The archipelago of the Cyclades, in the middle of the Aegean Sea, owes its name to the fact that the islands forming it encircle the rocky islet of Delos (‘cyclade‘ is ring in Greek), which in ancient time was considered the political and religious centre of the known world. 21 bigger islands and 20 smaller ones: among them many places still uninhabited and wild. All of them are delightful and each of them expresses its own nature. The Cyclades are considered and known all over the world as the most typical part of Greece. Unique distinctive features are the stony houses painted in white with their deep blue domes, ancient windmills, gorgeous beaches of golden sand, ancient ruins surviving time, typical little restaurants called tavernas that serve excellent meat and fish dishes with locally produced wine.

Every time we cross over to this area each summer we are amazed by the outstanding nature of this archipelago and their people – our friends, their cuisine, the stories and experience we live and accumulate every summer. When approaching this sea we are also sort of cautious and curious about the wind we will find there and how it will treat us. Some things to bear in mind in this area, especially the Flexibility Factor (read more) before you make your plans with regards to the destination. The area is  known for the Meltemi wind  in July and August. Having an exceptionally knowledgable and skilful crew is a must, therefore, if you are to enjoy these islands in all safety and tranquility of a secure navigation and anchorages.

The islands are stunning and you will want to explore every single one of them from the boat and from ashore. This brief itinerary offers an outlook on the these incredibly interesting islands packed with history, unspoilt and otherwise unreachable bays, coastlines and beaches, unique architecture of these white villages on isles tops (strategically positioned to protect themselves from attacks of the pirates in the past), and also nightlife, if that is on your bucket list.


  • Relax 100% 100%
  • Nature 100% 100%
  • Nightlife 80% 80%
  • Adventure 90% 90%
  • Shopping 90% 90%
  • History & Archeology 70% 70%

Kea Island

Makronisos Island

Kythnos Island

Serifos Island

Sifnos Island






Antiparos & Despotico


Naxos South








7 Days Itinerary West

Paros Island

is the central hub and the perfect arriving spot, in the very heart of the Cyclades islands archipelago. The main town is Parikia which is also the ferry port. For us, pleasure yachts the marina is tiny and always very busy. Being exposed to the prevalent wind during the summer season we suggest embarking on the other side of the island instead, easily reachable by taxi or public transport. This mundane and buzzing island is typically Cycladic, with whitewashed houses and narrow streets adorned with marvellous bougainvillea flowers, nice boutiques and countless caffees, lounges and restaurants. For archeology lovers, there is an interesting museum with  ceramic artwork and sculptures of archaic and classical periods. The Katapoliani church, literally the 100 doors church, is the most important monument of the town. Paros is the third biggest isle situated in the centre of the Cyclades. It is a modern holiday resort and will be one of our bases for boarding and landing. The profile of the mountains is gentle and it is difficult to believe that the whitest marble in the world comes from here. The rest of the island is flat and covered with endless vineyards. There are picturesque little towns with dazzling white houses, paved alleys, arched churches and wonderful beaches. We include this island in our Small Cyclades Archipelago Route which are considered to be an ideal getaway for those looking for peace and rest. The wild beauty of this barren scenery, the rocks always lashed by the sea, the indented beaches and a desire to escape from the madding summer crowds, are all reasons that attract the more connoisseurs type of visitors to these islands.

Naoussa Town 

This is the second largest town on the island, but first in beauty. The marina is modern and comfortable. Restaurants are located directly on the docks with fishing boats just a few inches from the table. The little castle on the sea, the narrow streets with their white-washed houses and a myriad of boutiques and typical restaurants, make this an extremely stylish night out spot. The town comes alive in the evening with a cheerful atmosphere and happy ambiance.

We will welcome you onboard with a drink or two, get to know each other, see what our itinerary looks like and where the winds will take us. Dinner in a superb inner village taverna, you will fall in love with. You can round up the evening with a cocktail on the port, in one of beach lounges.

Despotico and Antiparos Islands

After our breakfast and when you have gotten yourself accustomed to the boat, we will head towards our first destination:  this deep beautiful bay between the Antiparos and Despotico islands closed to the West by a small isle. We then anchor in the Western part of the bay adjacent to the wide and picturesque wheat fields. This is a fascinating site reaching its pinnacle at sunset while sipping your favourite cocktail awaiting for the dinner to be set on the cockpit. Great anchorage for the night. On the coastal side of Antiparos, home to hollywood celebrities vacation villas, you will notice a few typical villas, always in tune with the local architecture: cube-shaped, white with blue windows. But on the uninhabited Despotico island we are in contact only with nature, fields, horses, wild goats and the omnipresent white Greek chapel with deep blue doomed roof. Read more about the Greek Christianity here.

Sifnos Island

A swimming pool-like bay surrounded by marvellous cliffs embraces our arrival in the North cove of the isle. The harbour is situated in a tiny little town on the shores of the Kamares bay. It is well preserved and delicately developed into a more connoisseur type of traveller. The dock has but a handful of berths, so we must get there in the late afternoon or spend the night at the anchor on the nearby beach bay. The port is a quiet hideaway and allows for a tranquil walk, for a hike or for a morning jog along the seaside and up the hill on both sides of the bay. There is a wide and beautiful sandy beach within the port where these cozy lounges spread their tables and deckchairs on. A perfect spot for a relaxing cocktail as you sit on the first row for the beach sunset view over the harbour horizon. Check out the few boutiques on the harbour and come back to the boat to get ready before we make our way to the Chora for dinner. We will hop on the bus up to the main town: Apollonia. Sophistication is the type of atmosphere of this town which attracts art, design and crafts graduates from the the capital, Athens. They exhibit their works in galleries and boutiques throughout the narrow mews of Apollonia. Cafes, restaurants and lounges populate the main walk in the very heart of the town as you go for some great jewellery shopping and local designers showrooms. Our favourite place for drinks is a restaurant beyond the main street, in a secluded area, overlooking the entire town and offering a magnificent view on the moon and the starlit sky. For a traditional cuisine dinner we recommend a family-run taverna a few steps away. Delight yourself with local specialities, the unbelievable lamb chops, selected fresh fish and traditional Greek dishes. In the morning we will sail to Vathy, a village characterised by this circular and well sheltered bay for breakfast. We will then slowly make our way to Fakidha, an impressive fjord, digging deep into a couple beaches and hosting an exquisite white chapel with its own private pathway and beach. Picturesque windmills and not less than 365 churches pop out like white mushrooms.

Serifos Island

Bare mountains, interrupted by fertile little valleys, cover this evocative island, which ends in a sequence of rocky blocks forming indented bays. Clutched at the top of a hill the Chora, with its square little houses, the simple island churches and the Venetian castle, looks like a fairy-tale town. The next isle we will head to is this marvellous place with a breath-taking view of the handful of white houses on the hillside disclosing the Chora overlooking Livadhia, the port. Before hitting the port we will stop by in one of Southern bays for a swim and for lunch. Later on in the late afternoon we will aim for the port. The island has a reputation of being a haven for the intellectuals where tranquillity and silence were much cherished. Imagine a scene of these poets, writers and artists quietly sitting in cafes, reading or writing their books… a Greece of a long time ago. This atmosphere has slightly changed into a joyous noise. The moment you step on the ground, you will find the buzzing cafes and restaurants, relaxed crowds of both locals and tourists, children playing. The restaurants tables are right on the beach, with your feet in the water if you will, enjoying refreshing waves and the air from the sea throughout the evening. The real adventure is the Chora village, awaiting us and impatiently looking for our arrival on the top of the island. From our bus ride you will gaze a stunning view of the sea as we climb uphill and leave the harbour lights on the palm of our hands. This is yet another gem of the Cyclades Islands archipelago. Another unique experience of watching the sun disappear behind the horizon, from up the church roof, its massive bells hanging down the towers. There is something about the sunset colours of Greece that will be an unforgettable memory you will cherish for a life time. As we get lost in the labyrinth of small streets at the magnificent shades of the sun leaving us for the day, and  before you know it you will feel like you have never belonged anywhere else but in that lifestyle. We will keep exploring these narrow streets all strategically heading up to the Chora main square. Once you get out in the plain of this ‘platia‘, the square, you will be astonished by the beauty and timelessness of it. This truly magical place, year after year, makes us feel like we had never really tasted and seen the real beauty of life. The square is dominated by a vast yellow-façaded Greek church building where the kids play night and day. Cafes and restaurants tables and sofas are scattered throughout its every corner to as the locals and the tourists sip their drinks and nibbling on the mezzes starters. The evening is yet to begin and to expand into the fulness of this ‘Mediterranean as it once was’ atmosphere. No where else on the planet can you feel something alike. Pick up a place and people-watch as you are sampling your ouzo spirit. When ready, we will head down a slow descent by foot along an interesting serpentine footpath through the village streets, an open-air cinema, past by tiny museum and art exhibitions. The elderly ladies sitting on their front door porch benches chit-chat and greet to  wish good health to the passers-by. The harbour life will go on until late so you can enjoy its lights and sounds until you please. In the morning we will visit yet another cove, Psili Ammos literally ‘fine sand’, a golden reflections sand beach.

Milos Island

The island of the Greek goddess Aphrodite this is a place of a thousand colours. Its impressive cliffs have been coloured throughout millenniums by the sediments of iron, copper and sulfur manifesting in a spectacular scenario from red to yellow to green, exhibiting the volcanic nature of this land. The South natural cove of Kleftikos a beauty hard to describe with mere words: a frame of white rocks,  the whitest of whites arches peeking out of the light blue water. We will spend a night here at the anchor just so that you would take back home a once in a lifetime experience of the starlight night reflected not only on the ocean surface, but on its dazzling white sand bottom! A surreal atmosphere. There are a few perfect spots to anchor in seclusion and enjoy the private show. Upon awakening and before breakfast, a nice dip in these turquoise waters. We will then head on to visit to the caves that the erosion has carved, creating tunnels on the surface of the water. Our next stop is Kimolos Island and the dive in the past in its town: the Chora. Perched on a hill above the windmills, with narrow and winding streets, one shop and tavernas. There is also an ancient castle to visit.

Polyegos Island

An uninhabited island of white cliffs that nature has carved creating a true artwork. We discovered this place a few years ago, and the idea of not sharing it with the world is just unfair. This place is totally unknown amongst the tourist-paths, and it is only reachable by the sea. We call it The Grand Canyon of the Mediterranean, just replace the red rocks with the whitest of the white. Circumnavigating the Southern Coast, you will have a chance to take amazing pictures of these stunning coves. Amongst so much beauty, it is sometimes a challenge to pick one of them for our lunch break. One of our favourites is on the West side, a beach protected by a small island.

Folegandros Island

Although increasingly a popular destination, this island is still keeping the authentic Greek looks. Interesting areas to visit: the Karavostasi port, the main village Chora and another small village, St Mary, and only one road connecting them all. Due to the nature of its tiny port which is exposed to the prevalent wind in the summer season, w usually opt for taking you for a short walk in the town and then head off the next island for the night. The Chora is wonderfully composed of narrow streets around an ancient castle, three charming squares adorned with most exquisite cafes and restaurants in the shade of a huge tree in the centre of it. The island is renown for its stylish boutiques and craftsmen artwork. An infinite peace. The hibiscus and bougainvillea flowers color the white-wooden balconies of the houses. When you happen to be there in the morning, the fragrance of freshly baked bread and freshly ground coffee fills the streets as the village awakens to yet another beautiful summer day.

Sikinos Island

Secluded in the South of the archipelago, this is another attractive island for those who are seeking peace and authenticity. The port is probably the smallest in Greece, and it is a home to the picturesque fishing boats. Sikinos is still one of the unspoiled islands of Greece. The lifestyle of its inhabitants is faithful to the rhythm of the past centuries. The Chora, the main village, is situated on top of the island, in the mountains. With its genuine and welcoming spirit, the village stretches along a ravine, almost perpendicularly to the ocean. Particularly interesting the refined stony houses as well as the Pantanassa church. There is plenty of olive groves from which a variety of tiny olives are grown to produce the oil of best quality. A hike to the Zoodochos Pigi monastery on the pinnacle of the island is a must, an austere fortress with a magnificent view. The most exquisite dinner in the local taverna on the streets of this pearl island amongst the typical white-washed houses with blue windows, narrow alleyways and buzzing squares where people gather in traditional cafes.


Ios Island

Picturesque little creeks make its coasts very attractive to those travelling by sea. The island is mostly mountainous with countless little churches, olive trees and vineyards. The atmosphere here seems transparent and the beautiful beaches are sandy in a crystal clear sea. The main town climbs up the hill, all in white with its narrow alleys, little shops, cafés and restaurants: everything is tiny as if it had been built for a dolls’ house. For many years, Ios has been one of the most loved islands in the Cyclades and rightly so. This isle releases a real rare energy which is a mixture of natural beauty, nightlife and history. It has all the elements of a traditional Greek village, combined with a buzzing nightlife and most renown sandy beaches. The coastline of Ios has wonderful beaches with soft sand and emerald waters, such as the most well known Mylopotamou and Manganari beach. We will reach the main village on top by bus or by a motorbike/AVS. You will love walking along the narrow paved streets of the Chora, one of the most picturesque villages in the Cyclades Archipelago, decorated by the typical white-washed houses with deep blue windows and its famous windmills. From the highest point of Chora, the church of Panagia Gremiotissa, you will enjoy a breathtaking view of the sea all the way to Santorini island. According to the ancient tradition, Íos was the homeland of Homer’s mother and the final resting place of this epic poet, precisely located in Plakato village. On the Southern shore of the island we will stop for lunch at the Tris Ekkliseis Bay (the three churches bay), one of the undiscovered and hidden coves split into three branches where the sea water takes on an infinite gradation of shades of blue and green. A unique spectacle. Luckily for us, not many yachtees know about it and this makes it even more interesting.

This will be our last stop and disembarkation point on this excellently connected hub for those staying with us only for one week. It is also a good connection place to those travelling to Santorini or back to Athens.

Get Started

We are excited you are gaining an interest in trying out our sailing vacation tours. Let’s start working towards it together and have fun arranging it to the very last detail.

Call on (+1) 201-253-1848 or email us here.

Sandra, London Boat Show 2013 portrait