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Incredible sailing holidays
that people love. It’s what we do.
Cyclades Islands + 1
5 - 12 Oct - Adults: 6
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Sailing the Cyclades Islands, iconic Greece at its very best
Great for:
  • Early/late season
  • Exciting winds

Blue domed roofs, sandy beaches and winds with a bite, the Cyclades Islands are stunning. See a postcard of Greece and it will inevitably boast the blue domed roofs of Santorini or the iconic windmills of Mykonos. Gorgeous sandy beaches, wonderful traditional architecture, stunning landscapes & fascinating ancient history litter its many gorgeous & idyllic islands. While Mykonos and Santorini grab the tourist limelight (and their numbers), there are over 200 islands in the Cyclades. The beauty of a sailing holiday to this area is the ability to cast away from the 'beaten track' and visit undiscovered beauties such as Folegandros, Sifnos, Serifos and Kythnos. Picture relaxed gentle tourism that tends to stand back and observe the sights and sounds, rather than the mass sprawl that imposes itself on the busy islands.

Cyclades Islands Sailing Holidays that Guests Rave About
RC

Rex Chalmers

September,2019

Seamaster were again very helpful. We were looking at the Cyclades and I mentioned that my wife is not great in rough waters and we had two friends who haven't sailed before. Seamaster suggested that we sail from Lavrion so that we had the choice of sailing west to the Saronic Islands if the winds were too strong. They also recommended trying the 4.1 Bali rather than the Lagoon 45 as the interior was more modern. It was a great Cat except for the reefing lines always got caught. Seamaster were fantastic from start to finish.

MSM

Mrs S Milner

July,2021

We returned from Greece yesterday having had a fabulous holiday on the charter yacht Seamaster arranged with Olympic Yachting in Lavrion. We decided to go the Cyclades route and although we had a number of days in port due to the meltemi, we really enjoyed it and felt safe throughout from a Covid perspective.Olympic Yachting were by far the best charter company that we have ever used, and can’t recommend them highly enough. Thank you Seamaster for arranging the charter for us and for supporting our decision to go on holiday in spite of Greece’s amber status.

SF

Susan Forde

June,2023

Fabulous company with very personal service from true experts. Always willing to help and answer questions. Wouldn’t hesitate in recommending. Can’t wait for our next trip.

MG

Mr Gomm

June,2023

Arrived early at the Olympic Marina Lavrion, easy check in and document check, early departure was well managed by friendly base staff.Good and well maintained yacht: Surya - visited lots of interesting locations and had a great holiday.

IM

Ian Mitchell

June,2023

Seamaster very helpful throughout the booking process and the staff of the actualk charter company could not have been more helpful.The yacht was immaculate on handover and no probelms were experienced duringa week of great sailing.

Our Cyclades Islands Yacht Selection
Best for 6 people - 05 Oct - 12 Oct(Change)
  • Premium
  • Super Premium
  • yacht-imagewhishlist

    Premium

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    Lavrion, Cyclades Islands

    Elba 45
    • Size: Large
    • Age: Mid-aged
    • Catamaran
    • 2020
    • 6 Cabins
    • 5 Toilets
    air_conditioninggeneratorwatermakerautopilot
    £4,046was £ 5780
    Including Boat only
    -30 %
  • yacht-imagewhishlist

    Premium

    flag

    Lavrion, Cyclades Islands

    Lagoon 46
    • Size: Large
    • Age: Modern
    • Catamaran
    • 2021
    • 6 Cabins
    • 5 Toilets
    air_conditioninggeneratorwatermakerautopilot
    £2,975was £ 5950
    Including Boat only
    -50 %
  • yacht-imagewhishlist
    flag

    Lavrion, Cyclades Islands

    Bali 4.6
    • Size: Large
    • Age: Modern
    • Catamaran
    • 2022
    • 6 Cabins
    • 5 Toilets
    solar_panelsautopilot
    £5,967was £ 6630
    Including Boat only
    -10 %
  • yacht-imagewhishlist

    Super Premium

    flag

    Lavrion, Cyclades Islands

    Elba 45
    • Size: Large
    • Age: New
    • Catamaran
    • 2023
    • 5 Cabins
    • 5 Toilets
    air_conditioninggeneratorautopilot
    £4,457was £ 5865
    Including Boat only
    -24 %
  • yacht-imagewhishlist

    Super Premium

    flag

    Lavrion, Cyclades Islands

    Lagoon 51
    • Size: X-Large
    • Age: New
    • Catamaran
    • 2024
    • 7 Cabins
    • 5 Toilets
    air_conditioninggeneratorwatermakerautopilot
    £7,293was £ 9350
    Including Boat only
    -22 %
  • yacht-imagewhishlist
    flag

    Lavrion, Cyclades Islands

    Bavaria Cruiser 46
    • Size: Medium
    • Age: Mid-aged
    • Sailing yacht
    • 2020
    • 4 Cabins
    • 3 Toilets
    solar_panelsautopilotbow_thruster
    £2,636was £ 3468
    Including Boat only
    -24 %
  • yacht-imagewhishlist

    Premium

    flag

    Lavrion, Cyclades Islands

    Jeanneau 54
    • Size: X-Large
    • Age: Mid-aged
    • Sailing yacht
    • 2020
    • 6 Cabins
    • 4 Toilets
    air_conditioninggeneratorsolar_panelsautopilotbow_thruster
    £4,373was £ 5755
    Including Boat only
    -24 %
  • yacht-image
    On-Hold
    whishlist
    flag

    Lavrion, Cyclades Islands

    Bavaria Cruiser 46
    • Size: Large
    • Age: Economy
    • Sailing yacht
    • 2016
    • 4 Cabins
    • 3 Toilets
    solar_panelsautopilotbow_thrusterfurling_mainsail
    £2,196was £ 3230
    Including Boat only
    -32 %
  • yacht-imagewhishlist
    flag

    Lavrion, Cyclades Islands

    Lagoon 42
    • Size: Medium
    • Age: Mid-aged
    • Catamaran
    • 2019
    • 4 Cabins
    • 4 Toilets
    solar_panelsautopilotfurling_mainsail
    £3,876was £ 4845
    Including Boat only
    -20 %
  • yacht-imagewhishlist
    flag

    Lavrion, Cyclades Islands

    Lagoon 39
    • Size: Compact
    • Age: Economy
    • Catamaran
    • 2017
    • 4 Cabins
    • 4 Toilets
    solar_panelsautopilotbow_thruster
    £2,550was £ 3400
    Including Boat only
    -25 %

What makes the Cyclades Islands so Special

Picture postcard perfect Greece
Picture postcard perfect Greece

The Cyclades Islands are the most famous of the Greek islands, counting Mykonos, Naxos, Ios and Santorini amongst its ranks. With the famous blues domed buildings, white-washed villages, iconic windmills, and the golden sandy beaches, sailing the Cyclades is a life experience.

An incredible array of islands
An incredible array of islands

For every island that you’ve heard of in the Cyclades, there’s five that you probably haven’t and each of them has an incredible experience to share with you. Many of guests argue that these lesser-known islands, such as Folegandros, Amorgos, Milos and Koufonisia outshine the tourist hotspots. Will you agree?

Wind with a sting in its tail
Wind with a sting in its tail

The Cyclades Islands come with a warning, however. During the main body of the summer (June-September) there is a higher risk of strong winds that can verge on fierce. Therefore, sailing this area is best in May and October or you can use our base at Lavrion, which can also be used to sail the Saronics if the winds are strong.

Exclusive yachts and crew
Exclusive yachts and crew

Seamaster has a fantastic modern portfolio of yachts and catamarans from Athens that will suit all needs, including at the very luxury end of the market. We are particularly proud of our exclusive Seamaster crew, who are friendly and professional and thoroughly focussed on providing you with a stunning sailing holiday experience.

Cyclades Islands sailing itineraries
  • 1 Week - Mykonos Route ( via Sifnos)
  • 1 Week - Lavrion Route (Mykonos)
  • 2 Week - Whole Cyclades (Lavrion)
1 Week - Mykonos Route ( via Sifnos)
Day 1 - Mykonos (Mykonos Island)

Along with Athens and Corfu, Mykonos is probably one of the most well known places in Greece. Famed for its cosmopolitan atmosphere, exciting nightlife and picturesque architecture it is a must visit place for anyone sailing in this area. The island is located in the heart of the Cyclades and promises vistors plenty of things to do. We'd recommend hunting out Little Venice or perhaps one of the renowned beaches.

Day 2 - Naxos (Naxos Island)

The largest of the Cyclades, Naxos packs a lot of bang for its buck. Its main city of Hora is a web of steep cobbled alleys, filled with the hubbub of tourism and shopping. Yet you needn't travel far to find isolated beaches, atmospheric villages and ancient sites. It is a big beautiful island, rich in agriculture, tradition and some of the finest beaches in the Cyclades.

Day 3 - Nauosa (Paros Island)

Nauosa is considered to be one of the prettiest villages in the Cyclades. The village has kept it authenticity even though tourism has grown rapdily here. It's whitewashed and flowered little houses coupled with tiny churches, chapels and labyrinth like streets combine to give an enchanting atmosphere to the village. The port is at the heart of the village and is full of local fishing boats and the remains of an old Venetian castle.

Day 4 - Kamares (Sifnos Island)

Kamares is the port of Sifnos and lies on the western side of the island. Sifnos is one the the best known ceramic production centres in Greece meaning you'll find plenty of workshops dotted around the town. The main settlement lies on the right of the bay and has plenty of tavernas, shops and bakeries where you can stock up. The beach has a watersports centre on it if you fancy trying your hand at something smaller than your yacht.

Day 5 - Loutra (Kythnos Island)

The town of Loutra is famous for its hot springs which flow right into the sea. You can see where the water runs in a stream on the edge of town and empties into the sea at the town beach. For those who want a free cure you can go to the spot where the hot water pours into the sea and there is a tub built with rocks where the sea water mixes and makes the temperature bearable.

Day 6 - Finikas (Syros Island)

Finikas is a large and lively village in the southwest of the Syros Island. The harbour has plenty of space for visting yachtsmen and the town offers a wide selection of tavernas. You'll also find a fantastic beach close to the harbour where many of the locals head to during the peak season.

Day 7 - Mykonos

If you didn't have an opportunity to explore Mykonos on your first night then we strongly recommend heading into the town centre on your last night. Mykonos has something for everyone including: restaurants, traditional tavernas, bars, clubs and beaches.

Typical Cyclades Islands Weather
Typical Cyclades Islands Weather
May Weather 18°C Sea temp: 16°C

Warm days, cool evenings. Changeable weather improving

June Weather 25°C Sea temp: 22°C

Hot days, warm nights with the wind stronger later in month

July Weather 26°C Sea temp: 24°C

Strong winds, choppy seas with hot & dry conditions

August Weather 26°C Sea temp: 25°C

Strong winds, Choppy seas with Hot & dry conditions

September Weather 24°C Sea temp: 23°C

Warm days, warm nights, Weather becoming calmer

October Weather 21°C Sea temp: 21°C

Warm days & cooler nights with occasional stormy weather

April Weather 18°C Sea temp: 16°C

Cool calm seas and chilly evenings changeable conditions

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Frequently Asked Questions

We have three dedicated bases for the Cyclades Islands; Lavrion, Mykonos and Paros. Lavrion is based on the Greek mainland and is perfectly placed to sail the northern and western Cyclades Islands. Mykonos is located in the northeastern Cyclades Islands and is well placed for the eastern, central and northern Cyclades. Paros is the best located Cyclades base, with excellent access to the entire island group.

There are several ways to get to the Cyclades islands. You can fly into Athens and transfer directly to Lavrion or take a connecting flight to Mykonos or Paros. Alternatively, you can fly directly into Mykonos to sail directly from there or ferry to Paros. Finally, you can also fly into Santorini airport and ferry from there up to Paros primarily, or Mykonos.

The weather in the Cyclades Islands is hot and dry, explaining the arid landscape that you’ll experience there. During the early and late months of summer – May and October -temperatures reach the mid-twenties. During peak season – July and August – temperatures are in the mid-thirties. PLEASE NOTE: THE WINDS IN THE CYCLADES ISLANDS CAN BE FIERCE, ESPECIALLY FROM LATE JUNE TO MID SEPTEMBER During the peak season when winds tend to whip down the Aegean sea, it can stop ferries from running with Force 8-9 winds (strong gales). 70% of the time winds will be greater than Force 4 (moderate winds). Earlier and later the winds are much more bearable, particularly in the mornings.

There are generally no mooring fees in Greece other than the main centre marinas such as Mykonos, but even these can be avoided by mooring in the sheltered bays of the island. Given its popularity, it’s important to note that Santorini is a very difficult to moor overnight.

If sailing without a Seamaster skipper, for charters in Greece you must have an ICC (International Certificate of Competence). Those with an RYA Day Skipper, or above, can apply to the RYA for an ICC with no additional assessments required.

As a dynamic yacht charter agency headquartered in the United Kingdom, we take pride in offering expert guidance and fantastic deals on Mediterranean sailing vacations. We look forward to arranging your next sun-soaked sailing adventure!

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