Greek Island Cruises
Explore the cradle of Western civilisation on a Greek Island cruise, where ancient history meets turquoise waters. Our 2026/2027 collection focuses on small ship experiences, allowing you to access boutique ports like Mykonos and Santorini that larger vessels often miss.
The Greek Islands offer a fascinating history laced with legend and spectacular landscapes, with olive groves, small villages clinging to hillsides, and clear turquoise seas. It is a winning combination for a refreshing island-hopping holiday.
At Cruising Holidays, we specialise in a wide choice of Greek Island cruises on a variety of small ships, including megayachts, tall sailing ships, traditional gulets and luxury small ship cruises in the best Greek Islands to visit. Whether you are looking for a family cruise or a quiet private cruise in the Greek Islands, our expertise helps you find the right vessel for these storied waters.
Finding your perfect Greece cruise starts with choosing the right itinerary and ship size. Our curated collection for 2026 and 2027 focuses on immersive experiences that go beyond the typical tourist trails. From 7-day Greek Island cruises from Athens to longer explorations of the Dodecanese, these voyages are designed for those who value authenticity and comfort.
Last updated: 16 March 2026
Greece Cruise Collection
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Lavrion Port (Greece) , Delos - Mykonos , Naxos , Ios - Santorini , Milos - Kimolos , Sifnos, Serifos, Lavrion Port
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Athens (Greece) - Cape Sounion , Ikaria , Patmos - Lipsi , Kalymnos , Levitha - Amorgos , Amorgos - Koufonisia - Iraklia , Serifos , Athens
Civitavecchia (Italy), Positano - Sorrento, Sorrento - Capri, Syracuse, Valletta (Malta), Itea & Transit the Corinth Canal (Greece), Paros, Hydra, Piraeus
Piraeus (Greece), Delos - Mykonos, Bodrum (Turkey), Rhodes (Greece), Santorini, Chania, Hydra, Piraeus
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Piraeus (Athens, Greece), Mykonos, Patmos, Chios, Dikili (Turkey), Bozcadda, Istanbul
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Lavrion Port (Greece) , Edipsos & Oreoi, Volos & Meteora, Skiathos, Mamma Mia! Skopelos, Alonissos & Skyros, Andros & Kea, Lavrion Port
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Venice (Italy), Cres (Croatia), Hvar, Dubrovnik, Kotor (Montenegro), Corfu (Greece), Katakalon, Santorini, Mykonos, Athens
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Lavrion Port (Greece), Delos - Mykonos, Kusadasi (Turkey), Samos, Patmos, Paros, Sifnos, Lavrion port
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Piraeus (Greece), Kusadasi, Patmos (Greece), Amorgos, Mykonos, Spetses, Piraeus
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Piraeus (Greece), Rhodes (Greece), Bodrum (Turkey), Dalyan River, Santorini (Cyclades, Greece), Hydra (Saronic Islands), Piraeus
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Piraeus (Greece), Dikili (Turkey), Myrina (Greece), Skiathos, Skopelos, Poros, Piraeus
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Safaga (Egypt) , At Sea , Suez Canal, Port Said , Alexandria , At sea , Rhodes (Greece) , Santorini , Milos , Hydra , Piraeus
About Cruises Around the Greek Islands
When planning cruises around the Greek Islands, it’s helpful to understand the different island groups, as each offers a distinct "flavour" of Greek culture. The Greek Island cruises 2026 season is set to be one of the most diverse yet, with many operators returning to smaller, less-frequented ports to avoid the peak-season crowds of the larger mainland hubs.
Why choose a small ship for your Greek Islands cruises?
You may find that choosing Greek Island cruises on small ships offers a refreshingly different experience compared to a standard big-ship voyage. While larger liners are often restricted to major ports, smaller vessels can dock in the heart of the village or anchor in secluded bays for swim stops. This makes it ideal if you prefer a more relaxed, intimate atmosphere where the destination remains the star of the show.
Exploring the Cyclades and Sporades
The 200 islands of the Cyclades circle the sacred island of Delos. Fashionable Mykonos cruises are renowned for the iconic windmills and vibrant waterfront, while Paros offers wild spring flowers and a more relaxed atmosphere.
The volcanic Santorini cruise remains a bucket-list staple; however, we often recommend visiting in the shoulder months (May or September) when temperatures average a comfortable 23°C, and the famous cliffside paths are easier to navigate.
Further north, the Sporades Islands, including Skiathos and Skopelos, offer a more verdant, rugged landscape. With over 70 beaches in Skiathos alone, this area is perfect for those who want to combine ancient history with time spent by the water.
The Dodecanese and Crete
In the Dodecanese, a Corfu cruises itinerary might seem far away, but many routes connect the southern islands like Rhodes and Patmos. A stop on one of our cruises to Rhodes allows you to walk through a unique walled old town, while Patmos offers the serene Cave of the Apocalypse.
If you are looking for Greece island cruises that offer significant hiking opportunities, Crete is the fifth largest island in the Mediterranean and is criss-crossed with ancient donkey trails and the dramatic Minoan Palace of Knossos.
Greek Island Highlights
The beauty of a Greek Island cruise is the ability to wake up in a new, sun-drenched port every morning. While the larger hubs are well-known, our itineraries often focus on the authentic charm found in smaller seaside towns.
Is Athens the best place to start your Greek cruise?
For many, the answer is a resounding yes. Most 7 day Greek Island cruises from Athens depart from the historic port of Piraeus. We recommend arriving a day or two early to explore the Acropolis and the winding streets of the Plaka district. Starting your journey here provides the perfect historical context before you sail toward the islands.
What can you expect from a Santorini cruise?
Santorini is famous for its dramatic caldera views and whitewashed villages perched on volcanic cliffs. While it is undeniably popular, visiting via a small ship allows for a more tailored experience. You can spend your afternoon sampling local Assyrtiko wines or visiting the prehistoric ruins of Akrotiri before returning to the ship to watch the sunset away from the heaviest crowds.
Why are Mykonos cruises so popular?
Beyond the iconic windmills and boutique shopping, Mykonos cruises offer access to some of the most beautiful beaches in the Aegean. If you prefer a quieter experience, we suggest taking a short boat trip to the nearby island of Delos, an uninhabited archaeological site that serves as one of the most important mythological locations in Greece.
Exploring Corfu and Rhodes
Further afield, Corfu cruises reveal a fascinating blend of Italian and Greek heritage, visible in the Venetian-style architecture of its Old Town. Meanwhile, a stop on one of our cruises to Rhodes is like stepping back in time; the walled Old Town of Rhodes is one of the best-preserved medieval settlements in Europe.
Finding Your Perfect Greek Island Voyage
Everyone travels differently, which is why we offer a range of voyage styles to suit your specific needs. Whether you are seeking a quiet escape or a trip for the whole family, there is a Greek Island cruise designed to match your rhythm.
Luxury Small Ship Experiences
Our luxury voyages are ideal for those who appreciate the finer things in life, such as exquisite dining, high crew-to-guest ratios, and elegant surroundings. These ships provide a sophisticated base from which to explore, ensuring that your time on the water is just as memorable as your time spent discovering ancient ruins or boutique seaside villages.
Family Adventures in the Aegean
If you are planning a multi-generational trip, we select specific vessels that offer enough space and variety to keep everyone happy without the overwhelming scale of a massive "resort" ship. These cruises perfectly balance educational shore excursions with plenty of relaxed time for swim stops in turquoise bays.
Private Charters and Exclusive Groups
For a truly exclusive experience, a private charter allows you to set your own pace and itinerary. By booking a traditional gulet or a sleek megayacht, you can create the ultimate small group cruise experience in the Greek Islands, sharing the journey only with your chosen companions and a dedicated professional crew.
Social and Cultural Small Group Cruises
Our scheduled small ship departures foster a warm, social atmosphere among like-minded travellers who share a passion for history and culture. These voyages are designed to be intimate, often carrying fewer than 50 guests, ensuring you never feel like just another passenger and have plenty of access to our expert guides.
Romantic Honeymoon Voyages
There is something inherently romantic about sailing into an Aegean sunset on a smaller vessel. These cruises offer the intimacy needed for a special celebration, providing plenty of opportunities for private dinners on deck and quiet exploration of idyllic, white-washed villages. It is a spectacular and tranquil way to start your married life together.
Plan Your Greek Island Voyage
Preparation is key to getting the most out of your time in the Aegean. From choosing the right season to knowing which local delicacies to sample, here is our guide to the essential practicalities.
Best time to visit the Greek Islands
When it comes to deciding on when to cruise the Greek Islands, most travellers find that the season between May and October offers the best conditions. For a more detailed look at weather patterns and seasonal crowds, you can read our full guide on the best time to cruise the Greek Islands here.
Discover the best beaches for small ship cruises
One of the greatest benefits of a small ship is the ability to drop anchor in secluded bays that larger liners simply cannot reach.
- Sarakiniko, Milos: Often described as having a lunar landscape, the white volcanic rocks and turquoise water make this one of the most photographed spots in the Cyclades.
- Elafonissi, Crete: Famous for its pink-tinged sand and shallow, crystal-clear lagoon, it is a spectacular stop for those seeking natural beauty.
- Agios Prokopios, Naxos: A long stretch of golden sand with crystal-clear, glass-like waters that are perfect for a relaxing afternoon swim.
A taste of authentic Greek cuisine
Food is central to the Greek experience, and you’ll find that the best meals are often the simplest ones served in family-run harbourside tavernas.
- Fava (Santorini Speciality): A velvety purée made from yellow split peas, typically garnished with capers and red onion.
- Pastitsada (Corfu Speciality): A rich, slow-cooked beef or rooster stew seasoned with cinnamon and cloves, reflecting the island's Venetian heritage.
- Fresh Seafood: Look for grilled octopus or mussels saganaki (cooked in a spicy tomato and feta sauce). On a small ship, the seafood you enjoy for dinner was often caught by locals that very morning.
- Meze Culture: Don't be afraid to order several small plates to share, from dolmades (stuffed vine leaves) to kolokythokeftedes (courgette balls).
Frequently Asked Questions
Most itineraries visit the famous hubs of Santorini, Mykonos, and Crete. However, by choosing a small ship, you can also access boutique ports like Milos, Patmos, and Symi, which larger liners often bypass. This variety allows you to see both iconic landmarks and authentic, quiet villages in a single trip.
Yes, they are an excellent choice for first-timers. Because the islands are relatively close together, the voyages involve short sailing times and very little time in open water. This makes it a gentle introduction to cruising while ensuring you get to spend the maximum amount of time exploring on shore.
While 7-night voyages are the most common, we also offer shorter 4-night "taster" cruises for those on a tight schedule. For travellers who want a more immersive experience, we recommend our 10 to 14-day grand itineraries that cover multiple island groups and include mainland highlights.
Many itineraries starting in the Dodecanese or Cyclades include a call to the Turkish port of Kusadasi. This is a highlight for many, as it serves as the gateway to the impressive ancient ruins of Ephesus. Some longer routes may also visit the coastal town of Bodrum or the historic city of Istanbul.
They are ideal for those who prefer a comfortable, organised way to see multiple destinations without the stress of managing ferry timetables and luggage. We specifically select itineraries with a relaxed pace, though we can also advise on which ports are easiest to navigate if you have mobility concerns.
Why Book With Cruising Holidays?
Choosing the right Greek Island cruise is a big decision, but you aren't doing it alone. As your trusted travel partner, we combine decades of personal experience with a passion for finding authentic adventures that offer exceptional value. From your first enquiry until you return home, our team provides the honest, expert advice you need to book your 2026/2027 voyage with total confidence.
Explore our latest Greek Island cruise collections or speak with one of our cruise specialists today to start planning your perfect getaway.
Customer Reviews and Blogs
Classical Greece On Harmony V
by JulesI hadn't been to the Greek Islands for a few years so was really looking forward to my week of island hopping on the megayacht Harmony V. Im not a fan of large ships, so this sounded perfect - a relaxed, casual cruise with just 40 or so fellow passengers. Im pleased to say that from the minute we boarded Harmony V, we were instantly made to feel very welcome on this immaculately maintained yacht. Moored at Marina Zea in Athens, the ship was easy to find and so much easier than setting off from Piraeus, the main port of Athens. From the outside, Harmony V looks exactly like a large private yacht, and the inside didnt disappoint either! My cabin was small but very well designed with lovely furnishings, flat screen TV and DVD player, a great shower/wet room and was very clean.
We met the cruise co-ordinator, Iossef immediately, who was absolutely fantastic - his knowledge of the islands we stopped at was amazing, he was very helpful and friendly and his briefings really made the cruise flow very easily. As on any small ship, the weather dictates the route to a certain extent and the itinerary is never set in stone. The captain had a wonderful knowledge of the Greek Islands, and ensured that the route we took was always the best
Mykonos and Santorini were the ports of call for the first two days with optional visits available to the impressive classical ruins of Delos, and an exploration of the island of Santorini. Excursions were not pushed on us - if we didnt want to take them we were given information about the places we moored and could spend relaxed days discovering for ourselves. However, we did take a couple of excursions which were good value for money and very informative, obviously in small groups as Harmony V is a small ship!
The cruise is on a half board basis, which is a perfect way to enjoy all that these lovely islands had to offer. We had a great buffet breakfast on board (fruit, cereals, pastries, plus all the usual hot food like bacon, eggs, sausages, toast) and then either had lunch or dinner on board depending on the schedule, meaning that we were free to enjoy a Greek salad in a harbour side taverna for lunch, or a great moussaka for dinner in the evening. The food on board was fabulous - lunch buffets were enormous and freshly prepared - a wide variety of salads and grilled fish, chicken and Greek specialities. Most of the time we had dinner on land, but enjoyed a memorable Greek night, complete with Greek dancing, plus excellent five course Captains Dinner on board ship.
Where this cruise really excels is the ports this superb small ship can visit. We ventured far off the tourist trail and visited islands untouched by the large cruise ships - tourist-free places that the Greeks keep a well-guarded secret. My favourite of these was Kythira, with its stunning double bay, wonderful beaches, and amazing views from the top of the island. Another memorable highlight was sailing past Monemvasia and seeing this medieval walled town from the sea - a unique view that not many people get to see. This was a wonderful evening as we walked the short distance from Harmony V for a delicious meal in this atmospheric old town.
Another benefit of this relaxing cruise was being able to stop for a refreshing swim. Several times, the yacht cruised into a secluded, picturesque bay and dropped anchor so we could swim off the very useful platform at the back of the ship. There is no better feeling than swimming in the clear, warm waters of the Aegean sea in a tranquil and incredibly beautiful location! Floats, flippers and snorkels were always available - as was a small kayak for the more energetic guests!
With an interesting mix of Americans, Australians, Europeans and Brits on this cruise (just 40 guests altogether!), there was always someone to chat to, or a quiet corner of the ship to relax in. The crew were friendly and helpful, always working hard to make sure everything ran smoothly. Whilst not a luxury ship, Harmony V is classy and well-designed, superbly looked after, and has all the comforts you need. However, the real benefit of being on a small ship was the unique itinerary and superb destinations we could visit - this really felt like a tailor-made cruise on a private yacht and I recommend it whole-heartedly.
Honeymoon On Louis Majesty In The Med
by CorinthThe Louis Majestys standards were very impressive, excellent and friendly staff, fantastic food (far too much). As this was for our honeymoon, we decided to splash out and reserve an XG outside deluxe cabin (deck 7). Great standard, double bedded, plenty of storage space and good size shower room. Louis Majesty provided plenty of areas for people who wanted to relax, read a book or play cards and people tended to congregate around the pool bar/swimming pool area. I enjoyed a daily Jacuzzi dip. Even though on our departure the majority of passengers were German, French and Italian we didnt feel left out. The staff spoke a variety of languages with English as the main language. Signs, announcements, entertainment and menus were all in English. Entertainment was provided throughout the day from ping pong and dart matches to dance lessons and towel folding demonstrations. There was evening entertainment twice an evening, which was colourful and exciting. Our itinerary covered Italy, Greece, Ionian Islands and Albania. Each port of call allowed you plenty of time to look around. The time ranged from an hour and a half to a few hours. We particularly enjoyed Messina in Italy and Zante. I do have to say I found that the organised excursions to be a little expensive and not necessarily available with an English speaking guide we therefore went off on our own accord everytime we were in port. Overall I would highly recommend this to anyone who enjoys a relaxing style cruise with a continental feel. This was my husbands first time cruising and he is now hooked on the cruising style holiday. We cant wait for our next cruising adventure.
Splendours of Greece and Turkey
by TurrellThe MV Cristal is a small ship by current standards but very impressive, not least in the proportion of staff to guests. All the staff were smartly turned out, cheerful and very attentive, and spread over some 40 nationalities. The food was on the whole very good, with a choice of restaurants.
The itinerary was busy but well balanced, we enjoyed Istanbul very much, were very impressed with the very cheap and frequent tram system and would like to go back to sample the delights of this unique city in more detail. Ephesus too justified a further visit. We found the organised excursions to be very expensive but with some homework online prior to your holiday it is possible to use the local transport systems and to meet the local people. We personally find this sort of experience most rewarding and economical, and would be happy to pass on all the tips we accumulated.
We have already recommended Blue Water Holidays and the ship to some friends.
Related Blogs
A Greek island-hopping cruise is the most effortless way to explore the Aegean, acting as a floating hotel that visits a new destination each morning. Whether you're looking to visit world class beaches or ancient historical sites, our guide is here to help you choose the right Greek Islands cruise holiday to suit you. Fri 10 Apr 2026 Choosing which of the Greek islands to include in your itinerary can be a delightful challenge, as each island group offers a distinct personality, read our guide to choosing which islands best suite you and your travel style. Mon 30 Mar 2026 For travellers planning to cruise in the Greek Islands, the decision often hinges on what they value most: the vibrant energy of peak season or the quiet authenticity of the cooler months. Here is a guide to what you can expect when you cruise through the Greek Islands across the different seasons. Mon 09 Feb 2026
