Kea Veranda View
Syros at night
Syros beachfront taverna

Two Week Sailing The Cyclades from Lavrion

Two Week Cyclades Lavrion Map

220 Islands in the Cyclades to Explore

This route is a great extension from our one week starting in Lavrion. Giving you more time to explore as many of the 220 islands that make up the Cyclades and you can in two weeks!

Beginning in Lavrion is ideal as it’s only a 35 minute transfer from the airport and from here you can start with islands such as Kea and then make your way down to Irakleia and Katapola on the island of Armorgos in the south.

The Cyclades are made up of a group of islands in the Aegean Sea that are all clustered around the sacred island of Delos. We all know in Greece there are cats everywhere but did you know that the native Greek breed of cat or the ‘Aegean cat’ actually originated in this area.

Without a doubt, this is the windiest area in Greece to sail during the height of summer, July/August and also the beginning of September. This area is very open to the meltimi, which can blow a force 6 and above during the summer. We would only recommend this sailing ground to very experienced sailors, or if you were looking out of season in May or October.

Typical Itinerary & Highlights

Days 1 - 3, Arriving in Lavrion

After you have arrived in Lavrion and done your check in with the local charter company you can enjoy your first evening in Lavrion.

From here why not spend your first day on a short 5 mile sail to Kea. Kea is one of the largest islands in the Cyclades archipelago; home to stunning beaches, clear waters and traditional Greek villages. If you're a keen walker, then you're in luck as Kea is a walker's paradise. Explore a myriad of ancient paths throughout the island, which lead you through olive, fruit and oak trees so you can marvel just how lovely Kea is.

  • Kea Town View Kea
  • Lavrion Marina, Cyclades Lavrion

Days 4 - 7, Relaxation At It's Best

Head South from Kea for the next few days where you will come across some gorgeous islands to moor in for the evenings. Kithnos, Serifos, Sifnos and Irakleia are perfect places to visit for some relaxation with stunning beaches and lovely secluded bays. You will find traditional Greek tavernas amongst little bars with gorgeous views, perfect for an afternoon drink as the hot sun goes down.

  • Kythnos Marina Kythnos
  • Sifnos church, Paros Sifnos
  • Livadi Town, Mykonos Serifos
  • Irakleia shore front, Paros Irakleia

Days 8 - 12, Creating Waves Island To Island

Short hop sailing is common in the Cyclades but you will find some spots where you may be doing over 10 miles at a time. This is a great time to get those sails up and enjoy some exciting sailing. 

Head to Armorgos, Naxos, Paros and Syros, the more Northern islands in the Cyclades. 

Naxos, the largest island in the Cyclades is located in the centre between Paros and Mykonos. According to Greek mythology this was the nuptial isle of the god Dionysus, god of wine. Which sounds like a great spot for us if that is anything to go by.

  • Syros Promenade Syros
  • Naousa Paros Fishing Boat and cute quay Paros
  • Naxos Town by night, Mykonos Naxos
  • Katapola church view, Paros Armorgos

Days 13 - 15, Last Sail Back To Lavrion

As you head back to Lavrion with your last couple of days it's a great opportunity to explore a different port in Kithnos. We recommend visiting Loutra or Mericha depending on where you went the first time. 

Get back to Lavrion with plenty of time to enjoy your final night before checking out early the next morning.

  • Kythnos Marina Kythnos
  • Lavrion Marina, Cyclades Lavrion


What's Included

    • Return flights
    • Transfers
    • Diesel
    • Linen & Towels
    • Dinghy
    • Harbour Guide
    • Starter Pack
    • Full Financial Protection

What's not Included

- Yacht Security Waiver (£80-£270)
- Mooring Fees (£40-£120)
- Food & Drink
- Personal Holiday Insurance
- Child Discount -£65 for one week 
- Child Discount -£115 for two weeks
- Infants travel for just £50

One & Two Week Optional Extras - South Ionian Highlights, Paxos, Whole and South Ionian Flotillas

  • Manchester Flights £25
  • Brimingham Flights £25
  • Stansted Flights £25
  • SUP (paddleboard):
  • One Week £95
  • - Two Weeks £155
  • Dinghy Outboard:
  • - One Week £70
  • - Two Weeks £95
  • Cruising Chute



One & Two Week Optional Extras - Corfu, Paxos & North Ionian

  • Manchester Flights £25
  • Birmingham Flights £25
  • SUP (paddleboard):
  • One Week £95
  • - Two Weeks £155
  • Dinghy Outboard:
  • - One Week £70
  • - Two Weeks £95
  • Cruising Chute


Two Week Optional Extras - Saronic Islands & Sporades Flotillas

  • SUP (paddleboard) £155
  • Dinghy Outboard £95
  • Cruising Chute

Quick Yacht Price Search - For prices simply select party size and date

Below is an indication of the yachts that will sail on this flotilla. Please call us on 020 8459 8787 to check live availability.

Our Shore to Sail holidays are a combination of a one or two week flotilla sailing holiday with another relaxing week or two ashore.

These holidays will appeal to those who enjoy sailing but have family or friends who are not quite so enthusiastic about sailing - a compromise can now be made!

Most people opt for a week of sailing followed by a week of winding down on shore. However it is entirely up to you to do what you want to do (and when!)

Iris Hotel and Apartments

The Iris Hotel has been a popular choice for flotilla sailors for many years. This accommodation option will fit in with any of our flotillas starting and finishing on Lefkas Island. The hotel itself is a small family run hotel located close to Nidri Town. It has a combination of studio rooms for two or three people and apartments that can sleep up to 4.

Salvator Spa Hotel & Villas

The Salvator Spa Hotel is perched in the hills above Parga town and is a slightly more luxurious offering. The rooms on offer range from the Deluxe Room for two people, up to the Superior 2 Room Villa for up to 6 people. The hotel itself has an excellent restaurant, pool and spa facilities and all villas come with their own private pool.


Villa MeandrosDJI 0202 copy

Our brand new villa in Sivota on Lefkas is exclusive to Sailing Holidays Ltd. Built with families and groups in mind, the 3 double bedrooms all feature en-suite bathrooms. Built into the hill the ground floor level comprises of the master bedroom, a large kitchen and living space. On the same level you will find a huge outdoor seating area and a private pool. 

Images from Flotilla


  • Kea

  • Lavrion

  • Kythnos

  • Sifnos

  • Serifos

  • Irakleia

  • Syros

  • Paros

  • Naxos

  • Armorgos

  • Kythnos

  • Lavrion


Tell us about your holiday


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