This is a small‑group, expert‑led cultural journey that offers a rare chance to explore the Cyclades islands in depth. In stark contrast to being aboard a large cruise ship or having to wait for ferries, you’ll travel slowly on an 8-cabin traditional wooden gulet with plenty of time to discover the most famous sites together with smaller islands and hidden coves along the way. You’ll have the opportunity to truly appreciate the landscapes and seascapes of this part of the Aegean and and explore each island’s history, landscapes, and living traditions personally escorted by two specialist guides.
A unique opportunity to explore the islands of the Cyclades aboard a Greek gulet with a maximum of just 14 guests.
For most of us, islands are things you sail to, something distant and exotic, a place away from here that grows on the horizon. And, of course a lot of that’s true, especially on a trip like this where each day brings a new marvel, a new seascape filled with other islands, or one apparently far from everything. There’ll be hidden quiet coves where there’s no noise but the splash of swimming, or busy little havens where houses of all hues stand happily in polychrome tiers throwing themselves against a hillside and threaded with winding lanes that disappear into enchantingly mysterious nooks. There’ll be volcanic landscapes and the relics of prehistoric civilizations, masterpieces of ancient Greek art and architecture, landscapes unmoored from other planets, and the forbidding blank walls of fortified places of worship. So yes, this is a tour that more than answers the desire for a peaceful odyssey: some new memorable book to be written in the memory with every passing day. But in some ways its quite the wrong way to look at the Cyclades.
Because for great swathes of history, they’re not at the fringe at all. Far from being the record’s edge, they’re the spindle around which everything revolves, around which the music is made. And that is the other strand that makes this such a fascinating tour. It might not be the story that’s usually told, but these pretty islands, famed now for their gleaming white villages and pretty windmills, have often been at the core of Greek history and culture, right back to its very beginnings. As a result, our tour will have a layer upon layer of history to tell, with experts to do it justice, and a rich seam of art and culture to explore. We’ll have the Bronze Age world of the Cycladic Culture, precocious seafarers and artists famed for inspiring those of more recent times with their magnificently distinctive sculpture; the venturesome Greek cities of the Archaic period whose ambition produced some of the most breath-taking experiments in her art and architecture, brilliant pulses that supercharged the Greek world long before Athens’ dominance; and, as Greece took its place in an ever more interconnected Mediterranean, we’ll encounter the staggering remains of the greatest trading centres of the ancient world just as Rome entered it. There’s more to tell – frescoed Byzantine churches, Venetian castles, prosperous neoclassical mansions, but that’s surely enough to tempt you to make the crossing.
This is a tour that allows you to expansively sample the full breadth of the Cyclades’ history. You’ll discover historical powerhouses that few know exist as well as secluded villages where tradition marks every sinuous alley and which it takes a lifetime, or a passionate guide, to find; you’ll see sights renowned around the world like the awe-inspiring island of Santorini, and have the time to relax and think about them at a sublime islet that rarely sees a living soul and keeps its beauty to itself. An island is always a chapter in itself, and a destination in someone else’s tale. Here, you get to see both in a truly rich compendium.
Prefer a shorter tour? We have a 1-week version of this trip – Cruising the Cyclades
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We welcome you to Paros, and have our first meal together, on board our gulet.
In the afternoon we moor at the tiny harbour of Sikinos, a quiet and peaceful island. We’ll enjoy the beautiful unfolding views as we drive along its single winding road, making our way to Episkopi and a breath-taking surprise. Pressed into the flanks of Mont Troullos, just below a ridge that gives marvellous views of Sikinos’ neighbours, is a grand and near-complete Roman building from the height of the empire, temple-like and standing to the beginning of its roof. Saved in part by becoming a church in later centuries, it’s an unexpected and impressive survival. We’ll consider what it originally was amid gorgeous surroundings before taking in a truly stunning sunset over the western Cyclades.
We drop anchor at Akrotiri, and transfer ashore to make our way to the town of Fira and the archaeological museum that is home to the famed treasures of Bronze Age Akrotiri, among which are some of the finest frescoes of the ancient world. The saffron-gathering women and leaping blue monkeys await us here, surrounded by a wealth of other finds from this outstanding place.
After a little free time to stroll around the town and take in the majestic views from the crater rim, we continue on to the east of the island where we have lunch and a wine tasting at a historic estate before rejoining our gulet for a swim or a pre-dinner cocktail.
Our journey to the rim of the Cyclades has been breath-taking, but with a last gaze at the spellbinding Theran archipelago we make our way out and head north, this time to Ios, where we take a swim in quieter waters where the Cyclades seem to have found yet another wonderful form of blue.
Milos at time feels unexpected not just for the Cyclades, but entirely unearthly: a Sci-Fi landscape. This would be enough reason to come, but the usefulness of these gifts, particularly the superb shining black obsidian that first drew humans here and that still lies in shards and slabs on the surface has given the island a role in history out of all proportion to its size.
We begin our exploration with the Greek and Roman city of Melos, and in particular the theatre on its high perch with suitably dramatic views over the wide harbour. We descend down the slope to explore the Roman catacombs – a funerary landscape almost completely unheard of within the borders of Greece, their galleries filled with bow-vaulted niches and giving the impression of being from long ago and far, far away. We continue on to enjoy a well-deserved lunch and then have a little free time to allow the heat of the day to dissipate before continuing our exploration of the geology and history of this island in the wonderful Mining Museum, just a short walk from our mooring. Here, the incredible wealth of the island is on display in wonderful display cases and interactive exhibits.
A short drive takes us to the celebrated village of Artemonas where winding whitewashed alleys are artfully brought to perfection by an impressive local talent with floral decoration, bougainvillea and the like forming a perfect combination with the Aegean sky in a village given added distinctiveness by the presence of nineteenth century mansions, the product of a prolific relationship between the sea and the island’s ship-captains.
Lunch completes a great morning ashore, followed by a relaxed waterborne afternoon in a favoured cove.
Syros has a formidable recent past in trade (the modern name of the capital, Ermoupolis, derives from Hermes, the god of commerce) and shipbuilding – hence the impressive earlier nineteenth century cast to much of the splendid capital that we’ll spend some time exploring. As well as its more modern prominence, Syros was a major centre of the ancient Cycladic Culture, to the extent that a major phase (the Keros-Syros Culture) is named for it. As a result, the museum has some particularly fine Bronze Age artefacts, from the distinctive folded-armed sculptures to the enigmatic but wonderfully attractive swirl-bedecked “frying pans”. Since we’ve much to see, we’ll be overnighting in this picturesque and bustling harbour.
As are we, because after our final swim in the sacred waters of Apollo’s isle, we take to the same seaways as those the merchants of the second century BC plied and head back to Paros and our final meal onboard.
Transfer to Paros Airport or Harbour.
I would like to book, what else do I need to know?
For information not covered below please refer to our FAQ’s or contact us directly on [email protected]
Arrival and Departure Information
Arrival Airport – Paros
Departure Airport – Paros
Arrival Location – Paros Port (approx. 10 mins from airport)
Departure Location – Paros Port (approx. 10 mins from airport)
Embarkation and departure is planned for approx.17:00. 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 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 Athens 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 Greece. The cheapest way to book flights is directly with the airline online.
Please note:Â 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.
The European Union’s Entry/Exit System (EES) and the European Travel Information and Authorisation System (ETIAS).
The Entry/Exit System (EES) is a new digital border management system for registering non-EU nationals travelling for a short stay, each time they cross the external borders of 29 European countries using the system. The EES will modernise border management of the Schengen countries, gradually simplify border controls and prevent identity fraud. ETIAS travel authorisation is an entry requirement for non-EU visa-free nationals.
You find out more about EES & ETIAS using the link below
https://travel-europe.europa.eu/pb
Visas
For UK Nationals, You can travel without a visa to the Schengen area, which includes Greece, for up to 90 days in any 180-day period without a visa.
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 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 for any of the Greek islands, we are happy to offer information and advice.
Nature of the Cruising 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.
Food: As well as meals on board the gulet 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 guides will introduce you to some of the best beverages (alcoholic and non-alcoholic) the Greek islands have to offer.
Tour Includes:
Cruising aboard the 8-cabin gulet Athen A
Full board accommodation with water, tea and coffee and wine with dinner
Airport transfers on the first and last day of the tour
Travel by private minibus
Harbour fees and crew services
All entrance fees and tips on land
The services of your expert tour leaders throughout the entire trip
WiFi (coverage permitting)
Not included:
Flights and airport taxes
Visas
Travel insurance
Gratuities on the gulet. It is customary to tip the crew at the end of a tour (we recommend a minimum of 20Euro per day per guest)
Tips for guides
Michael Metcalfe
Michael earned his PhD at University College London, focusing on the ancient Greek cities in the Eastern Aegean Islands and Western Turkey. While finishing this research, Michael lived and worked in Athens and Ankara as well as London, and took up his first academic post as Assistant Professor in Ancient History at The Mediterranean Center for Arts and Sciences in Sicily, before joining Peter Sommer Travels full time in January 2009. A specialist in Greek and Latin inscriptions and social history, Michael is currently studying the unpublished diaries of early British Travellers to Greece, Turkey and Sicily, and is involved in publishing inscriptions from many parts of the Eastern and Central Mediterranean. Michael co-edited the Blue Guide to the Aegean Islands and has been contributing editor to the last two editions of the Blue Guide to Sicily.
Michael has designed and led many of our tours, and received rapturous praise. Not only is he 'enthusiastic, charming, and knowledgeable', he is also a natural born organiser. We are delighted to have him as one of our key team.
What previous guests have to say about Michael:
"Michael was an outstanding guide / tour leader. He was a delight to listen to. He brought the archeological sites to life with his passionate interpretation and stories. His love for the land he stood upon was evident throughout our travels." Yvonne McGrath
"Michael was excellent. He has a great sense of humour and was a wonderful and engaging story teller with extraordinary recall of detail. I have done many guided tours with other companies but this one was certainly the best ever. I am unable to suggest any improvements!" Dianne Truss
"Michael's subject matter knowledge, ability to connect with all the tour guests, organizational and interpersonal skills was an absolute highlight of the tour. An amazing guide, super knowledgeable with the latest research. I learned more about Greece in 2 weeks than I learned in school and in the last 60 years! Michael (and his fellow guide Nota) were the BEST EVER guides we had (and we have travelled with many from other companies before)." Constantin Delivanis
"This is the first organized tour we have ever participated in. I think the bar is very high for us now! Michael (and his fellow guide Nota) were wonderful tour guides, so knowledgeable, patient and considerate of all of the participants. We couldn't have asked for better guides. They managed to convey a huge amount of history in an organized way, brought it all alive with stories, and took us to local tavernas with delicious food." Alison Kibrick
"Michael was an exceptional guide. His 'stories' - carefully planned potted histories based on the sites visited - seamlessly knitted together to provide, by the end, a comprehensive survey of the history of the Peloponnese from Neolithic cave burials to post-war Greek politics. I particularly admired his ability to incorporate the uncertainties of scanty evidence and interpretations in talks designed for an intelligent but general audience. Excellent." Nigel Berry
"This was our third trip with Michael and valued his usual flair for imparting his knowledge with such verve and expertise. It was good to be in his company once again. The exceptional guiding by Michael and his fellow guide Nota was a higlight of the trip, they shared their passion and knowledge of the Peloponnese in such an engaging way. We were immersed in the history and archaeology so completely that we felt ourselves back in ancient times. It was a sheer pleasure to tour the Peloponnese in its springtime glory in the company of our enthusiastic, knowledgeable and charismatic guides Michael and Nota who brought history, archaeology and culture to life with such verve. We loved every moment of this trip - it exceeded our expectations!" Margaret Woods
Nota Karamaouna
Born and bred in Athens, Nota has been travelling to Turkey, especially Cappadocia, for many years, captivated by its multicultural history, the spectacular landscape and the warm local hospitality. With a degree in Archaeology and Art History and a Masters in Byzantine Archaeology, she is currently finishing her PhD. at the École Pratique des Hautes Etudes in Paris, focusing on the Byzantine churches of Cappadocia.
Nota has excavated and surveyed at a number of sites in Cappadocia and elsewhere in Turkey, and at sites in Greece, ranging from the island of Kos to central Athens. Alongside her academic studies she has worked for a specialist Byzantine photo-library and the Byzantine Museum of Athens. A native Greek-speaker, she is fluent in English and French (and is picking up Turkish too) and puts her language skills to use as a freelance translator and editor. We are very pleased Nota will be sharing her passion and expertise with our guests.
What previous guests have to say about Nota:
"My husband and I thought the guides/ tour leaders were sensational. You could not ask for better. Nota was so lovely, friendly and extremely knowledgeable ! I have nothing but praise for Nota. My husband and I consider Nota and fellow guide Michael highlights of the tour!" Yvonne McGrath
"Nota was top notch. Nota's enthusiasm and profound knowledge of all things Byzantine was a wonder. Its hard to improve on perfection. This was our favorite tour ever! Nota made sure that people with special dietary needs were accommodated and went above and beyond by looking after a member who had to go to the hospital. Nota and Mike, our guides, were exceptional; very knowledgeable and accommodating. This tour really was an investment in memories. It was expertly crafted, perfectly executed, and delivered an unforgettable journey through the Peloponnese rich with culture, history, and natural beauty. Thanks to Nota and Mike, this tour was truly an experience of a lifetime." Clint Cragg
"Nota has vast and detailed knowledge of the ancient sites, and her explanations are engaging and interesting. I really appreciate the way she went the extra mile to ensure that I had special dietary food, which was of the highest quality. Both Nota (and her fellow guide Michael) were friendly, kind and excellent company. Cruising the Cyclades with Michael and Nota was my second Peter Sommers trip, I cannot recommend it too highly: all the site and museum visits were interesting and informative, and the whole trip was great fun. I am looking forward now to a third Peter Sommers experience." Eilidh Macleod
"This has been my 2nd tour with Nota. I would do another with her any time. One of her many talents is an ability to relate personally with people without losing her professionalism. She is especially caring. Ten out of 10!" Anne Lancashire
"Nota's passion for the history and culture are always evident, and her energy was admirable. Always friendly and engaging. As regular travellers on Peter Sommer tours we were delighted to find the Dodecanese cruise offered the same winning combination of a fascinating itinerary with excellent guides. Their grasp of the history, archaeology and culture added enormously to the experience." Ian Suckling
"Nota was outstanding, she couldn't have been a better tour guide - her knowledge was very wide and she was engaging. She was very kind and helpful. Her organisational skills were exceptional. I would definitely travel with her again." Elizabeth Whyte
"Nota (and fellow guide Michael) were extraordinary, individually and as a bonus, as a team. They were both SO knowledgeable and obviously passionate about Greek history matched by their enthusiasm to show and share that passion. Nota was always on top of how each person was doing - thank you!! Excellent." Daryl Fields
"Nota is the most passionate subject matter expert that I ever met. Her knowledge about Byzantine history and iconography was simply amazing. Nota and fellow guide Michael were the BEST EVER guides we had (and we have been with many other guides with other companies). My wife and I have travelled to Greece many times; the 2 week Peloponnese tour we took with Peter Sommer Travels was the most educational, fun and best organized tour we ever had. The guides were simply amazing. We plan to take many more of their tours." Constantin Delivanis
What makes this Cyclades cruise different from other Greek island holidays?
What is life like on board the gulet during this cruise?
Your gulet is a beautifully handcrafted wooden vessel, offering comfortable ensuite cabins, generous deck space, and a relaxed, sociable atmosphere. Days unfold at an easy pace: gentle cruising between islands, swimming stops in clear Aegean waters, freshly prepared traditional meals onboard and ashore, and evenings anchored in peaceful bays or moored in small harbours. It’s an intimate, unhurried way to experience the Cyclades — scenic, restful, and wonderfully immersive.
Who leads this tour?
Your journey is led by two of our expert guides, specialists in the history, archaeology, and culture of the Greek islands. They accompany you throughout the voyage, offering insightful explanations at every site. Guests often tell us that travelling with passionate, knowledgeable and erudite guides is what makes a Peter Sommer Travels cultural cruise truly exceptional. Please click on the tour experts’ names under the tour dates to read full bios and testimonials.
Who typically joins this Cyclades gulet cruise?
Guests tend to be curious, culturally minded travellers who enjoy archaeology, history, good food, and the pleasure of exploring in a small group. With a maximum of around 14 guests, the atmosphere is friendly and sociable, and the presence of two expert guides ensures plenty of personal attention and in‑depth interpretation throughout the journey. It’s ideal for solo travellers, couples, and friends seeking a thoughtful, and life enriching holiday.
What kind of food will we enjoy on this Cyclades cruise?
Food is central to the experience. You’ll enjoy a mix of traditional Mediterranean meals prepared by the onboard cook and you’ll dine at carefully chosen tavernas and restaurants ashore, showcasing Greek specialities and the distinctive flavours of the Cyclades. Expect fish and seafood, a range of meats, seasonal vegetables and fruits, and local Greek specialities unique to each island. Dietary needs can be accommodated with advance notice.
How physically demanding is the itinerary?
This Cyclades cruise is designed for travellers who enjoy gentle walking and exploring historic sites. Distances vary but many visits involve uneven and broken ground, steps, and uphill or downhill paths. The pace is relaxed, and there is always time to enjoy the expert commentary, absorb the atmosphere of a place, or take photographs or appreciate the views. Good walking shoes and a reasonable level of fitness will ensure you get the most from the experience. The tour is rated 2 out of 5 on our intensity scale, meaning it is classed as moderate. You can find out more by visiting the fitness levels page on our website.


