The Greek islands had been on our list for a while before we actually got there. When we finally did — partly by cruise, partly independently — we understood why so many people go back. But we also understood that how you visit makes a big difference to what you actually experience.

We've sailed into Corfu, Katakolon, Santorini and Athens on MSC cruises, and we've also explored Mykonos and Santorini independently by ferry from Athens — plus spent a week in Athens itself. So when clients ask us about Greek island cruises, we can give them an honest answer rather than a brochure one. Here's what we'd actually tell you.

Why a Cruise Works Particularly Well in Greece

The Greek islands are famously scattered — there are over 200 inhabited ones, spread across a wide stretch of the Aegean and Ionian seas. Visiting more than two or three independently means juggling ferry timetables, different hotels, and a lot of luggage movement. A cruise solves all of that. You unpack once, wake up in a different port each morning, and spend your days ashore rather than in transit.

The other advantage is the season. The Greek islands are at their best from late April through to October, which maps almost perfectly onto the Mediterranean cruise calendar. That gives you a long window to choose from — whether you want the buzz of peak summer or the quieter, slightly cooler shoulder months, which we'd often recommend for a more relaxed experience ashore.

The Islands — What Each One Actually Offers

Corfu is often the greenest and most lush of the Greek islands — heavily influenced by its Venetian history, with an elegant old town that's a UNESCO World Heritage Site. It's a good port for those who enjoy wandering, good food, and architecture as much as beaches. We found it one of the most immediately charming stops on our cruise.

Katakolon is a smaller, quieter port — most people use it as a jumping-off point for ancient Olympia, the original site of the Olympic Games. If you have any interest in ancient history, this excursion is genuinely worth doing. The site itself is atmospheric in a way that photographs don't quite capture.

Santorini is the one everyone has seen in pictures — the white and blue buildings clinging to the caldera rim, the sunsets over Oia. It lives up to the image, but it's worth knowing that Santorini is a tender port, meaning the ship anchors offshore and passengers are ferried in by smaller boats. This can mean queues, particularly in peak season. Going early or booking a ship excursion that gives you priority tendering makes a real difference. We've also visited independently by ferry from Athens — the approach by sea, watching the caldera come into view, is one of those travel moments that stays with you.

Athens (Piraeus) is typically an embarkation or disembarkation port rather than a day stop, but it's worth building in extra time here if you can. The Acropolis and the National Archaeological Museum alone justify a full day, and the Plaka neighbourhood at the foot of the hill is a very pleasant place to spend an evening. My husband spent a week here and found it endlessly interesting — a city that rewards slowing down.

Mykonos divides opinion, and it wasn't actually the island I was most excited about — Santorini had always been the one on my list. The caldera, the sunsets over Oia — that was the dream, and it didn't disappoint.

But when I visited both islands independently — three days each, arriving by ferry from Athens — it was Mykonos that caught me off guard.

It wasn't the scenery, because both islands are genuinely beautiful. It was the energy. There's something about the atmosphere in Mykonos that's difficult to put into words — it just feels alive in a way that stays with you.

It's also worth knowing that Mykonos tends to attract a particular kind of traveller — mostly adults, couples, groups of friends out to have a good time. The general vibe leans toward a more grown-up crowd, and you notice it in the atmosphere. Just something to keep in mind when deciding how long to spend on each island.

Rhodes is one of the most historically rich islands in Greece — the medieval old town, built by the Knights of St John, is remarkably well preserved and still very much lived-in. People actually live and work within those walls, which gives it a completely different feel to a purely preserved historic site — it's not a museum, it's a place.

It's also one of the few Greek island ports where large ships can dock directly, which means no tender boats and a much smoother arrival. And because it's one of the larger islands, there's enough to fill a proper full day ashore — history, beaches, good food — without feeling like you've rushed through it.

What to Think About When Choosing Your Cruise

Duration matters more than people expect. A 7-night cruise typically visits three or four islands — enough to get a real feel for the region without it feeling rushed. Longer itineraries of 10 to 14 nights can take in a wider spread, sometimes combining Greek islands with Turkey, Croatia, or Montenegro.

Departure port is a practical consideration. Flying to Rome or Athens to join a Mediterranean cruise opens up a wider range of itineraries. Sailing from Southampton means no flights, which suits many of our clients — and MSC operates Greek island itineraries departing from both Athens and Rome, so there are good options whichever you prefer.

Ship size is worth thinking about for Santorini specifically. The island has strict limits on how many cruise passengers can come ashore on any given day, and larger ships can mean longer waits for tender boats. A mid-sized ship often gives you a smoother experience at the more sensitive ports.

Time of year shapes the whole trip. May, June and September tend to offer warm weather, manageable crowds, and often better pricing. July and August are peak season — hotter, busier, and more expensive, though the atmosphere is undeniably vibrant.

Why We Often Recommend MSC for Greek Island Cruises

MSC has one of the strongest Mediterranean programmes of any cruise line available to UK travellers, and for Greek island itineraries in particular they tend to use smaller ships. That's not a coincidence — several Greek ports, including Santorini, limit how many cruise passengers can come ashore at any one time, and a smaller ship simply makes the whole experience smoother, both on the tender and once you're ashore.

As an MSC specialist agency, we're able to offer our clients better value than booking direct — and more importantly, we know these itineraries from personal experience.

Ships like MSC Orchestra, MSC Splendida, MSC Fantasia and MSC Sinfonia sail Greek island itineraries from Athens (Piraeus), while MSC Divina does similar routes from Rome (Civitavecchia) — so there are good options whether you'd rather fly into Greece or Italy to join your cruise. We can also advise on Voyagers Club membership and how to make the most of it.

If you're weighing up options, it's worth a conversation before you commit.

One Thing Worth Knowing Before You Book

Since July 2025, the Greek Government has introduced a cruise passenger fee as part of its Sustainable Tourism Programme. The amount varies depending on which ports you're visiting and the time of year — with Mykonos and Santorini carrying a higher charge than other Greek ports, and peak summer being the most expensive period.

It's worth factoring this into your overall budget when comparing itineraries, and confirming how it's handled with whichever cruise line you're booking with.

Thinking About a Greek Island Cruise?

If you're considering it, we're happy to talk through the options — which itinerary suits your dates, which ship fits your style, and whether flying to join or sailing from Southampton makes more sense for you.

There's no pressure and no obligation. Just get in touch and we'll take it from there.

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