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“One of Greece’s top three cultural holidays 2014” – The Telegraph

“One of the top 10 cultural holidays in Greece 2015” – The Telegraph

Join us for the ultimate Greek Islands tour and explore the astonishing historical wealth and natural beauty of the Aegean Sea in spring when the sites are carpeted with wild-flowers or in autumn when the shores and coved are inviting us to swim in lovely warm waters. Clear blue seas, vast island-dotted horizons and a stunning range of prehistoric, ancient and medieval treasures combine to make Cruising to the Cyclades the quintessential Greek Islands experience.

This two-week cruise through the Dodecanese and Cyclades archipelagos includes about a dozen Aegean islands in its itinerary. Our visits are a carefully chosen mix of the world-famous (such as glorious Santorini, laid-back Kos, mountainous Naxos and UNESCO-listed Delos) and rarely visited secrets of the Aegean (such as remote Astypalaia, picturesque Nisyros and tiny Anafi), each one with its own distinctive character and beauty.

This region has been a crucible of history from the very earliest times. Its archaeological sites range from whole Bronze Age cities to Classical temples, Roman towns, Byzantine monasteries and Crusader castles, as well as countless traditional villages and towns. Our expert guides will bring them all to life, and as the islands glide by you will travel through the pages of history.

Avoiding the hectic crowds and the hustle and bustle of conventional island-hopping, you will travel in style aboard a beautiful and traditional gulet. The delicious meals prepared by the on-board chef will be a constant highlight of your journey, as will the many lunches and dinners ashore, all carefully chosen to showcase authentic Greek cuisine and traditional hospitality.

On this tour you will feel the excitement of discovery, crossing wide open seas or narrow straits to drop anchor at a new island, be it in a bustling port town, a tranquil seaside village or a peaceful cove, and there will be plenty of time to relax, swim, snorkel or kayak, or just lie back and watch the ever-changing island scenery.

Why not join us for a unique experience of exploration and relaxation, a perfect mix of culture and nature, in a truly epic maritime setting?

Our tours receive an average rating of 5 out of 5 from 659 reviews, according to AITO reviews.

Day 1: NB: The itinerary on this cruise is likely to change slightly according to the weather conditions. Some modifications regarding the order or days of crossings, or visits are likely to occur.

Day 1: Our gulet is about 40 minutes from Bodrum Airport in the beautiful harbour of Bodrum, ancient Halicarnassus (in Latin) or Halikarnassos (in Greek). If possible, we set out into the Aegean in the late afternoon. We serve welcome drinks and dinner on board.
Day 2: We make an early crossing to Greece, entering it in Pothia, the capital and port town of Kalymnos in the Dodecanese Islands. The attractive settlement, surrounding the harbour in a strikingly theatrical setting, is dominated by houses and mansions from the 19th and early 20th centuries, witnesses to the island's erstwhile wealth acquired by its large fleet of sponge-diving vessels in that period. After an island lunch, we walk through the streets and lanes to visit the excellent local archaeological museum, the biggest surprise in the Dodecanese! It serves as a great introduction to the archaeology of the Aegean Islands and is especially notable for its unusually fine collection of Archaic and Classical Greek sculpture, including the stunning Lady of Kalymnos, a near-fully preserved bronze statue of a woman recovered from the seabed near the island. Back in port, we learn about the tradition of sponge-diving (Kalymnos is the last Aegean Island to retain a sponge-diving fleet) and about the properties of that unique natural product. Weather permitting, we continue westwards to the tiny islet of Levitha, halfway between the Dodecanese and the Cyclades.
Day 3: Wonderful maritime scenery abounds often permitting great views across large swathes of the eastern Aegean as we make the long westward crossing to the picturesque harbour of Katapola on the stupendously rugged island of Amorgos in the Cyclades. Katapola was the harbour of Minoa, one of the three independent city-states of Amorgos, and physical remains of its distant past are visible here and there. We make our way to the interior of the island, where we visit the supremely picturesque Chora, the island's historic capital village or town, with its wealth of whitewashed houses and chapels set along labyrinthine lanes, all overlooked by a tiny but imposing Venetian castle. It is the first of a series of Cycladic Island towns on our itinerary and a great opportunity to introduce how people lived in these places, villages to our modern eye, but urban in their own self-perception. Later, we continue to the island's southern shore, where a stepped path leads to the astonishing Chozoviotissa monastery, a most extraordinary post-Byzantine marvel perilously clinging to a cliff-face overlooking the stupendously blue waters of the Aegean. The Chozoviotissa is unique: its top floor is the oldest part of the building!
Day 4: An early crossing takes us through the Little or Lesser Cyclades. We might stop for a view of the islet of Keros, a protected archaeological zone not currently open to the public, where recent British and Greek excavation have discovered important evidence of the Cycladic Civilisation of the Early Bronze Age. We continue to Naxos, the largest of the Cycladic Islands, and to its capital town and main harbour, also called Naxos. First settled some 6,000 years ago, it is one of the oldest continuous urban settlements in the world. It was also the seat of the Classical Greek city-state (polis) of Naxos and the capital of the Venetian Duchy of the Archipelago, or Duchy of Naxos, from the 13th to the 16th centuries. In the early afternoon, we walk up to the Venetian castle, surrounded by another labyrinthine settlement, to visit the Archaeological Museum with its rich displays of Cycladic material, including a thought-provoking collection of Cycladic figurines (sometimes called Cycladic Idols), the famous stylised marble figurines that characterise the Early Bronze Age culture of the islands during the 3rd millennium BC. Up in the Castle, we also learn about Marco Sanudo, the Venetian adventurer who founded the Duchy in the early 13th century. In the evening, we take a stroll to the Portara, the enormous marble gateway that stands on a headland just outside Naxos port, which was probably meant to be the entrance to a never-completed 6th century BC temple. The Portara and its striking vista of Naxos Town and Castle make a perfect setting for an atmospheric sunset!
Day 5: Naxos deserves more exploration, so we make our way to the interior of the island. We visit the site of Yria, the legendary birthplace of Dionysos, the god of wine, theatre and many other things, where we can trace the development of Greek temple building from its very beginnings to the 6th century BC, from mud and wood to marble, in the very place where stone architecture was invented. Time and other factors permitting, we also drop by the 6th century BC Temple at Gyroulas/Sangri, sacred to Demeter and among the earliest marble buildings in Greece. Our next stop is the 1,500-year-old church of the Panagia (Virgin) Drosiani with its unusual and very early frescoes, fascinating in themselves and even more so when we consider the cultural and theological background that produced them. After a village lunch, we explore the ancient marble quarries at Flerio, where unfinished 2600-year-old statues lie as if asleep on the ground, accidental witnesses to an essential element of Greek culture and to the central role Naxos played in it – stone sculpture also started here! After returning to our boat, we set out northwards for Rhineia, near the more famous islet of Delos.

(Note: Delos is located close to Mykonos. While we occasionally anchor off Mykonos for the night, the island and its main town are not a regular part of our itinerary. Our tour experts will be happy to explain more).
Day 6: We make a short early morning crossing to Delos. One of Greece’s and the world's most important archaeological sites (it is listed as World Heritage by UNESCO), the islet is nearly entirely covered in unusually well-preserved ancient ruins. As the mythical birthplace of two Olympian gods, Apollo and his twin sister Artemis, Delos was a place of great sanctity, which attracted one after another ambitious city state to make its mark on the sacred island. Initially, Paros and Naxos appear to have competed for standing there, with Naxos prevailing, but in the Classical era it was Athens that put its very sophisticated stamp on the place, making it the nominal headquarters of the Delian League, the military Alliance that brought Athens to its greatest height and subsequently its lowest fall in the 5th century BC. Later, the island was treated as a tax haven by the Romans, bringing great wealth and making it a major commercial centre. We walk the island to see its shrines, its multiple temples to Apollo, but also the streets, lanes and private houses of the affluent trading city that existed here in the last two centuries BC, as well as public buildings like the theatre, and we admire its rich array of sculpture, but also of household items, on display on the local museum (currently closed for renovations). Delos makes for a long and fascinating visit. In the afternoon, we cross southwards to find an anchorage in a region of beautiful seas and many islands.
Day 7: This is the mid-point of our cruise, a time to relax and savour being where we are. Weather permitting, we enjoy a leisurely day among the “Little Cyclades,” the small islands scattered south of Naxos. Today is devoted to taking in the beautiful scenery, to swimming in blue waters, and also to processing the many things we have seen already and to preparing for the unique sights that await us. In the afternoon, we set out southward to reach a cove off Ios or Sikinos in the southern Cyclades.
Day 8: In the morning, we continue southwards to Santorini (or Thera), entering the enormous volcanic caldera, a stark witness to the huge volcanic eruption that tore the island asunder about 3,600 years ago. Reaching Santorini by boat is a unique experience, both awesome and beautiful, as sheer cliffs of lava and pumice rise from the deep blue waters of the Aegean, with the toy-like clusters of whitewashed houses and blue-domed chapels that mark the famous crater-side villages sitting atop like some other-worldly icing. We take the cable-car up to Fira, the island's capital. Here we visit the wonderful Museum of Prehistoric Thera, housing a fascinating array of finds from the Bronze Age settlement of Akrotiri, which we visit tomorrow. The astonishingly lovely painted household pottery from the site, the wealth of imported objects and most of all the samples of the famous Akrotiri frescoes (having their own floor in the museum since 2021) with their rich and very mysterious narrative content combine to throw some light on the affluence of the Bronze Age city, and on its refined and joyful aesthetics. There is ample time to explore the bustling lanes and shops of the town, or to relax on one of countless caldera-side terraces, before we dine in a well-hidden local taverna serving the typical Santorini specialities, after which we finally return to our gulet.
Day 9: We make our way up to Fira a second time, to set out for further exploration of Santorini. Our first and most important stop is Akrotiri itself, the site sometimes described as a 'Bronze Age Pompeii', since it was both destroyed and preserved by the eruption of the 16th or 17th century BC. A modern shelter protects this archaeological miracle, where we can view 3,600-year-old houses, built of mudbrick and wood, which are still standing to the height of up to three storeys, representing only a part of what must have been a larger town. Our thorough tour of the site reveals the similarities and differences between the houses, shows how they are arranged along lanes and around at least one small square, and explores their public and private roles, their religious and secular functions, all of which remain major topics of lively scholarly debate, as does the very identity of Akrotiri's inhabitants. After a tasting session at one of Santorini's finest wineries, where we learn about the characteristic Assyrtiko grape. Following a delightful local lunch, we return to our boat and, if weather permits, cross to the remote island of Anafi, an off-the-beaten-track gem that is the exact opposite of popular Santorini.
Day 10: Conditions permitting, we start our day on the small, rarely visited, and unspoiled island of Anafi, perhaps just to have a little walk through its single village, or maybe to visit the post-Byzantine Kalamiotissa monastery, built over an imposing ancient temple of Apollo. We continue to the remote island of Astypalaia. Administratively part of the Dodecanese, historically more closely connected with the Cyclades and geographically part of neither, Astypalaia is a place apart, or a place in between. We find a lovely cove to relax and enjoy the soothing waters of the Aegean once again.
Day 11: We spend the morning and early afternoon in one or several coves of Astypalaia, devoting our time to the joys of sea and scenery, of swimming and relaxing. In the late afternoon, we ascend the island’s superb traditional Chora, another labyrinth of twisting stepped lanes, whitewashed houses and countless chapels, a place of supreme serenity and beauty, crowned by the mighty castle of the Venetian Querini clan. From the castle, there are stunning views across Astypalaia and the surrounding seas, on a clear day to distant islands.
Day 12: Continuing eastwards (and early), we return to the Dodecanese. We usually make our first anchorage off the tiny island of Yiali, between Kos and Nisyros. Giali is well-known in prehistoric archaeology as one of only two sources of obsidian, natural volcanic glass, in the Aegean. It was first settled in the Neolithic, when Yiali obsidian was traded throughout the surrounding islands and adjacent mainland. Today, it has quarries exploiting the island's excellent pumice and perlite, unique materials that result from the area's volcanic history. Our main reason to stay there for some time, are the pristine waters around it, inviting us to indulge in a day of leisurely swimming. Later, a short crossing takes us to Nisyros, another little-known island, which is a semi-extinct volcano rising above the waves of the Eastern Aegean. We moor at Mandraki, the main settlement, and one of the most attractive in the Dodecanese, our final labyrinth. Stretched out along the coast and the twisting main lane, its squares decorated with lovely pebble mosaics, a Dodecanesian tradition, Mandraki is peaceful and atmospheric, picturesque, and steeped in tradition. After a short visit to the Archaeological Museum of Nisyros, with its fascinating collection of finds from the island's ancient cemeteries, we offer our guests some free time to explore and relax at their own pace. Later, an inland excursion takes us first to the great Classical fortification of Paliokastro, one of the finest examples of Ancient Greek defensive architecture in the region, and then to the caldera, the collapsed crater at the core of the Nisyros volcano. There, we visit the phreatic (steam-volcanic) crater of Stefanos, as place that is both weird and fascinating, before dining on the caldera rim.
Day 13: We make an early crossing to Kos, the second-largest island of the Dodecanese, where we moor in what has been the island's main harbour for nearly 2,400 years, overlooked by the great castle of the Knights of Saint John since the 14th century AD. Kos Town is fascinating. A major earthquake in 1933 led to extensive excavations of the Greek and Roman remains beneath the town on the one hand, and to its rebuilding by the Italian authorities then in control of the island on the other, resulting in a place where surprisingly attractive modernist architecture rubs shoulders with a series of archaeological parks that act as windows into the past. We visit the agora, formal core of the ancient city, founded in 366 BC, when the preceding multiple city-states of Kos decided to unite into one city. The agora combines commercial (market), administrative, religious, and representative functions. In the Casa Romana, we discover a luxurious Roman-era home that has been reconstructed on its original foundations: its architectural refinements and especially its decorative mosaics are a joy to behold. Our tour finishes at the Archaeological Museum, with a wonderful collection of high-quality Greek and Roman sculpture from various public buildings and private homes. (Note that the order of visits on Kos, as on any other island, can change, according to various factors).
Day 14: We make our way inland, to the island's most famous site, the sanctuary of Asklepios, the god of healing, set on the verdant slopes above Kos Town. There, we admire the sanctuary's complex design, indicating the sophistication of the designers who planned it, and marking one of the earliest examples of a fully integrated architectural ensemble, planned from scratch, in Greece. Enjoying the panoramic views it offers across the narrow straits between Kos and the Bodrum peninsula, we also learn about the functioning of an Ancient Greek healing shrine, about ancient Greek medicine and about Hippocrates, the most famous denizen of Kos. Later, there is a final chance to shop, snack or just relax in the bustling town square before our final crossing, back to Bodrum and to our last dinner on board.
Day 15: Transfer to Bodrum airport.

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For information not covered below please refer to our FAQ’s or contact us directly on

Arrival and Departure Information

Arrival Airport – Bodrum Milas

Departure Airport – Bodrum Milas

Departure from Bodrum Harbour (approx. 40 mins from Bodrum Airport) is planned for approx.17:00 in order that the gulet can clear customs and enter Greek waters. Embarkation is from 15:30 onwards. You are more than welcome to arrive earlier to drop off your bags, but please be aware that the crew will be busy cleaning and tidying making everything ready for your group so you will not be able to settle into your cabin.

If your travel plans or flights do not allow you to arrive before 17:00 we recommend arriving in Bodrum the day before the tour starts. This would also allow time to relax, recover from any jet lag and arrive at the boat on time for embarkation and departure.

If you arrive at the gulet after 17:00, we will do our best to enable you to join the tour at a later time and place.

Please Note: Departure time is subject to change depending on weather, harbour or other conditions.

Disembarkation is around 09:00. We will arrange local transfers on the first and last day of the tour.

Booking Flights: If you are staying in or connecting via Istanbul then the easiest way to get to and from the gulet is to fly. There are a number of airlines that offer domestic flights in Turkey. The cheapest way to book flights is directly with the airline online.

Please note: Flights are subject to change. Please contact the airline for exact details.

If you prefer to book with a travel agent, we are happy to recommend specialists in a number of countries around the world, please contact our office for more details.

Travel Insurance:We consider adequate travel insurance to be essential. You should ensure that you take out a suitable policy, to make sure that your trip is properly covered.

A Visa is required to pass through Turkish customs during the cruise. Visas are easily obtained online at eVisa and must be purchased before you travel.

From 2 March 2020, British nationals travelling to Turkey for tourist or business purposes will no longer need a visa for visits of up to 90 days in any 180-day period.

For UK Nationals, travel to the EU will change from 1 January 2021. Please check the current situation regarding visa requirements before you travel. You can find more information online here.

Citizens of European Union or Schengen Treaty member states need no visa for Greece, those from the United States, Canada and Australia do not need to apply for a visa to visit Greece for trips of less than 90 days duration.

Athens, Kos and the Greek islands If you are planning to stay in Athens before or after your tour we have included below links to more information and things to see and do. If you intend to add time on Kos or any other Greek island, we are happy to offer information and advice.

Nature of the Cruising to the Cyclades itinerary

Cruising and Itinerary: This remarkable cruise has a character very different to that of most of our other gulet cruises. We will be crossing some stretches of wide open sea between the islands and covering considerable distances on some of the days. In so doing you’ll gain a wonderful appreciation of the nature and beauty of this part of the Aegean, a thoroughfare for sailors since the Bronze Age. There will be some early starts so we can make passage in the early morning before the wind picks up in the afternoon. While the average travelling time will be longer than our normal coastal gulet cruises, there will be opportunities to swim nearly every day (schedule and weather permitting), but occasionally they will be quite early in the day or quite late.

As with all of our gulet cruises, we have spent a great deal of time crafting the itinerary to be as good as it can be, but we are travelling aboard a boat and may need to make changes according to the weather and the captain’s authority.

Overnights: Compared with our coastal gulet cruises in Turkey and Italy, where we tend to spend a good number of nights moored out in isolated bays, on this trip we will be spending more nights in harbour on the islands. This means you’ll have the chance to explore not only as part of the expert led outings, you’ll also be able to go ashore and wander in the mornings and evenings when we are tied up in the picturesque Greek harbour towns.

Food: The boat is a Turkish gulet with a Turkish crew including a chef who will be cooking up wonderful meals throughout your cruise. As such the food served on board will be traditional ‘Turkish’ or Eastern Mediterranean. We will be going ashore to eat authentic Greek food in family run tavernas at intervals along the way and your tour leader will ensure you’ll have the chance to sample a good many of the local Greek delicacies of the islands. The gulet will be stocked with Greek wine and spirits and your guide, Heinrich, something of a Greek wine connoisseur, will introduce you to some of the best beverages (alcoholic and non-alcoholic) the Greek islands have to offer.


AITO Tour Operator of the Year 2015 Gold Award AITO Tour Operator of the Year 2017 Gold Award AITO Tour Operator of the Year 2018 Silver Award AITO Tour Operator of the Year 2019 Silver Award Best Travel Company for Arts and Culture Holidays Silver British Travel Award 2022 Member of AITO The Specialist Travel Association Member of ABTA the Association of British Travel Agents Member of ASTA The American Society of Travel Advisors Member of ABTOI the Association of British Travel Organisers to Italy

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