The Mediterranean cruise map is getting more interesting.

For years, the same heavyweight names dominated itineraries. Barcelona, Santorini, Dubrovnik, Naples. They’re still there, but smaller ships are increasingly filling the gaps with places many passengers will need to Google before booking.

Star Clippers has just added 27 new Mediterranean ports for summer 2027, the largest expansion of new calls in its history. They include Astypalea, Datça and Kekova, while earlier additions brought Monopoli and Crotone into the programme. The line says demand is growing for smaller, less familiar ports that its sailing ships can reach more easily than large cruise vessels.

That makes these destinations worth knowing, particularly if you’ve already done the Mediterranean greatest hits.

Astypalea: Greece without the greatest-hits feeling

Astypalea sits in the Dodecanese but has much of the whitewashed, blue-shuttered look associated with the Cyclades. Its Chora climbs towards a Venetian castle, while beaches and small settlements spread across an island narrow enough in the middle to resemble a butterfly.

The appeal on a cruise day is simplicity. You can wander the old town, climb to the castle, swim or have lunch without building the entire day around a transfer. Greece’s tourism board positions Astypalea around exactly that combination of traditional settlement, sea and relatively unhurried island life.

For repeat Greek-island cruisers, that may be enough. Not every port needs an archaeological site requiring three hours and a laminated headset.

Skopelos: the green Greek island with the Mamma Mia problem

Skopelos is greener than the Cycladic islands cruise passengers tend to know best, with pine forest reaching down towards beaches and a traditional town of white houses and churches.

It is also, inevitably, “the Mamma Mia! island”. Several scenes were filmed here, and Star Clippers is leaning into that connection on its new Skopelos calls.

The film is a perfectly legitimate reason to visit, but the island works without ABBA. Spend the day in Skopelos Town, head for Panormos or Kastani beach, or make the pilgrimage to Agios Ioannis chapel if your relationship with Pierce Brosnan’s singing remains uncomplicated.

Datça: Türkiye at a slower pace

Datça sits on a long peninsula where the Aegean and Mediterranean meet. Türkiye’s tourism board sells it with the instruction “don’t be in a hurry”, which is perhaps slightly provocative when addressed to somebody whose ship leaves at six.

Fortunately, the town works well on a short call. Old Datça has stone houses, cobbled lanes and bougainvillea, while the peninsula is known for almonds, coves and beaches. If the timetable allows, ancient Knidos at the far western tip adds a major archaeological site without turning Datça itself into another museum-with-a-port attached.

The sensible alternative is to stay close, eat, swim and accept that occasionally a shore day can simply be nice.

Kekova: where the approach is part of the attraction

Kekova is the clearest example of why smaller ships matter. Off Türkiye’s Lycian coast, ancient walls, stairways and harbour remains lie partly submerged around Kekova Island. Nearby Kaleköy rises towards Simena Castle, and the whole area is better understood from the water than from a coach park.

Star Clippers plans to sail between Kekova and Simena before anchoring, with passengers able to continue by small boat towards the submerged ruins or go ashore nearby.

That makes the journey into the port part of the day itself. You haven’t sailed somewhere beautiful only to immediately get into a vehicle and leave it.

Cruising occasionally remembers what it’s good at.

Monopoli: Puglia without the Bari transfer

Monopoli’s harbour pushes directly into its historic centre, which immediately gives it an advantage over ports where the interesting place is described as “approximately 75 minutes away, traffic permitting”.

The old town brings medieval buildings, defensive walls, the Castle of Charles V and a Baroque cathedral, while the surrounding coast has small coves and beaches. Italy’s official tourism site also points to the town’s long history as an Adriatic trading hub shaped by Byzantine, Norman, Venetian and Spanish influence.

You can use Monopoli as a base for the Valle d’Itria or Alberobello, but you don’t need to. The harbour, old streets and seafood provide an unusually low-administration port day.

Crotone: Calabria gets a turn

Crotone brings cruise itineraries into Calabria, a region far less familiar to international cruise passengers than neighbouring Puglia, Campania or Sicily.

Ancient Kroton was an important Greek city, and the modern town still has its archaeological museum, the Castle of Charles V and easy access to the Capo Colonna archaeological area overlooking the Ionian Sea.

There’s also a strong local food identity, including sardella, the spicy fish speciality associated with the Crotone coast, and the nearby wine country around Cirò.

It’s perhaps the least obviously glamorous name on this list, which is part of its appeal. A working Calabrian city with Greek archaeology and very serious lunch makes a refreshing change from another harbour full of luxury boutiques.

Why smaller Mediterranean ports are appearing on cruise itineraries

The practical explanation is ship size. Star Clippers’ vessels carry between 166 and 227 passengers and can anchor or berth in places inaccessible to today’s largest cruise ships. The line says its 2027 expansion reflects demand for smaller, less familiar ports as well as the physical flexibility of its fleet.

For passengers, the result is a Mediterranean itinerary with more contrast. Famous ports still matter, but they become more interesting when mixed with somewhere you haven’t already seen on twelve brochure covers.

Astypalea instead of another Cycladic repeat. Monopoli as the destination rather than somewhere passed on the way to Alberobello. Kekova, where the ship itself is one of the best places from which to see the attraction.

The Mediterranean hasn’t suddenly acquired new towns. Cruise lines have simply started putting more of the existing ones on the map.