Ancient Cretan harbours, the clifftops of Santorini, Byzantine walls, coastal Castles – you’ll find all of these and more when you explore the most beautiful cities in Greece.
Greece is better known for its beaches, small towns and villages than its cities, especially with the spread of apartment blocks from the 1950s onwards. But the cities that have largely stayed intact are stunning, as beautiful as anywhere else in the Mediterranean. This is my guide to the best of them.
In this article I’ll give you an overview of each city, its history, setting and what to see there, and I’ll also suggest places to visit and stay while you’re there. I hope you find it inspiring and helpful.
Most Beautiful Cities In Greece
Chania
The west Crete city of Chania is my tip for the most beautiful city in Greece. It has everything you could want, from thousands of years of history, a gorgeous Old Town, a breathtaking coastal setting and a few great town beaches to top it all off. And then it’s the best base for exploring the wild west of Crete.
Chania – ancient Kydonia – is on the north coast of Crete, two and a half hours by road from the capital Heraklion. A strip of coastal resorts has sprung up to its west since the 1960s, but you’re never far from the most dramatic landscapes in Crete, with the White Mountains (Lefka Ora) fifteen miles (25 km) to the south.
Chania Old Town is the place to start, a beguiling warren of narrow lanes and alleyways with traces of long-distant Minoan and Byzantine past, with more recent Venetian and Ottoman-era buildings more prevalent. One from the latter period, the Mosque of the Janissaries, dominates one side of the old harbour, which is lined with restaurants a few steps from the shore. On the other side of the harbour, your eye is drawn towards the 19th-century Egyptian-built lighthouse, one of the most famous landmarks in Crete.
There are many more things to do in Chania besides, with the popular Nea Chora beach a short walk from the Venetian fortified walls on the western edge of the Old Town. There are more beaches to the west, the best of which are Iguana and Agioi Apostoli. Chania is right up there in select company with the likes of Cefalu and Tenby as one of the loveliest historic beach towns in Europe. And it’s a great place to start if you’re dabbling in Crete for the first time.
Where To Stay – Casa Delfino Hotel & Spa – beautiful 17th-century Venetian mansion in superb Old Town location, close to the historic harbour
See Also: 15 Best Day Trips From Chania
Kerkyra (Corfu Town)
The majority of these most beautiful cities in Greece have many tales from to tell from various periods in history. So it is with Corfu Town, though it has had its unique mixture of influences, having been under both British and French protectorates. Despite great damage inflicted by the Luftwaffe in World War Two, Corfu Town is one of the most elegant cities in Greece, and a UNESCO World Heritage Site to boot.
Kerkyra’s Old Town is the huddle of narrow streets and lanes between the two Venetian fortresses, Paleo Frourio (Old) and Nea Frourio (New). This is where you’ll find the church of St Spyridon, home to the shrine of the island’s patron saint, and the Mitropolis, the Orthodox Cathedral, where another saint, Theodora, also supposedly rests.
Near the northern end of the Old Town, the Byzantine Museum houses some superb mosaics discovered at the nearby ancient site of Paleopolis. A few streets also survive from the old Jewish quarter.
You can see the city’s later influences in the modern part of the city close to the seashore and Nea Frourio. The Liston is one of the most famous streets in Greece, its arcades reminiscent of those of the Rue de Rivoli in Paris. The British also built the Palace of SS Michael and George in the 19th century.
While visiting Corfu, don’t miss the beautiful Vlacherna Monastery on an islet at the entrance to the Halikiopoulou Lagoon just south of the city near the airport.
Where To Stay – Bella Venezia – luxury hotel in elegant 19th-century mansion a few steps from the Spianada, the city’s main square
Fira
Fira, the capital of Santorini, is more of a town than a city, but it has made this article as it’s unquestionably one of the most beautiful places in Greece.
Fira grew from the 17th century onwards, as the main settlement nearby, the town below the Skaros fortress, was damaged over the course of several earthquakes, and eventually abandoned.
The town is by far the largest on Santorini, where all bus routes converge, and it has outstanding views over the caldera towards the volcanic islands of Nea Kameni, Palea Kameni and Thirassia.
It’s where you’ll find some of the most beautiful churches in Santorini, most famously the iconic Three Bells of Fira at the northern end of the town, and also the likes of the 16th-century St John the Theologian Church, and the Orthodox and Roman Catholic Cathedrals.
The highlight of a visit to Fira – and for that matter the island as a whole – is the chance to watch a Santorini sunset. The crowds flock to Oia, a few miles up the coast, and crowd into the Byzantine Castle for the sunset behind the village’s windmills. Fira is a busy place, but there’s plenty of room for everyone to spread out and literally hundreds of vantage points to choose from. One for your Greece bucket list for sure.
Where To Stay – Porto Fira Suites – 5-star luxury suites, some cave-style, and all with spectacular caldera views
Thessaloniki
Greece’s second largest city, Thessaloniki is fascinating. It’s by far the biggest city in northern Greece, a melting-pot rich in millennia of history, and was also the second city in the Byzantine Empire after Constantinople. Rather more modestly, it is one of my three favourite cities (along with Krakow and Budapest) from my first Inter Rail trip in 1991.
The main reason I travelled there (apart from needing a last-minute visa for nearby Bulgaria!) was to see its early Christian churches, many of which are included in the city’s Paleo-Christian and Byzantine Monuments World Heritage Site. The 4th-century AD Rotunda of Galerius is the oldest of these, and the remains of the mosaics therein, and the more substantial examples in Hosios David and St Demetrius Churches are among the most important examples of early Christian. Art, along with those in Ravenna, Italy.
The churches included in the World Heritage Site span over a thousand years, with the churches of Agia Ekaterini and Agios Panteleimon from the late Byzantine period (14th century).
Some of the 4th-century Byzantine city walls survive, especially up the hill in Ano Poli (Old Town), a maze of steep cobbled lanes. These walls are magnificent, even predating the Theodosian Walls of Constantinople by a decade or two. The Trigonio and Portara Gates are particularly impressive. The Byzantine-built Heptapyrgion is also an imposing sight, a fearsome citadel that served as a prison until 1989.
Thessaloniki’s most recognisable landmark, the Ottoman-built White Tower, guards the beautiful city waterfront. It’s a wonderful spot for an evening stroll, especially around sunset when the city’s lights twinkle on for the night.
While around the seafront, it’s worth taking a few minutes to contemplate the effects of the Great Fire of Thessaloniki in 1917. Prior to this, the city was home to a thriving Jewish community, which made up over half Salonica’s population. Their district was the worst affected by the fire, leaving tens of thousands homeless and many of their most important buildings destroyed. Many left the city in the years afterwards, including thousands for Palestine. The Nazis then murdered 90% of Salonika’s Jews during the Second World War.
I left Thessaloniki after three days, thinking I needed to spend at least a week there to get under its skin as it had quickly got under mine. One of these days….
Where To Stay – Electra Palace Hotel – iconic 5* hotel on Aristotle Square, close to many of the main Thessaloniki sights
Nafplio, Peloponnese
Nafplio is a gorgeous small city in the northeast Peloponnese, with one of the best-preserved Old Towns in Greece. It’s the capital of the Argolid region in the north of the peninsula, and was, from 1829 to 1834, the first capital of independent Greece. After this date it was moved to Athens.
The oldest part of Nafplio is the Acronauplia, a fortified area with sections of ancient walls largely built by the Byzantines, Franks and, later, Venetian occupiers. The Venetians also built the impressive Bourtzi Castle on an island in Nafplio harbour, and, after recapturing the city in 1685, added the imposing Palamidi Castle on the same hill as Acronauplia. It was the last major overseas fort built by the Venetians before the decline of their Empire in the 18thcentury.
Nafplio Old Town is a rarity in modern Greece, in that many old houses, dating from the 16th to 19th centuries, have survived largely intact. This is unusual because of property laws first introduced in 1929, which led to a profusion of apartment block building around the country, combined with often deliberate neglect of historic houses which were too costly for small property owners to maintain. This led to a catastrophic loss of Greek built heritage across the country.
Thankfully Nafplio – thanks to the heroic efforts of Evangelia Deilaki – was mostly saved, and this is one of the main reasons, the best part of a century later, why it’s one of the most beautiful cities in Greece.
Nafplio is also a great base for exploring Ancient Greek sites, including nearby Mycenae and Tiryns, and the later Sanctuary of Asklepios in Epidaurus.
Where To Stay – Aetoma Hotel – beautiful family-run hotel in an 18th-century mansion in the Old Town
Ano Symi, Symi
Ano Symi, also known as Gialos, is the smallest of the cities I’ve included in this article – indeed, many would suggest that with a population of around 3,000, it’s the size of a small town. No matter – as it’s the capital of the island of Symi, that’s good enough for me.
Gialos Harbour is one of the most beautiful places in the Dodecanese islands off what is now the Turkish west coast. Symi struck it rich in the 19th century, thanks to thriving sponge-diving and shipbuilding industries. Hence the many stunning colourful mansions clustered around the harbour and up the hill towards the village of Horio.
Symi is one of the most popular day trips from Rhodes, and many just stick to the picturesque harbour, Horio is fascinating, and partly ruined, but it’s over 500 steep steps up the Kali Strata stairs, enough to deter even the most determined in the searing midday heat.
There are some small museums to seek out, including the Nautical and Folklore Museum (good for more background on Symi’s sponge-diving history) and the Archaeological Museum.
Tours: This Symi speed boat tour from Rhodes gives you three hours in Symi and a swimming stop in St George’s Bay on the way back.
Where To Stay – Thea – aparthotel very close to the port in a gorgeous old Symi mansion
Rethymno
Rethymno is the third largest city on Crete (after capital Heraklion and Chania), and a subtle slow-burner. It’s busy in the summer season, but not crowded to the extent of some of the resort towns (like Malia and Hersonissos) to the east of Heraklion.
Its position in central-west Crete – roughly midway between the two larger cities – makes it easily accessible for a day trip, or a great base if you’re planning a longer stay.
Rethymno’s Old Town – between the beach and harbour to the east and the Fortezza (Castle) to the west is one of the best-preserved Venetian-period towns in Greece. Many townhouses have survived, as has the Porta Guora, the entrance gate at the southern end of the Old Town, and the ornate Rimondi Fountain, in a small, busy square surrounded by restaurants. Exploring the small side streets around this part of the Old Town is one of the most enjoyable things to do in Rethymno. There are also reminders of the city’s Ottoman past, including the Neratze Mosque on Plateia Mikrasiaton.
The Venetian Fortezza atop the small hill above the Old Town was built in the late 16th century to repel raids from Ottoman Turkish ships and pirates. It survived around seventy years before succumbing to Ottoman forces in 1646. It’s one of the most extensive castles in Crete, with much empty space within its walls but plenty to investigate, including the Sultan Ibrahim Mosque (originally St Nicholas’ Cathedral) and two 19th-century churches.
Even if you have little interest in history, I recommend the short uphill walk to the Fortezza for the astonishing views it commands. To the east, Crete’s second-highest peak, Psiloritis, presides over the central part of the island with the town and beach below. And the Castle is also an awesome sunset spot, with the sun sinking below the rugged mountains to the west at the end of the day in the summer months.
And there’s the main Rethymno city beach. It’s one beach where you can’t complain about the crowds because it’s so vast, swallowing them all up with plenty of sunshades and sunbeds available even in peak summer season. The beach extends over six miles (10 km) to the east, to the resorts of Adelianos Kampos and beyond.
Where To Stay – Neratze Hammam Suites – luxury Old Town retreat with superb views over Rethymno from the roof terrace
See Also – 20 Best Rethymno Beaches and 20 Best Day Trips From Rethymno
Ermoupoli and Ano Syros
Unlike everywhere else in this article, Ermoupoli doesn’t have an ancient history to uncover – rather a short but highly intriguing one. The city was only founded in 1821 – essentially as the expansion of the older Ano Syros – during the Greek War of Independence.
Ermoupoli grew because as a port and shipbuilding town, soon becoming the largest port in newly-independent Greece. Thousands of ships were built there, and the Greek Steamship Company was founded in the city in 1856. It was eventually superseded as Greece’s main port by Piraeus, but remains the capital of the Cyclades region of Greece.
Many beautiful houses were also built in Ermoupoli in the 19th century, many with pastel-painted facades, perhaps more influenced by the region’s Venetian past and more Adriatic in appearance than the likes of Fira and other Cycladic towns and villages.
The focal point of Ermoupoli waterfront is the twin-towered, blue-domed Agios Nikolaos Church to the north of the port, close to Vaporia and Asteria beaches. Staircases lead up from the shore to the church, and it’s a short walk from there to the Neoclassical Town Hall, one of the grandest buildings in the Greek islands, on Plateia Miaouli.
For something a little different, I strongly recommend the walk up to Ano Syros, the much older part of town, founded in the 12th or 13th century. There are no grand squares to be found here, just a maze of narrow, steep stepped streets full of cafes, tavernas and local life. A wonderful place to just wander.
Where To Stay – Hotel Aktaion Syros – beautiful 19th-century Neoclassical waterfront mansion with exceptional views of the port and city
Xanthi
Xanthi is beyond where most visitors to Greece venture, in the far northeast of the country in the region of Thrace, close to the Turkish border. The area is a relative melting pot compared to most of the rest of Greece, with many Turks living in Xanthi and the surrounding area, and Bulgaria is also pretty much on the doorstep.
Thrace is one of the best unexplored regions in Europe, and among the least explored in Greece. Xanthi is the largest city in the region, which grew rich on tobacco cultivation in the 19th century. Tobacco is still grown widely in the countryside nearby, and the income from it accounts for the many beautiful 19th-century mansions in the Old Town. Two of them – once owned by tobacco-rich brothers – now comprise the city’s Folk and Historical Museum.
The character of the city changes as you head north from the Old Town, with church domes replaced by mosque minarets. The city has one of the largest Turkish populations in Greece. A few miles further north and you’re into the Rhodope Mountains and, beyond there, neighbouring Bulgaria.
Xanthi is also popular with birdwatchers, as it’s the main jumping-off point for the Nestos River Delta and nearby Lake Vistonida, where flamingos are a regular sight. It’s also worth the 150mile (25 km) trip there to see the ‘Floating Monastery’ of Agios Nikolaos, which occupies two small islands on the Lake.
Where To Stay – Hotel Xanthippion – one of the best hotels in the centre of Xanthi, only five minutes’ walk from the old Two area
Most Beautiful Cities In Greece – Final Thoughts
I hope that you’ve enjoyed this article and that it encourages you to explore some of these cities. Some are well-known, others some way off the beaten track.
I’ve spent around nine months travelling in Greece, and written extensively about the country, particularly its largest island, Crete. Here is a selection of my articles on Greece:
Landmarks In Greece
30 Most Famous Landmarks In Greece
10 Best Landmarks In Santorini
Best of Santorini
Santorini sunset – the ten best locations on the caldera and rest of the island
Black Beach Santorini, also known as Mesa Pigadia
Best Of Crete
Things To Do In Chania – the most beautiful city in Crete
Things To Do In Heraklion – Crete’s greatly underrated but fascinating capital
One day in Heraklion – 24 hours in the capital of Crete
Visiting Knossos Palace – the most famous Minoan palace site in Crete
Heraklion Archaeological Museum – the best museum on the Minoan civilisation in the world
Things To Do In Rethymno – Crete’s beautiful third city
Balos Beach Crete – stunning remote lagoon beach on the west coast of Crete
Elafonissi Beach – pink sand paradise in the southwest corner of Crete
Falassarna Beach – perhaps the most beautiful beach in the Mediterranean, even the whole of Europe
Best Beaches in Crete – 26 astounding beaches around Greece’s largest island
Kedrodasos Beach – glorious pristine beach and coves in a grove of rare juniper trees
Hersonissos Beaches – the 15 best beaches around the busy Crete resort
Malia Beaches – the complete guide to Malia’s famous beaches
Voulisma Beach – gorgeous tropical beach near Agios Nikolaos
Bali Crete Beaches – all 5 beaches in this north coast seaside village