enjoyment of the island-by-island adventure is the highlight.

 

Sailing yacht anchored in a sheltered Cyclades cove, with pink flowers in the foreground.

 

Table of Contents

Full-on sailing vs taking the ferries around

 

I’ve now done both and there are obviously pros and cons. Even with the same two weeks, the trips look different because of how much time you spend getting between the islands.

 

KEY points to factor in

 

  • Athens is the major hub for multi-day yacht rentals. Alimos and nearby Lavrio are useful starting points. It isn’t the only option, though: there are established charter bases on islands such as Paros, with both bareboat and skippered boats.
  • The Cyclades can be very windy. Great if that’s the sailing you’re after, less great if you were imagining two weeks of gentle pottering. The northerly Meltemi can still be strong in September, so the route needs some flexibility.
  • For either option, I’d give yourself at least a day in Athens for the Acropolis, two days for the Mykonos glam and a full day with a car on Naxos. Keep the rest flexible as you make your way around.

 

What does a two-week trip cost?

 

For a useful comparison, the figures below assume four adults travelling in September, sharing a 40-45ft sailing yacht or two mid-range hotel rooms. Bareboat means you sail it yourself. These are 2026 planning estimates, not what I paid or a live booking quote.

For the two weeks Renting a sailing yacht Ferries + hotels
Total time travelling at sea Roughly 50-65 hours for the loop below, before extra exploring or weather delays. Roughly 15-25 hours overall (if the western-island connections line up).
Boat / ferry cost, all four adults Yacht hire: €6,000-€10,000 for two weeks. Passenger ferry tickets: allow €1,000-€1,500 for the whole route.
Boat extras, all four adults Allow €800-€1,300 for fuel, cleaning, water and mooring costs. None.
Skipper, if wanted €2,800 at €200/day, plus roughly €200-€400 for the skipper’s food. Reserve a cabin for them. None.
Land accommodation, all four adults €0 if you sleep aboard throughout. Any extra Athens hotel nights cost more. €3,640-€6,160: two rooms × 14 nights × an average €130-€220 per room.
Transport + accommodation, per person Without skipper: €1,900-€2,900.
With skipper: €2,800-€3,750.		 €1,160-€1,940.
Approximate USD equivalent, per person Without skipper: $2,200-$3,300.
With skipper: $3,100-$4,200.		 $1,300-$2,200.

 

That covers getting around and somewhere to sleep. Obviously food and drink, car hire, transfers, sightseeing and whatever damage you do in Mykonos needs to be added.

For a fuller budget, adding €40-€70 per person per day for food and drink, plus €100-€200 each across the trip for local transport and sightseeing, brings it to roughly €1,850-€3,150 per person by ferry, €2,650-€4,100 sailing without a skipper or €3,450-€4,950 with one.

 

Option 1: renting a sailing boat and making your own way

 

What it looks like: rent a boat from Athens and make your way between the islands, mooring in sheltered spots and taking the dinghy ashore. You’re looking at roughly €1,975-€2,900 per person for the boat and running costs, or €2,780-€3,740 with a skipper.

Pros: It is magical being on the boat, wind in the hair and watching the world go by. You also get the flexibility to pull into little hidden coves.

Cons: The cost. The extra time and faff of everything. You’ll need the sailing qualifications and experience accepted by your charter company, or to hire a skipper. It can get bumpy, and there is a limit to how far you can sensibly go in two weeks.

 

The 41-foot, three-cabin sailing yacht anchored in a sheltered Cyclades bay.

The 41 foot sailing boat we took, with 3 cabins and comfortably enough for 2 or 3 couples.

 

Option 2: taking the ferries

 

What it looks like: fly into Athens and take the ferries between the islands. Mykonos and Santorini are also options for flying in; compare the connections and fares from your own airport rather than assuming Athens will always be cheaper. On the assumptions above, allow around €1,160-€1,940 per person for ferries and accommodation.

Pros: way, way simpler. Usually cheaper for this sort of trip. The main island routes have frequent services in season, and the faster boats make it possible to fit more in.

Cons: less of that magical at-sea feeling. You’re also working around a timetable. The smaller western-island connections aren’t as frequent as the Mykonos / Santorini / Naxos / Paros routes, and strong winds can disrupt both options.

Verdict: there isn’t really a bad option here. Both are brilliant. If money isn’t so much of a problem and / or you have a passion for boats, do the sailing trip. For the standard traveller, just take the ferries.

 

Mykonos Little Venice small lanes

Mykonos’ Little Venice lanes . . . still there waiting for you whether you sail or ferry . . .

 

Highlights

 

After doing this a few times now, here were my highlights:

 

#1 The walk between Fira and Oia on Santorini ⭐️⭐️⭐️⭐️⭐️

 

Caldera views of Santorini whilst on the Fira Oia hike

 

Despite all of the island options to the north . . . and the crowds . . . it is the most famous of them all that blew me away the most and was truly mega wow.  Fantastic views of the world-class caldera, the gorgeous streets at either end and a middle stretch where the buildings disappear and you’re out in the rugged landscape. Our highlight of Santorini.

 

#2 Sailing past the picture-perfect islands ⭐️⭐️⭐️⭐️⭐️

 

Sailing yacht off a rocky Cyclades island, viewed from the water.

 

Wind in the hair, hand on the wheel and those white villages appearing as you make your way along. Magical and, of course, a large part of why you’d choose the sailing option in the first place.

 

#3 Finding little coves for lunch ⭐️⭐️⭐️⭐️

 

Sailing yacht and small dinghy in the clear waters of Cheronissos bay on Sifnos.

 

There are just so many little coves with their own small restaurant for a long lunch and chance to gawp at the beauty.  Some of those spots are far easier to access from the water, which makes having your own boat rather handy. This example was Cheronissos on Sifnos and was just gorgeous.

 

#4 Finding some of the more isolated beaches ⭐️⭐️⭐️

 

Kolona Beach on Kythnos, with a sandy strip between two bays and a terrace above the shore.

 

I would suggest typically the beaches in the Cyclades are only so so (south of Spain and Crete tend to beat them).  But there are some that are super pretty. Kolona on Kythnos would be my pick. A strip of sand with sea on both sides and a wonderful spot to stop.

 

#5 The glitz and lash of Mykonos

 

Crowd at an outdoor beach club in Mykonos at dusk, beneath palm trees and lights.

 

Beautiful white lanes and magical sunsets meet 8am finishes and x10 show off. Great combo. Little Venice and one of the beach clubs like Scorpios will give you the taste . . . then plough on if you want more.

 

#6 Hiring a car and driving around Naxos

 

Restaurant terrace overlooking the hills and coastline of Naxos.

 

Easy to do and a great combo of views, beaches, wine tasting, old towns and lunch spots. The day out I’d make sure to leave room for and 100% just rent a car in Naxos Town.

 

#7 The Acropolis in Athens

 

Athens and the Acropolis

 

Not exactly the Cyclades, but if you’re in Athens you simply must check it out.

 

Individual best-of tips

 

  • Best beach: Kolona, Kythnos. Kolona Experience is a wonderful restaurant spot for views right by the beach.
  • Best secluded cove: Cheronissos, Sifnos. Also spelt Herronissos. Be sure to walk around the edge of the bay for the pretty views.
  • Best ancient history spot: Akrotiri, Santorini. Utterly incredible, even if you’re not a history fan. The Temple of Poseidon at Cape Sounion is also not to be missed if sailing.
  • Best sunset dinner spot: Fira, Santorini. Oia, the famous bit, is obviously nice but x10 busy and expensive.
  • Best lunch spot: Rotonda Restaurant, Naxos. Eat on the terrace. Perhaps the best views on the trip.
  • Best beach bar: Scorpios, Mykonos. Expensive, but worth it. Earlier reservation times are still good.
  • Best late-night bar: Skandinavian Bar, Mykonos. Perfect combo of an outside area and inside Full Send.

 

What route would I suggest?

 

Two weeks sailing

 

Athens → Kea → Mykonos → Naxos → Paros → Sifnos → Serifos → Kythnos → Kea → Athens.

This is an active sailing trip rather than a different beach every morning with no effort in between. Allow roughly 50-65 hours underway at an average 5-6 knots, based on a broad 275-325 nautical-mile planning allowance. Your actual anchorages, the wind and any tacking will change that. Kea to Mykonos is a long passage, so don’t treat every leg as an easy half-day hop.

 

Map of a two-week sailing loop from Athens via Kea, Mykonos, Naxos, Paros, Sifnos, Serifos and Kythnos, returning through Kea to Athens.

The sailing loop. Kea appears twice, on the way out and on the way back. This is a route overview, not a navigation chart.

 

Give Mykonos and Naxos the longer stops, use the western islands for the smaller coves and beaches, and keep time in reserve for getting the boat back. If the Meltemi is making the return awkward, drop a stop. Most charter weeks run Saturday to Saturday, with the boat due back the previous evening, so check the handover times before booking flights.

Athens needs its own sightseeing time around that schedule. You may be able to use a marina night at the start or end, but add a hotel night if your flights and handover don’t leave you a proper day. Santorini is deliberately left off this loop; the sailing distances make it a different proposition from the ferry trip.

 

Two weeks taking the ferries

 

Athens → Mykonos → Santorini → Naxos → Paros → Kythnos or Kea → Athens.

For 14 nights, a starting point would be: Athens 1, Mykonos 2, Santorini 3, Naxos 3, Paros 2, Kythnos or Kea 2, and Athens 1 at the end. That final Athens night gives you some breathing room before flying home.

 

Map of ferry route A from Athens to Mykonos, Santorini, Naxos and Paros, with a timetable-dependent choice of Kythnos or Kea before returning to Athens.

The ferry route, with Kythnos or Kea as the final island. Dashed links need timetable checks and may involve a connection.

 

Check the Paros → Kythnos / Kea leg first. It is the awkward bit of this route. You may need a connection through Syros, and a suitable sailing might not run on the day you want. Treat the western stop as conditional until you’ve found workable tickets. If it doesn’t line up, give those nights to Naxos or Paros and return to Athens from there.

For the main legs, typical crossing times are roughly 3-6 hours from Piraeus to Mykonos, 2-3.5 hours from Mykonos to Santorini, 1-3 hours from Santorini to Naxos and around 30-60 minutes on a direct Naxos-Paros sailing. Slower services can take longer. Allow a substantial extra travel day for the western connection, plus the return to the mainland. The 15-25 hours in the comparison is a broad allowance for time afloat, not a verified set of connecting departures.

Athens has several ports. Piraeus or Rafina can work for Mykonos; Lavrio is useful for Kea and Kythnos. They aren’t interchangeable, so include the road transfer when checking your timings. Check your dates with the operators or a route planner such as Ferryhopper before booking the hotels.

 

General tips

 

Ubers and taxis on the islands are expensive.

 

Not too far off the most expensive in the world from what I saw. Renting cars, though, can be quite cheap: roughly €40-€80 per day for a medium-sized car in my experience, and you then get the freedom to explore. Treat that as a guide rather than a current quote; prices vary by island and date. Don’t be afraid to use some of the smaller companies rather than the Europcars and Avises of this world. Google reviews are a useful indication, and you can often get far friendlier service.

 

Mykonos and Santorini are also super expensive

 

Heaps of the islands are reasonable prices and naturally you can do some of this quite cheaply. But Santorini and Mykonos hot spots must be some of the most expensive places on the planet.

I remember asking for a nice bottle of wine at Scorpios . . . that’ll be €19,900 sir . . . second thoughts I’ll just have the house wine.

 

A drinks menu in Mykonos showing wine, champagne, beer and spirit prices.

Example menu in Mykonos

 

Naxos day-trip

 

I’d structure the day around these six stops. It’s a full day if you do all of them, so give yourself an early start:

  1. Naxos Town: most likely where you’re staying or arriving.
  2. The Temple of Demeter: a stunning location.
  3. The Vallindras distillery in Chalki: for sampling kitron, Naxos’s local liqueur, made by distilling the leaves of the citron tree. You’ll also see it called Kitron Naxou. Leave the tasting to the passengers if you’re driving.
  4. Rotonda Restaurant: some of the best views on the trip and a great atmosphere on the terrace.
  5. Apeiranthos: for pretty lanes and views.
  6. Agiassos Beach: long and chilled. It’s just that bit further than most tourists are prepared to go, with a lovely restaurant at the top for beers.

We hired a car from Marios (+30 694 882 0568) and would recommend him.

 

More tips for the individual stops

 

Each of the below are links to more detailed travel entries, each with their own detailed tips:

 

Experiences nearby
Wow Factor Score Two scores: first is the wow factor which ranges from ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️, and a separate category for the truly "gash". The second is the more analytical travel experience score, which considers 6 varied criteria to give an overall score out of 100. LowHigh
  • Elite, unmissable
  • World-class, downsides
  • Meets the Wow Factor
  • Worth it
  • Meh
  • Gash

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Score Detail

The scores above are the real point of this site.

Over 20+ years and 100+ countries, I’ve tried to rank the world’s best travel experiences - from genuinely mind-blowing ⭐⭐⭐⭐⭐ to the properly gash.

Every one of the 500+ places on this site has both a Wow Factor rating and a more analytical Travel Experience (TE) score based on the things that actually make travel memorable.

If you're curious about the thinking behind it, head to the About page.

Otherwise, explore the map above or on the Home page and see which places truly deliver maximum wow.

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