I was sprawled on our flying bridge in a quiet cove among the Greek Islands one evening, gazing at the brilliant stars dotting the black sky. Suddenly I wondered if a Greek sailor, perhaps on the verge of sailing into the battle of Salamis against the Persians nearly 2,500 years ago, had watched these very same stars from this same cove and hoped he would survive to see another night.

One of the pleasures of bareboat chartering in the Greek Islands is that the history of ancient civilizations is everywhere you look, anywhere you moor. Greeks, Romans, Persians, Turks—this is the land of Homer, Aristotle, Plato and Sophocles.
In an amphitheater built more than two millennia ago, we stood on marble steps worn smooth by the sandals of the toga-clad men who conceived philosophy, law, mathematics, astronomy—indeed, the very civilization that we now know. On another day, we moored in the shadow of the oldest maritime academy in the world in a harbor from which the Greeks once rowed into battle on triremes.
When Greece opened their waters to bareboat chartering, it was an irresistible opportunity to explore centuries of legends among the Saronic Gulf Islands that are close to Athens, yet a world apart. For our time machine, we chose a French, Jeanneau-built, 36-foot flybridge cruiser with two staterooms and twin Volvo Penta diesels.
Aside from the boat, the most important decision we made was to hire a captain. Unfamiliar with the waters and dealing with a language that was literally Greek to us, it proved to be a wise choice.
We flew into Athens and, after a traffic-clogged taxi ride, arrived at the charter base to find it closed. As we stood wearily with our bags, a motorscooter zoomed up. With a courtly bow, the rider greeted us in perfect English: “Hello! I am your captain, Thrassos.” In moments we were tucked aboard our boat and Thrassos was showing us where he had stowed the provisions we ordered, pointing out the cold drinks and a pile of fresh linens, and leaving us to sleep off our jetlag.

Over the next week, Thrassos proved to be worth far more than his daily rate of $154 USD. When we arrived in a crowded harbor, Thrassos grabbed his cellphone, called his dockmaster friend, and the perfect space magically appeared. Did we need more water? A hose was connected in an instant at a price far below tourist rates. He pointed out wonderful local restaurants unsullied by tourists, gave us a running lecture on island history, and showed us his private swimming coves. Not only was he a charming companion but, when we returned from exploring ashore, it was to a boat that had been washed down and polished. Best of all, he handled the sometimes tricky Med-mooring process with a practiced certainty. And, with a captain, there is no insurance or security deposit.

Experienced Caribbean charterers will find the Greek islands different for several reasons. First, there aren’t as many coves so you’ll spend most nights tied stern to the quay in a small village, where you’ll shop for fresh food daily rather than stock up in advance. Second, the terrain is different, with silver-leafed olive and cypress trees covering the rocky hillsides along with groves of lemon. Because of the antiquities, scuba diving is restricted to certain areas and snorkelers won’t see tropical fish, but they may catch a glimpse of an ancient vase (amphora) untouched for thousands of years.
Distances between islands are short, and we chose the tiny fishing village of Perdica on the island of Aegina for our first night. We were just 20nm from Athens, yet the whitewashed buildings and winding streets were ageless. The Greeks have four names for the west wind but, whatever they call it, we had it in buckets that night. Tucked behind the quay with the fishing fleet, we spent a rolly night and were ready to leave early for Poros, just 12 nm distant.

Poros is on a narrow passage next to the mainland, so don’t be surprised when huge ferries slide past just feet away from your mooring. It was pleasant dining in the cockpit in the evening as tourists and locals strolled the quay, and we had a frappe (a chilled Greek coffee) for dessert at one of the tavernas that set up tables on the waterfront. Later, I went ashore to nearby Café Remezzo, which offered hot showers for three Euros, which brings up a point about our boat.
European boats, like our Jeanneau, are built for European tastes. Americans may find the showers are smaller and staterooms are a bit tight. Our boat was impeccably maintained and, though two seasons old, seemed brand new, but American charterers need to keep an open mind when it comes to space. Our yacht had a double berth forward with limited dressing area, Thrassos staked out the twin cabin to starboard, and we all shared the smallish head.

From Poros we cruised another dozen miles to Hydra, which has remained almost the same since Greek triremes moored in its amphitheater-shaped harbor. Hydra is memorable for blindingly whitewashed homes (Greek white with blue doors) climbing a hillside colored by bougainvillea, but it is also the nautical equivalent of a Greyhound bus station with streams of ferries arriving every few minutes to spew teenagers and tourists.
If you’ve seen the film, Boy On A Dolphin, you’ve seen Hydra, since it was filmed there. In case you don’t remember the film, it introduced Sophia Loren to American filmgoers and, for some of us who were teenagers at the time, the image of Loren in a wet and thin shirt as a Greek sponge diver remains engraved in our memories.
No cars or motorscooters are allowed on Hydra, so all deliveries are by donkey convoys that meander along the quay where you’ll also see Pan, the bearded Greco-American who is the unofficial harbormaster. If you spend the night, be sure to walk to the western point to watch the spectacular sunsets from the small restaurant while savoring an aperitif. In the morning, Kostis Bakery on the waterfront has to-die-for chocolate-filled croissants.

When it comes to island dining, seafood (including octopus) reigns king. Dolmades are spicy meats in grape leaves, tzatzikis is garlic-laced cucumber yogurt, and olives come in hundreds of varieties. If you dare, wash it down with retsina (white wine mixed with paint remover), and ouzo is diluted with water and sipped.
From Hydra we cruised west seventeen miles to Spetses, detouring to explore a quiet bay at Dokos, where Jacques Cousteau found a 3000-year-old sunken ship with its cargo intact. From there, we moved to another cove (Thrassos swore us to secrecy about its location) where the water was so clear we could see the bottom more than 60′ below.
Spetses also has no cars but motorscooters are rife on the pebble mosaic promenade and streets. Known for a female admiral who helped rout the Turks, Spetses is covered with pine trees and the town is dotted with large homes from the trading days when prosperous ship owners called the island home. Moor far back at a quay in Baltiza and you’ll be surrounded by shipyards still building fishing vessels of pungent pine.
From Spetses, we retraced our wake to Poros, where we discovered that Greece is all about time. A Greek morning lasts until one, then lunch and a nap until late afternoon, and some restaurants don’t open until 9pm for dinner. Our first visit to Poros was on a weekday but, when choosing your quayside mooring, remember that the clubs on weekends are noisy until dawn.
For relief, Epidavros on the mainland is just the opposite: you moor next to a quiet park and enjoy blessed silence at night. Don’t miss Epidavros Theater (see sidebar below).

Heading back toward Athens on our last day, we stopped at Aegina Town, where strings of octopus hang outside restaurants to entice diners. Aside from being close to Athens, Aegina is where Zorba The Greek was written, and it is famed for its pistachios.
Tucking into the Kalamaki marina near Athens, we said goodbye to Thrassos and spent our last night aboard organizing our gear. The next morning, there was Thrassos to see us off and make sure our cab driver would take us the short route to our hotel in Athens.
To Captain Thrassos, we’ll use one of the Greek words learned during our voyage, “Efharisto!” Thanks!

Greek Sites Not To Miss While Cruising
Aegina: The Temple of Aphaia (6-5 BC) is a mini-Acropolis on the northeast corner of the island and has been called the most perfectly developed classical temple in Greece. It’s a short cab ride from Aegina Town.
Poros: As you approach from the north, you’ll see the remaining pillar of the Sanctuary of Poseidon (520 BC), who was both god of the sea and island protector. To explore, take a cab from town.
Epidavros: Not to be missed is the superb Epidavros Theater, a 2,400-year-old Greek amphitheater that still hosts an annual festival of classic dramas. Hire a taxi on the waterfront for 30 Euros (the driver includes waiting an hour at the site). Drop a coin or rustle a script on the stage and someone sitting in the last row of the 14,000 seats can hear it clearly. Included in the admission are a museum and the ruins of Askeplion, a temple of healing. Get there early to beat the tourist busses.
Hydra: The museum on the quay not only celebrates ancient times, but also the more recent heroes: 19th Century Hydra shipowners who sent their fleets to defeat the Turks who occupied Greece for 400 years. If you’re feeling athletic, hike up to the monastery of Profitis Ilias for a spectacular view and hand-woven fabrics at the nearby convent. Heads up: the nuns and monks observe the midday siesta from 1-5pm.
Athens: Since you’ll fly in and out of Athens, save a day or two to see the Acropolis, Syntagma Square, and the many ancient ruins in the area.

This article originally appeared in the Summer 2012 edition of CHARTER SAVVY; a free, quarterly publication that focuses on the wide world of chartering, both under-power and with the wind. CHARTER SAVVY covers everything from destinations to boat reviews to insider tips on all aspects of bareboating. Visit www.chartersavvy.com to read more and pickup a free subscription. Chris Caswell often contributes to PassageMaker magazine, and can be seen both online and in print. Most recently he appeared in the October 2014 Issue.