Just south of Athens is one of the Mediterranean’s premier sailing destinations – the eastern shores of the Peloponnese and the Saronic Gulf. It makes a fascinating route to explore by boat; culture and beauty will vie for your attention, unless the endless blue of the Aegean and the skies above capture you entirely. 

The variety along this route is tremendous – lush Green islands, historic cities, elite cosmopolitan sports, cultural hotspots, and finally a mesmerizing medieval village make for a stunning array of experiences. 

Poros

Actually an island pair – Sphaeria and Kalaureia (a little bridge connects them) – beautifully green Poros is just a short distance from the coast. The hilly island with its low-key charm has also traditionally attracted a cultural crowd, including Patrick Leigh Fermor, who lived here with his lover the Romanian Princess Balaşa Cantacuzino. Henry Miller was also enchanted, describing the port with characteristic surreal vividness in the “Colossus of Maroussi.”

Hydra

This is where Miller was headed after stopping briefly at Poros. Elegant, laid-back Hydra has one of the finest cultural pedigrees of Greece. Not only was this the home of the famous painter Nikos Hadjikyriakos-Ghika and also of the great choreographer Rallou Manou and her husband the famous architect Pavlos Mylonas, it was in later days home to the songwriter and performer Leonard Cohen, and home of many artists today. It’s still a cultural hotspot: The DESTE foundation arranges fascinating contemporary art projects at the former slaughterhouse. 

Hydra has more than a proud cultural pedigree; it also has an enormously proud heritage, its great merchant fleet turned to warships in service of the revolution for Greek independence. Elegant mansions attest to the island’s prowess at sea.

Spetses

Our next stop is one of the most beloved destinations of well-heeled Athenians looking for some peace and quiet (no cars- just horse carriages). Spetses is glamorous and elegant. Fine dining, famous accommodations, and boutique shopping compete with its natural gifts, namely spectacular beaches. 

Spetses is also central to the Greek War of Independence. It is home of the heroine Laskarina Bouboulina – her statue graces the main dock. Spetses honors its proud heritage each September by commemorating a famous sea battle with the Armata – a reenactment of high drama and excitement.

Porto Heli 

Another elite destination, the cosmopolitan and glamorous Porto Heli, on the mainland directly across from Spetses, is within easy reach of Athens and of the northern Peloponnese’s cultural wealth, such as the ancient theater of Epidaurus. This makes it an ideal port for Athenians of means. Expect some fabulous pleasure craft in the harbor, and superbly elegant dining.

Nafplion

Now sailing west into the embrace of the Argolic Gulf we come to a city beloved by all Greeks. This is Nafplio. The Venetians called this the Napoli of the East, crowning it with the Palamidi Fortress, 999 steps above it is beautifully preserved, and the elevation of 216 meters come with some spectacular views, including of the “Bourtzi” – an island fortress in the bay.

This was the first capital of Greece upon the liberation from the Ottomans. Steeped in history and charm, its winding alleys festooned with great boughs of bougainvillea make one of Greece’s most romantic destinations.

Astros

South of Nafplion, our next stop is an under-the-radar destination for a sweet taste of everyday seacoast Greece. With its long beach and larger town inland, Astros has plenty of life year-round.

It’s a perfect place to stop off for some excellent regional cooking and for cultural diversion, perhaps a look at the villa of Herodes Atticus – this 2nd century Roman senator is better known for having a marvelous theater constructed at the foot of the Acropolis, which is still in use today.

Kyparissi

And a bit further south as we make our way down to Monemvasia is Kyparissi. As the name implies (it comes from the Greek word for Cyprus tree), Kyparissi is lush and green, with a pristine beach.

Lovely vernacular architecture adds to the beauty. As to the quiet, it was relatively recently added to the road system. That wonderful sense of remoteness lingers still.

Monemvasia

Honestly, nothing will prepare you for your first sight of Monemvasia. Cleverly concealed from behind, a maze of enchanting alleys and Medieval stone buildings descend towards the sea. This was a key location on the Mediterranean trade routes, connecting the east with Sicily, and as such it prospered in the Byzantine era.

And it prospers today – on the remote southeastern edge of the Peloponnese, it attracts visitors seeking out a unique experience of history, architecture, and a magical natural setting, all while enjoying the finest Greece has to offer in its elegant boutiques and excellent places for wines and cuisine.

Have you ever enjoyed a boat trip along the Peloponnesian coast?