Eastern Mediterranean Islands Itinerary: Santorini, Crete, Rhodes and Cyprus in 21 Days

Santorini, Crete, Rhodes and Cyprus are four of the great eastern Mediterranean islands, and taken in that order they tell a single long story: a Bronze Age port buried by a volcano, the palaces of Minoan Crete, a medieval fortress city of crusading knights, and an island where Neolithic villages, Roman mosaics and Byzantine painted churches lie within a day’s drive of each other. Our 21-day Santorini, Crete, Rhodes and Cyprus tour follows that sequence, from Athens to Larnaca, with time on each island to see it properly. This guide explains how the route works, what each stop adds, and where to read more about every site along the way.

Why these four eastern Mediterranean islands, in this order

There are many ways to visit the Greek islands and Cyprus, and Odyssey’s broader overview of the Greek islands and Cyprus introduces the region as a whole. This itinerary is narrower and more deliberate. It chooses four islands whose histories connect, and visits them in an order that lets each one build on the last.

Broadly, the journey moves forward through time as it moves east. Santorini and Crete belong above all to the Bronze Age, the second millennium BC, when Minoan culture spread across the southern Aegean. Rhodes carries the story through the classical and Hellenistic Greek world into the Middle Ages, when the Knights of St John made it their headquarters. Cyprus, the furthest east, gathers almost everything together, from one of the oldest Neolithic villages in the Mediterranean to Roman villas, Byzantine churches and Venetian and Ottoman cities.

The pace is designed for curious, mature travellers. Rather than a different island every night, the tour spends three nights on Santorini, five on Crete, four on Rhodes and seven on Cyprus, travelling between them by local flights and ferries. That leaves time to see a museum and the site its finds came from on the same or neighbouring days, which is the single most useful thing an itinerary like this can do.

Athens: the starting point

The tour begins in Athens on Day 1 with a meeting and welcome dinner. Travellers arrive individually, and we recommend arriving a day early to allow for any flight delays. On Day 2 we travel to Santorini.

Santorini: volcano, Bronze Age town and Dorian city

Santorini is the only stop on the route whose landscape is itself the main event. The island is the rim of a vast, partly flooded caldera, and the villages of Fira and Oia sit along cliffs of layered volcanic rock above the water. Before a great eruption in the Late Bronze Age, Santorini was a single larger island; the eruption buried it under metres of pumice and ash and helped give the caldera its present form.

On the afternoon of Day 2 we visit the Prehistoric Museum of Thera in Fira, and on Day 3, after a morning in Oia and lunch at the small harbour of Ammoudi, some 300 steps below the village, we walk through the site that the eruption preserved. Akrotiri, a Bronze Age port town beneath volcanic ash, still has streets and houses standing two and three storeys high, and its wall paintings are among the finest surviving from the prehistoric Aegean. The same afternoon we climb to a very different settlement: Ancient Thera, a Dorian city on the ridge of Mesa Vouno, founded centuries after the eruption, used as a Ptolemaic naval base in the Hellenistic period and abandoned in the eighth century AD. Seen on the same day, the two sites span nearly two thousand years of the island’s history.

Day 4 turns to the volcano itself. After a walk through Fira, we take an excursion to Nea Kameni, the young volcanic island at the centre of the caldera, built up by eruptions over the last two thousand years, most recently in 1950. In the afternoon we visit a winery to see how Santorini’s growers have adapted to wind, drought and volcanic soil, training their vines into low baskets on the ground; our article on Assyrtiko and Santorini’s basket-trained vines explains the practice. For the island’s longer history, from first settlement to the Venetians and beyond, see our history of Santorini.

Crete: Minoan palaces, a great museum and Venetian harbour towns

On Day 5 we fly to Heraklion, and the next five days explore the island that gave its name, through Arthur Evans, to the Minoan civilisation. In July 2025 UNESCO inscribed six Minoan palatial centres on Crete on the World Heritage List, and three of them fall on consecutive days of the tour.

Day 6 is the heart of the Cretan section. In the morning we visit Knossos palace, the largest Bronze Age centre on Crete and the place where Evans’s excavation and concrete reconstructions shaped the modern image of the Minoans. In the afternoon we see its finds at the Heraklion Archaeological Museum, which holds the frescoes, figurines, stone vessels and clay tablets excavated across the island. Seeing the palace and its contents on the same day is the best way we know to understand both.

Day 7 begins at the Nikos Kazantzakis Museum, devoted to the author of Zorba the Greek, and continues with a wine tasting and lunch before an afternoon at Malia, the Minoan palace on the coast east of Heraklion, the third largest on the island. On Day 8 we cross to the south of Crete for Phaistos, above the fertile Mesara Plain, and the nearby Minoan site of Hagia Triada, before moving on to Chania.

Day 9 shows a later Crete. In Rethymno and Chania we see Venetian fortifications, a church converted into a mosque under Ottoman rule and later returned to Orthodox worship, and the covered market, and the day ends at the Allied War Cemetery at Souda Bay. Many of those buried there died in the Battle of Crete in May 1941, among them soldiers from Australia and New Zealand, and for many travellers from those countries it is one of the most moving stops on the journey. For the full sweep of the island’s past, from the Neolithic to the twentieth century, see our guide to Crete’s history.

Rhodes: harbour city, acropolis and the Knights of St John

On Day 10 a local flight takes us to Rhodes, the largest of the Dodecanese islands and for most of its history a meeting point of sea routes between the Aegean and the eastern Mediterranean. Rhodes has been an important centre since antiquity, and its medieval walled town, a UNESCO World Heritage Site since 1988, is one of the most complete fortified cities of its age.

The Knights of St John, also known as the Hospitallers, made Rhodes their base from 1309 until the Ottoman conquest of 1522, and the upper town they built is still dominated by their buildings. On our first afternoon we enter the Palace of the Grand Master, which tells a more complicated story than its Gothic appearance suggests: largely destroyed by an explosion in 1856, it was rebuilt by the Italian authorities who then governed the island between 1937 and 1940. The same day includes the Archaeological Museum and the ancient acropolis of Rhodes town.

Day 11 visits the Kallithea Springs, used since antiquity, with the rotunda built there by the Italians in the early twentieth century, and Day 12 is spent at the acropolis of Lindos, on the east coast about 40 kilometres south of Rhodes town. Here, on a high rock above the sea, the sanctuary of Athena Lindia, a long Hellenistic stoa and the walls of the Knights’ fortress stand together, a compressed history of the island in a single climb. On Day 13 we visit two more ancient Rhodian cities, Ialysos and Kamiros, along with a museum of the island’s long beekeeping tradition and the wooded Valley of the Butterflies. Our article on ancient Rhodes covers the island’s classical history in more depth.

Cyprus: from Neolithic village to Byzantine mountain church

On Day 14 we fly from Rhodes to Larnaca, and spend the last week of the tour on Cyprus, the third largest island in the Mediterranean and the one with the longest and most varied visible history of the four. After a walk around the old port of Limassol and its castle, we continue to Pafos by way of the medieval castle at Kolossi.

Paphos and the Roman west

Day 15 is devoted to the ancient city of Nea Paphos, part of a UNESCO World Heritage listing since 1980. In Paphos Archaeological Park we see excavated Roman villas whose mosaic floors are among the finest anywhere, along with the theatre, the Odeon and the Asklepieion, and the rock-cut tombs of the necropolis known as the Tombs of the Kings. After lunch at Kourion we visit its archaeological site, with remains from the Hellenistic, Roman and early Christian periods.

The Troodos Mountains

On Day 16 we leave the coast for the Troodos Mountains. At Omodos we visit the Monastery of the Holy Cross and taste commandaria, a sweet wine with a very long history on the island. In the afternoon we see some of the painted churches of the Troodos, ten of which are inscribed together as a World Heritage Site. Their plain, steep-roofed exteriors give little hint of the cycles of Byzantine and post-Byzantine wall painting inside, spanning some five hundred years. On the way to Nicosia on Day 17 we stop at another of them, the small church of Panagia tou Araka, whose frescoes date from 1192.

Nicosia, Salamis and the east

Nicosia, the capital, occupies Days 17 and 18, with the Cyprus Handicraft Service, the Ottoman-period Kornesios Mansion, the Archbishop’s Palace, and the Cyprus Museum, the island’s oldest and largest archaeological museum. On Day 19 we take a full-day excursion to the north-east of the island, to the ancient city of Salamis, near Famagusta, its Royal Tombs and the Shipwreck Museum, and to Famagusta itself. Salamis was one of the city-kingdoms of ancient Cyprus, with royal burials from the ninth century BC onwards and a Roman gymnasium and theatre; it was rebuilt after earthquakes in the fourth century and abandoned in the seventh. Arrangements for this excursion are confirmed before each departure.

Khirokitia and Larnaca

The last full day, Day 20, reaches furthest back of all. After the lace-makers of Lefkara we visit Khirokitia, a Neolithic village occupied from the seventh millennium BC, whose round houses of stone and mudbrick were inscribed as a World Heritage Site in 1998. The day continues to Larnaca Salt Lake and the Hala Sultan Tekke mosque on its shore, Larnaca’s archaeological museum, the Church of Saint Lazarus and the ancient site of Kition, before a farewell dinner. The tour ends after breakfast on Day 21.

How the route connects the islands

Taken together, the four islands form one continuous argument about the eastern Mediterranean. The sea was never a barrier here, but a road. Akrotiri on Santorini traded with Crete and Cyprus three and a half thousand years ago; Minoan culture shaped its art and religion. Rhodes became wealthy because ships passing between the Aegean and the Levant had to pass it, and the Knights fortified it for the same reason. Cyprus, closest to the coasts of Anatolia and the Levant, absorbed influences from every direction and kept the evidence of each.

Several threads run through the whole journey. The first is the Bronze Age, from Akrotiri and the palaces of Crete to the royal tombs of Salamis. The second is the relationship between sites and museums: the Prehistoric Museum of Thera and Akrotiri, the Heraklion museum and Knossos, the Cyprus Museum and the sites of the island. The third is the way later powers, Venetian, Hospitaller, Ottoman and Italian, rebuilt and reinterpreted what they found, so that a building such as the Palace of the Grand Master, or Evans’s reconstructions at Knossos, is itself a historical document. Following these threads is what turns a sequence of famous places into a coherent journey.

Why spend a full week on Cyprus?

Cyprus has the longest stay on the tour because it has the most to see across the widest span of time. In a single week the route runs from Khirokitia, a village of the Neolithic, through the royal tombs of Salamis and the Roman city of Nea Paphos, to mountain churches painted between the eleventh and sixteenth centuries, the Venetian walls and Ottoman houses of Nicosia, and the mosque of Hala Sultan Tekke on the edge of Larnaca’s salt lake. The island also changes character as you cross it, from the coast around Paphos to the pine-covered Troodos Mountains and the plain around Nicosia, and the tour moves between bases in Paphos, the Troodos, Nicosia and Larnaca rather than returning to one hotel each night.

Seven nights also gives the final week room to breathe, which matters at the end of a three-week journey, and the excursion to Salamis and Famagusta is a full day on its own.

How do you travel between the islands?

By a combination of local flights and ferries, with coach transport on each island, all included in the tour. The longer crossings are flown: to Heraklion on Day 5, from Crete to Rhodes on Day 10, and from Rhodes to Larnaca on Day 14. Travel days are organised for you, so they become a chance to watch the islands go by rather than a logistical exercise. International flights to Athens and home from Larnaca are not included.

Food and wine along the route

The four islands also have distinct food and wine traditions, and the tour builds several into the days rather than treating them as an afterthought. On Santorini we visit a winery where the vines are trained into low baskets against the wind. On Crete, Day 7 includes a wine tasting and lunch on the way to Malia. Rhodes has a long tradition of beekeeping, explored at a small museum on Day 13. On Cyprus, at Omodos in the Troodos, we taste commandaria, a sweet wine made in the region for centuries. Most meals are included, 20 breakfasts, 7 lunches and 15 dinners in all, with group dinners at local restaurants along the way.

How much walking does the tour involve?

A moderate amount. The tour is rated Level 2, Moderate: participants need to carry their own luggage, climb and descend stairs, and manage three to five hours of activity a day, the equivalent of walking up to eight kilometres on uneven ground. The most demanding days are those with hill sites and climbs, such as Ancient Thera, the crater of Nea Kameni and the acropolis of Lindos, while museum days and the Troodos churches are gentler. Several sites have worn or uneven paving, so sturdy, flat shoes are essential.

When does the tour run, and is it suitable for solo travellers?

Departures are scheduled in April and October, outside the peak of summer heat and crowds. For April departures, note that Orthodox Easter can bring changed opening times or closures at some sites. Solo travellers are welcome, and many join our tours on their own; groups are kept small, with a maximum of 14 travellers, so the group dines and travels together without becoming impersonal. Current dates, prices and single-room options are on the tour page.

Reading more before you travel

Each stop on the route has its own guide, linked in order above, and together they make a reading list for the journey. If you have time for only a few, start with Akrotiri and Knossos for the Bronze Age, the Palace of the Grand Master for medieval Rhodes, and the painted churches of the Troodos for Byzantine Cyprus. For practical questions about travelling in Greece more generally, see our answers to common questions about Greece.

Twenty-one days across four islands is not a short journey, but it is a coherent one, moving from a buried Bronze Age town to a Neolithic village, by way of palaces, sanctuaries, fortresses and mountain churches, with time on each island to understand what you are seeing. To travel it in a small group of 6 to 14 travellers, with a Program Leader and local guides throughout, explore the Santorini, Crete, Rhodes and Cyprus small group tour.