Greek Island Cruises from Athens

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 starting Athens

Athens – Lavrion

This marina is a good embarkation base for the starting of your sailing week. Located only twenty minutes drive from the Athens airport, this is the closest marina of Athens. The moment you get on your journey from the airport, you will start loosing up to the perfumes and the view of the drive along the shores of the Mediterranean Sea, its colours, its incredible and persistent sunshine that lights up even the dullest of greys. Cafes and restaurants are situated in very heart of in the town creating a pleasant buzzing atmosphere. You can start your culinary experience of the Greek food, on the way to yet the most amazing restaurants to be tasted on the islands. A good place to start getting your taste buds ready for the rest of your trip and get acquainted with Greek flavours. We will welcome you onboard with a drink or two, you can unpack and settled in your cabins, your vacation starts with this first excursion to this 700 BC monument, the Greek temple to Poseidon, mythologically believed to be the god of the sea. The famous Cape Sounion Temple of the Ancient Greek civilisation, is our first stop for the night. You will soon know why this impressing size structure was built in such a strategic site – enjoy it best at sunset. A majestic view to the closest islands you are to sail to from the next day onwards. You will find it resembles the world-famous  Parthenon in Athens.


Makronisos Island 

Is a convenient stopover for our crossing to the Cyclades isles as it is only a short navigation distance from Lavrion. This will serve as a preparation for you to get used to the boat and the sailing for the rest of the week. Passed a bank of outcropping rocks, we drop the anchor for the first plunge in the Aegean Sea. This place is fascinating if you think of this lonely island where the only inhabitants are a dozen goats and sheep. This bay is in a secluded South corner of the island, a well sheltered anchorage with a long beach and a cave so that you will find yourself swimming and sunbathing in the proximity of an ancient Byzantine church with original frescoes and an ancient village ruins where only the goats shelter from the sun – an extremely funny sight! At a lunch time, while enjoying the environment you will get to know your crew in these first days. We will then head off East across the Kea Island channel.

Kea Island

Thea island is the nearest big island to Athens. Starting from the little harbour, through picturesque arched alleys and old Cycladic houses you will reach the Chora, the main town situated on top of the island. Built as an amphitheatre, you will be impressed with its tile-roofed little houses, steep little streets paved in stone, and adorable chapels. The West coast opens to picturesque little bays, adorned with the Mediterranean vegetation, the bushes, the oleanders and the laurel plants. This is where you will first spot your Greek white houses with blue windows, in this tiny island that opens up the itinerary to this marvellous archipelago. You will be amazed to see its coast as you make your way to the port. The entrance is generous and well sheltered by a naturally crafted bay, the wide Agios Nikolaos (St Nicholas) bay hosts Livadhi, the ferry port. Further down is where our secret escape lays – Vourkari village at the end of the bay. Right opposite the local restaurants, buzzing cocktail bars and lounges. This wonderfully hospitable place will allure you in an instant and you will really start living this country and its people. After drinks and a short walk to the port village, we will hop on the bus or on a taxi to reach our dinner venue: the main town located uphill. You will find this the trend of these central Greek islands, you can read more about the historical reasons for building main towns uphill in this page.  The Chora is quiet and cozy. It gives you a spectacular sunset of the entire bay, taking on all nuances of red and purple. The village is a spectacle of white houses with deep blue windows and red tile roofs. Just as you start your walk up to the centre, you will bump into the smallest chapel in Greece: just about three square feet of Byzantine architecture. The main square, opposite the neo-classical town hall hosts The restaurant of the island – a tavern under a large Platanus tree. Lamb chops is a must here and this speciality of the house is amongst the best in the area of the Cyclades, so you better not miss it! The bus will take us back to the port even at a late hours. Lounges and bars on the port are open until late for a midnight cocktail before you hit back home. The morning buzz of the village will wake you up to its sounds and whispers. You can chose between having a cosy breakfast on your private balcony -the cockpit of the yacht- or step off for a local patisserie experience and a Greek coffee. We will then set off towards our next destination: Kythnos island.

Kythnos Island

This is a mountainous and generally arid island with a lot of little closed bays, still far from big tourist flows and therefore very good for those who want to enjoy the sea and need peace and quiet. The little villages on both sides of the island are typically Cycladic; two little ports alternate with bays with sandy beaches and one of these is well-known for its thermal hot springs. What is so specifically unique to this isle is a perfect double beach – two magnificent basins separated by mere 60 feet of pure white sand stripe connecting a desert rock to the main island. The great thing about this is that we have the choice of anchoring on either sides, jump off the yacht, swim to the beach and walk over to the other side or go for a drink at the bar. Bare feet, that is. This is our first encounter with this splendid island. After we have had our lunch there and a chilled in the warmth of the Greek sun, we can sail off to the other side of the beach, go for a few plunges and then slowly start making our way to the port. Given the sun is still high up, actually until 10pm in the summer months, we usually rent cars or motorbikes if you are up for some fun, and explore the island uphill. Drive to the other side, and to the remote villages. We will then get ready for the evening and go to the Chora for a delicious dinner. Our recommended restaurant on the island is right before the entrance to the centre. A short walk in one of the most picturesque towns of these islands is a must and so are the drinks in the islands nightlife capital. This is one of those places where each corner is a painting, and you are amazed by the singular beauty of every alley and row. All streets are paved with sparkling white-washed stones, carefully delineated designs of traditional Greek looks. The Mediterranean bouganvillea vine flowers with their deep fuchsia and purple colours contrasting the whites of house walls and falling down off their balconies and roofs, is a sighing experience at every step. Lively cafes and restaurants, live music and traditional dances invade these labyrinth-like mews and bring everything to life. It is an irresistible vibration of such remote and authentic places so far away from our Western city world. Here too, the big happenings take place in the uphill Chora (Greek for village). Ladies will love the boutiques and craftsmanship reflecting Greek summer fashion traits as to the fabrics and their most colourful prints. There is little life on the port as well, and an alternative for the morning breakfast can be the tavernas right on the beach. A short distance from our boat where you can dip your feet in the sandy beach waters as you are enjoying your coffee.



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.


Syros Island

Alternatively to Serifos island, we can go the Eastern route towards Mykonos passing by Syros. In the past this island was amongst the most important centres both from the commercial and cultural point of view. Now it is the most densely inhabited island. Its main town, Hermoupolis, is also the capital of the Cyclades. Shaped like an amphitheatre with neo-classical buildings, old exclusive houses but also with dazzling white houses sloping down the surrounding hills and reaching the harbour. It gets a particular greatness in the central square. The villages on the mountains and along the coast are a fascinating sight.

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.

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.

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