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Cobbled medieval streets, Byzantine architecture, wine tasting, and soaring sea views, in Greece’s Gibraltar of the East.

Rising steeply from the Myrtoan Sea, Monemvasia is a sheer-sided chunk of land off the Peloponnese’s southeast coast. Settled in the 6th century thanks to its strategic location (it was only accessible by sea and not visible from the mainland), The Rock, as locals refer to it, is now connected to the rest of the peninsula by a short causeway. Its medieval fortress town is enclosed within thick walls that have stood for centuries.

As you stroll the maze of cobbled streets, you’ll notice Frankish, Byzantine, Venetian, and Ottoman influences in terracotta-roofed buildings, domed churches, and stone mosques. A guide can explain the history behind what you see on a walking tour. And, with winemaking a thriving pastime here, you can taste your way through the narrow lanes.

Meanwhile, a walk up to the highest point of the Ano Poli (upper old town) will reward you with far-reaching views over the tiled roofs and sparkling sea.

Things to see and do in Monemvasia

A private walking tour of Monemvasia town

Just a handful of people live permanently within Monemvasia’s kastro (fort), and its narrow, winding streets are better suited to donkey and cart than motor vehicle, making the town feel as if it’s been suspended in time. Much of the joy of visiting comes from strolling the cobbled pedestrian lanes, and pausing at small tavernas to sip coffee, beer, or local Malvasia wine alfresco.

A private walking tour with a local guide can help you delve deeper, though. As you wander the streets, your guide will highlight the history of Monemvasia and how the fort developed based on its strategic location.

Among the highlights is a visit to the main Byzantine square, where you’ll see the stone bell tower of the Christos Elkomenos (Church of Christ in Chains). It was built in the 13th century by Byzantine Emperor Andronicus on the site of an earlier Christian basilica.

You can also zig-zag up to the 12th-century Agia Sofia church, positioned high on a clifftop looking out to sea. Octagonal in shape, it was built by Emperor Andronicus, but was later converted into a Catholic cathedral during Venetian rule, and was used as a mosque during the Turkish occupation.

Wine tasting in Monemvasia

Monemvasia’s wine-making roots go back to the 13th century, with the region’s Malvasia grapes still ripening under the warm Mediterranean sun to this day. You’ll find this wine on the menu at many of the town’s tavernas, and we can arrange for you to join an informal but informative tasting at one located within the castle walls.

Here, the bar’s owner will talk you through five different wines as you sip on each, accompanied by a few traditional mezze plates that complement their taste. They can tell you more about the wines’ history, cultivation, and subtle differences, as well as chatting more generally about life on the island.

Archaeological Museum of Monemvasia

Located opposite the Christos Elkomenos in the town’s main square, this museum is housed in a well-preserved 16th-century Turkish mosque that was later turned into a Frankish church, a prison, and a Greek kafeneion (café).

Inside, you’ll find a rich collection of archaeological findings that help tell the story of Monemvasia’s long history. Expect to see sculptures, ceramics, remnants of the old fortress walls and marble temples, as well as objects used in everyday life over the centuries.

Best time to visit Monemvasia

To enjoy warm, sunny weather without grappling for space among summer crowds and Athenians away for the weekend, visit midweek during spring (April to June) or early autumn (September and October). Attractions will be open, the lanes will be quieter, and you can take in the island’s sights without enduring the heat that July and August often bring.