Escale Yachting
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Sailing Charter Holidays 2018 In The Cyclades Islands, Greece


Island hopping with action

With our skippered sailing charters in Greece you will discover a country of the bright sunshine and unparalleled hospitality.

In the middle of the Aegean, the Cyclades are the most famous of the Greek islands shaped by Greek history since the ancient times. Usually with distances less than 20 miles, hundreds of islands are located for the seafarer to head to. You will find pleasure in leaving one island in the morning and to discover another, barely visible on the horizon later in the day. An unforgettable island hopping experience where you can get to know not only the famous islands of Mykonos and Santorini but also the big blue Amorgos and other special spots of the Cyclades. The Aegean Sea and the Cyclades are a paradise for the sailor due to the special weather conditions.

Learn how to sail

If you already have a sailing license or if you want to learn to sail, we offer you the opportunity to complete your experience and to accrue sea miles required for your training. Our skippers are on board to teach you or to refresh your sailing skills.

Check below our Itineraries to sail the Cyclades. You can create your own charter with skipper or charter a yacht without crew.

For more information please contact our office in Syros, Cyclades.

Prices & Dates

Low Season: 710 € per person
Sunday 15 April to Sunday 24 June including
Sunday 26 August to Sunday 21 October


High Season: 820 € per person
Sunday 1° July to Sunday 19 August including

Single supplement: +70% (single occupancy cabin)

Children’s fares (7 to 12 years): 70%

In these prices are included: Your accommodation on board, bedding & linen and the services of the skipper.

An on-board kitty 320 € /week per person is set up for the meals aboard and at the tavernas (skipper included), port fees, water, fuel and the end cleaning of the boat. A board kitty for children: 200 €

Bar bills, transfers, vehicle rental, tours of sites and museums are not included in the board kitty.

*) Other charters are possible before & after these dates…

Itineraries are given for orientation but may be changed according weather conditions.

Departures are guaranteed for a minimum of 4 participants. It’s possible to combine charters in case the required minimum has not been reached.

Other Itineraries On Request

On request, we can organise other charter programs: other periods, different itineraries and navigation areas. Feel free to contact us if you want to sail elsewhere. Let us know where you want to sail in Greece, the dates you are available and the number of people interested to participate in this charter. For a minimum of four participants we organise charters in the Cyclades,the Saronic Gulf and the Peloponnese, the Dodecanese, the Turkish coast, the islands of the Ionian Sea and the Sporades.

When To Travel?

April / May / Mid-June: Sunny spring weather with moderate winds for easier sailing. The sea starts to warm up from April and is perfect for a fresh morning dip!

Mid-June / July / August: Warm and dry. Good sailing weather thanks to the prevailing ‘Meltemi’, a strong challenging north wind. Enjoy beautiful evenings watching superb sunsets from remote anchorages.

September / October: Autumn is a very pleasant season in which to sail especially for those who do not enjoy the summer heat so much. The winds become more moderate ensuring a restful and peaceful time. The days become shorter with even more enchanting sunsets. The sea which has been warming up the whole summer is ideal for swimming. This is an excellent time for sailing.

Practical Information

How to reach the boat

Departure from Mykonos: The meeting point is at 6 pm at “Matthew’s Taverna” at the marina of Tourlos (10 minutes from the airport and 5 minutes from the ferry-boat) where the skipper will wait for you. Mykonos has an international airport with direct flights from many countries and several daily flights from Athens. You can also arrive by ferry or high-speed ferry from Piraeus or Rafina (ports of Athens).

Departure from Santorini: The meeting point is at 6 pm at the taverna “Limanaki” at the marina of Vlichada (15 minutes from the airport and from the ferry boats) where the skipper will wait for you. Santorini has an international airport with direct flights from many countries and several daily flights from Athens. You can also arrive by ferry or high-speed boat from Piraeus (port of Athens).

Welcome and transfers

When you make your reservation please let us know at what time and place your arrive Greece in order for us to give you all the information on how to reach your yacht. Transfer from the airport to your choice of destination has to be arranged and paid by you. Embarkation is at 6:00 pm and disembarkation at 10:00 am.

Life aboard a sailboat

Live on a sailboat is a little different from life ashore. There are some rules you have to respect but also a lot of joy to be discovered! The following information and suggestions will help to make your stay on board as pleasant as possible.

A Typical Day on Board:

Waking up between 8am-9am: Breakfast, shopping, tidying up and preparation for sailing.

Departure is around 9am-10am, it usually takes from 4 to 6 hours to arrive on the next destination, depending on the distance and the wind. If possible, we stop for a swim and lunch on board. The aim, of course, is to make the thrill of sailing a pleasant experience for everybody, every day. The skipper will be on your constant call to help you improve your sailing skills.

In the afternoon the sailing boat will anchor in a traditional Greek harbor or remote bay where you can either discover the local charms or just relax on board the boat while enjoying the beautiful Aegean sea.

Evening: At the end of the day you can share your experiences with the rest of the crew while tasting a traditional Greek ouzo. In the evening we can dine in an island taverna where we will introduce you to traditional Greek cuisine. As an alternative we can cook a meal on board - the choice is yours. Before nightfall the skipper and the crew will discuss the itinerary of next day’s voyage.

What To Bring And Formalities

Take your luggage in a light flexible bag, it's easy to store on board

  • Light clothes for protection against sunburn
  • Filter sunglasses
  • A hat to keep the sun from your head
  • Sunscreen & after sun
  • Towels
  • Pullover or sweatshirt
  • Sleeping bag for the early and late seasons.

Don’t forget:

  • Your passport or identity card
  • your sailing license (if you have one).
  • If you are on prescribed medication ensure you travel with it as it will be difficult to find the equivalent on your sailing charter. No specific vaccination is required. An anti-mosquito lotion can be useful for evening ashore. Please tell us of any medical conditions such as allergies when booking.

  • We can attest your sailing certificate.

You don’t need:

  • Blankets, pillow, linen however a towel will be provided.
  • Vaccinations are not required.

Cyclades: Santorini / Santorini

Santorini sailing map /

Starting from Santorini our new trip allows you to explore the Small Cyclades – the most untouched and quiet islands of the Cyclades. During this sailing charter you may also visit Amorgos – the island of the Big Blue. A change of scene and relaxation is guaranteed by swimming in bays with crystal clear waters.

Sunday: Santorini – Embarkation at Santorini at 6 pm. Meeting point at the taverna “Limanaki” at the entrance to the marina Vlichada. Welcome on board of the sailing yacht. Possibility to visit the village of Fira with a splendid view to the Caldera … Meal at the taverna.

Monday: Santorini / Oia / Ios – 25 miles (5 hours of sailing). A unique experience: sailing in the Caldera of Santorini (ancient collapsed crater). Lunch at noon at the foot of the village of Oia. In the afternoon arrival at Ios island where Homer is buried … From a deep bay you will discover on the summit Ios’ beautiful Cycladic village with the same name as the island and called Nios by the locals …

Tuesday: Ios / Folegandros – 20 miles (4 hours of sailing). A late morning departure to Folegandros anchoring in the little port Karavostati. At the top of the hill you will discover the picturesque Cycladic village Chora. Don’t miss out on a visit to its church dedicated to the Virgin Mary, its medieval castle Kastro and its impressive cliff line. In the evening meal in a lively taverna at Chora.

Wednesday: Folegandros / Sikinos / Small Cyclades – 20 miles (4 hours of sailing). Sailing downwind close to Sikinos and anchoring around noon in a small bay with swimming and meal on board … Heading to the Small Cyclades – a group of islands in the south of Naxos, Iraklia, Skinoussa, Koufounissi…. Anchoring and excursions on these islands barely touched by tourism, wild bays and magnificent beaches of fine sand and crystal clear waters.

Thursday: Small Cyclades / Amorgos – 25 miles (5 hours of sailing). Amorgos – Island of the “Big Blue”, arrival in mid-afternoon at the southern Port of Katapola. Visit the village of Chora which dominates the vast bay of Vathy. Do not miss the monastery of Haroviotissa built in to and clinging to the cliff on the south-east of the island, a nice walk with fantastic panoramic views.

Friday: Amorgos / Ios – 20 miles (4 hours of sailing). In early afternoon sailing to the beautiful beach Manganari in the south of Ios and mooring in the bay at night. Meals on board or at the taverna.

Saturday: Ios / Santorini – 30 miles (6 hours of sailing). Sailing to the island of Anydros. If the weather conditions are good we will anchor and swim. Back to Marina Vlichada at Santorini possibility of organizing a visit of the wine-cellar at Pirgos and tasting of the famous wines with a long tradition (1700 BC) as Vinsanto the Assyrtico the Nykteri …

Sunday: Santorini – Tidying up the boat and disembarkation 10 a.m. If you wish, the skipper can take care for your transfers from the port taverna Limanaki Vlichada (bus, taxi, rental car…).

Cyclades: Mykonos / Mykonos

Mykonos sailing map /

A circuit that will allow you to discover the traditional aspects and diversity of the Cycladic islands. An island hopping from Mykonos, heading south to Paros and then west to meet picturesque islands of Sifnos and Serifos.

Sunday: Mykonos – Embarkation from 6pm at the new marina of Mykonos, Tourlos (meeting point at “Matthew’s Taverna” at the entrance of the marina). Welcome aboard of the sailing yacht and presentation of the charter. Possibility a visit Mykonos Town, the most cosmopolitan place of the Cyclades, famous for its windmills, pelicans and its nightlife. Dining at the taverna in the evening.

Monday: Mykonos / Paros – 25 miles (4-5 hours sailing). Sailing along Delos – the largest archaeological site in the Cyclades dedicated to Apollo. Anchoring in a remote bay of Rhinia for swimming and lunch. In the late afternoon arrival at the marina of Naoussa at Paros. Visit and walk through this charming Cycladic village with Venetian history. Evening meal at a taverna by the sea.

Tuesday: Paros / Antiparos – 20 miles (4 hours sailing). Departure in the morning, sailing between Paros and Antiparos, with a stop halfway in a wild creek for swimming and lunch. In the late afternoon anchorage in a sheltered remote bay – one of the most protected of the Cyclades. Walk on the wild and uninhabited small island Despotiko. The evening meal is on board.

Wednesday: Antiparos / Sifnos – 18 miles (3-4 hours of sailing). Departure in the morning for Sifnos arriving at mid-afternoon in the bay of Vathy. Very well protected from prevailing winds#, with its chapel and it is long sandy beach it is one of the most beautiful mooring places in the Cyclades. Do not miss a visit to beautiful Venetian Kastro small citadel on the east coast and the village of Apollonia that never ends to stretch on the crest of the island.

Thursday: Sifnos / Serifos – 20 miles (4 hours of sailing). After traveling along the west coast of Sifnos, we cross to the island of Serifos. Anchor in the main harbor of the island Livadhi. You may climb up by stairs to Chora, a beautiful village with white painted stairs and houses. On top of this rock you have a fantastic panoramic view of the surrounding islands.

Friday: Serifos / Syros – 25 miles (5 hours of sailing). In the late afternoon arrival at Syros, the pearl of Cyclades. Visit of the City Ermoupolis, the capital of the Cyclades, whose name is dedicated to Hermes, the God of commerce but also God of thieves … a beautiful place with neoclassical buildings. The city is famous for its sweets (Loukoumia and Chalvadopita) and its cozy tavernas.

Saturday: Syros / Delos / Mykonos – 20 miles (4 hours of sailing). The morning before leaving for Mykonos you should make the effort to climb the steps up to the settlement of Ano Syros, the first Catholic village of the Aegean, with its narrow alleys and natural fortress – you will have a fantastic view to the harbor of Ermoupolis. After about 2½ hours of sailing we moor at Rhinia (sister island of Delos) and then back to Mykonos in the late afternoon.

Sunday: Mykonos – Tidying up the boat and disembarkation 10 a.m. If you wish the skipper can take care for your transfers from the port taverna Matthew’s at Tourlos (bus, taxi, rental car…).

Choose Your Itinerary

Itinerary /

Other itineraries may be available upon request. We can organise other sailing programs, other dates, different itineraries and navigation areas.

Feel free to contact us if you want to sail elsewhere…

Let us know where you want to sail in Greece, the dates you are available and the number of people interested to participate in this charter.

For a minimum of four participants, we organise charters in the Cyclades, in the Saronic Gulf and the Peloponnese, the Dodecanese and the Turkish coast, the islands of the Ionian Sea, or the Sporades.

Sailing vacation in Greece /Cyclades Yacht Holiday Charter /