In the Footsteps of the Knights of St. John – A Maritime Journey Through the Dodecanese

For over two centuries, the Dodecanese islands served as the seafaring frontier for the Knights Hospitaller. Known as the Knights of St. John, this military order transformed the Aegean into a formidable network of stone fortresses and naval watchtowers.

The magnitude of this maritime reach is highlighted by the journey of Grand Master Guy de Blanchefort. In November 1513, Blanchefort departed the Port of Nice, sailing south-east toward the Order’s headquarters in Rhodes. Tragically, he fell ill during the passage and never reached his destination, passing away near the island of Zakynthos in the Ionian Sea.

Following the ship’s arrival in Rhodes in mid-December, Fabrizio del Carretto was elected as his successor. During Carretto’s seven-year tenure, he significantly bolstered the defences of Rhodes and the surrounding Dodecanese islands, ensuring the fortresses were well-provisioned with artillery and supplies to withstand naval siege. Carretto died in 1521, the last Grand Master to pass away in Rhodes before the Order’s eventual departure.

Today, there is no better way to explore this seafaring legacy than from the deck of a private yacht, mooring in the same historic harbours where the Knights’ own galleys once sought shelter.

The Grand Master’s Legacy: Rhodes
The journey truly begins at the heart of the Order: Rhodes. As you approach Mandraki Harbour, the massive stone walls of the old city rise from the water, a direct testament to the reinforcements made by Grand Master Carretto.

Stepping ashore, you can walk the Street of the Knights, one of the finest examples of Gothic architecture in the Mediterranean. Unlike the bustling modern port, the walled city remains a silent witness to the Knights’ final stand. A Dodecanese yacht charter offers the unique opportunity to view these bastions from the sea, providing the same perspective held by the Ottoman fleets that eventually laid siege to the city in 1522.

A UNESCO World Heritage Treasure: The Living Medieval City

In 1988, UNESCO designated the Medieval City of Rhodes a World Heritage site, recognising it as an exceptional architectural ensemble. When you step off your yacht and pass through the Gate of Saint Paul or the Marine Gate, you are entering what UNESCO describes as a “perfectly preserved” Gothic city that has remained virtually unchanged for centuries.

Landmarks of the Knights’ Sovereignty
As we follow the footsteps of Grand Master Fabrizio del Carretto, several UNESCO-protected landmarks stand out as essential viewings from both the land and the sea:

• The Palace of the Grand Master:
  Described by UNESCO as the focal point of the city’s defence, this “fortress within a fortress” was the administrative heart of the Knights. Its massive towers and monumental entrance remain the most imposing sight on the Rhodes skyline.
• The Street of the Knights
  This is one of the few places in the world where a complete medieval street survives with its original “Inns” (lodgings) of the different languages of the Order—Italy, France, Spain, and Provence. UNESCO highlights the “purity of its lines” as a rare example of 14th-century urban planning.
• The Great Hospital
  Now the Archaeological Museum, this building reflects the Order’s original mission as the Knights Hospitaller. It is a sprawling Gothic masterpiece that once cared for pilgrims and sailors from across the known world.
• The Fortifications
  UNESCO specifically notes the 4-kilometre circuit of walls reinforced by the Knights. For the charter guest, these are best appreciated from the deck of a yacht as you cruise the coastline, observing the bastions, moats, and “curtain walls” that successfully repelled enemy fleets for generations.
• The Gothic Grandeur of the Collachium
  The Church of St John of the Collachium, the order’s conventual church and a magnificent 50-metre Gothic structure, was converted into the city’s primary mosque following the Ottoman conquest in 1522. Though it survived centuries of conflict, the building was weakened by earthquakes in the 1800s and ultimately destroyed in 1856 when a lightning strike ignited gunpowder stored in the cellars. Today, while only small portions of the northern and eastern foundations remain beneath a modern school site, the site remains a poignant part of the UNESCO zone. As the burial place of the final Grand Masters to die on the island, including Fabrizio del Carretto, it serves as a reminder of the sheer scale of the Knights’ religious and military presence. Standing at the site today, one can still feel the weight of the Gothic style that celebrates throughout the city’s design and the spirit of the Knights remains etched into the coastline.
• Find out more about the UNESCO World Heritage Sites | Medieval City of Rhodes

The Sentinel of the North: Kos and the Castle of Neratzia

Sailing north across the Dodecanese, your yacht will arrive at Kos. Dominating the entrance to the harbour is the Castle of Neratzia, a formidable sentinel built to guard the vital sea lane between the island and the Halicarnassus mainland. For a yachtsman, the fortress remains a magnificent navigational landmark.

Construction began in the 14th century, and the Knights utilized a fascinating blend of local stone and repurposed ancient columns from the nearby Asklepieion (the world’s first hospital). This gives the bastions a unique aesthetic, where medieval military engineering meets classical antiquity.

The fortress is notable for its double-walled fortification, separated by a wide moat that was once flooded with seawater. Today, this moat is crossed by the iconic stone bridge of Phoinikon Street (Palm Tree Street), connecting the castle to the modern town. Stepping ashore, you can explore the four high corner towers and the heavy bastions, such as the Bastion del Carretto, designed specifically to protect the port. Much like the Knights who once kept watch here, today’s charter guests can enjoy an unhindered view of the Aegean from these ancient parapets, looking out across the blue waters where their yacht sits at anchor.

Beyond the Walls: Hidden Strongholds

The Knights’ maritime influence extended far beyond the primary ports of Rhodes and Kos. A bespoke itinerary allows you to navigate the lesser-known seafaring strongholds that once formed a defensive chain across the Aegean.

Kalymnos: The Sentinel of Chora

Sailing into the rugged coastline of Kalymnos, the Great Castle of Chora stands as a monumental landmark. Perched on a naturally fortified precipice, this imposing stronghold served as the island’s medieval capital and a vital sanctuary for the local population against persistent pirate raids. While hidden from the modern harbour of Pothia, a short journey inland reveals the fortress silhouetted against the sky, one of the most dramatic historical vistas in the Dodecanese.

The castle reached its final form under the Knights of St. John in the late 15th century. Inside the sprawling ruins, you can explore ten remarkably preserved post-Byzantine churches and the remains of stone dwellings that once sheltered thousands. The vantage point from the parapets offers a commanding view of the surrounding sea lanes, allowing today’s travellers to see exactly why the Knights chose this site to monitor approaching fleets. It is a place of profound stillness, where the “silence of the stone” speaks to a bygone era of constant maritime vigilance and seafaring history.

Kastellorizo: The Red Castle (Castello Rosso)

At the easternmost edge of the Dodecanese lies the small but historically significant island of Kastellorizo. Here, you will discover the Castello Rosso, the “Red Castle” that gave the island its name. Built by the Knights in the 14th century on a towering outcrop of reddish rock, the fortress overlooks one of the most picturesque natural harbours in the Mediterranean.

The castle served as a vital waypoint and hospital for the Knights as they moved between Rhodes and the Holy Land. Though the fortress is now in ruins, the climb to the top is rewarded with a panoramic view that stretches all the way to the Lycian coast of Turkey. Mooring your yacht in the turquoise waters below, you can appreciate the strategic brilliance of a stronghold that was once considered impregnable.

Bodrum: The Castle of St. Peter

Just a short sail across the blue waters to modern-day Turkey, Bodrum Castle (the Castle of St. Peter) was the Knights’ last and most significant mainland outpost. This massive fortification was constructed using stones from the Mausoleum of Halicarnassus, one of the Seven Wonders of the Ancient World, and it served as a refuge for Christians from across the region for over a century.

Today, the castle houses the world-renowned Museum of Underwater Archaeology. It is a must-visit for any yachtsman, as it displays treasures and entire hulls recovered from ancient shipwrecks in these very waters. Walking through the towers dedicated to the English, French, and German “tongues” of the Order, you get a true sense of the international cooperation that defined the Knights of St. John.

The Final Transit

History tells us that in 1513, Grand Master Guy de Blanchefort died at sea near Zakynthos in the Ionian, a reminder of the vast distances these medieval mariners covered. Tracing his path today, from the South of France via the lush Ionian to the rugged Dodecanese, reveals the Knights determination to protect the maritime path to the Holy Land. When you charter  yacht in Greece, you aren’t just visiting the Greek islands; you are navigating a seafaring history that has shaped the Mediterranean for centuries.

Get inspired of other Greek islands and coast line at our Greek Destination Page.